Practical Founders Podcast: Recent Episodes
Greg Head
Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with founders who have built valuable software companies--without big funding.
Mike Lyon is the founder and managing director of Vista Point Advisors, a boutique sell-side investment bank he started almost sixteen years ago. A former chemical engineer at Exxon and BP who later joined Citigroup's tech M&A team, he built Vista Point to solve a conflict of interest he watched play out on Wall Street: bankers quietly working both sides of a deal.
Vista Point Advisors represents founder-led software companies only — never the buyers — focusing on vertical SaaS with enterprise values between $30 and $300 million. Mike and five other managing directors run about a dozen deals a year, spending 50 to 100 hours cleaning up each company's data before launch and running a long, non-exclusive process built to keep multiple buyers competing to the finish.
Mike says buyer criteria changed this year for the first time in a decade, and changed fast. Buyers now demand roughly 90% gross retention as a proxy for AI resilience, favor systems of record with real data moats, and discount horizontal point solutions. His advice: understand exactly how you'll be graded long before you go to market, because the aperture for a premium exit keeps shrinking.
Key Takeaways
- AI Changed Everything — For the first time in a decade, buyer criteria are shifting week to week this year.
- Gross Retention Rules — Buyers now want 90%-plus gross retention as a proxy for AI resilience.
- System Of Record — Point solutions look exposed to AI; systems of record with real data moats win.
- Exclusivity Is Leverage — Once you grant it, the deal slows and power shifts to the buyer.
- Watch Spend, Not Talk — Every buyer says the right things; only diligence dollars prove real intent.
- Second Bite Pays — Most founders who sold majority to PE did as well or better on the rollover.
Quote from Mike Lyon, Founder & Managing Director of Vista Point Advisors
"For the first time in ten years, the rules hav changed — and they changed fast. If you called any private equity or strategic buyer over the last decade and asked what makes a good SaaS company, the answer barely moved. This year I've had conversations I've never had before, where the criteria shifted week to week — first it's X, then X plus Y, then X plus Y plus Z.
The first big change is a maniacal focus on gross revenue retention (GRR). Net retention (NRR) was the star for years, but gross gives you no credit for upsells — you only get dinged for downgrades and churn, so it's really asking what happens if you can't upsell anymore. Buyers want to see 90% or better now, and our read is that it's a proxy for AI risk: they don't fully understand the AI threat yet, but they know a business at 90% gross retention is probably resilient enough to take some hits and survive.
System of record is the other thing that suddenly matters more. Point solutions feel like they're at further risk from AI, so buyers want a system of record with a real data moat — not the fake moat where anyone can go get that data somewhere else — or a payments angle, which is harder for AI to route around. And if your business started eight years ago, it's hard to be fully agentic, but you at least need the ability to hang agents off the backbone of your software to keep delivering value."
Links
- Mike Lyon on LinkedIn
- Vista Point Advisors on LinkedIn
- Vista Point Advisors website
Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.
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The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Wayne Cartmel grew up on a small farm in the Lake District region of northwest England and was selling chickens by the age of four. He trained as a maths teacher in Bedfordshire and could not believe the process he had to go through to apply for jobs — hours of Word-based application forms, one after another. He asked why nobody had digitized it, and then decided to do it himself.
Funded by a £5,000 innovation voucher and built with a computer science volunteer who is still his CTO eleven years later, it took two years to reach a working prototype. Wayne took no funding, went over £100,000 into personal debt, and did not draw a livable salary for several years.
MyNewTerm is a specialized hiring marketplace and applicant tracking system that connects schools across England directly with job seekers. It allows educational employers to post vacancies and manage candidates using a streamlined workflow that supports part-time, full-time, and temporary roles.
MyNewTerm now partners with over 6,000 schools and 500 multi-academy trusts, has surpassed £5M in revenue, and processes over 100,000 candidate applications a month with just 20 employees. It holds roughly 45% market share among multi-academy trusts against a private-equity-backed incumbent.
Key Takeaways
- Distribution Wins — Anyone can build a product now; almost nobody can get it into customers' hands.
- Start Absurdly Small — He targeted five schools in one district of Luton, then moved to the next.
- Free Buys Evidence — Schools wouldn't pay for an unproven marketplace, so he gave it away to prove it worked.
- Focus Compounds — Sticking to the core, not chasing adjacent opportunities, is what built the market share.
- Hard Equals Defensible — The marketplace was brutal to start, which is exactly why nobody can replicate it.
Quote from Wayne Cartmel, Founder and CEO of MyNewTerm
"Distribution and execution are everything, because the market nowadays is going to be flooded with software products, EdTech in particular. The advancements in AI mean that you can spin up products really quickly. I almost wish that was available ten years ago when I was starting as a non-technical founder.
"Building the product is the easy bit; I thought it would be the hard bit. What I failed to realize, and I wish somebody had told me, is that it's actually the distribution and the sales and marketing, the go-to-market motion, that's the really tough bit, doubly hard with a two-sided marketplace.
"You can build a product on such a small budget now, but you've got to be really deliberate and disciplined to keep on going and generate momentum. That's why many don't make it: they don't have the ability and resilience to get through the really hard moments when people are continually saying no to you, and you're continually being rejected."
Links
- Wayne Cartmel on LinkedIn
- MyNewTerm on LinkedIn
- MyNewTerm website
Podcast Sponsor – Vista Point Advisors This podcast is sponsored by Vista Point Advisors, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Eran Galperin is a Brazilian jiu-jitsu black belt who had already had one VC-backed marketplace failure when he started Gymdesk. Originally called Martial Arts on Rails, it launched in 2016 as a naive version of what he thought a gym needed. He was training five or six times a week and every gym owner he knew hated the software they used.
For four years he couldn't acquire customers, so he took a job as CTO of an e-commerce company and built the product on nights and weekends. Growth finally came through organic SEO, which still drives over half of new leads. He hit $3M in ARR by the end of 2023 with 16 employees, no salespeople, and over 40% of free trials converting without a demo.
In May 2024 he sold a majority stake to Five Elms Capital for $32.5M in cash for his share. What they paid the premium for wasn't size — it was churn under 1% a month, three straight years of more than doubling, profit margins over 50%, and a payments business compounding underneath. He stayed on eighteen months and now lives in Tokyo, building a custom house and an AI vision product for real estate.
Key Takeaways
- Churn Ceiling — Churn is the cap on growth; under 1% monthly is what buyers pay premiums for.
- Slow Bake — Four years of nights and weekends let the product mature in ways funded companies never can.
- Payments Compound — Profit share from payment providers grows as volume grows, and buyers pay extra for those rails.
- Buyers Differ Wildly — One expert said 5X was his cap; Five Elms paid 10X because they buy outcome, not value.
- Get Representation — A $60K legal bill and a good M&A broker closed the information asymmetry with private equity.
Quote from Eran Galperin, Founder of Gymdesk
"What we did have was very low churn, and that's one of the factors that helped us get the premium when we sold the company. Everybody building SaaS eventually realizes that churn is the cap your company has on growth. Eventually churn, which is a relative number, grows to the point where it meets the absolute numbers of your growth.
"Because we had very low churn, less than one percent month over month, that definitely helped us start the conversation from a very good position. The other element was that growth was very consistent year over year. I think we more than doubled three years straight.
"That in combination with the low churn and high profit margins was the last big item. We had a lean team, and we were over fifty percent profit margins when we sold. This was a firm that had multiple other portfolio companies similar to us, so they had a pretty good idea what a successful outcome would look like for them, and we filled all those criteria."
Links
- Eran Galperin on LinkedIn
- Gymdesk on LinkedIn
- Gymdesk website
- Tinyseed.com website
- Five Elms Capital
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Cliff Sentell co-founded Compass Professional Health Services in Dallas in 2005, where he and two partners each put in $20,000 and bought a single server. They started in healthcare price transparency, reverse-engineering the cost of specific procedures on specific plans out of billions of insurance claims. The first idea, selling to consumers, flopped, because frustrated patients wouldn't pay $20 to $30 a month for guidance they saw as nice-to-have.
So they pivoted to employers, who were footing the bill for their workers' poor healthcare decisions, and wrapped the data in a tech-enabled service: an app, "health pros," and a custom CRM. Compass reached about $1 million in revenue in three to four years, grew from $3 million to $10 million fast, and scaled to roughly $30–40 million with 200 employees and Fortune 100 clients, T-Mobile its largest.
They turned down growth equity investors to keep control and equity, funding growth off their own balance sheet. In 2018 Alight acquired Compass — mostly cash with a multi-year earnout — and revenue tripled inside Alight within three years. Today Cliff is a partner at Cypress Growth Capital, where he invests non-dilutive capital to help bootstrapped SaaS founders growth faster. The Cypress thesis is simple: in the AI era, industry domain knowledge is the moat, not features.
Key Takeaways
- Sell To Payers — Frustrated consumers won't pay; find the customer whose real problem costs them money.
- Protect Your Equity — Declining growth equity kept control and made the eventual exit worth multiples more.
- Exit Isn't The End — After the acquisition, Compass re-found product-market fit and tripled revenue inside Alight.
- Flexible Beats Restrictive — Royalty funding flexes with cash, avoiding debt covenants and the loss of control equity brings.
- Outcomes Over Models — Value created, not the recurring-revenue label, now decides whether a company scales.
Quote from Cliff Sentel, Partner at Cypress Growth Capital
"The biggest thing that's changed now with AI in SaaS is differentiation. If you're really good at something, if you have domain expertise that other people can't do, and you add AI to that, your moat of better knowledge and capabilities gets wider.
"That's fundamentally our investment thesis right now at Cypress. Can we find companies that are really good at a very specific domain capability, that have proprietary data, that create the system of action their customers use — feeding that information back into the knowledge set and building the moat wider and wider?
"This is a moment where knowledge and expertise are at a premium. Not software, not how much you've built. How much do you know? That's what you're capable of achieving."
Links
- Cliff Sentell on LinkedIn
- Cypress Growth Capital on LinkedIn
- Cypress Growth Capital website
- Compass Professional Health Services (now Alight)
Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.
If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.
Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.
Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Matthew Bullis grew up in a mud-brick hut with no running water on a small island off South Korea, was adopted to the US at 11 speaking no English. After a dot-com near-miss, he took over his brother's struggling concrete-pumping software — down to about $20,000 a year — for 90% of the company. He taught himself to code and rebuilt it from scratch.
From 2016, Bullis built RapidWorks into the operational system of record for heavy-equipment subcontractors: concrete pumping, cranes, hydrovac, and other site services. RapidWorks helps contractors book jobs, dispatch crews, manage the field, and get paid faster with accuracy and speed, taking dispatchers' productivity from 20 jobs to 60+. Today the company is near $20 million in ARR, serving more than 80% of the concrete-pumping market.
In 2023, approaching $5 million in revenue, Bullis sold a majority to Wavecrest Growth Partners and brought in a new CEO Tim Curran with a new executive team. Matthew expected to be phased out within a year. Instead, by staying flexible and solving whatever broke, he became indispensable as chief strategy officer, taking on important strategic execution roles across the company where he was needed.
Key Takeaways
- Solve any problem — A bootstrapper's real value is surviving anything and solving whatever breaks.
- Stay flexible — Don't trade on past wins; credibility comes from the value you create now.
- Sit with customers — Weeks in their offices surfaced problems they never thought to ask for.
- Hire your boss — A ready-made CEO and team de-risk the scale a founder can't reach alone.
- Keep perspective — Nothing is as good or as bad as it feels in the moment.
Quote from Matthew Bullis, Co-Founder and CSO of RapidWorks
"To stay useful and relevant when you're not the CEO any more, you have to be flexible. People overemphasize the value of what they've done in the past: look at all the great things I did. But that's like living in your high school glory days. It doesn't merit much, and you can't expect people to give you credibility just for what you built.
"Your real value is surviving anything and solving any problems. Take that to heart — I can survive anything, I can solve any problem, I can create value for myself and the people around me. Under any difficult situation, people are drawn to people of value.
"So I stopped staying quiet. When I saw things weren't done right, I spoke up, and the seasoned leadership saw my opinions had value. When people see value in you, and you really help, they want you on their team — that's how I won the other executives over."
Links
- RapidWorks on LinkedIn
- RapidWorks website
- Wavecrest Growth Partners
Podcast Sponsor – Vista Point Advisors This podcast is sponsored by Vista Point Advisors, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Nick Olsen is the Head of AI Innovation at Mainsail Partners, where he works hands-on with 25 scaling vertical SaaS companies helping them adopt AI in engineering and product. Before joining Mainsail, Nick spent 20 years helping build ResMan from a 3-person startup into a scaled software company serving the multifamily property management market.
Today, Nick leads a team of engineers who embed directly inside portfolio companies to build AI systems alongside their teams. They don't just advise from the sidelines—they commit code, ship features, and help technical leaders redesign how modern software organizations operate.
Nick explains why AI-first engineering is no longer a competitive advantage for SaaS companies—it's becoming the minimum requirement to stay competitive. The winners won't just write code faster. They'll build better products, make better decisions, and deliver dramatically more customer value with AI-native teams.
Key Takeaways
- Table Stakes — AI-first engineering is no longer optional for serious SaaS companies. It's becoming the minimum operating standard.
- Roles Are Collapsing — Product, design, and engineering are moving closer together as AI removes slow handoffs and bottlenecks.
- Velocity Misleads — Shipping 3x more features doesn't matter if customers don't want them. Outcome beats output.
- Judgment Wins — AI makes building cheaper and faster. Strategic product judgment becomes more valuable, not less.
- Agents Matter — The best teams increasingly treat AI agents like teammates with jobs, accountability, and measurable performance.
- UX Is Changing — Customers may increasingly stop logging into SaaS apps and interact through agents instead.
Quote from Nick Olsen, Head of AI Innovation at Mainsail Partners
"We are well past any point of skepticism or any engineer that says, Hey, this isn't gonna be here forever, or this isn't my thing. Engineers no longer should be starting in the traditional code editor, the IDE. Engineering has moved to much more of an agentic approach where you're starting in the terminal or or some sort of Claude Code or Codex app.
"How we're building software has completely and radically shifted. Companies are starting to move past treating AI as a tool. They're starting to treat AI as the way that they actually operate. It's not a tool like Excel is for a financial analyst, but that's actually where I start.
"We're trying to see people transition to treat AI as an actual teammate and actually affecting change within their organization.. And that's from the product and management side as well as to the engineering side."
Links
- Nick Olsen on LinkedIn
- Mainsail Partners on LinkedIn
- Mainsail Partners website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Paul Hoeper founded InvoiceASAP after spotting a simple but painful problem in 2009: home service businesses couldn't easily create invoices or collect payments from the field using mobile devices. He started in New Orleans, launched during the earliest days of mobile apps, and built one of the first mobile invoicing products integrated with both Square and Clover. He also suffered through several payment platform providers who never lived up to their sales pitches.
Today, InvoiceASAP serves about 23,000 paying home service businesses and roughly 400,000 total users across HVAC, plumbing, roofing, landscaping, and other field service trades. The company generates just under $5M in annual revenue with only 12 employees, growing 20–40% annually through a mix of SaaS and embedded fintech revenue.
Paul shares why he shifted from a pure SaaS subscription model to embedded payments, increasing average revenue per customer from roughly $9/month to $80–$94/month. He also explains why he avoided VC funding despite operating in fintech, choosing debt financing instead to preserve control, protect optionality, and keep building on his own terms.
Key Takeaways
- Revenue Shift — Moving from SaaS subscriptions to embedded payments increased average revenue per customer প্রায় 10x, from $9 to $80–94 monthly.
- Control Matters — Owning payment rails gave InvoiceASAP more margin, product flexibility, fraud control, and freedom from platform dependency.
- Debt Over VC — Paul chose debt instead of institutional equity to preserve board control and avoid forced exits or founder dilution.
- Vertical Focus — Home service businesses have highly specific cash flow needs that generic payment platforms often misunderstand or ignore.
- Fintech Reality — Payments infrastructure remains messy, legacy-heavy, and full of poor actors despite modern APIs and slick branding.
Quote from Paul Hoeper, Founder and CEO of InvoiceASAP
"Most of our competitors are on stripe.we're just exceptionally technically proficient. So we built out our own entire PayFAC infrastructure as close to the line as you can get, but where we control basically all the payment rails.
Stripe is an out-of-the-box product. So if you're looking for a different way of doing payments and billing, you just have to use whatever products Stripe gives you. That's it.
And when you build it the way that we built our product and payments platform, we can do a lot--for our customer and our business model. We have the flexibility to develop instant deposit, merchant cash advances and all different types of products."
Links
- Paul Hoeper on LinkedIn
- InvoiceASAP on LinkedIn
- InvoiceASAP website
Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.
If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.
Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.
Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Jerry Alderman is the co-founder and CEO of Valkre Solutions, a SaaS platform built specifically for key account managers who oversee the largest and most strategic customers in global B2B companies. After careers in engineering, sales, leadership, entrepreneurship, and customer value consulting, Jerry discovered that key account managers were still managing critical customer relationships with spreadsheets and PowerPoint.
That insight led to Valkre, which helps large companies build account plans, coordinate teams, identify growth opportunities, and manage strategic customer relationships. Today Valkre serves major enterprise customers, has grown beyond $4 million ARR, and helps organizations move key account management from disconnected documents into a structured system that can leverage AI and organizational knowledge.
In this conversation, Jerry explains why key account management may be the last major sales role that remains deeply human in the AI era. He shares lessons from building a new software category, finding product-market fit after several pivots, raising more than $5 million in practical funding from Golden Section, and why the biggest opportunities often hide inside markets that look small from the outside. Based on the transcript discussion of Valkre's growth, funding, and AI-driven market shift.
Key Takeaways
- PowerPoint Problem - Hundreds of thousands of key account managers still run critical customer relationships in spreadsheets and PowerPoint.
- Human Workflow - Key account management depends on trust, judgment, negotiation, creativity, and relationships that AI cannot easily replace.
- AI Catalyst - AI isn't replacing account managers; it's finally forcing companies to digitize strategic account management processes.
- Category Creation - Building a new software category takes longer than expected, even with strong customers and product quality.
- Practical Funding - Raising minority growth capital helped accelerate sales and technology investments without sacrificing founder control.
- Product-Market Fit - The biggest startup challenge is getting product-market fit right and finding the right feedback sources.
Quote from Jerry Alderman, Co-founder and CEO of Valkre Solutions
"AI is automating a lot of processes now. I think that key account management will be the last sales role standing. I really do. I used Claude to investigate. Can AI take over key account management sales and disrupt Valkre? And here's what it says. 'No, because key account management is very relationship and trust dependent.
"It requires this trust of people and relationships in order to get this done. It can't replace that. It says real-world coordination, meaning teamwork. It involves having this team of people coordinated together. This is a very human role and it requires the human to be creative and think forward.
AI is very much an accelerator. And so you did this job. Building an account plan and doing SWOT analysis and doing white space analysis, that stuff takes time. With AI in Valkre, you can do those things so much more efficiently and effectively."
Links
- Jerry Alderman on LinkedIn
- Valkre Solutions on LinkedIn
- Valkre Solutions website
- Winning Customers book by Jerry Alderman
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
TJ Joosten is the co-founder of RevFixr, a pricing and monetization consultancy that helps SaaS companies improve pricing, packaging, and revenue growth. Before starting RevFixr, TJ spent a decade building and selling software, helping early-stage companies find customers, refine product-market fit, and navigate pricing decisions from small startup deals to multi-million-dollar enterprise contracts.
Today, he works with SaaS founders, private equity firms, and software companies ranging from $1M ARR to $20M+ in revenues. TJ and his team have worked with more than 100 software companies, helping them identify monetization gaps, redesign packaging, move upmarket, and capture more of the value they create without necessarily building new products.
In our practical conversation, TJ explains why most founders systematically underprice their software, why private equity firms often see pricing opportunities founders miss. We also discuss what's changing (and not changing) in pricing and packaging with AI and agents this year. He shares savvy advice on usage-based pricing, hybrid pricing models, AI agents, and why founders should continuously test pricing rather than treating it as a fixed decision.
Key Takeaways
- Monetization Gap - Most SaaS companies create more value every year but fail to capture it through pricing and packaging.
- Pricing Courage - Founders procrastinate price increases while private equity buyers immediately look for pricing opportunities.
- Hybrid Pricing - Combining fixed fees with usage pricing often increases expansion revenue while reducing buyer risk.
- Founder Ownership - Pricing works best when one person owns it while sales, product, and finance actively contribute.
- Constant Testing - Pricing is not fixed; every new quote is an opportunity to validate a better monetization strategy.
Quote from TJ Joosten, Co-founder of RevFixr
"If you rarely get friction on pricing, it's rarely a barrier to entry and closing sales, then you have a pricing opportunity. If at least 20% of your deals in the negotiating stage don't push back on pricing then you're probably charging way too little.
"If let's say 40 % keeps giving you pushback then of course you might want to go down. At that stage they have already invested time so they'll always also be honest about are you simply too expensive and therefore I'm not buying your solution?
"Or is there a different reason? You can just straight up ask someone like why didn't you buy? And if they don't give the reason of price, then you probably don't have a pricing problem."
Links
- Tjitte (TJ) Joosten on LinkedIn
- RevFixr on LinkedIn
- RevFixr website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Rupert Mayer is the founder of IPfolio, a vertical SaaS platform built for corporate intellectual property teams to manage patents, trademarks, renewals, and innovation workflows. Originally from Austria, Rupert stumbled into IP software while helping a patent law firm solve Y2K risks, then moved to Silicon Valley to build a modern cloud-based product on Salesforce for smaller in-house IP teams.
IPfolio started as a lightweight alternative to legacy enterprise systems but gradually moved upmarket as customers like Dropbox, Square, GoPro, and Alphabet companies adopted the platform. Built largely on Salesforce with a lean team, the company grew steadily, signed six-figure enterprise contracts, and expanded to roughly 40 employees while serving increasingly complex global enterprises.
After raising a small strategic investment to scale faster, IPfolio grew too quickly and burned through capital chasing larger enterprise deals that took longer to close. Rupert ultimately sold the company in 2019 to a strategic partner, stayed through multiple acquisitions, and helped position IPfolio as the flagship product inside a much larger global company. Today, he is building again—this time in climate tech.
Key Takeaways
- Go All In - Growing software companies need full-time focus once you know the opportunity is real.
- Move Upmarket - Lightweight SaaS products often evolve into enterprise systems as big customers reshape the roadmap.
- Enterprise Leverage - Selling to innovative companies like Google accelerated product maturity and credibility faster than expected.
- Growth Trap - Hiring ahead of demand after rapid growth can create painful consequences when pipeline assumptions fail.
- Platform Advantage - Building on Salesforce dramatically reduced enterprise security, compliance, and infrastructure complexity.
Quote from Rupert Mayer, Founder of IPfolio
"I think the US innovation culture, especially in Silicon Valley, is very different from the business culture in Europe. I think it's just the willingness to take risks.
When I started selling, I was basically now a solo entrepreneur. When I approached big companies to buy IP Folio, the early version, I did not have big names to go out with. I was a nobody.
And so I walk into, what was it at the time already, a public company in Silicon Valley. I do my demo and everyone likes the product. And then they ask the dreaded question, well, how big is your company?
We're two people plus a developer. And I thought that was it. This public company will never sell from, buy from this no name, more or less solo startup. And they said, wow, that's so cool. This is great. We'd love to buy from you because 15 years ago, this company was basically just three people in the garage and someone trusted them and bought their product."
Links
- Rupert Mayer on LinkedIn
- IPfolio on LinkedIn
- IPfolio website
Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.
If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.
Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.
Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Eric Ries is the entrepreneur and author of The Lean Startup, whose work helped software founders validate ideas faster and build companies without making huge bets upfront. After years helping startups, large companies, and governments apply Lean Startup principles, Eric built the Long-Term Stock Exchange and turned his attention to a bigger question: Why do so many successful companies lose their way?
In our conversation, Eric explains the idea of "financial gravity"—the hidden force that pushes companies toward short-term financial thinking as they grow. He shares cautionary stories of companies like Whole Foods, Johnson & Johnson, Silicon Valley Bank, and Costco to show how scaling, investors, boards, and even employees can gradually erode trust, mission, and long-term value.
Eric's new book, Incorruptible Why Good Companies Go Bad…and How Great Companies Stay Great, offers practical ways founders can protect the soul of their companies before it's too late--even when they don't have big outside investors. He explains why founders should explicitly codify their mission into governance structures, why trust is the most underrated asset in business, and how practical founders can retain optionality while building valuable companies that endure.
Drawing on two decades of work with founders, CEOs, and investors, Eric Ries reveals the forces that make companies vulnerable to destruction from within and without. Then he offers solutions that safeguard against them for the long-term. Incorruptible is the blueprint for companies that will prosper and endure without losing their soul.
Key Takeaways
- Financial Gravity - Every growing company faces pressure toward short-term financial thinking—even without outside investors.
- Trust Compounds - Companies that earn trust with customers and employees often outperform financially over the long term.
- Founder Regret - Many founders regret selling because the mission, culture, and soul of the company disappear.
- Mission Protection - Values on a wall aren't enough—founders need legal and governance structures to preserve mission.
- Question Best Practices - Many accepted business practices optimize short-term profits while destroying long-term value.
- Think Long-Term - Practical founders have more optionality when they intentionally design companies to endure.
Quote from Eric Ries, Author of the Lean Startup
"People have woken up to this reality. Given where we're at, if you can create a bootstrap company, if you can maintain control, it doesn't make you completely safe. The problem is actually not investors, but financial thinking.
"So I tell a bunch of stories in my book (Incorruptible) of companies where the issue wasn't investors, but their own employees. You start to bring in professional managers. You start to bring in a CFO, and the CFO has that extractive mindset, or even worse.
"Financial gravity is one of the most underrated concepts in business. It is like trying to direct our attention away from the surface characteristics of an organization to the deeper forces that act on it. Your business model, strategy, vision, culture, these things are very important, but they are the things that we have control over. Financial gravity is a force."
Links
- Eric Ries on LinkedIn
- Eric Ries on Twitter
- Eric Ries Podcast
- Incorruptible book on Amazon
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Marc Sanderson is the founder and CEO of INNERGY, but he didn't start as a software founder. After earning his MBA and searching for a company to buy, he and partner Walter Wilkie acquired a small architectural woodworking business in Minnesota in 1997. Running that business revealed a deep operational problem: there was no software built for how custom woodworking shops actually operated. So Marc built his own.
That internal tool eventually became Innergy, a vertical SaaS ERP platform for architectural woodworking and high-end residential millwork businesses. Today, Innergy handles everything from CRM and estimating to project management, engineering, fabrication, and field installation. In 2025, the company reached roughly $25M in revenue, is growing more than 50% annually, and expects to approach $40M in 2026.
After bootstrapping growth for years using profits from the original woodworking business, Marc sold 51% of Innergy to growth equity firm MainSail Partners in 2025 for more than $40M, while remaining CEO. In this episode, he shares practical lessons about vertical SaaS, customer intimacy, onboarding complex ERP systems, finding the right growth equity partner, and why strategy still matters more than AI.
Key Takeaways
- Deep Domain — Marc built software from firsthand pain inside his own woodworking business, not from an outside startup idea.
- Education Matters — INNERGY advantage isn't only software. Customer education and operational thinking drive adoption and retention.
- Growth Equity Fit — Marc rejected investment several times before choosing a partner that could help scale—not just provide cash.
- Meet Customers — ERP success came from meeting customers where they are instead of forcing "best practices" immediately.
- Customer Intimacy — INNERGY's onboarding, benchmarking, and peer learning approach helped create ~95% retention.
Quote from Marc Sanderson, Founder and CEO of INNERGY
"AI is just a tool. I see organizations creating a chief AI officer. I don't have a chief Outlook officer. I don't have a chief Internet officer. I don't have a chief Web officer. It's just a tool at the end of the day."
"Just because you can cook rice infinitely at no cost doesn't make you a Michelin star restaurant. It's all the other aspects of these integrated activities that make you who you are. And at the end of the day, as long as we are creating value for our customer, they will continue to write a check to us."
"A lot of the AI efforts that are going on across the industry is focused on cost reduction, expense reduction internal to the software firm. Great. That helps us get to a breakeven or beyond. It helps with the rule of 40. However, it does not create more intimacy with the customer."
Links
- Marc Sanderson on LinkedIn
- INNERGY on LinkedIn
- INNERGY website
- MainSail Partners website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Blakely Graham co-founded TaskRay, a project management and customer onboarding platform built inside the Salesforce ecosystem. After years working with Salesforce implementations and operations teams, she and co-founder Eric Wu saw a major gap between closing deals and successfully onboarding customers. They bootstrapped the company from a simple Kanban-style workflow app into a growing SaaS business serving increasingly complex enterprise implementations.
TaskRay started with self-serve AppExchange purchases and evolved into enterprise software with six-figure contracts, serving companies with sophisticated onboarding and delivery needs. The company stayed profitable from the beginning, grew to roughly 40 employees, and eventually reached nearly $10M ARR. A major turning point came when the team repositioned around "customer onboarding" instead of generic project management, dramatically improving focus, retention, and enterprise growth.
Blakely also shares the difficult founder realities rarely discussed openly: co-founder conflict, burnout, loneliness, identity shifts, and the emotional weight of leading a growing company for more than a decade. After stepping away following the 2021 sale of TaskRay to a search fund-backed buyer, she focused on recovery, advisory work, and co-hosting the Not All Business podcast to help founders and leaders feel less isolated during difficult growth stages.
Key Takeaways
- Focus to Grow Faster — TaskRay discovered its strongest positioning by focusing narrowly on post-sale onboarding instead of generic project management.
- Bootstrap Discipline — The company stayed profitable from day one by growing carefully, shipping quickly, and avoiding unnecessary complexity early.
- Founder Burnout — Burnout showed up as physical exhaustion, emotional numbness, and losing the energy to inspire teams or create new ideas.
- Co-Founder Conflict — Long-term founder relationships can fracture under pressure, but respect and self-awareness can rebuild trust over time.
- Invest In Yourself — Peer groups, coaching, therapy, and personal health practices are essential leadership tools, not optional luxuries.
Quote from Blakely Graham, Co-founder of TaskRay
"This is probably the most important thing I learned as a CEO, and, I swear founders can't hear it. They just can't hear it.
"You have to invest in yourself. The word "self care" drives me crazy because that's what people told me for 10 years. Self care. What are you doing for self care? I'm like, I don't know. Leave me alone. I don't have time, any down time.
"Well, of course sitting on the other side of burning out and selling my company, founders just have to invest in themselves in the journey. It can be a peer group, it can be a coach. can be therapy. Heck for me, it's nature walks and going to the gym. Just do it because people don't want you to burn out. They want your leadership, so you have to invest in yourself and don't feel guilty about it. There, I said it."
Links
- Blakely Graham on LinkedIn
- TaskRay on LinkedIn
- TaskRay website
- Plexus Capital website
Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.
If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.
Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.
Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Andy Alsop didn't start The Receptionist—he bought a small iPad-based visitor management app in 2013 for $250K and turned it into a real SaaS business. What began as a simple front-desk check-in tool evolved into a full visitor management system used across offices, schools, and manufacturing sites.
Over a decade, Andy grew the company to 5,500 customers across 8,000 locations and more than $7M in ARR with just 30 employees. He stayed mostly bootstrapped, focused on steady growth, strong customer retention, and a unique "employee supremacy" culture that emphasized trust, transparency, and long-term loyalty.
At an inflection point—needing more capital to keep up with a maturing market—Andy chose to sell rather than raise growth equity. The company was acquired by Sign In, a growth-equity-backed platform consolidating the category. In this episode, Andy shares how he evaluated buyers, avoided common exit traps, and built a company worth acquiring without chasing VC growth.
Key Takeaways
- Simple Product, Deep System: What looks like a basic iPad app becomes complex, sticky infrastructure with integrations, compliance, and workflow depth.
- Bootstrap Leverage: Growing with customer revenue forced discipline, creating a profitable, efficient business attractive to strategic buyers.
- Employee Supremacy Works: Trust, transparency, and benefits (like every-other-Friday off) drove retention, performance, and long-term value creation.
- Clean Books Matter: Meticulous financial discipline prevented retrading risk and made due diligence smoother and more favorable.
- Exit Optionality Wins: Not needing to sell created leverage—allowing Andy to choose the right buyer instead of taking the only offer.
Quote from Andy Alsop, CEO of The Receptionist
"I sold 100 % of the company. It was a full acquisition. I wasn't even looking for, and this is something that my brother in tech always said: Don't build a company to sell it, build a great company and somebody will want to come along and buy it. And I think that's exactly the way it played out. We didn't go and look for the acquisition. We were pursued by Sign In and that's what happened.
"Just build a great company and somebody will want to come along and buy it. Because I didn't want to just sell it. I mean, we're profitable. We're growing. We have very low churn. Great employees. We're doing great in the marketplace, I didn't really have to sell."
Links
- Andy Alsop on LinkedIn
- The Receptionist on LinkedIn
- The Receptionist website
- Sign In website
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Sharon Nouh built ProSpend, a spend management SaaS platform for mid-market companies, after seeing firsthand how broken expense processes were in corporate travel. Starting with an expense tool, focused on her home market in Australia, she bootstrapped the company and landed a global enterprise as her first customer with a simple but powerful product vision.
Over 10 years, she expanded ProSpend into a full spend management system covering expenses, accounts payable, purchase orders, and budgets. The company grew to about 1,000 customers and 50 employees, with annual contracts ranging from roughly $15K to $40K, driven by strong mid-market focus and channel partnerships.
In 2025 Sharon sold ProSpend to ISH (Invincible Software Holdings), a strategic acquirer. She still runs ProSpend but can now accelerate expansion into the UK. After years of staying independent, she chose a acquisition partner over VC funding to maintain control and execute her long-term vision, showing how a sale can be a strategic move—not an endpoint.
Key Takeaways
- Bootstrap Reality — It took five to six years before taking meaningful income, with constant cash flow pressure early on.
- Product Expansion — Growth came from adding adjacent modules CFOs needed, not chasing unrelated features or markets.
- Channel Leverage — Partnering with MYOB and resellers now drives about 50% of new customers efficiently.
- Control Matters — Avoiding VC preserved full control over timing and terms of exit decisions.
Quote from Sharon Nouh, CEO and Founder of ProSpend
"A couple of years ago, one of the visions that I had for ProSpend was to expand from Australia into the UK. The UK was always going to be the market that we wanted to move into, rather than the US, because it's a very aligned, very similar market.
"And also because one of our competitors, WebExpenses, had been bought and sold about four times, and they were the incumbent in the UK. They were suffering. They hadn't been developing their product. There was a real gap for us to go into the UK and start picking up the mid-market there.
"So the question was, do I get VC funding, even though we've always been bootstrapped. Or do I look for an acquiring partner, somebody from the UK who could take us in there with boots on the ground and market intelligence? And I chose the latter and sold the business that I still run."
Links
- Sharon Nouh on LinkedIn
- ProSpend on LinkedIn
- ProSpend website
- ISH website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Perry Rosenbloom, founder of LaunchBay, previously built and sold Brighter Vision before starting his second SaaS company focused on onboarding. After running hundreds of onboarding processes per month, he saw a consistent problem: what happens after the sale is messy, manual, and often ignored.
LaunchBay helps SaaS and professional services teams manage customer onboarding with structured workflows, shared client portals, and automation. The company has grown past $1M in ARR, doubling in 2025, with a focused approach on helping teams reduce onboarding time from 60–90 days to significantly faster activation.
Perry shares practical lessons on onboarding as a core growth lever—not just an operational task. He explains why onboarding debt compounds, why charging for implementation improves outcomes, and how better onboarding drives retention, expansion, and long-term revenue quality.
Key Takeaways
- Onboarding Debt Compounds - Most SaaS companies duct-tape onboarding early, but delays, inefficiencies, and churn risks compound quickly as sales scale.
- Activation Matters More - The real bottom of funnel isn't closed-won deals—it's when customers actually reach value and start using the product.
- Stop The Chase - Much of onboarding is manual follow-ups and coordination; removing this admin work unlocks higher-leverage customer success teams.
- Charge For Setup - Charging for onboarding improves completion rates, sets expectations, and ensures customers have real skin in the game.
- Segment The Process - Treating all customers the same breaks onboarding—different tiers and workflows are required for different customer types.
- Visibility Is Critical - Without clear visibility into onboarding progress and bottlenecks, problems are only discovered after deals are already at risk.
Quote from Perry Rosenbloom, Founder of LaunchBay
"There's only so long that you can duct tape a process like onboarding new customers, with just hustle to make it work. A lot of companies are using Google Docs, shared Slack spaces, shared spreadsheets, and it almost works, until it doesn't. And the biggest mistake is continuing to let it not work.
"When you're founder-led and you are doing one to three implementations a month, you can get by without a dedicated tool for that. It's not going to be the best customer experience, but you can get by without a tool for that.
"But when you want to start scaling, you need to build out repeatable processes that can enable every single customer to have a phenomenal experience that is consistent, that is unified and that delivers value. "That's when you start looking for a specialized solution to solve those problems and don't build up more onboarding debt. Onboarding debt is real and early-stage SaaS companies in their processes and customer experiences."
Links
- Perry Rosenbloom on LinkedIn
- LaunchBay on LinkedIn
- LaunchBay website
- Free ebook: The Paid Implementation PlaybookROI calculator: Implementation margins
Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.
If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.
Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.
Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Dina Nagalla built EmpowerMX over more than a decade to digitize aircraft maintenance for major airlines like American, Southwest, and United. Starting from deep domain experience inside aviation IT, he tackled a complex, high-stakes problem—replacing paper-based processes with a full execution system that improves efficiency and compliance.
The company grew into a mid–double digit SaaS business serving global airlines with contracts ranging from hundreds of thousands to several million dollars annually. With a lean early team and offshore development, EmpowerMX delivered measurable ROI—often saving customers 10% or more on maintenance operations—while expanding globally with growth equity support.
After surviving COVID (when revenue briefly dropped near zero) and accelerating post-pandemic digitization, Dina sold the company to IFS. He chose to exit not out of necessity, but to pursue a new purpose—now building multiple AI-driven products focused on improving human outcomes like mental health and education.
Key Takeaways
- Vertical Expertise Wins: Deep domain knowledge created credibility and trust—critical for selling into conservative, high-risk enterprise environments.
- Start Small, Scale Smart: Initial product built with ~12 people, proving capital efficiency can solve very large industry problems.
- ROI Sells Enterprise: Clear financial impact (10%+ cost savings) overcame skepticism and justified multi-million dollar contracts.
- Trust Over Features: Adoption depended more on frontline trust than functionality—especially replacing paper and manual workflows.
- Purpose Drives Exit: Founder sold from a position of strength, driven by personal direction—not investor pressure or company distress.
Quote from Dinakara Nagalla, President and CEO of EmpowerMX
"Why did I sell the company when it was doing well? Life happens, you know. Primarily it was a desire driven by me that I want to do something different. So do I look back and think about it? Yes, I do.
"It's just that my purpose in life kind of switched. I wanted to do more meaningful things. I wanted to do more things. We were extremely profitable the year we sold and my equity partners were really happy with how things were going. "When I exited I moved right into building new products with new teams. So I didn't like take a step back and said I need a week of break. I think I had better vacations with my family when I was still running the company. Right now I'm doing, I get up at three o'clock in the morning. I work till four in the evening.
"You know, there is always this thing I hear from people all the time in my last 27 years of being in US: If you like what you do, you're not working another day. I think that is true in my case. I truly love what I do. Even when it's hard."
Links
- Dinakara Nagalla on LinkedIn
- EmpowerMX on LinkedIn
- EmpowerMX Website
- IFS website
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Chad Ingram is the founder of Distro, an AI recruiting software company that helps mid-market and enterprise companies automate candidate screening, vetting, ranking, and scheduling. He previously built Jump, a venture-backed customer engagement software company, through a stressful growth and sale process that taught him painful lessons about fundraising, control, and acquisition pressure.
Distro started as a marketplace to help companies hire software engineers globally, then evolved into an AI-first recruiting platform that integrates with applicant tracking systems and helps recruiters handle far more open roles. When Chad sold the company,
Distro had 14 employees and about $3.5M ARR, with revenue shifting from marketplace margins toward SaaS subscription and consumption-based contracts. Distro was acquired by Vensure Employer Solutions, a large private HR platform company that wanted Distro both for its own recruiting needs and for its 161,000 customers.
Chad explains why strategic buyers cared more about healthy financials than SaaS vanity metrics, why he said no to the first offer, what he learned from selling Jump too early, and why a daily cash flow forecast gave him the freedom to choose instead of react.
Key Takeaways
- First Offers are not always the right offers, and founders with real options can politely say no and keep building.
- Manual First is often the smartest way to start, proving demand with spreadsheets, email, and humans before writing software.
- Product Evolution happened by following customer demand, turning a hiring marketplace into an AI recruiting SaaS platform.
- Cash Visibility gave Chad optionality, because daily cash flow tracking removed surprises and helped him make harder decisions earlier.
Quote from Chad Ingram, founder of Distro
"You gotta know your numbers in detail. There are so many founders who don't know their freaking numbers. How do you not know your numbers? You just hope it all works itself out in six months? That's not how it works. You will go out of business.
"I learned how to do a daily cash flow forecast when we started my 2nd company, Distro. And I've been running one every day. That might seem a little too microscopic for many, but guess what? There's no freaking surprises.
"I could tell you nine months from now, the day that we would go out of business if we didn't have enough cash, unless there was some change. It's a lot less stressful knowing the facts. When you know the facts, you can make things happen. You don't have to sit and wonder and hope it works out.
"I don't care if you have zero mathematical aptitude or your background is sales or something else. You have to know the basics of accounting. If you don't, you are at a huge, huge disadvantage, especially when you go to sell."
Links
- Chad Ingram on LinkedIn
- Distro on LinkedIn
- Distro website
- Vensure Employer Solutions website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Joseph Lee is the co-founder and CEO of Supademo, a fast-growing SaaS company solving a common pain: quickly creating new product demos. In just two and a half years, they built a modern, AI-powered solution that dramatically simplifies how teams showcase software.
Supademo has reached $3M ARR in 2.5 years and is growing more than 100% annually with a freemium model. The product enables teams to create interactive, annotated, and even translated demos in minutes instead of days or weeks. The freemium model, reverse trial onboarding, and viral product loops have driven strong PLG growth, while enterprise demand is now emerging as a second growth engine.
Joseph is a second-time founder with global experience from Korea to Vancouver to New York. He's raised a small amount of capital but is focused on practical execution. His approach reflects tghe broader shift of using AI to solve real workflow bottlenecks and grow efficiently without heavy funding.
Key Takeaways
- Speed Wins - Reducing demo creation from weeks to minutes unlocks more usage, faster iteration, and better customer understanding
- Do The Work - Early traction came from building demos for prospects manually, removing friction and proving value instantly
- Reverse Trials - With free plans drive high conversion by letting users experience full value before choosing a plan
- PLG + Enterprise - Bottom-up growth creates stability, while enterprise deals add larger revenue but less predictability
- Constant Reinvention - Product-market fit is temporary in AI—founders must ship fast, iterate weekly, and stay paranoid
Quote from Joseph Lee, Co-founder and CEO of Supademo
"There's no bread and butter GTM channel that is going to work permanently into the future. And the biggest learning that I took away was product market fit nowadays has a finite stamp when it comes to a period of time that it's valid for.
"You have to constantly reinvent yourself and be paranoid, because the market is changing, new competition is coming, and the dynamics are changing. You can't rest on your laurels, you got to be constantly innovating, like at a faster pace than ever before.
"Our team competitive advantage is the ability to move quickly and ship quickly. It's combining gut based on our intel and context of the industry and tribal knowledge with some data to act faster than anyone else. Not analysis paralysis or having everything planned out. Just shipping something that may be imperfect, but using that as leverage to learn quickly and iterate quickly."
Links
- Joseph Lee on LinkedIn
- Supademo on LinkedIn
- Supademo website
Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.
If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.
Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.
Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Tanner Kovacevich of Lighter Capital joins Greg Head to explain how non-dilutive financing works for practical SaaS founders. Since 2010, Lighter Capital has funded hundreds of recurring-revenue SaaS companies that want growth capital without giving up ownership or board control.
Tanner shares discuss how non-dilutive financing fits companies with $1M–$5M ARR that are growing steadily but don't want venture capital. He explains typical loan structures, underwriting factors like churn and revenue trends, and why capital-efficient SaaS companies are often better candidates than "grow-at-all-costs" startups.
We discuss several examples of practical SaaS founders who used debt instead of equity to retain ownership and build long-term value. The conversation focuses on how certain practical founders can use capital strategically—accelerating growth while preserving control and optionality.
Key Takeaways
- Non-Dilutive Capital – SaaS-specific debt financing allows SaaS founders to fund growth without giving up equity, board control, or long-term ownership upside.
- Capital Sequencing – Smart founders combine funding types over time, using non-dilutive capital early before considering equity later.
- Retention Matters – High churn or declining revenue trends are the biggest red flags when underwriting recurring-revenue SaaS businesses.
- Ownership Economics – Avoiding early dilution can preserve tens of millions of dollars in founder equity in successful outcomes.
- Capital Efficiency Wins – Many profitable SaaS companies grow steadily and still attract buyers without needing big VC funding.
Quote from Tanner Kovacevich, VP of Sales at Lighter Capital
"Often we fund founders that just want to have a little more cash on hand and not have to manage cash so closely. What does that open up for the founder's mindset alone? To just have some extra cash on hand, to go out and hire whoever they want, an account executive, SDR. Because a lot of it can be psychological.
"It's not only the grand initiatives; it can just be the ability to breathe, extend your runway to look ahead. Maybe you want to offload a couple of things you're working on as the CEO, like acting as an accountant when you're the strategic CEO and trying to manage sales day to day.
"Lighter Capital provides non-dilutive debt financing for B2B SaaS companies, but we also work with other recurring revenue types of model technology companies. With Lighter, there are no warrants on our loan, no personal guarantees that the founder has to place, and minimal financial covenants on it."
Links
- Tanner Kovacevich on LinkedIn
- Lighter Capital on LinkedIn
- Lighter Capital website
- Bootstrapped Podcast
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Vivek Bhaskaran is the founder and CEO of QuestionPro, a bootstrapped survey and customer-experience research software platform they have been building for more than 25 years. Based in the Bay Area, Vivek has grown the company globally without venture capital, staying deeply involved in product and running the business as both CEO and de-facto chief product officer.
As QuestionPro crossed $10M then $30M in revenue years ago, private equity firms and acquirers started calling. Vivek chose not to sell and instead kept building. Over the years he has completed about ten small acquisitions and expanded the platform while staying nimble as an independent company.
In this conversation, Vivek explains why having fun, liking your team, and taking some profits along the way makes it possible for founders to play the long game. He also shares how AI is changing market research and why most AI use cases still need experimentation.
Key Takeaways
- Founder Product Ownership – Vivek still acts as chief product officer, believing founders should stay close to the product and customer problems.
- Small Acquisitions Strategy – Rather than selling, QuestionPro grew through about ten small acquisitions that expanded capabilities and distribution.
- Practical AI Adoption – Most AI experimentation fails early, so the team tests many use cases and keeps the ones customers actually adopt.
- Sales Efficiency Gains – AI dramatically improves painful processes like RFP responses and compliance questionnaires that previously took hours.
- Synthetic Research Data – Vivek believes AI-generated personas and synthetic respondents will transform early-stage market research within a few years.
Quote from Vivek Bhaskaran, founder and CEO of QuestionPro
"Two things matter to me that have allowed me to be the founder and CEO for 25 years. Number one, can I wake up every day and have the same level of energy, enthusiasm, and fun? Work and fun, and everything has to be correlated at this point. There is just one life. "Number two is the people around me. I love the team that works with me and hopefully they like working with me too. These are the two things that matter to me: Am I having fun? Am I having fun with the people around me? You got one life, so can you mesh those two things together?
"Ask yourself, am I personally in the game? Do I really want to do this? If those two things are true, then I'd say keep going. How you feel, what you're doing in the morning, how you show up all day, and then who you work with. These are not external. You control both these variables reasonably well."
Links
- Vivek Bhaskaran on LinkedIn
- QuestionPro on LinkedIn
- QuestionPro website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Juan Ignacio Garcia Braschi is a partner at L40, a boutique SaaS M&A advisory firm with offices in Madrid, Lisbon, and Miami. After two decades in banking, private equity, and operating roles, including serving as CFO of ride-hailing company Cabify, he now helps SaaS founders sell companies typically valued between $20M and $200M.
L40 works primarily with B2B SaaS companies doing $5M–$50M ARR, most of them bootstrapped or lightly funded, including companies in Europe and Latin America. Juan explains how today's buyers evaluate SaaS companies, why Rule-of-40 performance still matters even with AI, and how growth rate, retention, and profitability determine valuation ranges of roughly 4–8x ARR.
Key Takeaways
- Growth Drives Valuation: Growth rate correlates most strongly with SaaS multiples. Companies growing 50% command much higher valuations than those growing 20%.
- Rule Of 40 Still Matters: Buyers increasingly expect SaaS companies to combine strong growth with some profitability.
- Financial Buyers Dominant: Private-equity-backed platforms acquiring add-ons are the most active buyers for $50M–$100M SaaS companies today.
- Sell During Momentum: Smaller companies growing 20–40% annually can be an ideal window for acquisition before growth naturally slows.
Quote from Juan Ignacio Garcia Braschi, Managing Director and Partner at L40
"If you think that you're going to sell your SaaS company, you should think of that two years ahead of when you want to sell. So don't wait until you're burned out.
"Keep in mind that you will have to make a profit at some point to sell to serious financial buyers. So when your company is growing at decent 20, 30, 40% year over year rates, that's probably the sweet spot for selling.
"Significant funds have been raised in the past 24 months and that has to be deployed. Traditional private equity firms are more more interested in tech. These days you see more and more traditional private equity firms going into tech and that's increasing competition and driving multiples up."
Links
- Juan Ignacio Garcia Braschi on LinkedIn
- L40 on LinkedIn
- L40 website
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Simon Swords founded Fundipedia after starting in a backyard shed building bespoke software. Originally a custom development shop, his firm built a data governance platform for major buy-side asset managers including HSBC, Barclays, and Legal & General.
Over time, Fundipedia evolved into a high-retention enterprise SaaS platform with strong net revenue retention and Rule of 40 performance. Simon navigated long consultative sales cycles, regulatory tailwinds, and a tightly networked financial services market to build a durable recurring revenue engine.
After turning down an initial offer, Simon grew ARR further and ultimately sold in 2024 at approximately 10x ARR. He exited fully, used ChatGPT extensively in diligence, and now reflects on endurance, discipline, and surviving long enough for luck to compound.
Key Takeaways
- Survive First — Don't make a mistake that kills you or the business. Staying alive creates the opportunity for luck to compound.
- Enterprise Patience — Two-year sales cycles are normal at the top end. Persistence and reputation matter more than speed.
- Rule Of 40 Discipline — Strong growth plus profitability gives founders leverage in exit timing and valuation.
- Problems Over Product — Founders obsess over product; buyers care about solving painful, expensive problems.
- Build To Exit Cleanly — Structure the company so it runs without you before you start acquisition conversations.
Quote from Simon Swords, Founder of Fundipedia
"I think the most important thing is not to make a mistake that kills you or the business. While you're in the arena and you've not been taken out yet, dragged off by the hyenas or lions, whatever they used back in the Roman days, you've still got a chance to make something magical happen. "You do something stupid, kill the business, kill your reputation, you're done. Entrepreneurs hate the word luck. I do feel luck. I am lucky. Of course I'm lucky. I have to be lucky. You make your own luck.
"But I'll tell you what I didn't do. I didn't make a mistake that killed me or the business and the entire way through. Even when I was going through hell, never, no matter how neurotic or anxious or all the negative kind of traits you can imagine would have flown through me. I never made a mistake that killed the business."
Links
- Simon Swords on LinkedIn
- Fundipedia on LinkedIn
- Fundipedia website
- FE fundinfo website
Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.
If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.
Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.
Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Steve Reynolds didn't start TripBam to disrupt the global hotel industry—he simply noticed that corporations weren't getting the discounts they negotiated, and no one was checking. After 30 years in travel technology, he saw a broken system hiding in plain sight. What began in 2013 as a consumer hotel re-shopping tool quickly revealed a much bigger enterprise opportunity.
When a corporate client offered to pay a subscription fee, Steve pivoted from B2C to B2B—and never looked back. TripBam went on to serve 250 of the world's largest companies, saving clients 5–10% on existing hotel bookings and up to 30% when switching properties.
TripBam grew to $8–10M in revenue, with 50 employees across the U.S. and Europe, and operated as a Rule-of-60 SaaS business. Then COVID hit, transactions dropped 95% in two weeks, and the company had to prove its resilience before ultimately selling in 2023 to Emburse.
In this episode, Steve shares why pricing for 8x ROI made sales easy, how profitability and subscription revenue protected the business during crisis, what it's like selling into private equity, and why founders should think carefully before raising multiple VC rounds.
Key Takeaways
- Disrupt Carefully – TripBam aligned with corporate buyers while disrupting hotels and agencies.
- Price for Stickiness – Targeting ~8x ROI made approvals simple and customers loyal.
- Profit Is Protection – Strong margins helped survive a 95% revenue collapse during COVID.
- Avoid Over-Dilution – Limited funding preserved founder ownership at exit.
- Deep Expertise Wins – 30 years in travel tech created a defensible moat.
Quote from Steve Reynolds, CEO and Founder of TripBam
"Fortunately for me, since I didn't take additional funding, I wasn't diluted multiple times. I've met so many founders and they go through rounds A, B, C, D, E, F, and next thing you know, they end up with 5%, 10 % of the company. And it just doesn't work.
"You might actually get to a rare big exit, but it's really not going to be all that meaningful for the founders, at the end of the day. I've never kind of fallen into that trap of just getting out in front of your skis. I tend to follow the cashflow and look guys, you know, we got to make it happen on the revenue that we're generating.
"We're not going to go out and bet the farm and borrow a bunch of money and create these crazy expectations, right? Once you start taking outside money, you get someone else starting to make those decisions for you, whether you like them or not."
Links
- Steve Raynolds on LinkedIn
- TripBam (now Emburse) on LinkedIn
- TripBam (now Emburse) website
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Keith Shields is co-founder and CEO of Designli, a custom software development company that's helped non-technical founders build over 200 digital products in 13 years. After struggling to build apps through unreliable agencies in his own early startup, Keith focused on fixing the many painful experiences most founders have when hiring software development teams.
Designli operates as a complete outsourced engineering department for practical software founders building SaaS and AI products, mobile apps, and web applications. Their SolutionLab program means founders invest $13,800 in a 2-week design sprint of prototyping and product planning before committing to full development, reducing the risk of expensive failures that plague most custom dev projects.
The company focuses primarily on vertical SaaS founders who understand their industry problems intimately but lack technical expertise. Keith recommends velocity to first revenue over perfect features, outside audits for struggling teams, and getting gut checks on your development situation, which is far less risky than making huge changes blindly when you feel stuck.
Key Takeaways
- Black Box Risk: Most agencies operate in the dark, leaving founders guessing what's being built, why it's late, and whether progress matches expectations.
- Dedicated Teams Win: Full-time focused developers outperform fractional freelancers because context, ownership, and velocity compound over long projects.
- Get Clarity Fast: Structured upfront design sprints align founders and teams on scope, timelines, and priorities before heavy coding begins.
- Audit Early: A quick external code and process audit can reveal hidden problems before they turn into year-long setbacks.
- Trust Your Gut: If a development relationship feels wrong, get an outside perspective and fix it before making risky, large changes.
Quote from Keith Shields, CEO and Co-Founder of Designli
"My advice for non-technical founders that already have a product is to trust your gut when you ask, Are we getting the value out of our development team in this situation?
"If you already have a product and your dev team isn't working, get an outside perspective. It's not that hard to go and get what you're doing audited by people, sometimes for free, like us, or you pay for it. You send off a copy of your code in a zip file. It doesn't even have to be the living, breathing version and say, Can you audit this and give me a gut check?
"Getting an outside review of your code doesn't happen that often, surprisingly. People feel stuck in their frustrating situation until they make a huge change, and then it's a risky, huge change. So get some outside perspective early and often."
Links
- Keith Shields on LinkedIn
- Designli on LinkedIn
- Designli website
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Will Caldwell started Snap after his first real estate software startup fizzled, pivoting from agent tools to regulated compliance data. He discovered lenders were required to buy hazard and flood certifications, and realized this was a "painkiller" product. He built Snap as a data and analytics platform for real estate and mortgage underwriting.
Snap grew from a single California compliance product into a national flood data business, reaching $5M in revenue and 30 employees. The company charged per-loan transaction fees and embedded via API into mortgage software systems. With double-digit market share, Snap focused on customer experience, automation, and expanding wallet share inside lenders' workflows.
In October 2024, Snap sold 51% of the company to Intercontinental Exchange, parent of ICE Mortgage Technology, at a double-digit revenue multiple. Will stayed on to scale the platform inside a much larger ecosystem. His key lesson: dominate a narrow niche, build a required product, and let strategic buyers find you.
Key Takeaways
- Required Beats Optional – Legal compliance products create urgency and retention because customers must buy to complete revenue-generating transactions.
- Micro-Niche Entry – Starting in a narrow regulated segment let Snap win trust, then expand into much larger adjacent markets.
- API = Distribution – Embedding inside legacy systems turned Snap into a one-click button that scaled through partners' existing sales teams.
- Customer Experience Wins – In commodity data markets, faster, cheaper, simpler delivery became Snap's main competitive weapon.
Quote from Will Caldwell, CEO and Co-Founder of Snap
"You don't need to build a huge business to get a huge, life-changing exit. Just stay laser-focused. Don't chase shiny objects. I see many founders trying to boil the ocean. It is about staying focusedon a single niche.
"I think vertical SaaS has many great niches, and horizontal software is challenging. You need a lot of money to go after horizontal solutions across industries. However, with vertical SaaS products and niches, there is a lot of overlooked opportunity; the real estate vertical is one prime example."
Links
- Will Caldwell on LinkedIn
- Snap on LinkedIn
- Snap website
Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.
If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.
Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.
Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Luigi Mallardo joined Woffu as an early angel investor and later became CRO, helping founder Miguel Fresneda shape a practical SaaS growth path. Based in Barcelona, Spain, Woffu has built a modern cloud-based time and attendance platform for SMEs and mid-market companies, replacing legacy tools and spreadsheets with a focused, mobile-first workforce solution.
Starting from just €2K MRR, Luigi led growth first through inbound, then outbound, and partner channels, increasing average revenue per account five to seven times. By 2025, the company reached nearly €500K in monthly recurring revenue, or about €6M ARR, with more than 50 employees and profitable, efficient growth across Spain.
Woffu sold to Visma in 2022 following a multi-year, proactive exit strategy, with a total reported value of €20–30M including the 3-year earnout. Luigi shares how early focus, diversified revenue, and optionality shaped every decision. His biggest lesson: clarity about your endgame determines your strategy early on, including your growth model and many other important decisions.
Key Takeaways
- Strategic Focus - Choosing one clear use case and market unlocked faster growth than chasing horizontal HR suite ambitions across Europe.
- Optionality First - Designing for multiple future paths gave founders leverage rather than forcing a sale based solely on valuation.
- Revenue - Layers Inbound, outbound, and partners created resilience while steadily raising average contract value and predictability.
- Exit Readiness - Warming buyers years early turned selling into a strategic process rather than a rushed financial event.
- Customer Success - Investing deeply in retention created low churn and made Woffu more attractive to long-term acquirers.
- Builder Mindset - Great CROs zoom in and out, connecting go-to-market execution with strategy, culture, and long-term outcomes.
Quote from Luigi Mallardo, Chief Revenue Officer at Woffu
"We chose our focus of ICP and focus of use case, to reduce the space of market optionality to get more business optionality. You see what I mean?
"The advice I give most often is to focus, which doesn't mean to close off the option of having more verticals forever, but you need 75% or 80 % of your pipeline on where you are already monetizing and building traction. And then you leave that 20 % of pipeline to do experimentations in a new vertical.
"It's one of the historical challenges, especially with young founders: the feeling of losing opportunities if they decide and don't do everything. But you are losing opportunities if you go too wide and you don't focus. Just be patient, postpone, and focus on what works."
Links
- Luigi Mallardo on LinkedIn
- Woffu on LinkedIn
- Woffu website
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Jordon Comstock is founder and CEO of BoomCloud, a vertical SaaS company serving dental practices with patient membership software. He started the company scrappy and bootstrapped, with no outside funding, after years in the dental industry managing his family's dental lab business.
BoomCloud now does about $3M in ARR with roughly 600 dental practices and an 11-person team. The company helps dentists replace insurance-driven revenue with subscription-based patient memberships, creating higher margins and more predictable cash flow. BoomCloud has been profitable since 2016 and continues to grow steadily.
Jordon shares hard-earned lessons about hiring too fast, why systems scale better than people, and how he uses AI to increase output without adding headcount. He also shares how narrowing ICP transformed sales and marketing and why he's committed to building a durable, profitable business instead of chasing a fast exit.
Key Takeaways
- Bootstrap Talent Gap — VC-funded talent often struggles in capital-efficient environments that require ownership, speed, and scrappy execution.
- AI Is Leverage — AI tools helped BoomCloud increase marketing and product output without rebuilding a large team.
- Profit Creates Buffer — Staying profitable provided margin for mistakes and reduced stress during periods of experimentation.
- Slow Markets Matter — Vertical SaaS wins by matching the pace of conservative industries instead of forcing VC-style growth.
- Exit Isn't Required — Steady profits allow founders to "exit slowly" through distributions without selling the business.
Quote from Jordon Comstock, Founder and CEO of BoomCloud
"We say systems scale, people don't. And we're learning that now. Let's implement the systems first. It doesn't mean people aren't important. People are important. But they have to have a system or a process first.
"We've got to build it as a company and build that foundation first. When we hired a director of marketing and said, okay, you got to generate, you know, a thousand leads a month is what we were trying to do. And he couldn't do it because he didn't have systems. Fast forward a year, we implemented SEO systems to drive consistent traffic.
And we convert that traffic into leads and now a thousand leads in a month is automatic. Because we have systems. We don't have a director of marketing anymore. I guess it's me, me with systems and AI.
Links
- Jordon Comstock on LinkedIn
- Boomcloud on LinkedIn
- Boomcloud website
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Deepak Sindwani is Managing Partner at Wavecrest Growth Partners, an active growth equity firm backing bootstrapped and lightly funded SaaS founders. They work with practical founders who've built profitable businesses to $5–$20M ARR and want help growing without VC pressure or losing control.
Wavecrest invests in vertical SaaS companies growing 30–60% annually, typically profitable or breakeven. They help founders scale sales, pricing, analytics, and leadership teams while staying capital efficient. Investments are usually $10–$30M total, with founders often taking some liquidity while continuing to lead.
Even with the excitement around AI-first companies from VCs, Deepak sees efficient growth equity in practical vertical SaaS as a great investment and a big opportunity for founders. AI is helping serious practical founders, not making them irrelevant.
Key Takeaways
- Capital Efficiency Matters — Wavecrest only backs profitable or breakeven SaaS companies that already respect the business model fundamentals.
- Founder Liquidity Helps — Taking some money off the table reduces stress and helps founders make better long-term decisions.
- Vertical SaaS Wins — Deep industry knowledge and data create defensibility AI-first competitors struggle to replicate.
- AI Is Additive — Software plus AI and data creates more value than AI replacing SaaS systems of record.
- No One-Size Playbook — Growth equity works best when strategies are customized, not forced by rigid PE-style playbooks.
Quote from Deepak Sindwani, Managing Partner at Wavecrest Growth Partners
"We don't think B2B SaaS is dead. It may create great headlines to say, AI eats software. We think software plus AI is the right approach. Software, AI plus data. So they're harvesting and creating that data moat that is going to help make them defensible.
"Then, using the AI tools, why not use the AI tools to provide more automation for customers? That's what we really think AI does: increase the ability to automate the use of their product and to get value. "Every company that we're involved with has some AI initiative. How am I changing how I run my business? How am I changing marketing and sales and finance and customer success using AI? Every company is doing something in every function in terms of new tools and tests."
Links
- Deepak Sindwani on LinkedIn
- Wavecrest Growth on LinkedIn
- Wavecrest Growth Partners website
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Tighe Burke is the founder of SRCH Partners, a boutique executive search firm that helps SaaS founders replace themselves as CEO without selling their companies. After years in large executive recruiting firms, Tighe built a practice focused on founders who want their business to keep growing while they step back from day-to-day leadership.
Tighe works with profitable software companies typically in the $5M–$50M revenue range, helping founders hire experienced and scrappy operators who have already scaled businesses through the next phase. His team has completed more than 75 executive searches, often placing CEOs who take full P&L ownership while founders move into chairman, product, or portfolio roles.
In this episode, we dig into when hiring a CEO makes sense, how compensation and incentives really work, and what founders must let go of for this transition to succeed. Tighe shares practical warning signs, real compensation structures, and why this "third door" can create more value and freedom than selling too early.
Key Takeaways
- Founder Readiness Matters — This only works when founders clearly know what they want their life and role to become next.
- $5M+ Reality Check — Most companies need real profitability to afford a strong CEO with authority and incentives.
- Operators Are Different — The best CEOs have already scaled similar businesses and don't need to learn on your dime.
- Let Go Or Don't Hire — Founders who keep control undermine the hire and drive away the right operators.
- Comp Isn't Just Equity — Profit sharing, bonuses, and transaction payouts often work better than stock alone.
- Shadow Period Is Normal — The first few months require intentional transition, not instant disappearance by founders.
- Value Can Multiply — Hiring the right CEO can grow valuation faster than selling too early ever would.
Quote from Tighe Burke, Founder of SRCH Partners
"There are three doors as a founder entrepreneur. Door #1is keep running your business. Maybe you love your business. Door #2 is to exit the business and sell your company whenever you either get a good multiple, or the time is right, or a good buyer. "
"Door #3 is where we come in. Hopefully, your business cash generating asset for you. There are a lot of founders who think of their business that way. Some particularly people who like start their own company, it's their baby, it defines who they are. That's great. But if for any reason you're feeling angst or like you think someone can get past 10 million when you've really struggled there, that's probably true.
"Let's bring in somebody else, an operator, a big O operator to run the business, to own the P &L, to make strategic decisions, to hire, to fire, to do all the things that you probably don't really like anymore.
"You don't have to sell the business. You can actually get a bigger multiple later on by having a strong management team in place if that is something you choose. And you get your life back. can be with your family. You can start another business. You can advise, invest, kind of do whatever you want."
Links
- Tighe Burke on LinkedIn
- SRCH on LinkedIn
- SRCH website
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Dan MacDonald is the founder and CEO of BIS Safety Software, based in Edmonton, Canada. He didn't start in safety or software—he came from retail and leadership training before an unexpected pivot led him into online safety systems. That shift eventually became a long-term bet on a "un-sexy" problem that companies can't ignore.
Today, BIS Safety serves more than 2.5 million users across high-risk industries like construction, mining, transportation, and energy. The company generates roughly $25M CAD in annual revenue, employs about 200 people globally, and runs one of the stickiest SaaS platforms you'll find—with less than 1% annual logo churn.
After nearly 20 years of bootstrapped growth, Dan is beginning a staged exit, starting with a minority secondary sale and planning a control transaction in a few years. Along the way, he shares hard-earned lessons about product obsession, compounding customer retention, and why steady execution beats hype.
Key Takeaways
- Extreme Retention Matters — Less than 1% annual churn created compounding growth without aggressive sales spending.
- Product Over Sales — BIS focused on usability and depth first, letting word-of-mouth drive most early growth.
- Customer-Funded Start — Early customers paid to build the first LMS, avoiding dilution and premature fundraising.
- Long Bootstrap Reality — The first decade involved no salary, deep personal risk, and constant financial pressure.
- Enterprise Power, End User Simplicity — Power users get depth, while users see an interface designed to feel effortless.
Quote from Dan MacDonald, Founder and CEO of BIS Safety Software
"So at that time when I started the business, there was an awakening kind of moment of realization. It hit me big. I'm reading hundreds of business books and reading about Bill Hewlett, Dave Packard, Sam Walton, and many others.
"I'm listening to the things they're saying, the ways they're thinking, And all I'm thinking is, my God, they think like me, they're just like me, they're normal people, they're just like me. And that was kind of the first awakening realization to say, they're not superhuman!
That gave me the confidence to build the business and believe in the future. I never thought there's a pot of gold at the end of the rainbow it was never about the money. It was just some burning thing inside me that just I need to do this.I was just driven to do to do this. I felt like it was just this is what I'm meant to do."
Links
- Dan MacDonald on LinkedIn
- BIS Safety Software on LinkedIn
- BIS Safety Software website
Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Robin Eissler is the founder and CEO of BoosterHub, a vertical SaaS platform built for high school booster clubs. After selling her prior business as a private jet broker, Robin volunteered to run a local booster club and discovered a messy problem run with spreadsheets, emails, and manual accounting. She decided to build a single system that could actually handle it.
BoosterHub now serves nearly 600 booster programs, representing over 100,000 users. With just two full-time employees and a small dev team, the company processes more than $40M in transactions across payments, fundraising, merchandise sales, and accounting. Annual contract value typically runs $1,500–$2,000 per customer, with strong retention and expanding usage.
Still independently-owned and bootstrapped, BoosterHub is approaching $1M ARR and profitability. Robin shares lessons on building complex software with a tiny team, selling to volunteer buyers, surviving seasonal revenue swings, and why slow, compounding growth can create durable SaaS businesses without venture capital.
Key Takeaways
- Tiny Teams Work - Two employees plus contractors can build serious SaaS with focus, systems, and modern tooling.
- Sticky Beats Big - Hundreds of small customers compound more reliably than a handful of enterprise deals.
- Seasonality Is Real Education-adjacent - SaaS must survive cash spikes and winter slowdowns without panic.
- Founder-Led Marketing - Consistent content from the founder still drives inbound growth in niche markets.
- All-In-One Wins in Verticals - Being the system of record makes churn low and customer value expand naturally over time.
Quote from Robin Eissler, Founder and CEO of BoosterHub
"The numbers are much better than what we projected. so we're starting to see that compounding effect is really what's happening is there's just enough users and enough people in the system that they're using more of the add-on products and we're processing more volume.
"So it's starting to have that compounding effect. And so I really just admitted to myself this month, like, I think we're seeing it.
"I think we're finally seeing it. I feel like, OK, maybe for me, it's almost that I can exhale. I've been holding my breath for four years, so maybe I can breathe."
Links
- Robin Eissler on LinkedIn
- BoosterHub on LinkedIn
- BoosterHub website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
As the year winds down, I want to share an end-of-year message for practical SaaS founders who want to make better progress in 2026. Based on my recent conversations with more than 40 CEOs in my Practical Founders peer groups, it's clear that growth rates alone don't define whether it was a "good" year. Founders experienced very different outcomes—and very different feelings about them.
In this episode, I walk through five practical questions I believe founders should ask as they look ahead to 2026 (or their next quarter). These questions focus on whether you're working on the right hard things, what you're deliberately changing next, what help you actually need, whether you have enough cushion in the business, and the story you're telling yourself and your team about progress.
This isn't about templates, quick-fixes, hype, or perfect planning. It's about making steady progress on the hardest, most important things in your business—while staying independent and resilient.
Success isn't final and failure isn't fatal. What matters is whether you keep going—and keep making progress. If you're still here, still building, still learning—you're doing something right. I respect practical founders who choose independence, solve real problems, and do hard things year after year.
Key Takeaways
- Progress Over Growth Rates - What matters is whether you moved the hardest, most important parts of your business.
- Focus Is a Force Multiplier - Trying many things without concentration is why most initiatives stall.
- Companies Mirror Their Founders - The company's strengths and weaknesses often mirror the founder's.
- Cushion Creates Resilience - Cash, energy, and upsides protect businesses when headwinds inevitably appear.
- You Make It Up - How you frame last year's results shapes decisions, morale, and alignment.
Quote from Greg Head, founder of Practical Founders
"Everybody's doing really hard things who are practical startup founders. I know you are too. The question isn't about what the perfect growth rate or planning process is for you right now. The question is, are you lined up to actually do enough of the most important hard things in your business next year?
Are you really set up to make the kind of progress you want along the bigger vision you have for the company? There are all kinds of ways to do it. You can go fast or slow, or it could be an invest year, a rebuild year, or a steady year. You can choose your growth rate, your profitability, and all of that.
"You get to do it your way. You've bought your independence, or you are paying for it the hard way. There's no one right way to do all of this, if you're making big progress and getting better every year in the eyes of your customers, employees, and the owners."
Links
- Greg Head on LinkedIn
- Practical Founders on LinkedIn
- Practical Founder website
Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Dave Hersh, co-founder and former CEO of Jive Software, shares the real story behind bootstrapping Jive to $12M in revenue before raising venture capital and scaling aggressively. He explains how fear, comparison, and the pressure to "go big" drove him to abandon his profitable core business and pursue a new upmarket strategy that ultimately cost the company its soul.
After growing to $60 million, Jive eventually went public, but not without internal strain, personal turmoil, and ultimately the realization that the company had drifted away from what made it successful.
Dave discusses how overexpansion, premature scaling, hiring missteps, and market-chasing derail both VC-backed and bootstrapped companies—along with the psychological patterns founders rarely acknowledge.
He shares lessons from his book "Reignition: Transforming Stuck Startups Into Breakout Winners" on why most stuck companies don't need a new strategy—they need a wiser founder who understands their inner operating system and is willing to grow alongside the business.
Today Dave coaches founders, writes about the emotional foundations of leadership, and acquires underperforming SaaS companies to "refound" them with more clarity, connection, and human-first strategy.
Key Takeaways
- Founder Psychology Matters — Most stuck companies trace back to subconscious patterns, not strategy failures, and founders must address these to grow.
- Premature Scaling Kills — Expanding markets or teams too quickly dilutes the core and creates complexity most companies cannot absorb.
- Core Before Expansion — Winning in a beachhead and protecting the core creates more durable growth than chasing adjacent market too early.
- Better Growth Pace — Sustainable companies grow at the pace the market allows; forced hypergrowth often destabilizes otherwise healthy businesses.
Quote from Dave Hersh, Co-founder and Former CEO of Jive Software
"I realized that 90% of stuck companies and failed companies are not the reasons that we say they failed. Like they didn't have product market fit or they ran out of cash or the founders didn't get along. It's the psychology underneath. If you actually look at the source of those problems, It was these very consistent psychological patterns that founders run into.
"So hero complex, warrior, imposter syndrome, over identification with the company. It was all of these things that I kept seeing over and over again that led to the decisions that got them stuck. And so, yes, while it's true, they got out competed. Why did they go after the big market? What led them to do that? Why did they try to compete against these companies they were competing against?
"And then you start to tap into what's really going on and you see: They're trying to earn validation. They are trying to get redeemed as an entrepreneur. They're trying to live up to their parents, their older sibling, their peer group. And it was that desire that led to them trying to go after this big market and raising too much money that got them stuck. And so I like to work with the source material, which is, Why did you do that?"
Links
- Dave Hersh on LinkedIn
- Book by Dave Hersh: Reignition: Transforming Stuck Startups into Breakout Winners
- Dave Hersh website
Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.
Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Josh Ho is the Founder and CEO of Referral Rock, a bootstrapped referral marketing platform serving SMBs that rely on multi-step, relationship-driven sales. Starting in 2015 as a solo developer consulting on the side, Josh built the first version himself, validated demand quickly, and landed early customers by doing demos and hands-on support.
Referral Rock has grown to roughly 500 customers, 20 team members, and about $3M in annual revenue. The company scaled through strong inbound SEO, founder-led sales, and a high-touch onboarding model for B2B businesses that value referrals. Over the years, the product expanded too broadly, creating UX and complexity challenges that later required a deliberate refocusing on core use cases.
Today, Referral Rock is profitable, founder-owned, and steady at its current revenue plateau as Josh rethinks pricing, packaging, product simplicity, and ICP focus. He shares practical lessons on avoiding over-complexity, hiring from what you've already figured out, returning to first principles, and treating plateaus as puzzles to solve rather than signs of failure.
Key Takeaways
- Charge Early, Not Late – His first startup delayed monetization; Referral Rock asked for payment within days of launching an MVP.
- Pricing For Segments– Good-better-best failed for SMBs with wildly different referral economics; switching to two specific lanes solved misalignment.
- Do the Job First – Hiring worked only after Josh personally figured out support, sales, or marketing enough to define the role clearly.
- Plateaus Aren't Failure – Post-COVID shifts and SEO changes slowed growth, but Josh treats plateaus as system puzzles, not existential threats.
- Profit Equals Freedom – With no investors and steady profitability, he optimizes for enjoyable work, long-term optionality, and building at his own pace.
Quote from Josh Ho, Founder and CEO of Referral Rock
"For me, a plateau or a pivot is a puzzle to be solved. Any time you try to build something, you hope to just keep hitting accelerators and different serendipitously find those things. But I've learned through my life, the most part, there are things that work only for a certain duration, right.
"For me, it comes back to how I think about the business and. my innate goals for the business which, are different from most founders. When I'm talking to another founder is, they'll ask me what my exit strategy is. And my answer is usually, Well, I don't really have one. That's not how I think about the business. It's a very clear.
"I enjoy my work and that's my North Star. Am I having fun? Do I enjoy this work? And I also continuously reinvent myself and my role to fit those changes.. There might be a job I had to do that I don't enjoy, but then I'll do that until it's no longer like the limiting step and then hire someone to backfill for myself."
Links
- Josh Ho on LinkedIn
- Referra lRock on LinkedIn
- Referral Rock website
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Shailesh Hegde is the CEO of Hubilo, a Bangalore-based webinar software company that initially started during COVID as virtual events tech and raised $150M in VC funding before the market shifted. Originally joining as head of product, he stepped into the CEO role during a chaotic downturn and led the company through a full strategic reset after returning all the remaining capital to investors.
When the virtual events boom collapsed, Shailesh and the team rebuilt Hubilo into a mid-market webinar platform serving B2B marketing teams. They shifted from large in-person event organizers to marketers running frequent webinars, emphasizing differentiated AI-driven content repurposing. Hubilo stabilized revenue, rebuilt its GTM motion, and reached a 50/50 split between new webinar revenue and legacy customers.
Earlier this year, Hubilo was acquired by BrandLive, a U.S. enterprise video platform seeking a complementary webinar product. About 80% of Hubilo's team moved over, and Shailesh now leads product integration and customer continuity during the transition. He shares hard lessons on pivots, returning capital, leading through uncertainty, and executing a practical exit when the original VC-scale vision is no longer realistic.
Key Takeaways
- Refounder Mindset – Shailesh stepped into the CEO role and reframed the mission from hypergrowth to survival, focus, and a practical exit.
- New ICP Reality – Moving from event organizers to B2B marketers required a complete repositioning and GTM rebuild that took longer than expected.
- AI as Differentiator – Hubilo used AI-generated content and repurposing tools to stand out in a crowded webinar category with entrenched incumbents.
- Practical GTM – LinkedIn thought leadership, SEO content, and product-led demos outperformed outbound or expensive Google ads in this competitive space.
- Strategic Fit Wins – BrandLive acquired Hubilo for complementary capabilities, product acceleration, and access to a strong India-based engineering team.
Quote from Shailesh Hegde, CEO of Hubilo
"Now that I just sold our company, I'm thinking about what's next for me. It comes down to, Will I be able to find a viable problem that people are willing to pay for and will I be able to use sort of all of this experience that I have in order to solve it really well and kick off a company off the ground?
"Now is probably the best time to start a company where there's so much action, there's so much happening in AI, and it's super exciting to be in this space. It's also a great time to not have like revenue pressure on your shoulders and just think out loud, have open conversations and just be free, before you really dive in and choose a focus.
"The same types of business pressures will come back as you start a company. But now is a great time to just help with transition, make sure the team is good, but at the same time, start thinking about the types of problems I want to solve in the future with a new startup."
Links
- Shailesh Hegde on LinkedIn
- Hubilo on LinkedIn
- Hubilo website
- Brandlive website
Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.
Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Raju Patel founded eShow over 25 years ago after building a speaker portal for a magazine company and realizing he had a repeatable software product. What began as a one-man shop in suburban Chicago evolved into a robust event-management platform serving associations that needed complex, multi-module functionality. His business grew steadily as he delivered registration, booth management, speaker portals, and onsite systems for demanding event teams.
Today eShow has 125 employees, more than 14 integrated modules, and supports hundreds of events each year for 300+ customers, including large association conferences with tens of thousands of attendees. The company has always been profitable, self-funded, and built through careful reinvestment, steady hiring, and deep product expansion. Raju rebuilt the platform multiple times, including a shift to a modern stack.
Still independent with over $10 million in revenues, Raju is now building a VP-level leadership team, exploring practical growth capital, and planning a hybrid event model that blends in-person and virtual experiences. His story highlights long-term passion, practical growth, and a deliberate shift from hands-on founder to capable CEO after decades in the game.
Key Takeaways
- Deep Domain Focus – Serving the most complex association events created defensible differentiation.
- Slow, Steady Compounding – Year-over-year growth came from incremental improvements, not big bet.
- Passion Over Money – Raju built for love of the work, not an exit, which sustained him through decades of change.
- Multiple Rewrites Needed – Long-term SaaS requires full platform rebuilds, and Raju completed two with a third underway on a modern stack.
- Late-Stage Professionalization – Hiring VPs, defining ICPs, and strengthening leadership came only after passing the $10M threshold.
Quote from Raju Patel, founder of eShow
"Looking back after 20 years running this as a small business in software, think I would have figured out how to pull a little bit more money out. It would have given me a better peace of mind."
"I wouldn't have even known how to spend if I pulled a million out back then, it would have been wasted. I was very frugal and investing in my business every year."
"But now I could figure out how to spend a million dollars, on savings and other personal spending that would be meaningful. It would be liberating. I deserve it, so I'm going to spend a little bit more, not be frugal. I can be frugal in my business and in my personal life not be so frugal!"
Links
- Raju Patel on LinkedIn
- eShow on LinkedIn
- eShow website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Dharshan Rangegowda, founder of ScaleGrid, left a decade-long engineering career at Microsoft to solve a painful database operations problem he had lived firsthand. After early missteps selling to enterprises, he shifted to helping developers manage MongoDB, Redis, and Postgres on the cloud, bootstrapping the business from scratch.
ScaleGrid grew steadily through product depth, technical support, and Dharshan's mastery of SEO—becoming the top organic result for many key searches. The company expanded into multiple database engines, added a distributed engineering team, and reached 20 employees by 2021, serving both SMB developers and some enterprise teams.
Dharshan sold a majority stake to Spotlight Equity Partners during the pandemic after receiving an unsolicited offer, later stepping out of day-to-day operations while remaining on the board.
In this conversation, Dharshan shares hard-earned lessons about product-led growth, support as strategy, SEO as a long-game advantage, and how bootstrapped founders can build meaningful outcomes in massive markets.
Key Takeaways
- SEO Power: SEO remains a long-term growth engine for bootstrappers because big VC-backed companies rarely have the patience to compound it.
- Support as Strategy: Deep, responsive technical support became ScaleGrid's differentiator and directly informed product innovation and content.
- Start at the Edges: Enterprises won't buy from a one-person startup, but edge users with urgent problems will — and they become your early beachhead.
- Bootstrap Constraints: Founder over-frugality can limit growth; strategic delegation and early team building prevent burnout and plateauing.
Quote from Dharshan Rangegowda, founder of ScaleGrid
"You can't take random people and make them an entrepreneur. You have to want to be an entrepreneur and want to be on your own. You have to enjoy the freedom and the risk and the upside that comes with it and the unmitigated downside as well. You have to accept and be comfortable with it.
"You want to be on your own so you can try things. You are constantly looking at problems and new solutions. You want to be around people who like that sort of process: Here's a new problem and here's a new solution.
"But the most important thing you have to do as an entrepreneur is you have to add value to your customers. And most people forget that."
Links
- Dharshan Rangegowda on LinkedIn
- ScaleGrid on LinkedIn
- ScaleGrid website
- Spotlight Equity Partners (acquirer)
- Allied Advisers (M&A advisor)
- AngelPad Accelerator
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Gaurav Bhasin is the founder and managing director of Allied Advisers, an M&A advisory firm whose principals have completed over 100 sell-side transactions for software and tech founders. After two decades in investment banking and tech M&A, Gaurav is a sell-side advisor to B2B software founders who have built successful businesses and want to explore selling their companies.
Allied Advisers typically works with founders selling their businesses for $20M–$200M, helping them prepare materials, run a competitive process, and negotiate terms.
We discuss how today's M&A market looks very different from the 2021 bubble. Valuations have normalized, deal timelines have increased, and buyers are more disciplined. But the demand for profitable, steadily growing SaaS companies is stronger than ever.
Gaurav breaks down strategic and private equity buyers, what metrics matter most, how AI influences valuations, and why most founders underestimate the emotional and operational effort required to sell. For practical founders thinking about an exit in the next few years, this episode provides clear expectations and tactical guidance.
Key Takeaways
- Profitable Growth Wins — Buyers prefer SaaS companies growing 20–50% with real profits over faster revenue growth fueled by burn.
- Metrics Drive Valuation — Net retention above 110%, gross retention above 90%, and >75% gross margins increase valuation and buyer interest.
- Run a Real Process — A single buyer gives you no leverage. Multiple qualified buyers improve pricing, terms, and closing certainty.
- AI Is Lipstick — But Real — You don't need to be AI-native. Practical AI that improves product, margin, or GTM still increases buyer interest.
Quote from Gaurav Bhasin, founder and managing director of Allied Advisers
"The good news for SaaS founders is that the private equity community has raised about $1.5 trillion of capital, and more is being raised. And they also have access to debt. So there's $7 trillion of dry powder to do deals. Private equity is not paid to sit on the cash. And they love recurring revenue software.
"Private equity investors will typically move much faster than strategic buyers. Strategics will take a while. You need a business unit sponsor to buy into the vision, and then they will push the corporate to do the deal. But with the private equity, they will look at your financial metrics and if you fit in, they can move pretty fast.
"The one caveat with private equity compared to strategic is they generally pay a little bit less than the strategics because strategics have established distribution and GTM for higher growth, so private equity will index more on the financials."
Links
- Gaurav Bhasin on LinkedIn
- Allied Advisers on LinkedIn
- Allied Advisers website
- 2025 Vertical SaaS Report - Allied Advisers
Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.
Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Natalie Barbu is the founder and CEO of Rella, a SaaS platform built to streamline collaboration and workflows for social media teams and agencies. She began as a YouTube creator, grew a following of over 300,000, and then identified the fragmentation of the creator tools market — which led her to build Rella 1.0.
With some small seed funding, the first Rella version focused on content creators and made no revenue with a freemium model. With $25K in the bank and no revenue, the four cofounders thought they would shut it down. But a viral video focused on social media teams immediately created paid users and revenue for a new Rella product.
"Rella 2.0" now offers all-in-one content planning, scheduling, collaboration boards, billing & analytics, an AI content strategist, and all in one workspace — for social media teams. In just 12 months, they went from having no revenue, no funding, and a hard pivot relaunch to almost $3M in ARR run-rate revenue — with only four co-founder employees.
Key Takeaways
- Charge Early: They learned the hard way that free users don't convert — monetization early was non-negotiable.
- Lean Teams Win: A small, focused team aligned tightly with a mission beats trying to scale prematurely.
- Community Is Fuel: Natalie shared behind-the-scenes of the product with early users — built trust + word-of-mouth.
- Pivot Smart: They transitioned from creator workflow tools to a full SaaS platform after validating demand.
This Interview Is Perfect For
- SaaS founders pivoting after a stalled product
- Founders learning how to find product-market fit
- Teams deciding when to hire or stay lean
- Builders designing tools for marketing and content teams
Quote from Natalie Barbu, founder and CEO of Rella
"It was about two years before we decided to pay ourselves. I was still making money from my social media. So that's how I supported myself. And then my co-founders had to find side things, which I know a lot of people say, you have to be a hundred percent all in and invested in it.
"But when you're not making money, you need to find a way to support yourself. So yeah, they had some side gigs that they were working on while still working full-time on Rella.
"Once we started making more money with Rella 2.0, we all bumped ourselves up and got some raises since we could afford it, which has been such an accomplishment. It's money that we're actually making from our customers and our users and the income that we're generating."
Links
- Natalie Barbu on LinkedIn
- Rella on LinkedIn
- Rella website - Use this 10% Discount Code for Rella - practical
Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
In this episode, the founder of Practical Founders, Greg Head, shares the most powerful insights from over 165 podcast interviews and working with 40+ bootstrapped SaaS founders in his peer groups. Greg breaks down the common but less obvious traits he sees in practical founders who are quietly building valuable software companies without big VC funding.
Greg shares how frugality and managed risk-taking coexist to create compounding steady growth, creating massive long-term value fpr practical founders. And independence and doing it your way are not just luxuries but real superpowers that fuel growth. These patterns have emerged across hundreds of founders he's worked with, representing over $10 billion in founder equity value created.
For SaaS founders skeptical of VC templates and PE playbooks Greg shares what all practical founders do to grow from $1M to $10M ARR without betting it all. Are you wired like a Practical Founder?
Key Takeaways
- Frugal yet bold – Practical founders are unusually frugal in life but make well-timed bold bets inside their companies.
- Managed risk – They avoid betting the whole company, instead making small bets that can compound into larger wins.
- Compounding focus – Long-term, steady 20–30% growth creates exponential outcomes in SaaS over 10–15 years.
- Independence premium – Protecting their ability to do it their way is treated as a strategic advantage.
- Optionality matters – Practical founders value flexibility to sell, go long, or change direction without outside control.
This Interview Is Perfect For
- Founders building SaaS without VC funding
- CEOs who value control and sustainable growth
- Entrepreneurs exploring long-term leverage vs. quick wins
- Anyone who wants to understand the practical founder mindset
Quote from Greg Head, founder of Practical Founders
"The simple math of a $1 million ARR recurring revenue business that grows at 30% a year, will become very valuable if it keeps growing. ? Not crazy growth, a reasonable pace. This is the fundamental principle of recurring revenue businesses, that it's a compounding machine.
"If you grow at 30% for nine years, you'll have a $10 million business. And if you do that for another nine years, you will have a $100 million business. That's probably worth a billion dollars by that time. That sounds simple and not everybody gets there, of course, but practical founders think in this way. Steady, healthy compounding.
"We know that in the long run, the 10 years, the 20 years, compounding makes the difference. It's a healthier approach. We actually like this approach, generally speaking. We understand the math and yes, we're doing it. Most people don't really sign up for this kind of thing."
Links
- Greg Head on LinkedIn
- Practical Founders on LinkedIn
- Practical Founders website
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Darryl Pahl is the co-founder of DFnet, a Seattle-based company providing clinical trial data management software and services. Along with his wife and co-founder, Lisa Ondrejcek, Darryl started the company more than 20 years ago after careers at Fred Hutchinson Cancer Research Center. They built DFnet around long-term client relationships in global health and clinical research.
The company runs DFdiscover, an enterprise-grade electronic data capture and management platform used in clinical studies worldwide. With offices in the U.S., Canada, and South Africa, DFnet has grown to more than 50 employees and is approaching $10M in revenue. Clients range from the U.S. Department of Veterans Affairs to nonprofits like PATH and major universities.
Still independent and bootstrapped, DFnet has made key moves to prepare for the future—such as bringing in a growth-focused CEO, diversifying beyond single-client risk, and shifting legacy software to SaaS and services. Darryl shares the lessons from running conservatively under debt, buying rather than building, and building a global company rooted in relationships and practical execution.
Key Takeaways
- Stability First Growth – Carrying a 10-year SBA loan forced conservative growth and taught the discipline of stability over risky expansion.
- Buying Not Building – Acquiring DataFax brought 35+ new clients overnight and proved that buying legacy software can be smarter than reinventing.
- Services Plus Software – Unlike pure SaaS, DFnet thrives by combining consulting, hosting, and software in a regulated field.
- Spouse Founders Structure – Their 51/49 ownership split avoided deadlocks and kept marriage and business aligned.
This Interview Is Perfect For
- SaaS founders balancing growth and control
- Founders considering succession or sale
- Bootstrapped entrepreneurs in niche B2B markets
- Anyone curious about global health data and impact-driven tech
Quote from Darryl Pahl, co-founder of DFnet
"The best position to be in is to say that in three to five years, we would be crazy to sell this company. It's doing so well. That would be the perfect thing. And what we're not looking for is a giant payout. We have a very modest lifestyle.
"But is an asset, it is a business, and there's a business aspect. It would have to be the right type of buyer. It has to be the right fit. It has to be the right person or group that is respectful to our clients, our employees, and us as owners.
"So the ideal would be to have the luxury of either not selling or being more selective rather than responding to random emails from some financial buyer or search funder."
Links
- Darryl Paul on LinkedIn
- DFnet on LinkedIn
- DFnet website
Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.
Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Vincent Serpico, veteran CTO and founder of Founders Workshop, is on the front lines of the AI revolution in 2025, reshaping software development and business operations. With more than 30 years of experience building software apps, Vincent is now dedicating himself full-time to AI coaching and workshops for teams and companies to create high-leverage impact quickly.
Vincent shares how practical SaaS founders are leveraging agents, vibe coding, and tools like OpenAI's Agent Kit to multiply output without adding headcount. He sees the shift from SEO to GEO, the rise of ChatGPT apps, and why domain expertise is the ultimate competitive moat for SaaS founders navigating this new economy.
Now leading Serpico.ai, Vincent describes how entire applications can be built without writing code, using natural language and iterative management. He stresses that daily AI use, human-in-the-loop workflows, and focusing on domain-driven innovation will give practical founders the edge in this seismic shift.
Key Takeaways
- Agents As Labor – AI agents perform multi-step workflows like employees, delivering productivity gains with human-in-the-loop oversight.
- Domain Expertise Moat – Deep customer and industry knowledge matters more than raw coding speed in the AI economy.
- Vibe Coding Skills – Non-coders can now build apps with natural language prompts, managing AI like junior employees.
- Practical AI Adoption – Founders should start with small use cases, building workflows before tackling complex projects.
- Great Arbitrage Period – Founders who embrace AI now gain massive leverage over competitors who resist change.
This Interview Is Perfect For
- SaaS founders ready to apply AI beyond experiments
- Product leaders exploring AI-driven workflows
- Developers curious about vibe coding and agentic design
- Founders building lean, AI-powered teams
Quote from Vincent Serpico, founder of Serpico.ai
"If you're not an expert in something, AI will probably make you two to three times better than you currently are. But if you are an expert in something, AI will make you 10x better.
"If you're already a domain expert, using AI will make you 10x better. Those are the ones that you should be hiring and paying outpaced salaries to, and build your tiny team—domain experts who are great at AI.
"If I want to use AI in real estate, I could do it, but a guy who's been a real estate agent for 30 years will do much better if he understands AI skills like how to prompt and context engineer.
"So we'll see hiring domain experts and paying them outsized salaries because they're utilizing AI and producing five, six times more than they could without it."
Links
- Vincent Serpico on LinkedIn
- Serpico AI website
Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Brett Gilliland, founder of Elite Entrepreneurs, joins Greg to discuss how they help ambitious founders navigate the tough leadership journey from $1M to $10M in revenue. Brett shares how co-creating a clear, practical Purpose, Values, and Mission form the foundation of scalable organizations.
He explains why moving from founder-led chaos to aligned leadership teams is the critical step that separates $1M experiments from $10M companies. With clear meeting rhythms, disciplined execution, and strong hiring practices, Elite Entrepreneurs has helped hundreds of founders become happy CEOs and build companies that run without constant founder involvement.
Brett reveals the personal transformation required for founders to evolve into true CEOs who can enjoy their business more as it grows. You can reduce chaos, scale your teams, and rediscover the fun of running your business once you shift focus from “I” to “we.”
Key Takeaways
- Growth Brings Freedom: Founders who learn let go in the right way often rediscover fun, profit, and time.
- Leadership Teams Required: Scaling past $3M–$10M depends on building a capable senior leadership team.
- Meeting Rhythms Drive Scale: Annual, quarterly, monthly, and weekly cadences keep teams aligned.
- CEO Core Roles: Set the vision, build the team, and secure resources—everything else gets delegated.
- Hiring as Marketing: Culture-fueled job postings act like a “bat signal” for the right candidates.
This Interview Is Perfect For
- SaaS founders at $1–5M in ARR
- Business owners feeling “stuck” at their current stage
- CEOs ready to build their first real leadership team
- Entrepreneurs who want growth and a life
Quote from Brett Gilliland, founder of Elite Entrepreneurs
“All of us get stuck in some way. We know there's a better way. We see other people figuring it out. I should be able to do this, we say, but we just didn't know what to do.
"You have to do work on your business in a deliberate way. And those who do the work consistently make progress. We help them lay out the path from $1 to 10 million. Here are the things that you do. It's proven, it's practical.
“Whoever has been consistent with it, quarter after quarter, month after month, week after week, doing the things that we're talking about, they start stacking wins.
“Then all of a sudden, 18, 24 months later, we're at a place where we've tripled in revenue, we've doubled in team, it's fun, I've got some time back in my life. It does take time, but it's totally doable. I've seen it over and over and over again.
Links
- Brett Gilliland on LInkedIn
- Elite Entrepreneurs on LinkedIn
- Elite Entrepreneurs website
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Praveen Ghanta, founder of Fraction and former CEO of HiddenLevers, shares how he turned his experience scaling a bootstrapped SaaS company into a fast-growing fractional talent marketplace. After HiddenLevers reached $8M in ARR and sold for over $100M, he realized that senior fractional engineers were the secret to delivering efficiently without expensive full-time hires.
Fraction now serves over 100 SaaS clients with a vetted pool of 500 senior U.S.-based engineers and CTOs. Typical engagements run 10–30 hours a week, helping founders tackle scaling challenges in vertical SaaS, AI engineering, DevOps, and legacy system conversions. The company has reached $10M ARR in just three years while keeping half its own team fractional.
Praveen explains how clients use Fraction to save costs, speed development, and even prepare for M&A due diligence with fractional CTOs. He also highlights how AI has boosted senior developer productivity by 4x, why U.S.-only context matters, and how fractional-to-full-time hiring often becomes a win-win path.
This interview is perfect for SaaS founders at $1M–10M ARR, hitting scaling issues, vertical SaaS leaders needing senior engineers without VC funding, and founders considering AI-powered product features and engineering talent.
Key Takeaways
- Fractional Individual Contributors: Not just execs—senior engineers deliver hands-on code, marketing, and DevOps part-time.
- AI Productivity Boost: Senior developers using AI tools are delivering 2–4x more than peers without them.
- Cost Advantage: Starting at $5K/month, founders access senior dev talent without $200K+ full-time salaries.
- Best ICP Fit: Vertical SaaS companies at $1–10M ARR facing scaling issues or legacy migrations.
- Developer Productivity: Fraction leveraged its experience with over 100 clients to build DevHawk.ai, a tool that manages fractional talent and delivers results even more efficiently.
This Interview Is Perfect For
- SaaS founders stuck at scaling challenges without a budget for big teams
- Bootstrappers and practical founders looking for senior engineering firepower
- Founders facing legacy code, scaling issues, or AI feature rollouts
- Non-technical founders struggling to manage offshore or junior dev teams
Quote from Praveen Ghanta, founder of Fraction
“There are a lot of very experienced engineers who get into a senior developer role, but if they’re not going to become the manager of the team, there's not a really good and obvious career path for them.
“They start to get bored because they know their job inside and out and it's relatively easy for them to keep delivering.
“So working on a startup on the side is actually a way for both for them to sort of enrich their career and see new things and have that creative satisfaction, but at the same time, not take the risk. There are plenty of folks that want to be full-time at the startup, but there's risk in being at a startup.”
Links
- Praveen Ghanta on LinkedIn
- Fraction on LinkedIn
- Fraction website (fraction.work)
- DevHawk website
Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.
Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Anthony Pierri and Rob Kaminski are the co-founders of Fletch, a positioning strategy firm for B2B SaaS companies. They started Fletch after observing that most founders often confuse positioning with copywriting and marketing, and built their business by helping SaaS leaders make the tough, strategic choices about who they serve and how they win.
Over the last three years, Anthony and Rob have collaborated with over 400 SaaS companies, ranging from early-stage startups to rapidly growing companies. Fletch helps founders and B2B SaaS leaders clarify their positioning, sharpen their messaging, and translate strategy into effective homepage design.
In our practical discussion, they help founders see that positioning is a business strategy, not copywriting, which forces clarity and tradeoffs to improve execution. They share why founders must (eventually) choose one clear path to scale efficiently and why bootstrapped SaaS leaders often make sharper bets than VC-backed peers.
Key Takeaways
- Positioning = Strategy: Positioning is a founder/CEO choice, not copywriting or branding.
- Almost Universal Problem: Most B2B SaaS founders struggle with positioning clarity.
- Anchors Drive Focus: Use category, use case, or alternative as clear positioning anchors.
- Bootstrappers Move Faster: Limited capital forces clarity that VC-backed companies delay.
- Execution Takes Time: Positioning decisions are quick, but discipline drives results.
- Homepage Test: Your homepage clearly reveals whether positioning is working or not.
This Interview Is Perfect For
- SaaS founders stuck at $1M–$10M ARR growth plateaus
- Bootstrapped operators needing sharper messaging to scale
- Founders unclear about marketing vs positioning strategy
- B2B SaaS CEOs rethinking go-to-market focus
Quote from Dave Yuan, founder of Tidemark Capital
“There is a difference between bootstrappers and VC-funded startup founders in successfully positioning their startups. Bootstrappers are willing to see a narrow opportunity and tackle it with focus, because almost every market is big enough to sustain a $10 million company. “I don't care how narrow you get, the world's a big place. So even with a hyper-focused, verticalized niche, or use case play, there's plenty of money if you do it well and that's very appealing to bootstrappers.
“Most VC-funded founders don’t focus as well, which creates problems. But the founders who truly understand positioning and the idea that it can evolve over time, whether they're venture backed or not, they start with a very narrow practice to start and succeed as a leader. “
Links
- Anthony Pierri on LinkedIn
- Rob Kaminski on LinkedIn
- Fletch Website
Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company’s future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Dave Yuan is the founder of Tidemark, an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful vertical software companies like Toast, ServiceTitan, Jane, and CCC.
Tidemark hosts its annual VSaaS Collective Live Event, featuring experienced speakers for hundreds of vertical SaaS founders, on November 5, 2025.
In this episode, we discuss the practical opportunities and risks of AI as it is currently developing in 2025 for vertical SaaS companies. Dave explains several powerful examples of how AI is being used in his portfolio companies and the new strategic questions that are being discussed.
Dave also shares:
- Why software companies are getting real results with AI and are not waiting for the AI revolution--it’s here now.
- How AI-powered “systems of action” have undue influence with important users and can potentially displace entrenched systems of record software.
- How fast-growing practical software company grow efficiently with well-timed product, channel, and regional expansion.
Quote from Dave Yuan, founder of Tidemark Capital
“There are a handful of examples where software companies with AI-powered solutions are getting two to five times what they got on a software seat with new outcome-based pricing. They are providing real hard to ROI that's measurable, oftentimes associated with revenue.
“And arguably, they're only getting started because the outcomes that they're measuring are relatively low value and they can increase the value of the outcomes and price accordingly.
“To capture that value, it depends on competition. Because you can add a lot of value to your customers, but you can only charge for that value unless there's not a lot of competition vying for the same thing.“
Links
- Dave Yuan on LinkedIn
- Tidemark on LinkedIn
- Tidemark website
- VSaaS Collective Live event
Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
Dr. Matthew Jones is a licensed clinical psychologist who specializes in working with co-founders to help manage critical conflicts that threaten their success. He is the author of the book, "The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup Success."
Matt has worked with hundreds of bootstrapped and VC-funded co-founder teams to help them repair and manage their relationships in the context of their growing business. In this episode, we discuss a wide range of co-founder relationship topics, including:
- Why co-founder alignment sets the floor and ceiling for entire company culture and employee performance.
- How most co-founder conflicts aren't about surface issues but deeper psychological needs for recognition and power.
- Why research shows companies founded by friends are more unstable than those started by strangers.
- The three communication languages of cofounders: operational (business), psychological (feelings), and archetypal (the vibe).
Quote from Dr. Matthew Jones, a clinical psychologist
“And those differences can start off and be quite positive. If we can manage that tension effectively. That's the magic of co-founders, right? Is the complementary skills and ways of operating that allows you to land somewhere even more effective than you could have individually.
“But those same differences that give you that magic sauce also can be sources of friction, like an arthritic knee that just aches every now and then, and sometimes gets worse and worse, right? And so that's where the tensions really have to be managed. And so that's why I advocate for making those differences as conscious and explicit as possible.”
Links
- Dr. Matthew Jones on LinkedIn
- Cofounder Clarity website
- Book: “The Cofounder Effect: How to Diagnose Fix and Scale Healthy Communication for Startup Success”
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Yuval Selik is co-founder and CEO of Promomash, a software platform and managed service for Consumer Packaged Goods (CPG) brands to manage their trade promotions and field marketing activities. Yuval is a former CPG founder who encountered the expensive, complex, and crucial process of managing trade promotions with stores and distributors.
Promomash launched in 2015 to serve mid-sized CPG companies that don’t have custom software and their own teams to manage promotion spend and budget compliance with retailers. With 125 employees, they now serve over 500 customers with their software and optional analysts who can perform complex sell-through reconciliation and spend analysis.
Yuval and his co-founder raised under $1 million from angel investors to get started, and the company is now profitable and growing steadily. Yuval also hosts The 7 Hats Podcast, which helps entrepreneurs master the seven key areas of their lives, ensuring both success and fulfillment.
Quote from Yuval Selik, the founder and CEO of Promomash
“That's really the reason why we did not raise funds from big investors, because I don't want to have the pressures of somebody on my board telling me that I have to grow 50%, 80%, or 100% year over year.
“Sometimes you need to pull back in order to fix your product. Sometimes you need to push forward and step on the gas a little bit. But that decision needs to be my decision, not a VC investor’s decision.
“Others in our market that raised big VC funding, in our competitive landscape. They are not run by their founders; they're run by their investors”
Links
- Yuval Selik on LinkedIn
- Promomash on LinkedIn
- Promomash website
- The 7 Hats Podcast
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Vince Mayfield is cofounder and CEO of TalkingParents, a co-parenting app for communication and coordination used by divorced parents raising children. Cofounder Stephen Nixon was a lawyer with family cases who recognized the need for a secure, unalterable communication record to improve co-parenting and family harmony.
He pitched a development company owned by Vince and Louis Erickson to build the first app. They came together to cofound TalkingParents in 2012. Stephen worked with judges, courts, and lawyers to build awareness and get their first customers. The app records and stores all communications between co-parents, including chats, message, phone calls, and calendars. The company started growing and eventually became profitable as word spread, they charged more for the product, and the app improved.
TalkingParents is now a profitable and growing company with well over $10 million in revenue, 65 employees, 100,000 paying customers, and 500,000 people using the app. They are self-funded with no outside funding.
Quote from Vince Mayfield, cofounder and CEO of TalkingParents
“The company you are when you have 5 million in revenue and maybe 40 people, it's not the same company you are when you've got 20 million in revenue and say 80 people. It's not. You've got to iterate and change.
“And you've got to have the stamina for that. You've got to be willing to put in the effort and do that. Yeah, exactly. There's no shortcuts to this.
“I love it when people tell me, I've got an idea and I'm going to start up and it's going to go viral overnight. And my first thought is bulls--t. It's not going to happen that way.
“It's much harder than everybody thinks. You hear about the overnight success, but what you don't see is the 10-year grind that it took to get there. And the sacrifice and delayed gratification that goes along.”
Links
- Vince Mayfield on LinkedIn
- TalkingParents on LinkedIn
- TalkingParent website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Alan Miegel is co-founder and CEO of BetterComp, a modern compensation management platform for larger companies to manage compensation datasets to set market-priced salary benchmarks. Alan and his cofounders started the company in 2019 with founder funding, then raised angel funding as convertible debt from his friends in the tech industry.
They shipped their first “minimum sellable product” in 2020 and grew revenues steadily, doubling every year from $1M in 2022 to almost $10M in revenue in 2025. BetterComp now has over 80 employees and 200 customers.
In July of 2025, BetterComp raised a combined $33 million in growth equity funding from Ten Coves Capital and venture debt from Silicon Valley Bank. Alan and his cofounders still own a majority of the company. Now they have more resources and support to build on what has worked so far, enabling them to grow even faster and become a market leader.
Quote from Alan Miegel, cofounder and CEO of BetterComp
“Early on I didn't pay myself anything. Then I paid myself enough just enough to max out my 401k contribution, with no taxable income. I made a promise to my founders, my co-founders that I was going to pay them before I paid myself.
“I always paid my co-founders more than I made. That's still the case now. As the CEO, you think of it like you are the last one to get paid in this equation. You're not doing this to make money now, you're doing this to make money down the line.
“And you ask a lot of other people to make sacrifices, you ask them to make less than what they're used to making, so you have to put them first. Because if they see you putting yourself first, they're not gonna think they're the most important thing in the business, which they are..”
Links
- Alan Miegel on LinkedIn
- BetterComp on LinkedIn
- BetterComp website
- Founderpath
- Ten Coves Capital
- Union Square Advisors
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Zvi Band is co-founder and former CEO of Contactually, which was CRM software for real estate and other relationship-oriented professionals. Contactually was founded in 2011 with initial funding and support from 500 Startups in Silicon Valley. In the next five years, they raised a total of $15.5 million from institutional VC investors.
Contactually grew to about $10 million in revenue before growth stalled, and it became clear they couldn’t raise additional capital or grow big without funding. The company was sold in 2019 to Compass, a major real estate technology company and brokerage, to power their internal CRM platform.
In this episode, Zvi candidly shares his personal experience with VC funding, their opportunities and challenges, and the strategic dilemmas they faced along the way. Zvi now owns and operates a bootstrapped contact management software business called Relatatable.
Quote from Zvi Band, co-founder and former CEO of Contactually
“I realized I spent seven and a half years of my life in survival mode as a CEO with VC investors.. And at no point did I feel that like we were safe and things were fun, because the bank account was always trickling down a little bit.
“We always had big growth goals. And we were always thinking about, How do we get through the next VC funding round? At no point did I realize and celebrate that, hey, we built something really awesome.
“We could have chilled out once in a while or taken the team to Mexico for a week or something like that. But everything was around short term goals and what we need to do to get there that month.”
Links
- Zvi Band on LinkedIn
- Compass on LinkedIn
- Relateable website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Shoanak (Sean) Mallapurkar is the founder and CEO of Recruit CRM, a complete CRM and business management system for global staffing companies and recruiting agencies. He started the company in 2017 with his father, a technical expert who had experience as a senior executive in large staffing companies.
Sean handled customer-facing jobs in sales, success, and product management, and his Dad managed engineering, finance, and marketing. They started in Pune, India, but both Sean and his father moved to Dubai in 2023 for lifestyle and tax benefits. Recruit CRM employs over 150 remote employees in India to serve thousands of customers in more than 100 countries.
Recruit CRM revenues grew quickly to nearly $10 million ARR in 2025. Their product suite includes CRM, billing, applicant tracking, AI resume parsing, financial management, and more. The company is very profitable and growing steadily (Rule of 70) and the co-owners/co-founders have no intention of selling. They see a steady path to a $100 million revenue business as an independent company.
Quote from Soanak (Sean) Mallapurkar, founder and CEO of Recruit CRM
“The one thing that really worked for us was keeping costs extremely low and having over three years of capital runway. That wasn't millions of dollars for us. It was $100,000. And we didn't even spend it. We only spent about $80K before we started selling and got to breakeven.
“When you have enough time,you can you can do more things, you can try more things, and make it happen. If you only have a year to succeed, you're screwed. Get through the really hard stuff and get to a million in revenue
“Then resist the urge to raise capital until you are at a million dollars in revenue. Then ask yourself if you need it. If you can resist the urge to raise capital, a lot of opportunities open up to you. And it’s a very different financial outcome than having investors.”
Links
- Shoanak (Sean) Mallapurkar on LinkedIn
- Recruit CRM on LinkedIn
- Recruit CRM website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Jesse Burrell is the CEO and co-founder of BatchService, now known as BatchData, a real-time data and API platform designed for prop-tech startups and enterprises requiring massive and current housing data. Jesse was a real estate investor who needed better data to target his marketing efforts. BatchService was launched in 2018 with data brokering and subsequently built additional tools and apps.
BatchService grew rapidly to $35 million in revenue by 2022, but regulation changes and economic shifts contracted their core business, forcing them to make drastic cutbacks and pivots. They launched an enterprise data service with APIs for larger companies in 2021, which is now known as BatchData.
In July 2025, BatchService sold its “B2C” software business, comprising two successful products — BatchLeads and BatchDialer — to PropStream for an undisclosed cash amount. Jesse and his co-founders retained the B2B BatchData enterprise data business, now with 30 employees.
Quote from Jesse Burrell, cofounder and CEO of BatchService
“I had a couple years where I was pinching myself with the amount of money I was taking home every month. It was pretty wild how fast we rose in the first years. So when things changed for us, the fall really hurt, especially when we felt invincible and every idea worked brilliantly for three years.
“When things changed, we stayed pretty patient. We stayed pretty calm, but there was a lot of nights, weeks and months. I went home feeling like a failure and I don't think I was failing. I just think it was the conditions that we got put in. But it was really hard on me mentally. It was very, very tough to get punched so hard in the mouth with like a multitude of things in a short period of time.
“You're not as good as you think you are when it's going good and when it's going bad. It's not typically as bad as you think you are. A lot of it has to do with conditions and things that happen that are out of your control. You're fighting that because you're an entrepreneur and you'll figure it out if you are just persistent and don’t give up.”
Links
- Jesse Burrell on LinkedIn
- BatchService on LinkedIn
- Batchdata website
- Stewart Title website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Brian Forbis is the CEO and president of Blood Bank Computer Systems, Inc. (BBCS), a business his mother created in the 1980s to serve the non-profit blood bank industry in the US. Brian started in sales, then transitioned to run development, and assumed the role of CEO in 2019 when he bought the company.
BBCS rebuilt its entire mission-critical ERP software as a modern cloud solution over the last five years and is actively converting customers from legacy on-premise systems. With 40 employees and nearly $10 million in revenue, BBCS serves the blood banks that supply 20% of the blood products in the U.S.
Their industry presents numerous unique challenges, including negotiating co-op pricing, complying with FDA regulations, and managing partner-based relationships with customers. Brian is running this as a private, long-term business that will support the important blood bank industry for decades to come.
Quote from Brian Forbis, CEO and president of BBCS
“We don't have churn in customers, and we don't have churn in employees either. The people we attract to our blood bank software business really get bought in that we're helping people. We tell our team that you are affecting the lives of tens of thousands of people every day
“There's a reason we're regulated because we make decisions on the safety and efficacy of blood. And that's a big deal. We're committed to what we’re doing. We build a key component of saving lives.
“I drive that home every time I can talk about it. Making quality personal is one of our key values that we emphasize and discuss frequently.”
Links
- Brian Forbis on LinkedIn
- BBCS on LinkedIn
- BBCS (Blood Bank Computer Systems) website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Chris Brisson is the CEO and co-founder of Salesmsg, a conversational two-way texting platform that enables businesses to engage with their customers through opt-in SMS. When his first software company stalled, he shut it down and developed the Salesmsg product for a different SMS use case that served his previous customers.
Salesmsg now provides secure SMS texting across all departments in the company, integrated directly with Hubspot CRM. It includes voice calling, sophisticated SMS automation, opt-in management, analytics, and deep CRM integration.
Salesmsg has grown rapidly, exceeding $10 million in revenue with 65 employees, leveraging its deep integration with HubSpot and promoting through agency and affiliate partners. The company is independent and has no outside investors.
Quote from Chris Brisson, the CEO and founder of Salesmsg
“In 2015, I wrote this post to our email list of 36,000 called The Death of Call Loop. I shared the story of how I created a business I secretly despised. We were shackled and couldn't innovate. I wanted to create a better company and reinvent the business from the ground up. My second chance startup became Salesmsg.
“When you start a company and it stalls, at what point do you say It's not the horse to ride? I've been there. At what point do you say, Enough is enough? Because you're only going to get older.
“I've always gone after solving problems, but some problems were worthy of the adventure, others not so much. Make sure you're choosing the right opportunity because it will take seven years of your life. And you can pivot along the way, but man, you want to find out early if it's worthy of the adventure.”
Links
- Chris Brisson on LinkedIn
- Salesmsg on LinkedIn
- Salesmsg website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Tracy Larson is President and CEO of WeSuite, a vertical sales automation platform designed for larger integrators who sell complete security systems for commercial and residential real estate. Tracy and the cofounders were in the security systems business before launching a sales software company for this market in 2008.
WeSuite is now a comprehensive solution that addresses the complex industry requirements for lead tracking, quoting, proposal management, contracting, commissions, and pipeline management. Hundreds of integrators in the US use WeSuite for their end-to-end quote-to-contract process.
WeSuite grew profitably to nearly $5 million in revenue in 2024, when the founders sold 100% of the company to Valsoft, a buy-and-hold acquirer of practical software companies. Tracy remains the CEO of the company, which operates independently in the Valsoft holding company.
Quote from Tracy Larson, CEO and president of WeSuite
“For founders in SaaS, especially women founders, you need to find the right people to become your personal board of advisors. You don't need money to pay them. Just pick five people who you've known over the years to help you.
Ask them, Would you do this for me and be a sounding board once a month? I'd like to get your perspective on topics like these for 30 minutes. It’s not a formal board, it’s just advice and perspective.
“Establishing a personal board of advisors is a great idea. They can be women or men. And you can switch it up every year or so. Don’t worry about what you don't know. We all have things we don't know.”
Links
- Tracy Larson on LinkedIn
- WeSuite on LinkedIn
- WeSuite website
- Valsoft website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Henry Valentino is the founder and CEO of EConnect, a leading provider of facial recognition software for casinos and stadiums, ensuring venue security and compliance. He founded EConnect in 2009 and pivoted several times before focusing on a security platform utilizing AI for casinos during the COVID-19 pandemic.
The Econnect platform offers facial recognition surveillance software that integrates with special cameras at venue entrances to identify known security risks and ensure compliance. Security teams get immediate identification of “known bad guys” in large venues.
Econnect is approaching $10 million in revenue with hundreds of customers as a profitable business, with no outside equity funding. EConnect secured a total of $2 million in venture debt in 2019 and 2020, repaid it, and is now a growing and profitable company.
Quote from Henry Valentino, CEO and founder of EConnect
“Make sure you know your financial numbers yourself as the CEO. It's great to lean on accounting or finance leaders, but if you don't know them yourself, that's a big hindrance to success.
“Cash is what it comes down to. If the bank account doesn't have enough cash, they're only calling one person to get that resolved and that's you. If you get into trouble, you'll be trying to cut costs, which is not a way to grow a SaaS business.
“To continue growing, you need to increase your spending and capacity to take on new customers. How much does it cost to keep these doors open every month? How much cash are we going to bring in? What do we need to billl to put us in a profit position every month?”
Links
- Henry Valentino on LinkedIn
- EConnect on LinkedIn
- EConnect website
- Costella Kirsch
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Josh Turley is CEO of RTA Fleet Management, a fleet management software company that his grandfather started in the 1980’s and ran as a small family business for decades. Then Josh’s father ran the business until 2015, never growing this slow, old-school business past $2 million in revenues. Josh had worked in the business before, but in 2016, Josh bought the business, to over as CEO and slowly began to make improvements—and mistakes—as they started to grow.
Josh had an ambition to grow the company and learn how to be a real CEO. They started retooling their code to build modern cloud software, investing heavily for many years. They transformed their leadership, staff, business model, pricing, marketing, tech stack, and culture as they grew faster. They also focused on state and local government fleets as they grew.
The bootstrapped company grew steadily, with 75 employees and a $15 million annual recurring revenue (ARR) run rate in 2024, supported by some debt. In 2025, Josh closed a $30 million investment round from Susquehanna Growth Equity, a practical growth equity investor that invests in steady SaaS businesses.
Josh is a long-time member of my Practical Founders CEO Peer Groups. He is an avid learner, attending conferences, reading books, hiring consultants, and continually seeking new knowledge.
In this episode, Josh also talks about:
- How difficult it was to transform an old business into a new one
- Why their Purpose, Values, and Mission drive successful hiring
- Why he chose to take on growth equity investors and de-risk with secondary investment
Quote from Josh Turley, CEO of RTA
“Every problem is a leadership problem. The biggest challenge in building a SaaS business is always the people—making sure you get the right people on the bus in the right seats. We’re at 90 people now, and there's no way I can manage 90 people myself. As the CEO, it all starts with you, then your leaders.
“Most problems I see are because we got the wrong person in the wrong seat. You can't outrun that, regardless of how good the product is or how strong your financial model is. It will always catch up to you eventually, and that causes more problems than anything.
“When you get a leadership team to be 100% aligned with one another, it doesn't matter what the market's doing. It doesn't matter what the product is doing. It will figure itself out. It's a forcing function to get that alignment, and then you just can't be stopped at that point.”
Links
- Josh Turley on LinkedIn
- RTA on LinkedIn
- RTA website
- Susquehanna Growth Equity website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Sameer Narkar is the founder and CEO of Konnect Insights, a global SaaS company based in Mumbai that provides an omnichannel customer experience platform to consumer brands in 100 countries. Sameer created Konnect Insights in 2015 to help customer service teams respond to customers who mention their brands on social media.
The product and company have expanded from a slow start working through marketing agencies in India to now distributing through ISV partners in all major global regions. The Konnect Insights product includes social listening, ticketing, reputation monitoring, and social media analytics. They have grown to 140 employees, hundreds of customers, and $7 million ARR--without any outside funding.
In this episode, Sameer talks about:
- Selling through agency and ISV partners to grow efficiently
- Competing with large, well-funded software companies
- How he thinks about how AI can help them compete
- Why he hasn’t sold the company or raised outside funding
Quote from Sameer Narkar, founder and CEO of Konnect Insights
“When you start a software company, you have all odds against you. You don't have enough money. There's no reason why customers would trust you against the established products. There is a 99% chance that you'll fail.
“But if you're really passionate about what you're building, then don't look too far ahead. Try to achieve your smaller goals or get from zero to one. So just build something and get some early customers. We figured out a way for agencies to be interested in selling our solution to bring it to market.
“Then meet directly with your end customers. It's very easy for tech founders to sit in the office and build a product the way they think. That doesn’t work. Many founders think that if they take a half-baked product, they won't get another chance. But that's not the case. You need to build relationships to help you improve and grow..”
Links
- Sameer Narkar on LinkedIn
- Konnect Insights on LinkedIn
- Konnect Insights website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Chris Erler was co-founder and COO of ComX, a sales pipeline generation for mid-market B2B companies in Germany and Europe. Chris and two other founders started the company in 2018 to conduct turnkey modern digital marketing and lead generation solutions for traditional German companies.
As a tech-enabled service that combines technology, data, and people-powered solutions, ComX delivers proven results through subscription and outcome-based pricing. They grew quickly to approximately $20 million in revenue in four years before being acquired by the private equity firm FLEX Capital.
In this episode, Chris talks about:
- Growing a team of 70 employees in South Africa
- Starting in Germany with mid-market companies
- The challenges of debt financing of private equity buyouts
Quote from Chris Erler, cofounder of ComX
“99% of the time, I ask the founder, Why are you raising money from investors that early? I'm very pushy on that one because I know the freedom that you can create when building a bootstrapped business.
“For me, raising money from investors and giving away shares very early means you’re not focusing on customers, but rather focusing on collecting capital to build the product without having it validated too early. I just share our bootstrapped story with ComX which I believe works well.
“That's why I'm a big fan of your podcasts. There's a huge education needed, especially in Europe. People need to be educated on how to found properly. Of course, it can go well, but the chances that something f*’s up are much higher. And then young people are in a very bad situation.”
Links
- Chris Erler on LinkedIn
- ComX on LinkedIn
- ComX website
- FLEX Capital website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Aaron Steffey is the co-founder and co-CEO of Propeller, an online platform that enables insurance agents and brokers to issue surety bonds instantly — without the lengthy paperwork or back-and-forth typically involved in bonding. Aaron was an insurance agent, and his co-founder cousin, Chris, was a surety bond underwriter before 2019, when they set out to revolutionize the way surety bonds are bought and sold.
They initially bootstrapped with a software development partner who accepted equity instead of fees. Their first version drastically simplified the process of buying and selling surety bonds in the digital world, allowing them to grow quickly. They raised $7 million in SAFE notes from strategic partners to accelerate growth in 2021 and grow to nearly $20 million in revenue. They sold 100% of the company to Arch Capital in a strategic acquisition in early 2024.
In this episode, Aaron also talks about:
- How this sleepy, paper-based market changed quickly in COVID
- Why they raised growth funding from strategic investors and not VCs
- Why they sold the company and are still leading the business after the sale
Quote from Aaron Steffey, co-founder and co-CEO of Propeller
“My biggest advice for startup founders is simply just that endurance wins. It’s the whole thing of getting back up after you're knocked down, like everyone says. I had to live that so many times. So many No's when it came to our first carrier pulling out. No, I don't want to invest. No, I don't want to use your surety product.
“There were so many times when I wanted to give up. And the same with my cousin. Had we not founded the company together, I don't know that we would have continued because there were probably times when I would have given up.
“As long as both of us weren't on the floor, one of us would just pick the other up when the other person usually was more sane, and we dragged each other along.
“A successful founder needs to have a pretty high pain tolerance and endurance to succeed. You just have to keep pushing forward. It just sounds so cliche, but that’s what it was for us.”
Links
- Aaron Steffey on LinkedIn
- Propeller on LinkedIn
- Propeller website
- Arch Capital website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Roy van den Broek is the founder and CEO of Rentman, a rental business management software platform for event and media production companies. Roy built software for his event equipment rental business in the Netherlands. He had over 100 software customers in Europe before selling his rental equipment company in 2015 to focus on growing his Rentman SaaS company.
Rentman grew slowly and profitably as word of mouth spread in the industry and their product evolved. In 2024, after growing to nearly 100 employees and 200,000 users across 100 countries, Roy raised a $22 million growth equity round from Expedition Capital to derisk the founder's investment and add growth capital to continue expanding.
In this episode, Roy discusses how they managed the painful growth stages as they expanded from one employee to 80 global employees, building a multi-lingual product and business, and why he chose to raise a significant growth equity investment.
Quote from Roy van den Broek, founder and CEO of Rentman
“We had a lot of interest in investing in Rentman after COVID, so we ran a quick process. We ended up with 3 term sheets. You have multiple ways to look at these term sheets. You can look at the numbers and the valuation, which is a big part.
“But what's often overlooked is the other terms. The other terms are as important as the valuation because they really determine the way you work together. I think these terms might even be important or more important than the valuation. You got to understand their game and really figure out if you could get some alignment.
“In essence, you are negotiating the amount of autonomy that you have as a founder. That's basically what we prioritized. Like the board seats and who makes certain decisions, what are the decisions that require a majority vote? And I think we were able to get 100% autonomy on our side.“
Links
- Roy van den Broek on LinkedIn
- Rentman on LinkedIn
- Rentman website
- Expedition Growth Capital website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Gopal Krishnamurthy is the founder and CEO of Lumel, which has a suite of products focused on enterprise performance management (EPM). Their apps allow users to plan, report, and analyze data using the modern native app framework vs. traditional SaaS on top of modern cloud data platforms such as Microsoft Fabric, Snowflake, Databricks, and others. Lumel’s products provide a full stack of integrated Planning, BI & data apps on the customers' data platforms.
He grew his enterprise services company, Visual BI, to over 200 employees and sold that company to Atos in 2021, as he described in his first Practical Founders podcast interview in 2023. Gopal self-funded Lumel with a VC-sized investment and has grown it to over 300 employees in four years. Lumel is already at a revenue run rate of over $12M ARR and is growing fast.
Lumel is building its apps using modern cloud data platforms, not siloed SaaS databases, allowing it to manage real-time data across applications. This bold new vision and architecture for enterprise software apps align with modern data approaches supporting AI, creating a billion-dollar opportunity for Lumel in the future.
In this episode, Gopal also discusses:
- The challenge of transitioning from custom services to a no-touch product-led approach selling to enterprises
- Why VCs wouldn’t understand their technology bet and why their patience is paying off
- What it’s like to grow a fast-growth and innovative technology company as a bootstrapper
Quote from Gopal Krishnamurthy, founder and CEO of Lumel
“The main thing is it’s a big market. It’s not like we are just trying to get our first $10 million revenue. We have done that with Lumel already. We are looking at how we can get to a billion-dollar ARR business. That’s the big, bold vision. We have invested tens of millions already, and we are almost profitable.
“We think we can absolutely create a billion-dollar business based on our customer feedback and traction from 3,000 customers. So, it’s not a question of product market fit. We worked with hundreds of our enterprise customers and perfected our data app products.
“The other thing is that our products can work for smaller and medium-sized businesses because of our architecture and approach. It's completely horizontal: it works for all industries and all customers of all sizes.”
Links
- Gopal Krishnamurthy on LinkedIn
- Lumel on LinkedIn
- Lumel website
- Power BI website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Phil Stern is the operating principal of Mainsail Partners, a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success teams.
Phil was an experienced SaaS sales leader at several companies before joining Mainsail to focus on helping their portfolio companies scale up to $30M ARR or more. Phil’s team helps founders solve challenging problems with sales leadership, rev ops technology, compensation, marketing analysis and planning, and more with deep operational insights customized for each company.
In this episode, Phil discusses these important topics.
- The five keys to hiring your first head of sales to graduate from founder-led sales to a scalable sales team
- How Mainsail specialists partner with founders and their leaders to help them solve their most important GTM problems quickly
- How Phil helps with due diligence on potential investments to assess the upsides and opportunities for revenue growth
- Why Mainsail is focused on vertical SaaS companies with founders who are experts in their domains
Quote from Phil Stern, Operating Principal at Mainsail Partners
“Hiring a first head of sales is typically one of the first roles we're going to hire. This sales leader needs to be willing to sell the product. You're not coming in at $5 million of ARR to be an armchair VP. You own part of the quota, you're going to cover for a rep at a trade show or on maternity leave, whatever it takes.
“You have to be willing to sell. So if you come in just to strategize and move chess pieces around, it's just not the job for you.
“If you don’t sell, you won't get close enough to the customer. For these customers in vertical end markets, you need to get close to them, learn from them, understand them, and speak to them.
“It's really back to a bootstrapper mentality. The CEO has been doing absolutely everything up and down the business. I'm asking a sales leader to do everything up and down the go-to-market.”
Links
- Phil Stern on LinkedIn
- Mainsail Partners on LinkedIn
- Mainsail Partners website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Sean Hoban was co-founder and former CEO of Kimble Applications, a leading professional services automation (PSA) software for organizations to manage their professional services business's entire operational and financial lifecycle. Sean and his co-founders had already started, grown, and sold a pro services organization before creating a PSA product and building a SaaS business.
With a little funding from the founders and a few angel investors, Kimble started efficiently and grew steadily, eventually raising a practical minority funding round from private equity investors Accel-KKR in 2018. The company grew to $30M ARR before selling most of the company to Accel-KKR in 2021, which merged two PSA companies to create Kontata.
In this episode, Sean discusses some of their deepest strategic opportunities:
- Learning to grow a SaaS business versus a professional services organization
- Building on the Salesforce platform and working in that ecosystem
- Starting in the UK and expanding to Germany and the US
Quote from Sean Hoban, former CEO and co-founder of Kimble Applications
“One of the most powerful ways I learned as a CEO is to find and talk to other founders in London who were in a similar situation. We would meet for beers, share ideas, and chat on WhatsApp.
“If you have a specific problem, it was valuable to talk to other founders in the same growth stage. And these were founders, not hired CEOs.
“It's a lonely job as a CEO. And being able to talk to somebody else who is in a similar position can be cathartic and very helpful.”
Links
- Sean Hoban on LinkedIn
- Kantata on LinkedIn
- Kantata SX (formerly Kimble Applications) website
- Accel-KKR website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Josh LaSov is the founder and former CEO of Satori Reporting, an advanced reporting and business intelligence (BI) solution for mid-market businesses that use NetSuite financial software. Satori provided pre-built reports and dashboards, a tailored data warehouse, and detailed data models that leveraged the popular Power BI software.
Josh launched Satori, his second NetSuite solution, in 2019 and grew quickly in the NetSuite ecosystem, with a savvy team and no outside funding. Satori was sold it to private equity buyer Insight Partners in 2022 and combined with another NetSuite provider, Zone & Co.
In this episode, Josh talks about the benefits and challenges of building add-on solutions in the NetSuite ecosystem, their ROI of non-dilutive funding and strategic angel investors, selling two companies then getting bored and restless, and starting his third company, Cauzzy.ai to provide AI-powered automated financial analysis and insights.
Quote from Josh LaSov, founder of Satori Reports and Cauzzy.ai
“When you have a good exit, you can assume the lifestyle that you desire to live, you can slow down. So from 2022 until starting Cauzzy.ai in 2024, I did that, I worked out every day. I listened to more podcasts than any human should listen to. I educated myself, read every newspaper and news site. I took time for myself
“What I found was...it wasn't fulfilling. I needed more. I didn't want to be on the sidelines. I felt myself getting slower, like I was retiree. I appreciated the journey more than the destination. But there's a balance and I could achieve that balance.
“I needed to do something, but I didn't want to just jump into something just to do it. I was to be patient until I found something that I was passionate about and that's realizable. I thought, I can do this again, I want to do this again. Let's take our time and focus a bit more on balance this time, but let's get back in the game.”
Links * Josh LaSov on LinkedIn * Zone Reporting (formerly Satori Reporting) on LinkedIn * Zone Reporting (formerly Satori Reporting) * Cauzzy.ai website * NetSuite website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Andrew Gazdecki is the founder and CEO of Acquire.com, a marketplace of buyers and sellers of smaller, profitable SaaS products with revenues between $100,000 and $5,000,000. Andrew sold his own software company and learned how little support and information was available to sell a software product for under $5-10 million in deal size.
Acquire.com has helped over 2000 entrepreneurs sell their software products for a combined value of more than $500 million. Acquire offers additional support to help founders package, promote, negotiate, and close their transactions. Potential buyers are vetted for financial viability and identity confirmation before getting confidential details for any deal.
In this episode, Andrew describes their typical seller and buyer profiles, the typical process for a founder to sell a small and profitable SaaS company, typical multiples of profit that financial buyers offer, and founder transition periods.
Quote from Andrew Gazdecki, founder and CEO of Acquire.com
"There are three buckets of active buyers on Acquire.com. The first is below $100,000 net profit. That's going to be an individual buyer looking for something with maybe a little bit of product market fit. They want to take the product, grow it a little bit, see what they can do from there. They're buying a very, very early startup. So some buyers will actually start small and then work their way up.
"From $100,000 to $1 million in net profit in our middle range, the buyer will a blend of "micro PE firms" and holding companies that want to get their hands on a business where there's a lot more going on. And then a $1 million in profit and above is going to be for the more traditional private equity or strategic buyers."
Links * Andrew Gazdecki on LinkedIn * Andrew Gazdecki on Twitter * Acquire.com on LinkedIn * Acquire.com website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many business ventures before launching Genius Monkey in 2009, leveraging their experience in digital ad technologies.
Genius Monkey grew steadily as a bootstrapped company, with the founders and team working hard for years to improve their platform, prove results to clients, recruit agencies, and grow their team. Most ad tech peers took VC funding and are no longer around, but Genius Monkey is still growing and getting more profitable every year.
In this episode, Seth and Clint talk about their unusual long-time partnership, the power of profits, competing with giants, building a strong company culture, and leveraging non-dilutive funding to grow faster.
Quote from Seth Hassell and Clint Ethington, co-founders of Genius Monkey
"Don't be afraid to fail with the smaller stuff. A lot of times, people don't take the chance of seeing, "What if we do it this way?" What happens? And all those little things that could become something big, they never pursue because they're comfortable with where they're at."
"Fail fast. Try stuff out. If you see it's not working, shelf it and go to the next thing. Move on until you find that one that's doing better than where you're at right now. Then, I will put the determination and the motivation behind it to see it through. Clint and I tried through lots of things that just didn't work out."
"If it wasn't working, we were okay. We wouldn't say, "It's all over, close the doors." It wasn't like that. It was like, "Okay, we know that doesn't work. What's our next thing we're trying?" And we always had different ideas in the background."
Links * Genius Monkey on LinkedIn * Genius Monkey website * Cypress Growth Capital website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Shalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many successful products from 2000-2010, then focused on HappyFox and moved to the US in 2011.
HappyFox is a mid-market product that sells across industries and departments with an efficient product-led growth (PLG) approach. The product has matured with successful add-on products for live chat, AI support, business intelligence, and workflows.
The company has over 2200 customers, 110 employees, and now $20 million in revenue. Shalin plans to keep growing and leverage modern AI technology to become a much bigger company based on the disciplined product culture they have created.
Quote from Shalin Jain, founder and CEO of HappyFox
“I think software and its pricing need to be deflationary, just like hardware, where memory prices, hardware prices, and server prices have all been deflationary. But we are now going through a phase where software is actually getting more and more expensive.
“With the advent of AI and automation, software will become cheaper and more usage-driven. So, the best survivors in that phase would be the efficiently run companies that have not bloated themselves by charging more today to have more employees and spend more on ads.
“I believe software needs to get cheaper because it's getting cheaper to run software every day; it's getting cheaper to outsource to AI and build stuff with the help of AI as well. So software cost should not go up; it should go down.”
Links * Shalin Jain on LinkedIn * HappyFox on LinkedIn * HappyFox website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Brian Kesselman is cofounder and now CRO of Skematic, a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance in this highly regulated industry. He took a job selling compliance software and broke sales records before starting Skematic with a coworker and launching in September 2022.
Skematic grew quickly by solving an acute problem for lawyers and compliance execs just like him in his industry. The company became profitable quickly as Brian focused on outbound selling with cold calls and savvy demos to busy compliance executives. They grew fast, were profitable in just over a year, and attracted attention from potential acquirers.
In June 2024, Financial Recovery Technologies, a fintech legal software company, acquired Skematic for an undisclosed amount, including some cash and incentives. Brian and his cofounder still run Skematic and enjoy being part of a bigger software company owned by a private family office that is highly aligned with their culture and values.
Quote from Brian Kesselman, cofounder and CRO of Skematic
"My co-founder Charles and I had worked at a number of PE-backed software companies. And we had our own opinions about what it's like to work at a PE-backed company."
"The family office structure is very different from a private equity firm across the board. They're looking typically to build profitable cash-producing assets. And so that enables our team to think long-term, which benefits not only the founders and the people that are still participating in the upside of the business."
"That also means that the clients will benefit because you are going to do things that will benefit the clients every step of the way, one year, two years, five years, 10 years. And that was paramount to us, given that we've grown up in this very niche industry and our reputations to us are pretty much everything we have."
Links * Brian Kesselman on LinkedIn * Skematic on LinkedIn * Skematic website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Rebecca Shostak is co-founder and chief brand officer of Flodesk, the popular email marketing software for small businesses that care about beautiful branded emails. After prototyping the product and validating the problem, they launched in 2019 with a viral explosion that still powers their bootstrapped growth.
Six years later, Flodesk has over $30M in annual recurring revenues with 75 employees and over 100,000 paid customers. They have been profitable since the second week after launch, driven by great product design, the email footer “viral loop,” and referrals from customers and influencers.
In this episode, Rebecca shares her insights on product design, their unlimited pricing model, working with her co-founder/CEO, Martha Bitar, why they haven’t taken outside funding, and where AI is showing usefulness in their products.
Quote from Rebecca Shostack, co-founder of Flodesk
“The reason you hire is never to solve a problem. You need to be sharp and figure out how to solve the problem on your own. Then, you hire people once you've proven something.
“When you want to hire someone to run your paid ads, for example, you first need to figure out the basics. Then, you can hire someone to come in to own that so they can scale that operation.
“But it doesn't work to hire someone to come in and figure out something that you can't figure out yourself. How can you hire someone to manage something you don't understand?”
Links * Rebecca Shostak on LinkedIn * Flodesk on LinkedIn * Flodesk website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
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Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard for key metrics for the Managed Service Provider (MSP) industry.
After his intense 9-year journey at BrightGauge, Brian “retired” to spend more time with his growing family. He enjoyed his free time but eventually returned to the software startup game with his second company, Strety.
Strety is a fast-growing SaaS business with a popular app for small businesses using the EOS® approach to manage their businesses. It has 10 employees, hundreds of customers and partners, and no outside funding. Brian brought back some of his previous team to build another sustainable and valuable software company.
Links * Brian Dosal on LinkedIn * BrightGauge website * Strety on LinkedIn * Strety website * Entrepreneurial Operating System (EOS) website * Traction book by Gino Wickman * Anything You Want book by Derek Sivers
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
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Dave Yuan is the founder of Tidemark, an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful companies like Toast, ServiceTitan, Karbon and Dutchie.
In this episode, Dave shares some of the most useful strategic growth frameworks for vertical SaaS companies to grow through winning market share, expanding with additional products, and even extending through an industry ecosystem serving new markets. We also talk about the impact of AI on established vertical SaaS players and how it’s both an opportunity and a thre
Tidemark supports the global community of practical vertical SaaS founders by publishing their strategic growth frameworks, their annual Vertical SaaS Benchmarketing Report, and they host the annual Vertical SaaS Collective Live conference for founders.
Quote from Dave Yuan, founder at Tidemark
“Vertical SaaS founders should not be asleep with AI. You can wave it off, view it as a toy, and say that no one’s going to trust that outcome or use it. That may have been the case, but things are changing really quickly.
“Lots of smart people are making it better every month, and you have a massive opportunity to improve it with your data and workflow.
“Jump into it to control your destiny. Don’t get caught sleeping without AI in your product in a useful way.”
Links * Dave Yuan on LinkedIn * Tidemark on LinkedIn * Tidemark website * Tidemark Vertical SaaS Knowledge Project * VSaaS Collective Live 2025 conference * Vertical SaaS Benchmark Report 2024
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Dori Yona is co-founder and CEO of SimpleClosure, a technology- and people-powered company that helps founders wind down and dissolve a startup or business that is no longer viable. Shutting down a business can be complicated, costly, and risky for founders. SimpleClosure manages the unique processes with automation and expert support.
SimpleClosure has helped tech startup founders wind down over 500 startups, businesses that closed or have gone through a sale of assets. It manages the important steps of a winddown, including legal, regulatory, employees, investors, intellectual property, customers, data, and more.
In this episode, Dori shares the key considerations for SaaS founders who have run out of VC funding or need to shut down their companies for other reasons.
Quote from Dori Yona, CEO of SimpleClosure
“The biggest thing for software startup founders and CEOs is to move fast. Your time is your biggest resource in life as an entrepreneur, whether you’re venture-backed or bootstrapping. You’re spending your time, you’re spending your energy, you’re spending the best years of your career.
“So move fast, learn fast, test fast, iterate quickly, grow fast, fail fast. Ultimately, when you’re building your own business, you’re sacrificing an easy, convenient, cushy job anywhere else to take this risk.
“The faster you can grow, learn, build, and fail, the better. It’s ultimately to your advantage to make the most of your time. Our time is our most expensive resource.”
Links * Dori Yona on LinkedIn * SimpleClosure on LinkedIn * SimpleClosure website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
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Howard Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business grew steadily and profitably without any outside funding.
Read-A-Thon helped over 4000 schools and students raise over $30 million in donations. Their platform has tracked over 30 billion reading minutes by students who have used it to earn donations.
Read-A-Thon was successfully acquired by private equity investors in early 2023 for an undisclosed amount. The business has continued to grow and expand with a new CEO and key executives, with Howard on the board as an advisor and now a minority investor in the company.
Quote from Howard Gottlieb, founder of Read-A-Thon
“I have been very blessed and very lucky in my journey with the success of Read-A-Thon. Everyone should realize that and have some humility.
“If you succeed at the game, you can be the smartest guy or the smartest woman with the most brilliant idea, but it still will take 50% or more luck for everything to align correctly to succeed. Just realize that. It takes a lot of good fortune.
“At Read-A-Thon, our lucky moment was COVID because online fundraising was only in its infancy. When COVID hit and schools were out, Read-A-Thon was almost the only viable option. Our growth went from 40% a year to 100%, then 150% a year. So that was luck after all these years.”
Links * Howard Gottlieb on LinkedIn * Read-A-Thon on LinkedIn * Read-A-Thon website
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Richard Change is co-founder and CEO of PFA Solutions, the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and carried interest.
Richard was a senior architect for a large private equity firm when he discovered this complex problem that was being managed on spreadsheets. He left to start PFA Solutions and bootstrapped the development of FirmView with consulting revenue. From inception, through growth and ultimately acquisition, Richard never took any outside funding.
FirmView adoption grew steadily, serving large private equity firms. PFA Solutions eventually grew to 34 employees before being acquired by Allvue Systems in 2024. Allvue is a private-equity-backed software company that serves the alternative investment industry.
Quote from Richard Change, co-founder and CEO of PFA Solutions
"Once you're in it, once you've decided to start a company, own it. No regrets. No one's going to save you. There's not a fairy godmother that will come and wave all your problems away. You have to own it.
"There's no magic wand that will come and wave a wand and say, OK, all your problems are solved. And that magic wand in my mind wasn't outside capital; it wasn't VC funding. That wasn't magic because what do when the money runs out?
"Is your product generating revenue? That's the real problem. If there's a problem to be solved and you have a great idea or solution, you can generate revenue from it. Prove to yourself and the world that this is viable and has product-market fit."
Links * PFA Solutions on LinkedIn * PFA Solutions website * Allvue Systems website * Vista Equity Partners website
Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.
The Practical Founders Podcast
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Rachit Khator is the founder and CEO of Stackby, a no-code spreadsheet and database app builder that allows business users to create powerful spreadsheet-like applications with data links, automations, and workflows. Rachit and his team of 34 employees live in Surat, India, north of Mumbai.
Stackby started when Rachit was working for a corporate venture firm in Michigan, doing repetitive manual data imports and analysis in Excel. He hired a developer to build a better tool and started to sell Stackby to early customers. They followed customer feedback to build an inexpensive and easy-to-use app that competes well with VC-funded competitors like AirTable for specific use cases.
This bootstrapped company has grown in 4 years to serve 75,000 free and paid business customers. Now they are profitable and growing at 15% per month, upselling free business users to paid plans. Rachit has big ambitions for Stackby to serve millions of customers–and be an example success story in the Surat software community.
Links * Rachit Khator on LinkedIn * Stackby on LinkedIn * Stackby website
Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
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Joe Hyrkin is the former CEO of Issuu, a content publishing platform for interactive marketing content. Issuu allows you to easily publish printable and PDF materials in various formats to websites and social media. It’s a global product-led success story with millions of customers and a successful and sustainable business.
Issuu was started by four Danish founders before the company was moved to Silicon Valley in 2013 when Joe was hired as the CEO. Joe ran the company for almost 12 years, growing it profitably most years to almost $30 million in revenue before it was sold in mid-2024 to Bending Spoons, an Italian holding company that is an active acquirer of software companies.
Joe talks about working with their early venture capital investors with a practical and patient approach. In 2021, Issuu raised $20 million in debt to invest in marketing and address technology issues, which helped them grow faster before being acquired.
Quote from Joe Hyrkin, former CEO of Issuu
“From 2016 to 2020, we ran Issuu profitably, with what I like to call a ‘pro-grow’ approach—profitable and growing. Then, we raised debt to grow faster to about $30 million in revenue. The final year before we sold, we got back to profitability. So we got to profitability twice.
“By being profitable, you’re committing to your customers that you’re going to be around and that they will not have to go find some other solution. You’re communicating to your team that this company can be counted on. In 2024 and 2025, everybody wants profitability, unless you’re an AI company.
“Not having a profitability plan actually creates a lot of risk. I’m not saying you always have to be profitable, but you always have to have a foundation to know how we get to profitability. It’s a different way of thinking.”
Links * Joe Hyrkin on LinkedIn * Issuu on LinkedIn * Issuu website * Bending Spoons website
Podcast Sponsor – Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Brian Hamilton is one of America’s most successful entrepreneurs and a leading expert on entrepreneurship. Today, Hamilton serves as chairman of software company LiveSwitch. He is known for his pioneering work in fintech, his advocacy for small businesses, and his commitment to criminal justice reform.
As the founder of Sageworks (now Abrigo), America’s first fintech company, Hamilton developed technology that translates complex financial data, empowering millions of small business owners.
Sageworks struggled and grew slowly for 10 years before pivoting to serve local banks and credit unions with financial tools to assess the creditworthiness of their small business loans. The practical SaaS company grew steadily and very profitably to more than 400 employees when it was sold in 2018.
Through Inmates to Entrepreneurs and the Brian Hamilton Foundation, he encourages entrepreneurship as a means to economic opportunity. Hamilton’s work has been showcased by major media outlets like CNBC and Good Morning America, and he starred in ABC’s Free Enterprise TV series, an award-winning show based on Inmates to Entrepreneurs.
Quote from Brian Hamilton, founder and former CEO of Sageworks
"Being the founder of a tech company is like this: You're in a tunnel, it's dark, you're on your hands and knees, you're going through that tunnel, you're groping your way through, keep moving forward.
"I know it sounds like such a BS, but we've all been there. I'm telling you, that is the picture: you're in this huge sewer tunnel, it's dark. You just gotta keep moving. Just keep chipping away. You do that, and you will get momentum somehow.
"It's like compound interest. You start with a dollar and how does it turn into $10? You build momentum a little at a time. I've got to listen every day. I'm knocking off making the product better. You develop the physical property of compound interest and things will get better."
Links * LiveSwitch website * Brian Hamilton Foundation
Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Scott Desgrosseilliers is the founder and CEO of Wicked Reports, a leading multi-touch marketing attribution software for SMBs who use paid online advertising. Scott is a data and analytics expert who saw the costly limitations of simple performance reports from popular ad platforms.
Wicked Reports was started as a bootstrapped software company in 2016 to serve smaller companies that spend millions on digital ads and other marketing, including email, SEO, and digital events. Determining which marketing activities drive incremental revenue is a tricky puzzle to unravel, but the payback of those insights is huge.
Scott raised a little angel funding and a little SaaS debt and is still going strong with 28 employees and is figuring out their growth and retention puzzle to accelerate growth.
Quote from Scott Desgrosseilliers, founder and CEO of Wicked Reports
"We had offers, and we could have raised VC funding early on, but then the growth rate we would have had to hit was too high, which didn't make sense for our business.
"A competitor of ours took $20 million from a similar VC, and then they had to cut a third of their team. I'm not saying anything against them. They have a nice product and they seem like good guys. They hired a ton of people and didn't hit the growth number, so they had to whack a bunch of them.
"Money isn't always the answer. I'm sure there are cases where it solved all sorts of problems, but most VCs want to invest when you already have growth and net revenue retention at 120% when the efficient growth problem's already solved!"
Links * Scott Desgrosseilliers on LinkedIn * Wicked Reports on LinkedIn * Wicked Reports website
Podcast Sponsor - Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Bryan Forrester is CEO of Boostlingo, a leading on-demand platform for language live interpretation services that is growing quickly and can become a very large company.
Boostlingo now has 160 employees and over 17,000 language interpreters who use their software to manage jobs, coordinate schedules, deliver interpreting services, and get paid.
Bryan raised some practical funds from angels to start the company in 2016. The company grew 50% or more every year since then. In 2021, Boostlingo raised a growth equity round of funding from Mainsail Partners to provide capital for efficient growth and buy out some early investors. Boostlingo has since made several small acquisitions.
Quote from Bryan Forrester, CEO and co-founder of Boostlingo
"Our customers love our software, and our NPS is very high. So when we have customers who love our software, we have high retention and low churn, and our customer costs are really good. When all of that is combined, why would you slow down the growth?
"Why would you take your foot off the gas pedal and be very profitable? And we raised a growth equity investment from Mainsail and started spending more on efficient marketing. And it worked. It worked.
"What would have happened if we didn't take that small investment with our growth equity partner? We could still have had a positive outcome. We may have already sold the business. But we wouldn't have grown as big as we have become in this very big market."
Links * Bryan Forrester on LinkedIn * Boostlingo on LinkedIn * Boostlingo website * Mainsail Partners website
Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Jason Fried is the co-founder and CEO of 37signals, makers of the popular Basecamp project management software, which is still growing and very profitable after 20 years. He is going long and still having fun as an engaged CEO, building great products with great marketing that stands out.
Jason has long advocated for software founders to avoid VC funding and build sustainable businesses that are great for customers and generate healthy profits for the owners. His best-selling book, Rework, shared his practical approach for entrepreneurs.
In this wide-ranging interview, Jason discusses these important topics:
- How the core principles of Basecamp remain focused on simplicity and essential tools for project management after 20 years.
- Why Basecamp targets small businesses, avoiding the enterprise market that many competitors chase.
- Why software should fit the needs of the user, rather than forcing users to adapt to complex tools for big companies
- How profitability, not growth, provides the freedom to innovate and explore new ideas.
- Why competing against your costs is more important than competing against other companies.
- How small teams have the agility to win against big companies.
Quote from Jason Fried, co-founder and CEO of 37signals
“My sense of independence has always been important to me. That’s why I became an entrepreneur: to do things the way I wanted to do them. Otherwise, why be an entrepreneur? It’s true when you work, you’re working for your customers. That’s always going to be true. But you still have a sense of independence. You get to make your own decisions.
“What people don’t realize is when you raise money, you don’t really work for yourself anymore. You really don’t. You work for someone else’s schedule, for someone else’s fulfillment, for someone else’s return. That never appealed to me.
“I want our products to explain themselves. I want our success to explain ourselves. I don’t want to have to explain myself on a quarterly basis to somebody who’s trying to get a return out of me. I’m not interested. So for all those reasons, it just wasn’t right to raise big funding.”
Links * Jason Fried on LinkedIn * Jason Fried on Twitter * 37Signals on LinkedIn * 37Signals website * Basecamp website * HEY website * Ruby on Rails website
Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Quote from Russ Perry, founder and CEO of Design Pickle
“The game for practical SaaS founders really comes down to recognizing that there is a large market size for very boring niche companies. Finding that niche is the fastest path to success. Don’t be afraid to be boring and specific.
“If I were to do Design Pickle all over again, I would have just picked a vertical niche, like we are the graphic design provider for feline mobile cutting trucks or something. There are easily 10,000 mobile pet grooming businesses in the United States, so probably just cat groomers.
“We just went super broad when we started, and it’s been fine, but it would have been easier for us to have focused on a niche. When you have such limited resources and time and money and capital, having that narrow niche makes it easier to maximize all those dollars and investments.”
Links * Russ Perry on LinkedIn * Design Pickle on LinkedIn * Design Pickle website * Colorado River Partners
Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Sunando Bhattacharya spent 13 years as a business leader in managed IT services companies in India before starting his own cloud tech services business. This company grew slowly and an opportunity arose to create a software product for one of their clients. Two years later, in 2019, they had a few more Apiculus product customers and focused more on the product.
Apiculus is a complete "cloud-as-a-service" software platform for data centers to offer, sell, deploy, and manage cloud data services for their own customers. They focused on smaller data centers in emerging markets, including Nepal, Oman, Rwanda, and others in the Middle East and Africa.
The Apiculus business grew as it turned into a product-first company. They overcame many challenges during COVD and with customers and partners that didn't work out. In 2024, the company was acquired by Yotta, and Indian cloud technology company, in a strategic acquisition.
Quote from Sunando Bhattacharya, founder of Apiculus
"Somebody asked me what one thing you want for your company. I said I wanted my company featured on Great Places to Work. It's very important that the team that works with me finds this a great place to work.
"The only secret ingredient for tech companies is people. It's people who make the technology. And if you take care of your team, you take care of your people, you will always do well.
"This isn't just for services companies. Talent and ability are important. But for somebody to bring their best every day to work and deliver something world-class, which is world-beating, it needs a very different level of passion. And that passion will only come from your team if you take care for them."
Links * Sunando Bhattacharya on LinkedIn * Apiculus on LinkedIn * Apiculus website * Yotta Data Services website
Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Steve Wolfe and Nate Grossman are co-founders at Growth Street Partners, a growth equity firm focused on investing in early-stage B2B SaaS companies between $2M-$6M in ARR. They discuss how growth equity funding works for SaaS founders and how it allows entrepreneurs to maintain control while still benefiting from investment and liquidity.
In this expert episode, Steve and Nate get specific and share real examples of how SaaS founders use growth equity to win bigger, when it can be a good fit for founders, and how founders scale their businesses and win with multiple exits. They also describe:
- Why Growth Street Partners focuses on practical founders with growth equity.
- How growth equity is different from traditional private equity and venture capital.
- Why successful founders are “learn-it-alls” with a growth mindset.
- How founders can achieve multiple exits through strategic partnerships.
- Why building a strong team is essential for scale-up success.
Quote from Steve Wolfe, co-founder of Growth Street Partners
“We know that when entrepreneurs have fun, their companies do much better. When founders continue to feel real ownership in their business and in the success of their company, they do a lot better, too.
“So we set up our whole firm to enable that. We are investing to own just 20% to 50% of a business, so the founder still controls the company. We go to them with execution ideas and proven frameworks and approaches, but we are really just giving them the tools to make better decisions themselves.
“They know they make the decisions in the end, so they will make sure that it’s successful. There’s something beautiful about that relationship and about helping that founder get to where they want to go while still feeling like they did it.”
Links * Steve Wolfe on LinkedIn * Nate Grossman on LinkedIn * Growth Street Partners on LinkedIn * Growth Street Partners website
Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Raj Bhaskar is a successful two-time practical software founder with one exit. In 2000, he started his first software company, VisualHOMES, to provide a comprehensive financial management software to public housing agencies. With no outside funding, the business grew to serve 65 regional providers serving 2 million residents before Yardi Systems acquired the company in 2010.
After he left Yardi two years later, Raj and his brother launched Hurdlr to reach the wider small business market with a simpler accounting and tax management software than Quickbooks. They started selling their online accounting software to small businesses, but eventually they returned to their original vision to build embedded (white label) accounting that works inside other software.
Hurdlr has grown steadily and has served over 1.3 million small businesses in its 13-year history. Raj invested his own money for many years and a little outside investment. The company is now “lifetime profitable” and growing quickly with 25 employees. Raj loves his work and has no intention of selling the business anytime soon.
Quote from Raj Bhaskar, cofounder and CEO of Hurdlr
“I ran my previous software business for 10 years before I sold it. And Hurdlr is now over 10 years old. These days, I’m talking about the next 10 years and the next 10 years after that. The next decade and two decades from now, because it’s relevant and because I think we’re just getting started.
“I’ve seen inflection points in markets, and our market is finally ready. That’s the part we didn’t have any control over. So, in my view, there is no finish line. This is the starting line where we now have all these assets and need to let more people know we exist.
“It’s crazy to say after 10 years that this is just the beginning. So I could say probably 20 years from now, looking backward, OK, these are the phases, but I’m in new territory and I know this will be a sustainable and growing business for a long time.”
Links * Raj Bhaskar on LinkedIn * Hurdlr on LinkedIn * Hurdlr website
Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Vince Hsieh is a two-time entrepreneur who has started, grown, and sold two industrial tech companies that included software and either an RFID or GPS device in the solutions. His second venture, Geoforce, raised a non-dilutive funding round to accelerate global growth before being successfully acquired by private equity investors LLR Partners in 2019.
Their royalty-based funding round allowed Geoforce to skip a VC funding round, preserving founder equity and fueling their growth. After their acquisition, Vince shares that the founders saved tens of millions of dollars in founder equity value with their non-dilutive funding from Cypress Growth Capital.
Vince eventually joined Cypress as a general partner, working with capital-efficient SaaS founders to help them build more enterprise value. Vince shares how royalty-based funding can be a very useful funding approach in specific situations.
Quote from Vince Hsieh, partner at Cypress Growth Capital
"Skipping a VC found by using non-dilutive funding made a huge difference to us at Geoforce, especially compared to my first startup where we did not have royalty-based funding in the middle from Cypress. We had just venture capital and then eventually sold to private equity.
"So the math of royalty-based funding is amazing because from the time of our funding from Cypress to the time we sold to private equity, our equity, our value more than 10x'd. But we didn't pay back Cyprus anything close to 10X.
"Had we raised several million dollars in VC funding with equity, there would have been easily tens of millions of dollars of difference between having done royalty-based funding and equity funding. And that tens of millions of dollars of difference went into our shareholders' pockets, including the founders and our friends and families who invested earlier."
Links * Vince Hsieh on LinkedIn * Cypress Growth Capital on LinkedIn * Cypress Growth Capital website * Geoforce website
Podcast Sponsor – Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Bill Spruill had a successful sales and executive career with two exits before he and his cofounder struck out on their own in the location verification market serving financial and e-commerce companies. Sales grew slowly for several years as they scraped by and kept going. Eventually, they pivoted the company to focus on identity verification and know-your-customer (KYC) with a new approach, and sales grew steadily every month.
Global Data Consortium (GDC) partnered with data providers and fintech companies who became loyal customers, trusted partners, and potential acquirers. The company grew over 100% for several years, acquiring new partners and adding experienced leaders to their small team. In 2022, the London Stock Exchange Group (LSEG) acquired GDC for $300 million in an all-cash deal.
Bill talks about the lessons he learned in their patient growth journey, the challenges of trying and failing to raise startup capital, their frugal focus, their incredible acquisition story, and what he is doing now as a successful former founder.
Quote from Bill Spruill, founder of Global Data Consortium (GDC)
“There was a low point in the business where we were just struggling with, Why are we doing this? Are we going to make it? So we stepped back and said, We’re gonna do something very simple. We’re gonna focus on 10% growth every month, which wasn’t a big number then.
“We focused on moving the needle 10% every month with revenue. And then you get into the power of compounding. Every month we moved it 10% and we would celebrate. We kept moving that needle 10%, 10%, 10%.
“Eventually, that number got to be very sizable where we cracked through $5 million in revenue and we paid off all of our debt. And we became profitable and we kept growing fast. That unleashed the ability to accelerate our growth, growing 100% a year as we got bigger.”
Links * Bill Spruill on LinkedIn * Global Data Consortium (GDC) on LinkedIn * Global Data Consortium (GDC) website, now called LSEG Risk Intelligence * London Stock Exchange Group (LSEG) website
Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
Troy Munson has been a successful enterprise SaaS sales rep for several years, but he wanted more control over his life—and eventual financial independence. So he launched his own small startup on the side. He learned a lot and sold it before launching his second side gig software company, which he sold for a little bit more.
He started his third side-gig startup, Dimmo, in 2023 to allow enterprise software buyers to watch product demos without talking to sales reps. With the help of co-founders, Dimmo is now live and revenues are growing fast. With a little angel funding, Troy was able to go full-time to make Dimmo successful quickly.
Troy is a fast-start SaaS founder, testing ideas and launching companies when traction starts. He and his cofounders don’t think about running this forever, but they do want to create a valuable company and achieve financial independence as successful practical founders.
Quote from Troy Munson, CEO of Dimmo
"I'm like this fast-starter person. I built Vocul and Refurl, my first two side gigs, from an immediate thought: This is annoying, this should be solved. Let me solve it, let me sell it. And then let me see if there's any interest.
"With Dimmo, I just wanted to create extra income on the side. The hope for Dimmo was to pay my mortgage with a side gig. I knew software buyers just wanted to watch software demos. So let's just make it like a YouTube for software demos and then we'll just take some sort of revenue.
"It blew up on LinkedIn when we launched and grew faster than expected. I had to go full-time and I'm so happy I did. It feels great. I hope I never go back to the side gig guy. I also hope I never go back to any sort of any sort of W-2 work. I'm buying my freedom."
Links * Troy Munson on LinkedIn * Dimmo on LinkedIn * Dimmo.ai website
Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Wes Bush is CEO of ProductLed, a coaching and education company that has helped almost 500 serious SaaS founders to succeed with product-led growth strategies, tactics, and execution. These include freemium products and free trials, where the product itself creates the awareness, engagement, and enthusiasm to buy before any human intervention (aka “the required sales demo”).
Wes has written two successful books, Product-Led Growth and The Product-Led Playbook, describing key ideas, frameworks, approaches, and examples for SaaS founders. In this expert episode, Wes shares his expertise for SaaS founders, including these topics:
- Defining product-led growth
- Transitioning from sales-led to product-led
- Common mistakes in product-led growth
- Identifying challenges and solutions for user experience
- Pricing strategies in product-led growth
- The future of product-led growth in SaaS
Quote from Wes Bush, CEO of ProductLed
“The PLG model you choose doesn’t matter. Not a bit. Freemium, free trial, credit card up front, whatever. You can make any of those work. That’s not the question. What matters in PLG is the actual outcome that we hope somebody will get from our product-led experience?
“Does your free motion actually have a transformation in it where they can feel they will grow bigger, save time, and do cool stuff? Because if you don’t have that, it’s literally just, “Hey, look around, see for yourself, see what you can do in this product. That’s not real value.”
“What is your PLG outcome that creates that transformation for the user? There has to be tangible value for the user before they ever consider buying. That’s what customers want when they buy software now–Show me value first before I think about buying from you.”
Links * Wes Bush on LinkedIn * ProductLed on LinkedIn * ProductLed website * Free Product-Led Growth book * Free Product-Led Growth audio book * The Product-Led Playbook book
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Michael McAllister is the founder and former CEO of The CE Shop, the leading provider of pre-licensing and continuing education for real estate professionals in the U.S. Michael started The CE Shop in 2005 by distributing existing training materials from a continuing education provider. They quickly created their own online education solution and proceeded to expand with specific content and compliance elements for each state.
The CE Shop grew steadily without outside funding for 15 years by building a 5-star team, adding partner channels, expanding to new states, and providing more content for the pre-licensing of new real estate agents. The company grew to over 130 employees and expanded faster during COVID.
Michael successfully sold the company to private equity investors in 2020 for a “9-figure exit,” meaning more than $100 million, to Waud Capital. On this podcast, Michael shares the realities of their growth journey, including their special emphasis on culture, people, and practical expansion as a bootstrapped technology business.
Podcast Sponsor – Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
Quote from Michael McAllister, Founder of the CE Shop
“When founders sell their companies, I'd suggest they need to do it when they hold all the cards. During our first experience with a serious potential buyer, we asked for a lot of information about their business. It was reverse due diligence since I’d be the biggest private investor in their company.
“We were two weeks before closing, and I called our banker and said, this is really frustrating that we’re asking for all this information and not getting it back. Unless we do, we may need to pull the plug on this deal. We held all the cards. We had a great business. We didn’t need to sell like we were completely in the driver’s seat.
“It was really difficult but we decided to pull the plug on the deal. The biggest thing was that there was a real mismatch in core values. Our core values were foundational to who we were and who we are as a company. One of them was doing what we said we’d do. And it was a $100 million question. It was a big deal.“
Links * Michael McAllister on LinkedIn * The CE Shop on LinkedIn * The CE Shop website * Waud Capital website (acquirer)
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Last year I interviewed three-time software founder Matt Watson on this podcast about his successful practical founder journeys. Matt leveraged offshore software development talent in his last two SaaS companies to staff up quickly and grow efficiently.
His top developers and designers were offshore in the Philippines, but they weren’t one-off contractors or difficult-to-manage outsourced agencies. He found an endless supply of top tech talent who became savvy members of his team, working hard every day to get things done fast.
So, for his fourth venture, Matt created Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who augment and extend your core dev team.
In this expert session with a Practical Founders Podcast sponsor, Matt shares what works and doesn’t work for practical SaaS founders who want to offshore some or all of their software development.
Links * Matt Watson on LinkedIn * Full Scale on LinkedIn * Full Scale website * Startup Hustle podcast * Product Driven video channel
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Eric Dill was a successful mortgage broker in Sydney, Australia, who struggled with the same painful problem as every other broker: manually checking with multiple banks to validate and price mortgages for homeowners. Eric and his good friend Angus Keatinge resolved to create a software product to solve this complicated and chronic problem.
Quickli was launched in late 2021 and it immediately gained happy customers and fans without any proactive marketing or sales. Three years later, more than 10,000 mortgage brokers use Quickli every week—that's over 50% market share. Quickli has AUD $5 million in ARR with 40 employees.
This is an amazing story of two product-focused entrepreneurs who solved a difficult problem and grew a successful software company without any outside funding. Quickli still has almost no marketing staff and no salespeople. Most of their employees are engineers working on the product and customer service.
Quote from Eric Dill, cofounder and co-CEO of Quickli
“We just cracked the $5 million ARR figure in just three years, which is a big milestone for us. We have 10,000 brokers on the platform, which is over 50% of the total market in Australia. We also have 40 employees, mostly in engineering.
“It’s been very, very much a story of product-led growth. Our product completely solves the biggest problem that every broker has every day. No other product has solved it. Brokers have been telling each other about Quickli, and we have some really big fans. It’s a very tight community of brokers who help each other.
‘How lucky did we get? Because we didn’t do anything. Almost marketing and no sales. We have a website. To say we have half a marketing person feels like an overstatement because we have a customer service person who also does some marketing on the side for us.”
Links * Angus Keatinge on LinkedIn * Eric Dill on LinkedIn * Quickli on Linkedin * Quickli website
Podcast Sponsor – Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Guy Rubin is the co-founder and CEO of ebsta, a revenue intelligence platform that works with Salesforce and Hubspot to automatically analyze existing data to improve sales performance. Started in London in 2012, ebsta found success in the early days of the Salesforce marketplace and addon economy as a data tool integrated with customer emails.
ebsta has since become a complete revenue intelligence platform, serving sales teams with 10-100 sales reps. With 400 customers, 30 employees, and no VC funding, ebsta competes with a focused approach to play in the massive Salesforce ecosystem and against huge competitors.
Guy talks about their many pivots, running the business with his wife as cofounder, and the benefits and challenges of not being in San Francisco with VC funding. With deep data across thousands of sales reps, ebsta publishes an annual ebsta Sales Benchmark Report with specific data about close rates, quota attainment, and data-driven factors to improve sales performance.
Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
Quote from Guy Rubin, CEO of ebsta
“We found ourselves in a place where we had some amazingly talented, very driven, very focused doers, and they were happy to work together as a common goal and get stuff done.
“What moved the bar for me as the CEO was bringing on board advisors. I’ve now got four board advisors and a chairman sitting around me. We also brought on a CTO, CPO, and CFO, who are very experienced.
“So bring in those experts around you, people independent of those doing the doing. Don’t get me wrong; you need the doers. They’re absolutely vital, but I also needed experts to help me at the running stage.
“That was the best thing I ever did: bringing those expert advisors in. And if you’re small, I would encourage founders to ask different people to be advisors to give you an outside perspective. You’d be surprised if people love being asked for help and ask you some difficult questions.”
Links * Guy Rubin on LinkedIn * ebsta on LinkedIn * ebsta website * 2024 ebsta SaaS Sales Benchmarks Report
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Stuart Draper founded Stukent, an innovative ed-tech company that provides simulated internships for business students. Stukent started by focusing on high-quality digital marketing education for colleges and universities using up-to-date digital textbooks and content. They then added a simulation system for students to practice their digital marketing skills.
Stukent grew steadily with less than $1M in outside funding, which helped them bridge the long and seasonal buying cycles of big schools. The team grew to over 100 employees and nearly $10 million in revenue serving marketing professors and their students.
In 2021, they engaged with Vista Point Advisors, an M&A advisor firm, to shop the company to prospective buyers and investors, eventually getting a majority investment from Tritium Partners. Stuart describes the M&A process, what worked well, and how he transitioned out of the company after two years of continued growth.
Podcast Sponsor – Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
Quote from Stuart Draper, founder of Stukent
“When we officially sold a major part of our company to investors, we had a brief celebration. My CFO and I called each other and screamed as loud as we could on the phone in a fun moment. We got there, we did this. My family also took a big trip and I got a break.
“But then it was back to work. I was still the CEO and I still run this thing and I’ve got new investors that also need returns. I’m going to go deliver for these guys. They gave me a big payday, so I’m going to make sure they have a win too.
“After the second board meeting with our investors, I realized this is way harder than I thought. After eight board meetings and doubling the business again, I wasn’t enjoying this as much anymore. The board meetings were hard for me. Prepping for them was super stressful.
“So we found a new CEO for Stukent, and he’s doing great. Now I get to sit back in my chair at the board meeting, listen in, share my advice and opinions and come back in three months.”
Links * Stuart Draper on LinkedIn * Stukent on LinkedIn * Stukent website * Tritium Partners website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Cree Lawson combined his curiosity for technology with his career in the travel industry to create Travel Ad Network, which connects advertisers with travel-related audiences online. Travel advertisers were frustrated with the inability to track whether ad viewers actually visited the destinations they promoted, so Cree figured out a solution and started his second travel tech venture.
Arrivalist was created in 2012 to provide offline visitor tracking and analytics to online advertisers in the travel industry. They bootstrapped and grew efficiently, with some revenue-based financing from Lighter Capital, not requiring big outside equity funding to build out their platform and acquire new customers.
They grew steadily and became was through 2019. After the COVID travel disruption faded, Cree sold Arrivalist to Alpine Investors, owners of AirDNA, another travel data company. John is no longer the CEO of Arrivalist, but he is still involved in the company as a board member and spokesperson.
Quote from Cree Lawson, Founder of Arrivalist
“New entrepreneurs need to answer three questions to see if they have a real business. Can you do it? Will people pay you to do it? Will you get paid more than it costs to do it? You can answer those without spending a lot of money.
“Once you answer those three questions, you are off and running. I could answer those questions at Arrivalist, and we didn’t need to raise outside funding. Bootstrapping was a bad word in 2011. People told me to stop calling myself a bootstrapper, but it worked well for us.”
Links * Cree Lawson on LinkedIn * Arrivalist on LinkedIn * AirDNA website * Alpine Investors
Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region.
Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
John Stewart created and sold an engineering services business, then grew a Salesforce integration services company before building some early software products. One of their software experiments allowed Salesforce customers to see and interact with their customer data on a map. When customers paid for it and revenue grew, he and his co-founder wound down services and focused on their mapping product.
MapAnything grew quickly to over $2M ARR as a bootstrapped software company, with some revenue-based financing from Lighter Capital to help test their growth plans. When they focused on field service route optimization and grew quickly, MapAnything raised several rounds of venture capital to grow even faster by focusing its sales and marketing efforts within the Salesforce ecosystem.
MapAnything reached $22 million in ARR before Salesforce acquired the company for $250 million. John stayed on with Salesforce for six months before moving on. John and a co-founder launched Fastbreak.ai three years later, a sports schedule optimization platform for professional and amateur sports leagues.
Quote from John Stewart, former CEO of MapAnything
“I tell founders most often that you really need to focus on sales and distribution. As a CEO of a startup in the tech space or SaaS, the only thing that really matters is revenue growth. Technology is technology. Even if you have unique IP right now, it won’t be unique soon enough.
“So you need to figure out your go-to-market motion. That’s the single most important thing. Revenue cures all ills. It doesn’t matter what’s going on in the company as long as revenue is growing. It’s all about revenue growth more than anything.”
Links * John Stewart on LinkedIn * MapAnything on LinkedIn * Salesforce website * Fastbreak.ai website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Landon Taylor created two successful digital marketing services businesses before starting a product-powered business with recurring revenues. His first agency drove traffic to its customers, which led to his second business, Best Company, which produced qualified leads for large home services businesses through its bestcompany.com consumer review site.
Their work in consumer reviews led them to his latest business, Snoball, a word-of-mouth marketing platform they use to predictably and efficiently drive customer referrals. With their systematic approach and some human-in-the-loop help, Snoball creates a scalable customer acquisition channel for large home services businesses in the US.
Landon speaks openly about his approach to “parlay” one business into another to create new businesses that are larger and more valuable than the last. Rather than raising big VC funding, Landon invests his own resources to find and create new businesses.
Quote from Landon Taylor, CEO of Snoball
“Fear can be debilitating for an entrepreneur. If you fear failure, if you take a leap and you’re gonna fail, you’ll be paralyzed. You won’t be able to move forward, see opportunities, and take risks that will open up doors.
“You’ve gotta get to the mindset that failure is not fatal. Everybody who’s been successful has failed multiple times, right? So just take the leap. It can be a small leap. Or it could be a mental leap of believing that I can build, I can create, I’ve got something unique.
“It might be as simple as wanting to do a LinkedIn post, but you hit this wall of ‘I can’t.’ So get beyond that to believe I can, I’ve got something unique, I can build, I can create.”
Links * Landon Taylor on LinkedIn * Snoball on LinkedIn * Snoball website * BestCompany.com website
Sponsor This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
Connect with Cliff Sentell at cypressgrowthcapital.com/practical to find out how they can help with your practical growth plans.
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Kyle York was the Chief Revenue Officer of Dyn, a bootstrapped cloud infrastructure that he helped grow and sell to Oracle for over $600 million. He then led product strategy and acquisitions in Oracle’s cloud infrastructure group before going out on his own to invest in SaaS startups and help them grow.
York IE is both an advisory firm with tech-enabled services to help early-stage B2B SaaS companies grow and an investment firm that has invested in over 60 practical SaaS companies.
In this expert session, Kyle discusses why his efficient funding approach appeals to practical SaaS founders and why it is different than traditional VC funding. We discuss the current environment for funding, growth, and exits for practical founders. We also dive into what’s working and not working in 2024 to drive growth in capital-efficient SaaS businesses.
Quote from Kyle York, Founder of York IE
“It’s gonna sound so simple, but founders need to set the long-term vision of what they want to be and what they want to build. Then make sure that every decision you make backward to today is working towards fulfilling that vision.
“What I see too often is companies pigeonholing themselves down a certain trajectory or path that isn’t even aligned exactly with what they wanted. This can create problems when you’re raising money from outside investors if what investors want is not the same as your vision and timeline
Links * Kyle York on LinkedIn * York IE on LinkedIn * York IE website
Sponsor This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
Connect with Cliff Sentell at cypressgrowthcapital.com/practical to find out how they can help with your practical growth plans.
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Mike Kovarik is the founder and former CEO of Attribytes, a software company he started, grew, and successfully sold in just over five years. Mike was a data analytics leader at large food distributors, where he discovered a chronic challenge with low-quality product data in their massive e-commerce systems. He quit his job, built a product with a friend, and his former employer became his first customer.
Attribytes grew steadily in the next few years, serving food distributors and retailers in the US, with Mike making the first sales and slowly adding new employees. He invested his savings in the company and raised just over $2 million from a strategic and several angel investors in Phoenix, Arizona. They grew to nearly $5 million in ARR in 2019 with just over 20 employees.
In 2020, Mike sold the company to Syndigo, a larger data management provider that served the same industry. He joined Syndigo for over a year to lead the acquisition of other data management companies to expand their product offerings. When their acquisition strategy changed in 2022, Mike left to take a break and then acquire and retool another vertical software company called ShopControlller.
Quote from Mike Kovarik, founder of Attribytes
"I built a little spreadsheet and I put in what our revenue was, what our current valuation was, and then what that exit would look like after taxes for me, just to see what that dollar amount was. We were at almost $5M ARR, and we were getting interest from acquirers, so it was already interesting.
"I created another spreadsheet to show what would happen if we raised big VC funding and invested that lover for 5-10 years to grow. What rate of return would I get? How would we be diluted? What annual recurring revenue would we need to get to, and what valuation would that be? What would my dollar amount be?
"The reality is that the amount for me would be pretty close to the same if we sold now or raised a big VC round. And I'm not trying to risk everything to potentially buy a plane. I could have a big exit now and have a lake house and a place in Flagstaff, and my kids' kids will be good. What else do I need?"
Links * Mike Kovarik on LinkedIn * Attribytes on LinkedIn * Syndigo website * ShopController website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Brothers David and Chris Sinkinson attended Queen’s University in Ontario, Canada, when David learned of the problems maintaining the blue emergency phones on campus. He proposed a location-aware mobile safety app, so Chris built it himself, and it worked great.
AppArmor grew steadily to become the most popular university mobile safety platform in Canada and the US, and over 250 universities use it.
With no outside investors, they bootstrapped the company to $6 million ARR with serious profits before selling the company to Rave Mobile Security for $40 million. They stayed on for another year in transition before writing a book and running a podcast called Startup Different.
Quote from Dave Sinkinson, CEO and co-founder of AppArmor
”The biggest advice I give new founders is to ‘ignore that startup noise.’ Throughout our experience, we had lots of people who I loosely referred to as haters. People who said we’re "just a lifestyle business” or our idea is never going to work. One person literally told my cofounder brother Chris that we weren’t even a startup.
“Just ignore those people. Don’t pursue validation from your peers. Instead, pursue validation in the market. A couple of years into the business, that realization was a big change that helped me stay on track. So, my advice for SaaS founders is to ignore the haters and enjoy the journey.”
Links * David Sinkinson on LinkedIn * Chris Sinkinson on LinkedIn * AppArmor on LinkedIn * AppArmor website * Rave Mobile Security website * Startup Different podcast and book
Sponsor This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region.
Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines, who can augment and extend your core dev team. Learn more at fullscale.io.
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Dan Balcauski is the founder and principal consultant of Product Tranquility, a SaaS pricing consultancy. Dan shares the core building blocks of SaaS pricing, including customer segments, value, competition, and positioning strategy. Dan also describes the common mistakes in pricing and the importance of having structured pricing conversations with customers.
In this expert interview, Dan shares his perspectives on key SaaS pricing challenges:
- Why CEOs need to be involved in pricing decisions as pricing and packaging affect everyone in the organization.
- How understanding customer segments, value drivers, competitive alternatives, and differentiation are key building blocks of SaaS pricing.
- Why choosing the right pricing metric and offer configurations can help target multiple customer segments.
- Why having pricing conversations with customers can provide valuable insights into their perception of value and willingness to pay.
- How pricing plays a role in positioning and branding.
- How AI is impacting pricing strategies in the SaaS industry.
Quote from Dan Balkauski, Principal at Product Tranquility “One of the healthiest ways to think about pricing is that price is a thing, but pricing is a process. Like any other process in your company, it probably will have a process owner and some sort of document to describe it.
“Your first pricing iteration is probably not going to be your best iteration. You’ll keep improving it. You don’t prevent your team from answering customer support tickets until you have the perfect customer support process. It’s the same with your pricing.
“You’re going to make mistakes. Those mistakes will be way less fatal than you imagine they will be in your head. But as long as you’re committed to improving that process over time, you’re going to start moving in the right direction.”
Links * Dan Balkauski on LinkedIn * Product Tranquility website * SaaS Scaling Secrets podcast
Sponsor This week’s podcast is sponsored by Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.
Learn more at cypressgrowthcapital.com, then connect with Cliff Sentell at Cypress to have a conversation about your growth plans.
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Rob Farrow was an experienced marketing executive and his wife Christina Farrow was a successful professional wedding planner. They discovered there was no good software for wedding planner pros, so they decided to build software themselves. They invested their savings, built a loyal team, and started Aisle Planner to serve other wedding planner pros with a complete solution to power their businesses.
Aisle Planner grew slowly as they overcame huge obstacles, listened to their customers, and built world-class software that changed how events are managed. Aisle Planner is now the leading all-in-one software for wedding planners and event professionals with over 4000 customers.
After struggling through the COVID-19 shutdown several times, Rob and Christina decided to sell Aisle Planner to Fullsteam, a software holding company. They stayed for several years to meet their earn-out commitments and run the company with the same team.
Quote from Rob Farrow, co-founder of Aisle Planner ”There’s a very fine line between arrogance and ignorance. And somewhere in there is where I was living in this. When we started, I was so sure we would succeed that I ignored obvious signs of failure. I just believed wholeheartedly. I believe in myself, I believe in my wife, and I believe in our team.
“If you have that belief, you can achieve things. And I know that sounds very cliche, but you have to have that belief. If you’re doing it for the right reasons, you’ll have that belief. If you’re doing it to get rich quick, you won’t.
“There’s a bunch of obstacles that you don’t even know are coming our way. With that mindset of belief and just forging ahead, you’re ready for any obstacle. They’re not obstacles; they’re just things you deal with.”
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Ian Manners was a successful consultant for pharmaceutical companies in the US when he discovered a major problem that needed a software solution. Big pharma companies provide financial assistance funding for patients who require their drugs but struggle with high costs, but these funds are difficult to access and manage for patients and healthcare providers.
Ian and his cofounder created Vivor in 2014 to connect this financial assistance funding to patients through healthcare providers like hospitals, medical offices, and healthcare networks. The bootstrapped software startup grew slowly at first but eventually became profitable as it scaled up. Since inception, Vivor has helped over 100,000 patients receive over $2 billion in financial assistance to offset the high costs of prescriptions.
During the COVID crisis that hit the US healthcare industry, Ian decided to merge Vivor with TailorMed, a VC-funded competitor, in a cash and stock deal. He stayed on for two years during the transition and is now looking for his next entrepreneurial adventure in healthcare software.
Quote from Ian Manners, cofounder and former CEO of Vivor “The overall idea of merging our companies and having stock and some cash in our acquisition structure made sense for both parties. If the company that’s acquiring your company is huge and they’ve got big cash reserves, they buy someone out. But if you’re combining with another startup, that cash is precious. They don’t want to spend all of it.
“So it really makes sense to do a combination of the two and to include equity in the deal. I think that part was absolutely a win-win, even when, as you’re going through that process, you negotiate all the details.
“It’s a huge bet for us to take equity as part of our deal, We became an investor in the company that bought us.. I think for anyone facing something similar, my advice would be to just slow down that part of it and really think about and digest the fact that you’re becoming an investor in the combined company. “
Links * Ian Manners on LinkedIn * Vivor website * TailorMed on LinkedIn * TailorMed website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Dave Lambert and the team at Right Side Capital Management are the most active venture capital investors, having invested in over 2,000 startups since 2009.
Right Side Capital is a “pre-VC” institutional investor that operates very differently from traditional VCs: investing when SaaS companies have just a little revenue using a submission form on their website, then responding quickly and making investment decisions in a week. They also invest in practical SaaS founders with capital-efficient approaches who expect to sell their companies someday for less than $100M.
In this expert episode, Dave shares practical insights for SaaS founders who don’t expect to play the big VC funding game:
- Why raising Series A or B funding rounds from VCs reduces your odds of a successful exit
- What founders should be focused on when they get their first customers and revenue
- Why most VCs don’t invest when you have just a few customers and a little revenue
- How the founders they invested in are using AI technology to grow more efficiently
- What’s happening right now with acquisitions of SaaS companies for $25-$100M enterprise value
Quote from Dave Lambert, Right Side Capital “More often than not, at the stages that we’re investing and someone has $4K, $8K, $20K MRR, the founders are still supremely confident and think they figured out their exact ICP and how it’s going to grow in scale. They think, We’re just going to take your money, and it’s going to be straight up from here. And it never does, or almost never does.
“We’re having conversations with founders where we’re sharing, Hey, just so you know, 90% of our companies miss their revenue targets massively in their first year. So you should assume that you are going to as well.
“But guess what? They all spend exactly what they thought they were gonna spend or more, usually. Just know that that’s gonna be the case and have a plan for where you’re still alive if things don’t go as expected.”
Links * Dave Lambert on LinkedIn * Right Side Capital Management on LinkedIn * Right Side Capital Management website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started as a videographer before joining a friend in 2007 to create a scrappy software business that made inexpensive photo-presenting and sharing tools for photographers.
The Showit company was created when Todd took one of their two products and half the small team in 2010 to spin off Showit as an independent business. The small revenue from the small customer base and his own savings allowed them to rewrite Showit for the cloud and then continue their fanatic customer focus to keep growing every year—without any outside funding.
Now Showit is used by 50,000 designers, photographers, and small businesses as their website platform using its elegant “Photoshop-like” no-code visual builder. The Showit company is growing quickly every year and is profitable, yet Todd has no interest in taking outside funding or selling his beloved company.
Links * Todd Watson on LinkedIn * Showit website * Showit website design marketplace: * Showit on LinkedIn
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Erin Fletter had a long career in the restaurant business before starting an after-school enrichment program to teach kids how to cook at her daughters’ school in 2011. Her cooking program became popular, and she improved and expanded it to become a paid program called Sticky Fingers Cooking. Soon, she had a sizable business with over 100 chef-instructor employees who conducted engaging classes daily in Denver.
Her team created custom software to help manage their complicated operations, from enrolling students, coordinating instructors, and building relationships with schools to handling payments and payroll. The software grew slowly initially but eventually became a powerful system that helped them scale their business and run efficiently.
Erin considered turning her business into a software company, as many tech-powered businesses do. Instead, they kept improving the software and expanding operations, serving over 100,000 students and thousands of schools and venues. Now Sticky Fingers Cooling is a fast-growing and successful franchise business with a software superpower.
Quote from Erin Fletter, CEO of Sticky Fingers Cooking
“Our business has a lot of logistics, coordination, and operations. Our own custom software, we call it the Dash, it takes about 85% of all operations off the table for humans. This enables our chef-instructors to connect with their students and our franchise owners and regional directors to focus on building relationships with schools and parents.
“Over the years, we have been contacted by very large organizations like YMCAs, Boys and Girls Clubs, and other after-school enrichments about our software. They would see our automatic rosters getting texted and emailed at the venues that we were teaching in, and they asked, What are you using? What is this? And we told them, Well, it’s our own software, sorry.
“We had talked for years about selling our software as a white-label solution because the demand is there. We’ve had inquiries for the last 10 years. That was a direction we could have taken.
“But I’m just laser-focused on Sticky Fingers Cooking. It’s a very simple business, and our technology helps us do it incredibly well. We want to be the best at what we do. I didn’t really want a diversion from the path of taking our business national through franchising.”
Links * Erin Fletter on LinkedIn * Sticky Fingers Cooking on LinkedIn * Sticky Fingers Cooking website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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In this second of two episodes, Practical Founders Podcast host Greg Head discusses the next five important things venture capital investors don’t tell new SaaS startup founders. Greg emphasizes that VCs invest in very few businesses and seek big wins. He highlights the importance of understanding the game of venture capital funding and the alternatives available to SaaS founders.
Check out last week’s episode, in which Greg discusses the first five things that VCs don’t tell SaaS startup founders about raising VC capital.
Quote from Greg Head, Host of the Practical Founders Podcast “Professional VC investors are expecting very big results when they invest. If you sell a piece of your company to get a $5 million Series A investment, that typically ends up being about 20 percent of your equity. So you’ve just valued your company after funding at about $25 million.
“$25 million is the point where the venture capital investor comes in, so you can’t sell your business for $30 million or $50 million anymore. That wasn’t why the VC invested. They probably don’t even want you to sell your business for $75 million. That’s just a 3X exit.
“That’s not what they invested their precious cash. They’re going for a 10x or 20x exit. So even when you just take $5 million from VCs, you can’t sell your company for less than $100 million and have everyone win. You have to sell for $500 million or more for everyone to be happy, including the founders.”
Links * Greg Head on LinkedIn * Practical Founders website * Practical Founders Podcast * Greg Head’s blog * Part 1 – The 10 Things that VCs Don’t Tell Startup SaaS Founders – Greg Head
In this episode, Practical Founders Podcast host Greg Head discusses the most important things venture capital investors don’t tell new SaaS startup founders. He emphasizes that VCs invest in very few businesses and are looking for big wins. Greg highlights the importance of understanding the game of venture capital funding and the alternatives available to SaaS founders.
Quote from Greg Head, Host of the Practical Founders Podcast “If you’re thinking about raising VC investment, do your homework so you know what you are signing up for before. VCs are not evil people, and it’s not a bad business model—for them.
“The world has changed for SaaS founders in the last 5-10 years, and it’s still changing. You no longer need VC funding to start most B2B SaaS software companies. It’s 10 times cheaper to create a sellable SaaS product and go to market now. And founders can get higher multiples earlier when they sell their companies. VC funds are also much bigger, so it’s riskier for founders to play that game.
“You just don’t need to make a crazy all-or-nothing bet that your company will create a billion-dollar exit in seven years, which VC investors require to win. The best case scenario for 80 to 90 % of software companies is NOT to raise big institutional venture funding.”
Links * Greg Head on LinkedIn * Practical Founders website * Practical Founders Podcast * Greg Head’s blog
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Mike Trasatti spent 10 years in the automotive dealer software business before he found an auto dealer in Iowa who had built is own complete software system. They partnered up in 2008, and Mike became the first CEO of the spinout software company, DealerBuilt.
DealerBuilt grew slowly as a bootstrapped startup in a market full of large incumbent competitors. They had a better approach to managing multiple dealers in a group with their dealer management system (DMS). DealerBuilt is powerful software that manages the entire financial operations of an auto dealer in the US.
They grew steadily to 450 dealer customers and 100 employees in 10 years before deciding to partner with ParkerGale, a private equity investor, to help them with their next growth stage in 2019. Mike continued as CEO until 2023, navigating through the COVID years and acquiring several “tuck-in” products to extend the DealerBuilt solution. Mike is now an independent advisor to DealerBuilt and other organizations.
Quote from Mike Trasatti, former CEO of DealerBuilt “You’re constantly challenged in the entrepreneurial world. Do you really know what you’re doing? Self-doubt can be tremendously harmful to CEOs. I don’t think you can get into this business without a strong image of yourself and real confidence.
“But you have to balance confidence with humility because you’ll make mistakes. You’re going to have setbacks every week, and some very big ones, too. You can’t lose enthusiasm: You need enough confidence that you’re on the right path and that will carry you more than anything else. Those who don’t lose enthusiasm win.
“When you have both confidence and humility, you won’t be afraid to be around people who are better than you. And you’ll feel comfortable in that space, leading smart people who are championing your journey. They will look at you and think, I want to be there with you to champion this for you. That’s success as a leader.”
Links * Mike Trasatti on LinkedIn * DealerBuilt on LinkedIn * DealerBuilt website * ParkerGale website – private equity investor in DealerBuilt
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Brian Abernethy, founder of Utopaya, is an expert in helping SaaS leaders navigate the complicated process of adding payments monetization to their product offerings and business strategies. With a long history in the payments industry, Brian has worked with hundreds of early-stage SaaS leaders and their investors to optimize their payments strategies.
In this expert podcast interview, Brian explains the basics of payments monetization for practical SaaS founders, answering questions like these:
- When should SaaS companies consider monetizing payments and when is it not a good fit?
- What are the first steps to adding a profitable payments offering to your SaaS product?
- What’s happening in the payments industry to make it easier or harder for SaaS companies?
- How do investors value payments offerings in a SaaS business?
- What are the biggest misconceptions and mistakes that SaaS companies make when get started with payments?
- How can SaaS businesses lower their payments bills for the credit card customer they take from their customers?
Quote from Brian Abernethy, principal at Utopaya “Most software companies are looking to include some type of fintech offering. Payments is typically the first one of those. These software companies want to own not only the bigger portion of revenue, of course, but also mprove the customer experience.
“Recent consolidation in the fintech and payments industry has created new options for SaaS companies to monetize payments. The big payments providers are now much bigger and have moved upmarket, creating a gap. Many new payments players are designed for smaller SaaS companies, with purpose-built platforms, APIs, and more support for integrated software solutions.
“There are more compelling solutions for SaaS companies to launch truly white-labeled, profitable, and easier-to-implement payments solutions. Also, the market data show that it does positively change the customer experience, so these smaller payment companies are winning share at a fast clip.“
Links * Brian Abernethy on LinkedIn * Utopaya on LinkedIn * Utopaya website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Jeff Corn is the co-founder and former CEO of Virtuance, one of the US's leading real estate photography and marketing providers. In 2010, Jeff was in the real estate investment business and wondered why it took $10,000 and nearly a month to get professional photos for new listings. He and a cofounder started taking photos to serve busy real estate agents to learn what was needed and improve the quality and speed of delivery with technology.
Virtuance started with the vision of a software-only solution, but the business started growing with a high-quality, done-for-you service with a fast turnaround, powered by its technology, partners, and systems. The company grew steadily every year without any outside funding to eventually serve more than 20,000 real estate agents with 100 employees and more than 300 local photography partners.
This tech-enabled services company has SaaS-like gross margins. re-occurring revenue, and some profits In 2022, Jeff successfully sold Virtuance to Diakrit, a global real estate marketing technology company backed by private equity investors. Jeff stayed on for two years after the sale, until last month.
Quote from Jeff Corn, co-founder of Virtuance “The biggest reason that founders fail is that they actually fail to launch. The hardest thing to do is to fricking push your product and get it out in the world– because it’s messy. It’s certainly far from perfect, and it may not even work very well. But getting that feedback is so important to figure out what to do next.
“I see too many founders try to perfect it before they get it into the market. And then when it gets into the market, they might think it’s perfect, but the market may not. And at that point, they already invested too much in it. It’s not that we’re shipping something that we don’t think works; we are shipping something that we know checks just one of the boxes that our customers need.
“It’s just human nature that we want to put out good work, we have pride in our work. It’s one of the one of the real paradoxes of entrepreneurship is that we are all perfectionists and Type A personalities. We want to control it and we want it to be right, but also to be successful. The only way to succeed is to let go of some of that, to allow our teams to do the work, and be able to ship an imperfect product to get real feedback.”
Links * Jeff Corn on LinkedIn * Virtuance on LinkedIn * Virtuance website * DIAKRIT website
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Adam Haynes is a managing director at GLC Advisors, an M&A advisory firm that helps bootstrapped founders to successfully sell their companies. The software advisor team at GLC has been working with practical software founders for over 15 years and has completed over 100 software transactions.
In this expert interview, Adam shares:
- What has changed in software acquisitions in the last 20 years and recently through 2024
- What are the valuation ranges and factors for practical SaaS companies under $10M revenue
- The 7 key areas that founders should be working on several years before an acquisition
- When should a SaaS founder consider using an M&A advisor
Quote from Adam Haynes, M&A Advisor at GLC Advisors “When you are selling your company and the buyer is looking at all your challenges and problems, founders should know that deal breakers are very rare. Buyer and seller want to get a deal done, and there are ways to navigate around them.
“You can’t have a software company without tech debt. That’s okay. Nothing’s perfect, but you need to have a remediation plan for it. If you were going to close a couple of big deals during diligence and you don’t, or they get delayed, the valuation may take a hit. Or they might inject some structure like an earn-out if you can get these two deals signed.
“But if you don’t own your IP and don’t own or clearly license all your code, that’s tough to navigate around. Or if you’ve infringed on somebody. That can be a dealbreaker, but it isn’t that common.”
Links * Adam Haynes on LinkedIn * GLC Advisors on LinkedIn * GLC Advisors website * GLC Software Capital Markets Report – Q1 2024
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Matt Wolach spent 15 years as a successful SaaS account rep, sales leader, and software founder before becoming a SaaS sales coach for early-stage B2B SaaS companies. He has worked with over 250 SaaS founders and sales leaders worldwide to improve their close rates and create repeatable sales systems quickly.
In this episode, Matt shares:
- How B2B SaaS founders need to learn to sell and understand their own sales processes before hiring salespeople
- Why technical founders can their sales using a helpful mindset of customer problem-solving
- Why he starts by analyzing the sales demo to understand what’s working and what needs to be improved in the sales process
- How successful founders and salespeople show their product less and follow up more than their peers
- Why software buyers are tired of buying software and don’t want to engage with commission-focused salespeople
Quote from Matt Wolach, B2B SaaS Sales Coach “The only way a buyer can be excited about your solution is if they are really emotional about their own problem. How can we get them to realize their problem is important and worse than they thought?
“If they’re gonna take action, they’ve gotta be emotional about their problems. They come in thinking, I just got this thing I want to take care of. And they leave saying, Whoa, I had no idea we were in so much trouble. We have to move now.
“We have to make sure that they prioritize the problem we solve instead of not doing anything and moving on to a different problem. When they realize how bad their problem is and feel the emotion, it helps them see they need to prioritize it and take action instead of putting it on the back burner and waiting till later.”
Links * Matt Wolach on LinkedIn * Matt Wolach SaaS sales coach website * Matt Wolach YouTube channel * Scale Your SaaS podcast
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Charlie Alsmiller is the founder and CEO of APIWORX, a powerful integration platform for mid-sized ecommerce companies. He is an experienced practical founder who has created and grown several software companies. His first venture was VC-funded and shut down quickly in 2001. His next software ventures were bootstrapped with funding from services revenue and his own savings.
APIWORKS is a powerful integration platform that connects Shopify data to accounting software and other applications. Charlie started the company in 2020, with well over $1M in annual recurring revenues and 30 employees. They are growing faster by focusing on key vendor ecosystems and specific customer problems where they have a unique advantage.
In this episode, Charlie shares:
- What happened when challenges arose in his first company, which was VC-funded
- Why he started a services business to find and fund his next software business
- What happened after his first successful exit that made him start another company
- How he ideated and validated to discover the best startup idea to invest in
- Why they are growing faster every time they niche down on specific vendor ecosystems
- Why startup CEOs should eventually focus on their superpowers and delegate everything else
Quote from Charlie Alsmiller, founder and CEO of APIWORX “As a startup founder, you need to really know yourself. Know your personality type, know your skills, and know your superpower. Focus on what you do best and where you add the most value.
“I have the superpower of whacking the machete to start new things, clearing the brush away in new markets, and figuring it out. And I’m pretty good at recruiting people who can do the things I don’t do well. Now my team tells me, Charlie, don’t do that, we’ll do it and you go do that thing over there.
As an early-stage founder, you start by taking out the trash, doing software development, doing marketing, and everything else. As soon as you can scrape together the pennies to outsource or hire those other things you’re not good at, you should do it because it allows you to double down and grow faster. That’s the game changer for your growth.“
Links * Charlie Alsmiller on LinkedIn * APIWORX on LinkedIn * APIWORX website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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David Evans, the managing partner of Sentiero Ventures, a seed fund focused on AI-focused software startups. David discusses the role of AI in software development and the opportunities it presents for practical SaaS startups. He shares his journey with AI and predictive modeling in his previous companies and the key factors he looks for when investing in AI-powered companies.
In this expert podcast interview, David discusses:
- The new questions about revenue models for AI-powered companies
- The challenge of cost in AI and the potential for innovation
- The importance of clean and relevant data to train models and machine learning
- Balancing AI in the go-to-market strategy
- The impact of AI on various industries
Quote from David Evans, Managing Partner of Sentiero Ventures “The biggest challenges and opportunities we see right now are in the revenue model. The traditional per-user, per-month model in SaaS is becoming increasingly difficult to justify in AI-powered companies because every time I interact with ChatGPT, there is an associated nontrivial cost. When I ask it a question with AI, there is a compute resource of OpenAI or whatever that is being directly accessed.
“This also leads to some opportunities to scale revenue more quickly because you can now charge based on utilization. With the right sort of unit economics, you have the opportunity to scale your revenue more directly with usage and value. Companies will scale their utilization very quickly when they see results. It gets really interesting fast.
“It’s obvious when you start viewing it through the lens of whether I need to run one more campaign. If they are making money, then yes, I’ll pay for the next campaign and the next one. We’re seeing a better scale with utilization-based billing. You have to figure out the unit economics to ensure you’re doing it profitably.”
Links * David Evans on LinkedIn * Sentiero Ventures on LinkedIn * Sentiero Ventures website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Phil Dur is cofounder and managing partner of PeakSpan Capital, a growth equity investment firm that works with bootstrapped SaaS founders who are scaling up to become sizable market leaders. Phil has been funding capital-efficient software founders for over 20 year and has served on 45 boards with those companies.
In this expert podcast interview, Phil explains:
- Why the practical growth equity approach is fundamentally different from the venture investment approach
- How PeakSpan and other growth equity investors support bootstrapped and capital-efficient SaaS founders
- Why founders should be taking money off the table with every funding or transaction event
- When can growth equity investment be a good fit for practical SaaS founders
- Why founders should be thinking about the risk-adjusted odds of successful exits at multiple milestones
Quote from Phil Dur, Managing Partner of PeakSpan Capital “It’s a big deal to bring an investment partner into your business because now you’re now collaborating with someone on your big decisions. Some founders only need to look themselves in the morning mirror to decide what will happen in their business this year. When you have investor partners, you will have more dialogue to align around important decisions.
“Unfortunately, I frequently see entrepreneurs picking their first investor partner without much time getting to know them and experience working with them. That’s why we start actively helping our founders 6 to 12 months before they make a final decision on a transaction.
“We want our founders to get a free trial of what the full experience is going to feel like before we work with them. Founders should be doing that with every other investor they are interested in.
“Don’t bring someone into your business with eight figures of capital at risk when you just met the partner two weeks before term sheets are due. That’s not a smart strategy for founders.”
Links * Phil Dur on LinkedIn * PeakSpan Capital on LinkedIn * PeakSpan Capital website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
Get weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
Joe McMenemon and his college roommate, Brendan, knew they wanted to start a business together. They had run their college fraternity chapter and saw the problem of managing members and collecting payments. So they lived frugally and built a software solution for fraternities and sororities to solve this problem.
ChapterSpot grew slowly over several years as they sold to local chapters. Eventually, the national associations came calling, requesting an enterprise solution to manage hundreds of chapters in one system. They rewrote the platform to run on Salesforce and grew faster with more employees.
ChapterSpot grew profitably to over 30 employees, with 40 large organizations managing thousands of chapters and millions of members on the platform. ChapterSpot was acquired in early 2024 by BillHighway, a strategic acquirer with a payments platform.
Quote from Joe McMenemon, CEO of ChapterSpot "Long shots are probably not as crazy as you may think they are, but they're just going to require time. If you think you'll make a bunch of money in three years, it's probably very unlikely. But if you're willing to put in the time and work at it every day, you're most likely going to be able to figure out the right path to success.
"My favorite quote is from James Clear: It's the courage to start, a few lucky breaks along the way, and a ton of hard work. That's the formula.
"Once you get started, are you putting yourself in a position where you can do it at a level that's best in the world for the problem you are solving? If you're the only one trying to solve the problem and you do it long enough to catch a few lucky breaks, well, eventually, you'll get there."
Links * Joe McMenemon on LinkedIn * ChapterSpot on LinkedIn * ChapterSpot website * BillHighway website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.
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Jeromy Wilson spent over ten years in the software business as a product management leader working for PE-owned and VC-funded software companies. When he decided to start his own software company, he focused on serving public libraries, like his father, who had created a successful library automation software company called Dynix.
Jeromy is the founder and CEO of Niche Academy, the leading learning and development platform for libraries in the US. With his savings and a little angel funding, Niche Academy struggled at first but eventually grew into a profitable and growing software company with 20 employees that is almost ten years old.
Jeromy and his co-founder have no intention of selling the company or raising big VC funding. They are focused on serving their customers, developing their employees, and living great lives with their families right now.
Quote from Jeromy Wilson, CEO of Niche Academy “Early on, I idolized VC-funded founders. Why aren’t I growing as fast as that funded company? But now, I say thank goodness. I’m not dictated to like they are, have the problems that they have, or have these massive crashes that some of them end up having. I don’t idolize them as much anymore.
“I love the freedom that I have now as the CEO of a profitable software company that didn’t take big VC funding. When you don’t have tons of outside funding, you make different decisions and choices. You do things in a way that is going to make a difference for the customer rather than how we can make more money today.
“I’m a real believer in being in charge of your own destiny, having this control, and being able to grow with your profits because you know it’s valid. Your solution is something that your customers see as valuable rather than something that some VCs see as valuable.
Links * Jeromy Wilson on LinkedIn * Niche Academy on LinkedIn * Niche Academy website
Learn more at practicalfounders.com.
Paul Van Metre was the co-founder of a successful machine shop that manufactured custom parts for the aerospace and medical device industries. Over 15 years, they created and improved software to run their entire business, which created huge efficiencies and helped them manage their growth. They sold that business in 2014 to focus on selling their complete software platform, called ProShop, to other forward-thinking machine shops.
ProShop is now one of North America's leading ERP (enterprise resource planning) software platforms for machine shops. The software manages every aspect of a machine shop business, from orders, finances, inventory, and shop floor operations.
The company grew quickly with no outside funding as happy customers spread the word in their industry. Their software company focuses on processes, customer service, and company culture. In 2024, ProShop received a $32 million growth equity investment from Mainsail Partners, which allowed the founders to take money off the table and fund new growth.
Links * Paul Van Metre on LinkedIn * ProShop on LinkedIn * ProShop website * Mainsail Partners website
The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies—without big funding.
Chris Savage is the co-founder of Wistia, a leading video marketing platform for businesses. Wistia was started in 2007 by Chris and a college friend when inexpensive cloud hosting and easy web video encoding became available. They created the first easy way to host and share videos with deep analytics and no ads for marketers to use on their websites.
With a bootstrapped approach and just $1.2 million in angel funding, Wistia grew quickly and profitably, becoming a leading video hosting platform used by thousands of small and mid-sized business customers. The company experienced typical internal challenges with leadership, culture, and focus as it grew to 80 employees by 2015.
In 2017, Chris and his cofounder Brendan received several significant offers to buy the company. They decided not to sell the business, and the company made a tender offer to buy out their angel investors’ shares and some employee options. Wistia got back to profitability the following year by refocusing on its core business and aligning its team around efficient long-term growth.
Wistia is still growing, with 180 employees, tens of thousands of customers, and millions of users. It is very profitable. The founders still love what they do and have no intention of selling the company any time soon.
Learn more at practicalfounders.com.
Rand Fishkin is the founder and former CEO of Moz, a leading SEO software for marketers created in 2007 that grew out of the active followers of Rand’s popular SEOmoz blog. Moz grew quickly to over $30 million in revenue by 2013, having raised $30 million in venture capital investment. When growth slowed in 2014, the company faced many internal difficulties and Rand dealt with mental health challenges, causing him to step down as CEO.
Rand left Moz in 2018 and later that year published his popular book about his difficult startup journey, “Lost and Founder: A Painfully Honest Field Guide to the Startup World.” He described in detail the growth of Moz and the exciting growth years, but he also revealed the painful challenges he and the company faced in their later years. In this podcast discussion, he is frank about the pitfalls and brutal realities of big VC funding for founders and the companies they created.
Rand created his second software company, SparkToro, in 2018 with an approach that was opposite to the funding, growth, and staffing he used at Moz. We discuss the benefits of practical funding and sustainable profits to create healthy software businesses that support the goals of founders, employees, customers, and investors.
Learn more at PracticalFounders.com.
Nathan Hirsch, co-founder of FreeUp, shares his journey of building and selling the company and his other business adventures. FreeUp provides clients with pre-vetted virtual assistants (VAs) and freelancers in an online marketplace.
Nathan discusses the importance of niching down and targeting specific industries, such as e-commerce, to attract clients. He also highlights the combination of software and people in FreeUp’s operations, with software handling recruitment and billing and people assisting with matching and customer service.
FreeUp achieved success through organic marketing strategies, niche focus, and great customer service. The business grew to $12 million in revenue in four years before being acquired by The HOTH in 2019.
Learn more at practicalfounders.com.
Ian Brodie, the co-founder and CEO of Levanta, shares his journey of building a successful SaaS company in the affiliate marketing space.
Levanta is an affiliate marketing platform for Amazon sellers, enabling them to connect with content creators, publishers, and influencers to drive sales and traffic to their Amazon storefronts. The company has experienced rapid growth, with over 700 brands and 3,000 affiliates on the platform. Ian discusses the challenges and opportunities of the affiliate marketing industry, working with Amazon, and the importance of building credibility and confidence as a young founder.
He also discusses his experience of successful selling his previous company, Grovia, an affiliate partner recruiting services company that was acquired by Acceleration Partners in 2022.
Learn more at practicalfounders.com.
Gregg Scoresby founded CampusLogic in Phoenix in 2021 to provide software for colleges and universities in the US to make it easier for students to apply for college loans and grants online. Initially self-funded, CampusLogic raised investment and grew faster, becoming a leading provider of software to universities with $50 million in revenue. In 2022, CampusLogic was acquired by Ellucian for an undisclosed amount.
In 2023, Gregg launched PHX Ventures, a $27 million seed-funded supporting early-stage B2B SaaS founders in Phoenix, Arizona. Unlike the traditional VC approach, PHX Ventures supports startups that are growing fast with a capital-efficient approach. PHX Ventures also helps the larger software community in Phoenix with educational events and networks to connect founders, talent, experts, and capital.
In this expert episode, Gregg answers common questions about when practical venture funding can be useful for founders and what it means to be capital efficient.
Learn more at practicalfounders.com.
Esben Friis-Jensen and his cofounder, Sebastian Seilund, teamed up in 2021 to create Userflow, a no-code user onboarding product for SaaS companies. This week, it was announced that Userflow has been acquired by Beamer, a maker of product user engagement software that also used product-led growth strategies just like Userflow.
Userflow is profitable and growing, with over $4 million in ARR, 750 customers, and just three employees with no outside funding. Techcrunch reported that Userflow was acquired in a $60 million deal, supported by Beamer investors Camber Partners and other investors.
Esben told the Userflow story on the Practical Founders Podcast in episode 42 last year. This is an update about the recent acquisition and his thinking behind selling the company.
Learn more at practicalfounders.com.
Antony Ceravolo is a successful two-time startup founder from Adelaide, South Australia. He started his career in investment banking but left in 2002 to start a DVD rental business in London that raised funding from big VCs and Amazon. It grew into Lovefilm.com, which was later acquired by Amazon in 2011 to become part of their movie streaming service.
He moved back to Adelaide and started Sine in 2013 to help schools, businesses, and large office buildings manage guest sign-ins more securely using iPads at their front desks. They also started tracking visiting contractors and vendors with their mobile app, allowing automatic check-ins and tracking for operations managers.
Sine grew quickly with global customers and large deals, eventually growing to 100 employees, mostly in Adelaide, with no VC funding or institutional investors. Sine was acquired by Honeywell in 2020 and became a critical product in their property management technology suite.
Antony speaks openly about the benefits and challenges of working with institutional investors and why he avoided raising VC funding with Sine.
Learn more at practicalfounders.com.
Raj Khera is an experienced practical SaaS founder who has used search engine optimization (SEO) to grow businesses very efficiently. Now he coaches entrepreneurs at MoreBusiness on how to use organic SEO as a core part of their marketing engine.
In this expert interview, I ask Raj to explain the basics of SEO for SaaS founders, what tools and techniques are most useful, and how SaaS founders can make the most of SEO investments to drive revenue faster.
SEO for Bootstrapped SaaS Topics Discussed on this Podcast
- How he used SEO to grow his previous software companies
- The basic concepts of search engine optimization (SEO) for SaaS founders
- Simple tactics for identifying search terms that would create qualified traffic
- His favorite tactic for gaining authority from Google for your organic website content
- Which search engine marketing tools are most useful to maximize your time and investment
- The simple ROI math that founders can use to measure their investment return with SEO
Learn more at practicalfounders.com.
Justin Hewett started in the software business as a territory sales manager for an education software company in Utah. The company grew and Justin eventually led the sales team as the senior executive. When the company was acquired by PE investors, Justin moved on in 2020 and thought about ideas for a new software business to serve K-12 schools in the US.
Flashlight Learning helps K-12 teachers in the US to quickly assess the speaking and writing progress of multilingual students who are learning English. The software captures data for teachers to provide students with improved feedback to accelerate language development.
Flashlight Learning grew 300% in 2023 to $4 million in revenue, with a growing team and an outsourced development partner. Justin raised some angel funding to get started and move fast, but they are expecting to be profitable this year with continued growth.
Learn more at practicalfounders.com.
Morgan Katz is the founder and CEO of Ticketnology. Morgan was an enthusiastic athlete with a degree in sports management who started her career in ticket sales for sports teams and front-line venue management. Morgan saw how companies with season tickets had difficulty managing their digital tickets after COVID, so she started her own company to solve it with a software solution.
Ticketnology is a fast-growing leader in the new category of season ticket management software. Started with a mix of hands-on concierge services and a software solution, Ticketnology is now a complete platform that helps season ticket holders manage and distribute tickets to maximize the value of their season ticket investment.
Ticketnology is a bootstrapped and profitable software company with just over $2 million in revenue, four full-time employees, and an outsourced development team. They doubled revenues this year and expect to double each year for the next few years. Morgan is a member of a Practical Founders Peer Group.
Learn more at practicalfounders.com.
Stephanie Betters was a practicing Nurse Practitioner in heart surgery and an active real estate investor when her frustration with disparate real estate CRM and marketing solutions hit a boiling point. Salesforce and a development partner proposed a project so expensive that Stephanie hung up and decided to build the solution herself. She learned to code and build a useful real estate CRM on Salesforce in three months.
Her business thrived with her comprehensive software. Other real estate investors heard about her software and encouraged her to launch the company in 2019 and start selling the software, now called Left Main REI. Word spread in the industry and hundreds of real estate investors signed up in the first year, transforming their businesses.
In just over three years, Left Main REI now has hundreds of customers, 20 employees, and nearly $3 million in annual recurring revenue. The company has been bootstrapped and profitable from the first day. Stephanie has a big vision for the company and loves her founder/CEO role; she will no longer be practicing as a Nurse Practitioner as of 2022.
Learn more at practicalfounders.com.
Shameem Hameed created several companies, including a medical billing services company, before starting ZH Healthcare in 2008 to provide billing and EHR software to innovative healthcare providers. Their BlueBriX software grew into a comprehensive and customizable platform used by hundreds of healthcare organizations around the world.
ZH Healthcare now has almost 200 employees in the US and India. The company has been profitable every year and has not taken on any outside funding.
Kevin McArdle spent 15 years working in large software companies before becoming a practical investor and acquirer of smaller SaaS businesses. Kevin is the CEO and co-founder of Big Band Software, a holding company that buys and holds small, profitable, and growing SaaS businesses—with no intent of selling those businesses. Kevin has acquired over 40 businesses in the last 10 years with this buy-and-hold model.
As an expert guest on the podcast, Kevin answers common questions from practical founders about the holding company approach as an exit path. Holding companies are common in other industries, including Warren Buffet's Berkshire Hathaway, but relatively new to the software industry.
Learn more at practicalfounders.com.
Harry Hopkins is co-founder and CIO of Viewgol, a medical billing technology software and services company based in Dallas, Texas. Viewgol was started in 2017 by three founders who got the product and revenues going before hiring additional staff. Their revenue cycle management (RCM) analytics software reveals medical billing problems and missed revenue opportunities at physician offices in the US.
As the company expanded its service offerings, Viewgol grew very quickly, from three employees in 2019 to almost a thousand employees at the end of 2023. Viewgol was acquired in October 2023 by CPSI, a public medical billing solutions company, for a reported $67 million in cash and earnouts.
Learn more at practicalfounders.com.
Hamed Mazrouie owned a security monitoring business and other businesses for many years before he started his first software and services business called Vivant Corporation. Vivant provides a complete multi-site internet phone system to thousands of restaurants and law firms across the US. Vivant grew steadily and profitably for 10 years and is now a maturing business with 50 employees.
In the last four years, Hamed and his growing team have been building Milagro, a complete restaurant management system to increase repeat customer business. They now have happy paying customers who use their powerful software which includes advanced data analytics. Their vision is expanding based on early customer results.
Learn more at practicalfounders.com.
Subramanyam Kasibhat has created dozens of products in many different industries. He and his wife were contracted by a friend to build a software solution for a manufacturing plant for a German company. Seven years after they started with their first customer, they rewrote the software to serve other customers and the Vegam Solutions business started to grow.
Vegam Solutions is smart factory software for digital optimization and control of complex manufacturing plants. Vegam now has 180 remote employees, primarily in India, with almost $10 million in revenue. They have grown without outside funding by selling to large customers with complex needs.
Learn more about practicalfounders.com.
Jafar Owainati was a mechanical engineer before he got an MBA in entrepreneurship and decided to start a software company with two friends. They looked at many ideas before building software to help sales engineers respond to Requests for Proposals (RFPs) faster and easier. They launched Loopio in 2014 and had paying customers within one year.
The three founders built the software and sold the first customers before adding more employees as they approached $1M ARR. They kept growing faster with a disciplined and frugal approach to $3M ARR before raising a round of VC funding from OpenView Ventures, a practical investor that aligned with the vision and approach of Loopio’s founders.
Loopio now has hundreds of employees and Sumeru Equity Partners made a strategic $200 million private equity investment in 2021. Jafar left to start a compensation management software company called Barley which is starting to grow quickly now.
Learn more at practicalfounders.com.
Miles Schwartz a cofounder of Zūm Rails, a fast-growing fintech based in Canada with a growing worldwide presence. In just 3.5 years and without any outside funding, Zūm Rails has grown from a focused startup to a credible open banking and instant payment gateway with $10M in ARR. Zum Rails also integrated KYC (Know Your Customer) technology which reduces fraud across all payment types.
Miles and his cofounder had experience with fintech payments before they started Zum Rails to improve EFT payment processing in Canada. As they worked with more partners and grew revenues, they expanded the Zum Rails solution and built relationships with larger partners.
Fast-growth, larger partner opportunities, and traction with a US expansion are causing Miles and his cofounders to think differently about the potential for the company and potentially raising growth capital from the right VC investment partner.
Learn more at practicalfounders.com.
Bernardo Carvalho Wertheim is a worldly entrepreneur who grew up in Sao Paolo, Brazil, and then moved to the UK to go to school and start his career in advertising. He kept traveling and eventually settled in Santiago, Chile, where he started a tech startup and participated in a tech accelerator.
The Bridge started as a community and jobs platform connecting UX designers in Latin America to work at startups and large agencies worldwide. They expanded the services offerings and eventually grew to $10 million in revenue by helping to employ hundreds of high-skilled remote creative professionals.
In 2023, the Bridge was acquired by Gi Group, a large Italian HR services conglomerate that wanted to expand its footprint in Latin America. Bernie stayed on to help The Bridge serve a global audience and work with other Gi Group organizations across Europe and Latin America.
Learn more at practicalfounders.com.
When Patrick Randolph discovered that doctors' offices lose 20% of appointments due to patient cancellations and no-shows, he set out to design and test a solution. QueueDr was created to fill those open slots with patients in the waitlist "queue."
With just a little funding and lots of hard work, they began by helping small practices and group practices fill open slots with no human intervention. Eventually, they sold to larger organizations and became profitable as they grew. QueueDR was acquired by Phreesia (PHR: NYSE) in March 2021 for an undisclosed amount.
Topics discussed on this podcast
- How he prototyped and designed the full product before writing any code
- The multiple challenges of selling technology to healthcare providers
- How they started by selling to small offices and eventually sold enterprise deals to large organizations
- Why he didn't want to raise another round of VC funding after raising $1 million from an investor
- How he developed the relationship with leaders at the company that eventually acquired QueueDr
- How he thinks about life after selling his company
Learn more at practicalfounders.com.
Raj Khera has had three exits as a software entrepreneur and leader in his long career. His first company, GovCon, grew in the late 1990s to help government contractors easily access new contracts up for bid by the US government. Their advertising and subscription revenues grew quickly, and he sold GovCon in 1999 for $12.5 million.
He bootstrapped one of the first email marketing software businesses in the early 2000s called MailerMailer to help small businesses send emails. Raj and his brother Vik ran this as a profitable small business for many years, giving them an interesting business challenge while not sacrificing time with their families. After running the business for 15 years, Raj sold MailerMailer to a public software company, J2 Global, in 2017.
Then Raj joined a struggling VC-funded software company called WealthEngine to help grow sales, create new products and exit. Wealth Engine was successfully sold in late 2020. Raj is now an active advisor to software founders. At MoreBusiness.com, he coaches software founders to efficiently acquire customers using advanced search engine optimization and marketing techniques.
Learn more at practicalfounders.com.
Robin Alex worked in a digital marketing agency in Dallas when he discovered their small business clients struggled to nurture and follow up with their website leads. In 2018, Robin and two developers prototyped a marketing automation and CRM software that could help other agencies solve this problem for their clients. They pitched the product and got a great response. They built their first product and HighLevel grew quickly.
HighLevel grew fast as word of mouth and referrals spread in the agency community. HighLevel is an all-in-one sales and marketing platform for agencies that serve small businesses. With marketing automation, CRM, and payment tools, HighLevel has an innovative “white-label” platform that their agency customers rebrand to deliver custom solutions to their customers.
HighLevel has over 60,000 agency customers, over 3 million small business users, and over 700 remote employees. HighLevel is adding 30-50 employees a month, yet they are still “moving fast and breaking things” to move fast and serve their agency customers. The founders took a practical growth equity round of funding in 2021 from PeakEquity.
Learn more at practicalfounders.com.
Mike Roberts is the founder and CEO of SpyFu, a leading competitive research tool for marketers and entrepreneurs with over 15,000 paid customers and hundreds of thousands of free users. SpyFu was launched in 2006 and has been a profitable and bootstrapped business for almost 18 years.
Mike is a happy founder who splits his time between leading the business and his personal pursuits, which include surfing and spending time with his family. He is still passionate about innovation, search marketing technologies, big data and AI, and creating new ways to help smaller businesses succeed.
Learn more at practicalfounders.com.
Raution Jaiswal grew up in India and then worked in management roles at large companies in the US before he discovered a problem experienced by small insurance agencies. He validated the problem, built an early solution, and didn’t quit his full-time job in 2018 until he had 50 paying customers.
InsuredMine provides an all-in-one sales CRM (customer relationship management) and marketing automation software for independent insurance agencies in the US. InsuredMine helps improve and automate marketing, sales, and service to help insurance agencies sell more, serve customers better, and become more profitable. It also integrates with many popular agency management systems (AMS).
The bootstrapped company is growing up quickly with almost 60 employees, a leadership team, and a growing reputation. In addition to over 1,000 small insurance agency customers, InsuredMine is now being used by some of the largest agency organizations in the US.
Learn more at practicalfounders.com.
Kelly Mann was a CPA and auditor for 15 years before leaving her employer to start her own CPA firm focused on 401K benefits audits. She discovered a need to automate this process, validated the market with other CPAs, and created the first AuditMiner software.
Unfortunately, Kelly was diagnosed with Stage 3 breast cancer just before launch and started aggressive chemotherapy immediately. After a year of treatment, AuditMiner was launched, and CPA firms lined up to buy it.
With her treatments and surgeries behind her, Kelly is now CEO of a fast-growing and profitable SaaS software company with 15 remote employees, hundreds of customers, lots of publicity, and suitors interested in buying the company.
Kelly openly shares her personal journey with cancer and how she thinks differently about running a software company than most founders.
Learn more at practicalfounders.com.
Praveen Ghanta graduated from MIT with computer science and economics degrees and worked for various financial services companies after trying his hand at a software startup. Working in his spare time, he built a product and recruited a cofounder to help sell it. After trying to sell it to different types of financial services companies, they finally found a valuable use case with individual wealth managers to help them sell new clients. They quit their jobs and launched HiddenLevers.
HiddenLevers was as stock portfolio and financial risk management software that helped financial advisors show their clients the potential impact of outside invents on their investments. Despite being bootstrapped and profitable, the company grew steadily to $8M ARR with 25 employees by selling to larger wealth management companies and solving bigger problems.
Orion Advisor Solutions acquired the company in March 2021 for a strategic valuation of 16X revenues. HiddenLevers is now Orion Risk Intelligence. After helping the acquisition transition, Praveen started Fraction to help software companies hire senior developers looking for ongoing fractional engagements.
Oliver Low worked for Microsoft and then MySpace in London before creating a successful digital agency in 2010 with two friends. Their agency grew fast and was profitable, so they invested in building software apps to solve problems that they faced helping big brands promote on the web. One of those products, Platform360, turned into a real SaaS product business which became their focus in 2013.
Platform360 was a programmatic ad platform for large brands to manage digital advertising in the changing digital privacy environment. They grew quickly with extreme effort and no outside funding, but eventually decided to sell the Platform360 business in 2018 for a modest exit.
Oliver is a savvy and practical “0 to 1” entrepreneur and business builder. He now runs Tiny Studio, the venture builder inside Tiny.com. Tiny is one of the largest “buy and hold” acquirers of bootstrapped and profitable SaaS companies, continuing to run those companies as independent and sustainable businesses.
We talk at length about what we are both seeing in the big wave of successful practical software companies that are starting, growing, and thriving without any VC funding.
Bootstrapped SaaS Topics Discussed on This Podcast with Oliver Low
- Why Oliver created a digital agency in 2007 after working at Microsoft and Myspace
- How they built and grew a programmatic ad-tech platform without outside funding
- Why they chose to sell the company at a challenging time rather than raise big VC funding
- How Tiny.com works as a holding company that acquires bootstrapped SaaS businesses and holds them long-term as independent companies
- What Oliver sees in the world of practical SaaS founders from his global perspective
- Why he started a venture studio inside Tiny.com to incubate practical SaaS businesses
Learn more at practicalfounders.com.
In this expert interview, Vik Thapar of Cypress Growth Capital explains revenue-based financing (RBF) and how it can be very useful for practical SaaS founders. In the last 10 years, Vik and the Cypress team have funded over 50 SaaS and tech-enabled services businesses that have steady recurring revenues and predictable customer acquisition approaches.
Revenue-based financing is a form of non-dilutive funding that is paid back as a fixed percentage of cash receipts until the investment is paid off.
Unlike raising funding from VC or other equity investors, founders with $3M-$10M ARR can use RBF as an efficient option to accelerate growth and increase the value of their companies without losing control or diluting their equity.
Royalty-Based Funding Topics Discussed on This Podcast
- What is royalty-based financing and how is it different than other non-dilutive funding options like venture debt or equity funding from VCs?
- When is royalty-based financing useful for practical founders by company size and capital needs?
- When doesn’t royalty-based financing make sense for founders?
- What time frame is typical for founders to use funding to grow and then exit at a much higher price?
- What has happened in the royalty-based financing industry in the last 10 years?
- What’s the typical process and timeline for a founder to receive funding and start paying it back?
Learn more at practicalfounders.com.
Bryan Clayton is the co-founder and CEO of Greenpal, a leading on-demand marketplace of lawn care services for homeowners across the US. With a team of 25 remote employees, they help 300,000 homeowners connect with 35,000 landscape service providers.
Greenpal is an “overnight success that took 10 years” while the founding team learned to build a software product and recruit homeowners and services pros to the marketplace. It grew slowly at first as they learned and made mistakes, but they didn’t stop and started to expand regionally. Greenpal has no outside funding.
Bootstrapped Marketplace Topics Discussed on This Podcast
- How long it took the founders to get the Greenpal marketplace going in his home city before adding other cities and going national
- Why they are laser-focused on one segment of this massive landscape maintenance industry
- How a two-sided marketplace business is different than a B2B SaaS business
- Why they resisted taking outside investment for all the years it took them to become profitable
- Why he has “fun” working so hard for so long to make GreenPal successful
Learn more at practicalfounders.com.
Ben Murray is a former SaaS CFO and finance professional who helps SaaS founders understand the basics of SaaS accounting, finance, and metrics for their growing businesses. Ben has a popular blog and podcast with free educational resources to learn advanced SaaS metrics, learn finance best practices, and hear stories from other founders.
In this expert interview, I ask Ben all the questions that I hear from startup founders and SaaS CEOs about finance and accounting operations. Ben is very experienced and very practical about doing the simple practices that help software companies grow efficiently and confidently.
Learn more at practicalfounders.com.
Wissam Tabbara is a serial entrepreneur who has created multiple software startups in Seattle since 2009 when he left Microsoft where he was a software development manager. He led multiple startup technology teams and now is an experienced CEO and business builder. In 2021 he founded Truebase, a B2B prospecting platform for revenue teams using the power of generative AI accelerates the prospecting journey.
Wissam steps back to assess his startup adventures more objectively and shares his biggest learnings around leveraging the latest technologies, funding, and acquisitions, and staying ahead of giant tech companies in the same space. He talks about his biggest learning as a technical founder: how the revenue and growth side of the business is where “all the action is at” when creating a valuable software company.
Learn more at practicalfounders.com.
Lloyed Lobo is the co-founder and former president of Boast.ai, a leading platform to help software companies in the US and Canada to redeem available government tax credits. Boast was started in 2017 and started as a services business that slowly grew into a product business as its technology evolved.
Boast.ai bootstrapped their growth to $10 million ARR before taking an investment from Radian Capital that also allowed Lloyed and his cofounder to cash out some of their equity for life-changing cash payouts. Their growth was fueled by the active startup community they built called Traction.
Lloyed faced many challenges as an immigrant, startup adventurer, starving entrepreneur, and hyperactive community builder. He also struggled after the investment when he finally had monetory wealth and went into a deep depression. With the support of his family and therapy, he moved forward to prioritize his health and family and limit his startup addiction.
Learn more at practicalfounders.com.
Ryan Goodman joined the startup in the early days of the business intelligence and analytics market in 2003 as a specialist helping large customers adopt this new technology. This startup was acquired by the successful BI company Business Objects, which was then acquired by the huge software company SAP. Ryan left to start consulting and build niche add-on "feature products" in the SAP Business Objects ecosystem.
They experimented with product ideas and consulting services before finding an opportunity to help Business Objects users easily visualize data on Google Maps. They grew fast as an add-on product selling to large companies all over the world, reaching 700 customers and $1.4 million ARR. But new BI platforms and technology changes slowed their growth and completely changed the market opportunity.
Ryan talks about the pivots and experiments they tried before deciding to shut down the company and sunset their core product. He shares his difficult decision process and the emotional journey, including lessons learned and perspective gained in hindsight.
In this episode, Ryan explains:
- How he started in the pioneering early days of business intelligence and analytics for big customers
- Why he left SAP after being acquired twice to start his own add-on software business in the Business Objects community
- How he experimented and survived long enough to find a compelling product opportunity that quickly grew to over $1M ARR
- How the market changed and how that eventually led him and his cofounder to shut down the business slowly
- How he feels about the successes and failures of his software startup journey
Learn more at practicalfounders.com.
As the host of the Practical Founders Podcast, I have interviewed 46 successful SaaS founders and 6 savvy experts in the first year of weekly episodes. In this episode, I share some of the deeper insights, surprising lessons, and useful perspective that I have learned after so many great conversations.
Practical founders are building valuable software companies without big funding all over the world and in every corner of the software business. It's an amazing time to be a practical founder. Practical founders are solving problems, changing the world, and doing it their way.
The founder equity value and founder wealth created by just the 46 founders I interviewed this year is over $1 billion. Tune in to this episode where I share what's going on right now and how these founders are succeeding in their own ways.
In this episode, Greg explains:
- What characteristics that all successful practical founders have in common
- Why there are so many variations and ways to create a successful software company when you don’t raise big funding
- What has happened in the last 5 years that makes it better for most new founders to grow a serious software company without big funding
- Why we don’t see the hundreds of billions of founder equity value and wealth that have been created by practical founders who have grown thousands of valuable software companies without big funding
Learn more at practicalfounders.com.
Patrick Fingles grew a successful roofing company with hundreds of employees in the Baltimore-Washington DC area. In 2013, they created their own software to help new salespeople estimate, quote, and close new roofing sales. They started selling the software to other contractors in 2016 and called it Leap.
Leap grew fast to $7 million ARR in 2021 with Patrick as the CEO. In 2021, they decided to take some growth funding from Nexa Equity to give Patrick and his cofounders their "first bite" of successful liquidity and support future growth and acquisitions.
Leap is now the leading contractor management software with CRM, project management, and point-of-sale functionality specifically designed for the unique needs of home improvement contractor and remodelers in the U.S. Leap is now over $20 million in ARR with over 150 employees and full-time contractors and is still growing fast.
Learn more at practicalfounders.com.
Jordan Fleming grew up in Toronto and New York, then lived in Edinburgh, Scotland for 15 years where he created a successful consultancy helping larger businesses automate and improve their processes. His experience developing workflow apps led him and his cofounders to create a tightly-integrated phone system solution called smrtPhone built just for the Podio workflow platform, which is very popular in several industries. Jordan now lives in Poland and most of the team works in their office in Romania.
The bootstrapped and profitable smrtStudio Global company is now growing fast with 2400 customers, 45 employees, and nearly $5 million in ARR (annual recurring revenue). They are very disciplined about company culture, building a scalable organization, growing employees, and preparing for growth before problems arise.
Learn more at practicalfounders.com.
Gregory Shepard is a serial entrepreneur who has created and sold 12 companies, including marketing software and ad technology companies. In 2016, he sold two of his bootstrapped software companies, AffiliateTraction and AdAssured to eBay for an undisclosed "f*ck-ton of money," as he describes it. He is now an author, speaker, philanthropist, investor, and the creator of Startup Science and BOSS, an open-source business operating system to help more startups succeed.
Gregory faced monumental challenges as a child growing up in poverty with a rare combination of autism, dyslexia, synesthesia, savant syndrome, and other neurodivergent conditions. He learned to develop himself and overcome big challenges, including creating, growing, and running many software companies over three decades.
In this interview, Greg shares his difficult personal challenges and his successful entrepreneurial journey as an experienced practical founder. He also shares several powerful insights and approaches for bootstrapped software founders that you won't hear from investors or the current startup education.
Learn more at practicalfounders.com.
Deepak Sindwani is a former software entrepreneur who has been a professional investor in software companies for over 20 years. Deepak is the co-founder and managing partner of Wavecrest Growth Partners, a growth equity investor in practical B2B SaaS companies. Wavecrest specializes in helping bootstrapped and capital-efficient founders of vertical B2B SaaS companies reduce risk and grow their companies from $5M-$10M ARR to $30M-$50M ARR and drastically increase the value of their companies.
Growth equity funding is a practical version of institutional funding that is different than traditional “Get Big Fast At All Costs” big venture capital approach. With more reasonable growth and exit expectations, more help for founders and their teams, and more secondary for founders (to take some money off the table), growth equity partners can help ambitious founders scale their impact with an efficient approach. Unlike private equity (PE) majority acquisitions and “roll-ups”, growth equity investors want to grow businesses organically and support the founders in their journeys.
This is an expert interview in which I ask Deepak to educate us about the growth equity funding game and answer typical questions for founders who are considering taking on a funding partner to efficiently accelerate growth after they reach $3M-$5M ARR.
Learn more at practicalfounders.com.
Sam Knight is the co-founder and former president of BOLT Software, a project management and scheduling software for the construction trades that build residential homes. Sam helped lead the BOLT team as it grew before the company was sold and now he guides the BOLT product in the larger company.
BOLT was created in 2015 after years of internal use at a large Dallas-based electrical contractor. Cofounder Josh Causey brought in Sam Knight to spin out and run BOLT as a separate software company and grow the customer base and improve the product. Through 2020, the company grew to over $1M in recurring revenues before it was acquired in 2020 by Fort Worth-based ECI Solutions to expand its construction software offering.
Built by the trades for the trades, BOLT is a SaaS solution that simplifies project management, scheduling, and estimating for new home construction subcontractors (electricians, painters, plumbers, etc.). BOLT helps those subcontractors truly manage their teams: from rescheduling due to unforeseen delays to scheduling out multiple crews simultaneously.
Learn more at practicalfounders.com.
Chris Kern is an expert independent M&A advisor who has helped over 150 growing tech companies get financing, obtain investment, or sell their companies. He is Managing Director of Windstream Partners where he advises smaller SaaS and tech business owners in selling their companies for successful exits between $10M-$50M.
Chris got his start on Wall Street working on large finance and acquisition deals, but he quickly shifted gears 20 years ago, moved to Phoenix, and started working only with small software companies with growing SaaS, software, and technology businesses. I have known Chris for over 15 years.
In this interview with an active M&A professional who helps many practical SaaS founders sell their companies every year. I ask Chris the most common questions I hear from practical founders who are thinking about selling their companies someday.
“There are a thousand times more companies getting acquired for less than $50 million than all of those that sell for billion-dollar valuations. You just don’t hear about these deals because they are smaller and often have confidentiality agreements in place," Chris explains.
In this episode, Chris explains:
- What’s happening right now in mergers & acquisitions of software, SaaS, and fintech companies that sell for $10M to $50M?
- What are common valuations ranges for software startups and small companies with revenues between $500K and $5M in ARR?
- What are the factors that affect valuation one way or the other?
- Can you really sell a startup for a multiple of revenues when it’s still small?
- Who is buying these smaller software companies and why are they buying them?
- What is the general process of selling your company?
- What should they be thinking about before they try to sell to maximize their outcome?
- Is it better to have outside funding or to have bootstrapped when selling your company?
Learn more at practicalfounders.com.
Joshua Strebel started a small SEO and website agency in the early 2000s after graduating from university. Joshua and his wife Sally experimented with website hosting using WordPress with low monthly fees while they ran their services business in Scottsdale, Arizona. WordPress became popular and eventually Pagely was formally launched as the first managed WordPress hosting platform in 2009 and they closed their services. business.
Pagely grew steadily until 2013, when dozens of inexpensive managed WordPress hosting competitors entered the market, all backed by big VC funding. Pagely was bootstrapped with no outside funding, so they slowly changed their focus to serve only the biggest companies the largest WordPress sites with the most complex needs. Pagely revenues grew 1000% in just 3 years after focusing on the top 1% of WordPress customers.
Pagely was profitable and sustainable with many big-brand large customers when they sold the company in 2021 to GoDaddy, the huge website hosting company also based in Arizona. With nearly $10 million in ARR, Pagely’s strategic exit created generational wealth for Joshua and Sally and life-changing wealth for multiple key employees.
Learn more at practicalfounders.com.,
Dave Savage was a top-producing mortgage loan officer in the early 1990s who used computers and software to help him sell more. He became a software entrepreneur by creating a new software solution for loan officers to help them educate their clients and sell more. He sold $120,000 of Mortgage Coach on stage at a conference on their first day, which started their 25-year growth journey in the software business.
Mortgage Coach helps loan officers transparently present loan options and educate their clients about the financial impact, which differentiates the loan officer and helps them increase sales and referrals. It started as Windows software then eventually transitioned to the web and mobile devices.. The company grew steadily until the mortgage meltdown in the Great Financial Crisis of 2008-2010 caused its sales to plummet, but it didn’t kill the company. After 2012, they started selling to large lending companies, not just individual loan officers.
Mortgage Coach was a growing and profitable software company with no outside investors when a majority of the company was acquired by private equity investor LLR Partners in 2021. Dave is no longer the CEO of the new company called Trust Engine but he is still is part-owner and an active executive leader helping to grow the impact of the new company.
Beth Sanders was selling computer software and equipment for a regional computer retailer in Ohio when she recorded her grandmother’s life stories on a tape recorder. It was so powerful she decided to create a website in 2001 that allowed anyone to journal and share their life stories. Many experiments led to her first paying customer in 2006: a senior care center that wanted to offer life journaling software to their seniors. The LifeBio software business was born.
LifeBio is a leading “agetech” software that uses Reminiscence Therapy Method and storytelling in various media to help older people to capture and share their life stories. LifeBio’s autobiography tools are also used by the Mayo Clinic and other organizations serving Alzheimer’s patients. During the COVID crisis, LifeBio launched MyHello, a new software app that helps seniors fight loneliness.
LifeBio has grown steadily and profitably to over $2 million in revenue with 48 employees, based in a small town near Columbus, Ohio. Mostly self-funded with a little angel funding, LifeBio serves the massive senior care industry in the US with its easy-to-use apps and tools. Their mission is to help people tell their life stories and share them with their own families.
Josh Haynam grew up in the Central Valley of California just 100 miles from the tech center of Silicon Valley--without any awareness of tech jobs or tech businesses when he lived there. He was a successful high school entrepreneur, then supported himself through his college years with his digital SEO agency. Their experiments with custom website quizzes showed promising results, so Josh and his cofounder friends started a company to build the first lead-generation online quizzes as a standalone plugin for websites.
Interact quizzes showed promise with great customer value, but they struggled to sell their new solution to small business owners or marketers who had never seen quiz software before. They experimented, pivoted, and kept going for seven years before they finally reached $1 million ARR with some profits. The ups and downs continued with well-funded competitors, COVID booms and busts, target market pivots, and more.
Interact now is profitable and growing with nearly $3 million in annual recurring revenues, 11 remote employees, and thousands of customers—still without any outside equity funding. Every day, users complete millions of Interact quizzes on their customers’ websites.
Learn more at practicalfounders.com.
Esben Friis-Jensen was a technology professional in Copenhagen, Denmark before he and three Danish friends moved to San Francisco in 2013 to start a new startup called Cobalt. Cobalt.io grew steadily and raised several rounds of VC funding to become a sizable cybersecurity software company in Silicon Valley. Cobalt serves large businesses with a platform and services for larger companies to efficiently test and find security holes in their websites and web applications.
Esben left Cobalt in 2020 to start Userflow to help software companies attract, sell, onboard and support their customers without human touch altogether using a product-led growth approach. Userflow is a no-code onboarding software to easily build in-app explanation guides, checklists, and videos for software product companies to improve free trial conversion and new customer onboarding for expanded retention. Userflow has a free trial and uses its own software to improve conversion and onboard customers without human intervention.
Userflow is profitable and growing with over $3 million in ARR, 600 customers, and just three employees with no outside funding. Esben handles all growth and lives in San Francisco and his cofounder Sebastian builds the product with their UX designer in Denmark, so about $1 million annual recurring revenue per employee.
Learn more at practicalfounders.com.
Massimo Arrigoni grew up in Milan, Italy, and moved to California 27 years ago to create software products and start a family, eventually moving to the San Francisco area in Silicon Valley. While leading product at the software company MailUp, a popular Italian email marketing software, his team built and tested a better visual editor for creating email templates and website landing pages. The free software tool called BEE ("Best Email Editor") became popular and a new product line was born.
BEE end users love the modern and easy-to-use no-code editor which doesn't require email or credit card to use the product for free. The company also sells to SaaS developers who want to embed the BEE builder into their own apps instead of building their own visual editors. BEE is growing with no paid advertising or marketing spend. New users find their free template library and start to use the product instantly with a frictionless experience.
Businesses now pay for the BEE Pro solution making up about half of company revenue and embedded plug-in makes up the rest. BEE is now a standalone company owned by parent Growens with 80 employees and over $10M in revenues. BEE has over 40.000 monthly users and 10,000 paying customers.
Learn more at practicalfounders.com.
“My B2B SaaS startup needs just more warm leads. But we have struggled when we hire junior salespeople to call on and email cold prospects to generate qualified leads that the CEO or salespeople can close.”
This is a common frustration for startup and early-stage SaaS founders when they hire sales development reps (SDRs) or business development reps (BDRs) to generate qualified leads. There are many misconceptions and pitfalls that make this even more challenging.
Christine Rogers shares her expertise on what is working and not working when hiring SDRs to generate or warm-up leaders in the modern software business. Christine is an experienced SaaS sales leader who has helped develop thousands of SaaS sales and SDR reps to succeed at growing software companies through her company Aspireship.
In this episode, Christine explains:
- What are the different tasks and roles of sales development reps (SDRs) and business development reps (BDRs) in growing SaaS companies
- What tools, processes, and ideal customer definitions are required before you hire your first SDR
- Which SaaS business models make the most sense to use SDRs in the sales process
- Which outbound lead development approaches are productive in generating qualified discussions
- What compensation ranges are typical for SDRs this year
- How to think about SDR business goals and targets
- If you should hire one SDR or a sales manager-doer as your first sale hire
- When should founders hire “full-cycle” salespeople instead of a lead gen-only SDR
Learn more at practicalfounders.com.
Dave Whorton is an experienced tech investor and funded founder who spent the first 20 years of his career at the highest levels of Silicon Valley venture capital and tech-boom startups. He started his career at Hewlett Packard and experienced the famous "HP Way" culture firsthand before he attended the Stanford Graduate School of Business. He joined the preeminent tech venture capital firm Kleiner Perkins and worked directly with John Doerr for several years before launching Good Technology and raising $63 million in venture funding in the early 2000s. He brought in a CEO to run the company before it was sold to Motorola.
Dave joined the large tech private equity firm TPG and directed many investments there before creating his own small venture capital firm and making several investments in the 2000s. Dave started to become disenchanted with the "Get Big Fast" of the venture capital approach. He talked to several founders who were growing businesses without any outside funding and who were building better businesses with better cultures and better outcomes with no intent to ever sell their companies.
In 2013, Dave started the Tugboat Institute, a membership organization that brings together Evergreen® CEOs across industry sectors to share best practices and unique insights, and to develop trusted bonds for their respective Evergreen paths. Evergreen leaders are seasoned entrepreneurs, CEOs, and presidents with the vision, creativity, resourcefulness, patience, and grit to build and scale a business that will stay private indefinitely.
Learn more at practicalfounders.com.
Windermere Real Estate is a large and well-known residential real estate broker in the Seattle area. In the late 1990s, they invested to build an internal software system to power their own business and differentiate their services. After using and improving their software for over 10 years, the family owners of Windermere spun out the software as a new company called MoxiWorks. They hired experienced tech entrepreneur and marketer York Baur to lead the new MoxiWorks business as CEO in 2012.
After rewriting the software from scratch, they started selling their solution to other large brokers in the US. They grew steadily and expanded their product platform and their team. MoxiWorks is now a leading platform system for large residential real estate brokerages, serving over 800 brokerages and 400,000 agents nationwide, which account for more than 20% of transactions in the U.S.
MoxiWorks started as an internal technology investment at Windermere Real Estate, but their early growth years were funded by the Windermere owners and customer sales. In 2019, Vector Capital made a major investment to help MoxiWorks expand beyond its current $50 million in revenue and 300 employees.
See the full-text transcript and show notes at practicalfounders.com.
Patrick Campbell wasn't expecting to be an entrepreneur when he grew up, but after his first few jobs, he struck out on his own in 2012 to create a software company to help SaaS businesses optimize their pricing. Price Intelligently quickly evolved into a tech-enabled service that allowed him to grow, build a team, and ultimately launch Profitwell.
Profitwell is a free and powerful SaaS metrics product that automatically calculates MRR, ARR, churn, and other import financial measures for SaaS and subscription companies from their payments data. It is now used by over 35,000 subscription businesses. Profitwell now offers paid products for managing churn, credit card failure, revenue recognition, and price optimization.
Patrick bootstrapped Profitwell with no outside funding, but they grew fast to 100 employees before being acquired by UK-based Paddle for $200 million in 2022. He openly shares the story of how they started, grew, survived, and eventually sold the company—and how the acquisition is going one year after the acquisition.
In this episode, Patrick explains:
- How it grew in the early day as Price Intelligently, a tech-enabled pricing strategy service for SaaS companies
- How they bootstrapped for 10 years with efficient growth and savvy pricing
- Why Patrick thinks now that he should have raised some funding and why they didn't at the time
- How they created Profitwell and gave it away for free, then created upsell products to monetize their large and loyal user base
- How they grew fast with an extensive inbound media model with episodic content on top of their inbound middle-of-funnel content
- Why he chose to stay with Paddle and contribute to achieving the big vision instead of selling for cash and moving on
- What it's like now for him and his team a year after their acquisition by Paddle, a UK company
Learn more at practicalfounders.com.
Jon Nordmark founded eBags.com in 1998 as one of the first Internet e-commerce companies and grew it into the largest online retailer of luggage, bags, and travel accessories. Jon was previously a successful corporate executive who led marketing for Samsonite.
eBags raised $30 million of VC funding in 1999 and survived the dot-com boom and bust era, but the crazy growth expectations of VC investors were misaligned with the profitable growth path of the company and the market. eBags was eventually acquired by Samsonite in 2017.
Jon’s second software company is Iterate.ai, a no-code enterprise innovation platform allowing big companies to integrate, test and scale new technologies quickly and efficiently. The company was initially funded by services revenue and then by customer sales. Jon eventually raised $3 million in angel funding and a strategic investment from a large customer.
Iterate.ai has grown to over $10 million in revenue and is now profitable, with no plan to raise outside funding from big VC or PE investors.
In this episode, Jon explains:
- How he started and grew eBags.com into one of the largest and the only profitable online retailers in the early 2000s
- The brutally frustrating challenges he faced after raising big VC funding when the company was growing but didn’t meet investors’ extreme expectations
- How he kept returning as CEO of eBags after retiring, then eventually sold the company
- Why he is staying away from big VC funding with his second company, Iterate.ai
- How they approached a strategic investment from their largest customer
- Why it took them 7 years to get to real, scalable product-market fit
Learn more at practicalfounders.com.
Perry Rosenbloom moved to Boulder, Colorado in 2011 and started a small business offering digital marketing and custom website services. After building a website for his mother-in-law, an independent therapist, Perry created a scrappy subscription-based website builder platform to make websites for other behavioral health professionals.
The Brighter Vision company grew steadily and efficiently without big outside funding and eventually provided custom mobile-ready websites and marketing tools to over 4,000 therapists.
The company grew to 35 employees with an all-new website-building platform before being acquired by EverCommerce in 2020 for $17.5 million.
Gopal Krishnamurthy was an early BI and data analytics expert working for a large company when he left to start a BI consulting company in Dallas called Visual BI in 2011. Visual BI grew to over 300 employees serving enterprise customers that use SAP Business Objects and Microsoft Power BI platforms. They also created several add-on products, which Gopal retained when he sold the Visual BI consulting company in 2021 to Atos.
Gopal now leads the growing product family in Lumel, the leading provider of add-on products for the massive Microsoft Power BI ecosystem. Lumel is funded by Gopal from the proceeds of the sale of the services business, but the company is almost profitable now with 10 employees in the US and 170 employees in India. Lumel products are currently used by most of the largest enterprises in North America.
This is Gopal's transformation story of growing from technical employee to successful consulting company CEO to now product CEO. Gopal is also leading change in the data analytics industry with Lumel's useful enterprise software products that don't require expensive salespeople or consulting services.
In this episode, Gopal shares:
- How he grew a fast-growing consulting services business called Visual BI by serving large companies in the US using SAP software
- Why they started to build add-on products for the SAP Business Objects ecosystem, then invested in cloud-based add-on products for Microsoft PowerBI
- How they sold their consulting business to Atos in 2019 and kept their products to start Lumel
- How they are transitioning from a portfolio of point solution products to a family of integrated solutions for large enterprises
- Why Gopal doesn’t think VC investment makes sense for Lumel even as they grow faster with marketing efforts, despite his big and bold vision that wouldn’t be a good fit for “get big fast” VCs
Find out more at practicalfounders.com.
Matt Watson was a two-time software company with two successful exits before he was 40 years old. He started his first company, VinSolutions, in his basement in Kansas City in 2006. VinSolutions started by helping auto dealers upload photos of their cars to sell in the popular Autotrader catalog and website. Matt was the first developer and product visionary who lead a team that build their popular CRM and lead management system to help those dealers manage internet leads and sell cars faster.
Their revenue doubled every year as they grew to eventually serve thousands of auto dealers with their pioneering web-based software.VinSolutions didn’t raise any venture capital or private equity investment as they grew to over 300 employees. In 2011, VinSolutions was acquired by Autotrader.com itself for a reported $150 million.
Matt started Stackify in 2012 as the CEO funding the startup with his own money. Stackify is a tool for software developers using cloud platforms to manage and optimize application performance, a problem Matt had experienced at VinSolutions. Stackify grew slowly and struggled at first before it grew steadily. Stackify was acquired by Netreo in 2021.
In this episode, Matt explains:
- How they started by taking photos of cars for auto dealers to sell those cars online, then bootstrapped a CRM software product to help dealers manage internet leads
- What it was like to be the CTO of a pioneer in web-based software with a recurring revenue business model back in 2008 when the auto industry was in a massive recession
- The benefits and drawbacks of growing a large vertical software company in Kansas City
- Why they tried to raise capital but started the process to sell the company instead
- Why Matt started a new company called Stackify as the CEO with a different customer focus, technology stack, and different sales model than his previous company
- Why did he self-funded Stackify and then raised venture debt as they grew, but didn’t raise big VC funding
- What it is like to be a two-time founder of software companies with successful exits before he was 40 years old
Find out more at practicalfounders.com.
Deb Muller was an experienced HR executive at a large global company who left her job to start a consultancy specializing in managing important employee incident investigations. Surprisingly, her customers asked her for a software solution that included her best practices, so she mocked up some screens and had someone build the first version in 2009. She started selling it to fellow HR leaders and her software company HR Acuity was born.
Professional management of employee incident investigations was new when HR Acuity started, but there was no shortage of employee incidents to track, especially in larger companies with more than 1000 employees.
She and her team built a community of HR leaders and led the global discussion about proactive employee relations and transparent HR incident management. Big changes like #MeToo, DE&I awareness, and remote employment during COVID increased the awareness of these HR issues and the tools to manage them.
HR Acuity is now a fast-growing company with over 100 employees. Deb took a small angel investment from a friend a few years after starting the company. They grew mostly from revenues with no interest in any major funding until 2019, when HR Acuity took a growth equity investment from Growth Street Partners. In 2021, they took additional funding from K1 Investment Management. The company is still independent and growing steadily.
In this episode, Deb explains:
- How she started her company as a law firm providing employee incident investigation consulting for large companies, then slowly transitioned to being a software-only company.
- Why she grew their community of HR leaders at large companies with roundtable discussions to share ideas, processes, and approaches with each other.
- How she bootstrapped the company with customer sales revenue, but slowly learned that some appropriate funding could help the company grow faster without being crazy about it.
- What has changed in the employee-employer relationship in the last 15 years that has helped them grow
- What women founders should be thinking about when they are serious about creating change in the world with a software company
Find out more at practicalfounders.com.
Vivek Bhaskaran was a computer science student in college who worked on an online survey tool for a professor in the marketing department. After school, he built a new survey tool with a fellow software developer while they still held their day jobs. QuestionPro grew slowly and profitably with efficient search engine optimization and viral marketing, avoiding the need to raise any money from outside investors.
QuestionPro grew steadily by expanding the product with more powerful features for larger companies to sell larger deals that required regional enterprise salespeople. They also expanded regionally with offices in US, UK, Germany, Australia, and Latin America. Recently, they have acquired several companies with survey products used by large global companies that added to their customer base.
Vivek talks openly about their key inflection points in their journeys of revenue growth, global expansion, recruiting leadership talent, developing systems and processes, and expanding their product portfolio. QuestionPro has 300 employees with $35 million in revenue. Vivek is enjoying the learning and professional challenges of being the CEO of a software company that is growing to over $100 million in revenues.
In this episode, Vivek explains:
- How they grew fast and profitably in the early years with successful search marketing with a freemium survey tool product and chat sales support
- How his role changed at important revenue inflection points at $1 million revenue with scrappy founders, then stalling at $4 million, growing to $10 million with an organized team, and now to over $30 million with a global organization with systems and processes
- How they have grown with regional expansion with autonomous sales offices and multiple products including several acquired products
- Why he doesn’t say they are a “US company” as they have fully remote employees around the world with no headquarters
- Why they charge an additional fee to big customers to develop new features that eventually enhance their core products
Find out more at practicalfounders.com.
Scott McCausland was an experienced software sales leader who decided to go out on his own in 2005 to build a new software business. His technical cofounder built the first version of their new software and Scott started selling it. MVP Systems Software was underway without any outside funding.
They kept adding name-brand customers who used their JAMS workload automation software in their IT departments for a variety of scheduling and automation tasks that saved time and money. It was an unsexy but mission-critical software for their users
The company grew to $13 million in annual revenues with 70 employees in 4 global offices before being acquired in 2018 by Forta. Scott left Forta in 2019 and is now working on his next software company.
In this episode, Scott explains:
- Why they sold their product aggressively, but grew the business steadily and managed cash conservatively
- How they generously compensated salespeople and employees rather than give incentive stock options
- Why they decided to sell the company rather than raise funding or keep growing organically
- What it was like to join their acquiring company and be part of a much bigger team
- How he helps tech founders understand the basics of selling and what is needed to create an initial sales machine
Find details for this episode and more Practical Founders Podcast episodes at practicalfounders.com.
Oliver Palmer helped start a mobile app development agency in Sydney, Australia that built simple apps for early mobile phones. When the iPhone launched, Tigerspike grew very fast by creating branded mobile apps for large companies with its high-end design and development services.
Tigerspike also created its own software product—a mobile application development platform with subscription fees—to try to transition into a product-based company to grow faster with VC funding. This was difficult as they prioritized their urgent custom software projects for big clients and chronically underfunded their software product development
Tigerspike eventually raised $11M of outside funding from strategic partners and kept growing. The software platform also grew, but Tigerspike never made the full transition to a product-first software company. They sold the company in 2017 for $85 million. Oliver is open about their vision and their challenges as they grew Tigerspike into a large and successful global company.
In this episode, Oliver explains:
- How their mobile app design and development agency grew into a large global provider serving large companies
- Why they created a SaaS software platform product to grow faster and make their company more valuable
- How they struggled to invest in and grow their software app with their “addiction” to services revenue and custom development
- How potential VC investors viewed their services and product revenue streams
- How they sold the company and what it felt like for founders to make that transition
- What he’s working on now to help practically-funded software startup founders in Australia and Southeast Asia
Find more episodes of the Practical Founders Podcast at practicalfounders.com.
Sandeep Kumar quit his job working for an Indian consulting company to start a software company in 2005 when product-focused startups were not common in India. For the next 10 years, they experimented with product features and customer profiles until they finally found an important buyer with budget power who needed their must-have software.
ProductDossier is now a comprehensive platform for enterprise consulting and IT services companies in India to manage project financials, project resources, and new opportunities in one system. Over 50 large consulting companies in India use ProductDossier to manage their global project portfolios to ensure high-quality and profitable project delivery.
The company has 100 employees and is growing steadily without any outside funding. Sandeep shares the important lessons he learned in his 15-year journey about product-market fit, building trust with big Indian customers, developing a great organization, and thinking big.
In this episode, Sandeep explains:
- What it was like to create a startup software company in India 15 years ago when it wasn’t common to create product-focused software companies there
- The critical product-market fit lessons learned to eventually build a must-have software for buyers with decision-making power in a specific industry
- How their vertical focus and product feature depth enabled them to sell to their first large enterprise companies as a small startup
- What’s happening in the SaaS startup scene in India right now and how startups are perceived there
- The advantages of not having big outside funding too early, include strategic flexibility, attracting the right talent, and patient growth
- How he defines work-life balance and how he manages time with his family
Read the full interview transcript and check out other interviews at practicalfounders.com.
Sarah Hum studied graphic design at university before she discovered she loved to help software startups create new products. She moved to Silicon Valley to work at Facebook as a product designer, but a side project helped her find a problem she wanted to solve. So she quit her job and built an initial software product called Canny with her technical cofounder while traveling the world together as nomading entrepreneurs. Within a year, Canny created enough revenue for them to live and travel frugally.
Canny is a customer feedback management software for product managers at SaaS companies to collect useful product feedback inside their products, then prioritize requests and communicate with customers about their requested features. The Canny product has evolved quickly using its own product to engage with customers and make decisions about the next product features and improvements.
Canny is growing steadily with over $3 million in annual recurring revenue and 13 remote employees. They continue to experiment with substantial pricing experiments for different customer segments. Sarah openly blogs about the ups and downs of their startup journey and their unique approaches to hiring, designing, and testing new tactics.
Mark Abbott was an active investor and board member for 20 years when he realized that most of the 100+ companies he helped were not good a their “business fundamentals.” The fundamentals of setting long-term goals, making short-term plans, and then aligning teams and individuals to make efficient progress. He thought of writing a book but discovered the book “Traction” by Gino Wickman and his branded EOS® (Entrepreneurial Operating System) system.
Mark worked with his cofounders in 2016 to create a software platform that aligned with the principles and processes of EOS and other “Business Operating Systems.” Soon Ninety.io (now just Ninety) was a popular software used by EOS coaches and business consultants. They licensed the branded terminology from EOS Worldwide, which presented both opportunities and challenges.
The company grew steadily, funded by revenues until Ninety had over a thousand customers and more than 50 employees. In 2021, Mark talked to just one tier 1 venture capital firm, Insight Partners, and then raised $20 million in growth capital from them. Mark and the Ninety team have a big vision to change the way businesses grow and thrive.
In this episode, Mark explains:
- How he discovered the need to manage business fundamentals better as an investor in 100+ companies
- Why he decided to license the EOS-branded terminology and name to get the company started
- The pluses and minuses of partnering with a branded methodology provider
- How they used Ninety software to grow faster and be ready for a major venture investment round
- Why Mark still participates in CEO peer groups and coaches other leaders in his “spare time”
- Why he decided to raise $20M in capital from a Tier 1 venture fund in 2021
- What are the “business fundamentals” that Ninety leverages to accelerate growth
Read the full interview transcript and find more episodes at practicalfounders.com.
Craig Letton quit his corporate sales job in 2011 to take over his parents’ small printing business in Scotland. It was his first time running a business and he learned hard business lessons quickly. Eventually, he discovered a huge need for custom-printed promotional materials by frontline salespeople in the global drinks and beverage industry. He sold their printing equipment to focus just on the software to solve this tricky problem for those salespeople, marketing departments, and regional printers.
Running the business for revenue and profit with no outside funding, Craig grew the MRM Global business slowly with big brands in the alcoholic beverage industry all over Europe. They worked hard and stayed frugal and started to grow. Then COVID hit and revenues evaporated. Their survival tactics helped them keep going and even grow faster when restrictions were lifted. They raised some practical funding from BGF Capital in the UK to stay alive during COVID lockdowns and expand quickly after that.
MRM Global is now a fast-growing marketing technology software company serving many of the largest global beverage brands in 20 different countries. This is a great example of a “small niche vertical market” with a very specific problem presenting a massive opportunity to create a large and valuable company. It’s also the story of grit, perseverance, frugality, and intense customer focus creating a huge opportunity for growth.
In this episode, Craig explains:
- Why he took over his parents’ small printing business in Scotland after he left a corporate sales job
- How he uncovered a major opportunity in the global drinks (beer and liquor) industry for salespeople to easily create custom, branded promotional materials for their customers using software
- How the small company grew profitably and steadily until COVID shut down restaurants and hotels, taking their revenue to zero
- What they did to survive the COVID shutdown and how he defines entrepreneurial resilience
- Why he decided to take some practical funding to survive the downturn and prepare for growth
- Why he thinks this business will be a £100 million business someday
Read the text transcript of this interview and find other Practical Founder Podcast episodes at practicalfounders.com.
Jeff Matlow is a serial entrepreneur and a crazy triathlete and a long-distance runner who found a way to put those passions together in a software startup that grew up fast. He saw an opportunity to create a better registration experience for endurance events like 5Ks, marathons, and triathlons.
In 2008, he sold the big deal to USA Triathlon and set out to build the website and registration platform he envisioned. The company I Am Athlete (now called imATHLETE) went live with their platform and started selling to hundreds, then thousands, of other endurance event managers all over the US. The company grew without big funding and the solution expanded to manage payments, social media promotion, and more.
In 2019 Jeff sold the company to a major endurance event company. Jeff shares the challenges in growing this company and the learnings from trying to grow with a strategic partnership. Like running a marathon or climbing Everest, the journey is hard and how you approach every day is critical.
In this episode, Jeff explains:
- How his experience as a marathoner and triathlete let him to the opportunity to create a better event registration platform
- How he sold his first big customer before he had a product and a website
- Why he didn’t raise any outside money until I Am Athlete was an established market leader
- Why growing a company is like climbing Everest or running a marathon
- His experience selling the company and what worked and didn’t work
- How the modern software startup and investor game is like his first career finding new bands in the music business
Read the full transcript and find other episodes of the Practical Founders Podcast at practicalfounders.com.
Howard Gottlieb created and sold several businesses before starting a school fundraising website in 2003 called Easy Fundraising Ideas. It grew into the most popular Internet website for school fundraisers. He experimented with many business models and ideas while the fundraising industry still wasn’t changing or growing.
In 2012, Howard started Read-a-Thon as a literacy-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business grew steadily and profitably without any outside funding.
Their relentless focus on elementary school fundraising and their culture of continuous improvement helped them grow faster and create a much bigger impact. In 2022, Read-a-Thon helped thousands of schools and students to raise over $30 million in donations. Their platform has tracked over 30 billion reading minutes by students who have used the platform to earn donations.
In this episode, Howard explains:
- How Read-a-Thon has impacted literacy in the US in a material way as they reach more schools, students, and donors
- Why they changed their business model from pledge-based to one-time fundraising
- How he experimented with many business models in school fundraising before starting Read-a-Thon
- Why he didn’t sell the company to a private equity buyer that had an offer on the table
- The power of specialized focus on elementary school fundraising vs. being a generalized platform for any type of fundraising
- Why he is constantly testing, improving, and optimizing everything inside the business and in the customer experience
- What he learned from the previous 6 companies he created and sold before starting Read-a-Thon
For more details and the full interview transcript, go to practicalfounders.com/podcast.
Scott Pickard didn’t know he was embarking on a 15-year software entrepreneurial journey when he signed on to manage a horse veterinary practice in Calgary, Canada. But they had built some internal software to help them manage their large practice that drastically improved their business results. Soon other horse vets wanted their HVMS software and the Business Infusions software business was created with Scott leading the small team.
Business Infusions grew steadily without big budgets, big funding, or a big team since 2006. Equine (horse) veterinary and hospital practices all over the world heard about their software and lined up to buy it. Now Business Infusions powers over 400 sizable veterinary practices all over the world. The company was acquired for cash by Merit Holdings in 2021 to run as a standalone company to expand its solutions to continue serving its clients.
Scott and his dedicated team weren’t in a glamorous industry with fancy modern technology, SaaS best practices, and big funding. They just served their loyal veterinarian customers and built a reputation in their tight-knit community for dedication, support, and focus on equine vets who have specialized needs.
In this episode, Scott explains:
- How their popular HVMS software was first created for internal use by a successful horse veterinary practice in Calgary, Canada
- How they grew steadily and efficiently with vet-to-vet referrals by their existing customers
- Challenges with board members who know their industry but weren’t savvy about the software business
- How Business Infusions grew to be the global market leader for large equine veterinary practices around the world
- The process of how they were acquired in 2021 and what happened to the company after that
Find out more and read the full interview transcript at practicalfounders.com.
Josh Cameron and three university friends started a scrappy software company in Brisbane Australia just after graduating. They had run the popular college bar where they discovered there was no simple software solution to track, onboard, and schedule hourly employees. They started Tanda in 2012 and it grew into a successful workforce management software company in Australia —without any outside funding.
The four founders moved to Chicago in 2019 to expand their North American business. Their product worked fine in the US, but sales, marketing, and operations all had to be rebuilt, which took years to figure out. They acquired the Workforce company and took on that brand and domain name outside of Australia.
Now Workforce.com is a leading workforce management software company that helps improve time and labor management for shift and hourly workforces. Their 130 employees serve 6,000 customers in 80 countries with employee scheduling, time and attendance, employee engagement, analytics, and automated compliance.
In this episode, Josh explains:
- How he and his university friends chose to start a scrappy software startup instead of taking big jobs after they graduated
- How they bootstrapped and grew their company in Brisbane in Australia for 5 years before the founders moved to the US and settled in Chicago to expand their North American business
- How they compete and win in a crowded marketplace against bigger competitors
- The growing pains they experienced growing from a small team in Australia to a global organization with 130 employees with offices in three countries
- The benefits of being frugal, growing at a steady pace, and not taking big VC funding
- Why they bought a 100-year old company to get the Workforce.com domain name and brand
Check out practicalfounders.com to read the full transcript from this episode.
Joe Griffin recently left his job of 8 years as co-CEO of ClearVoice, a company that he and co-founder Jay Swanson started in 2014 out of their digital marketing agency business in Phoenix, Arizona. ClearVoice was acquired by Fiverr in 2019 and has been operating as an independent subsidiary since then. Fiverr is now a large public company with a global reach.
ClearVoice was created in the fast-changing web search marketing industry in 2014 out of the need from larger companies for high-quality content to drive their organic website traffic. Joe and Jay previously ran their search marketing agency iAcquire and used profits to self-fund the first ClearVoice platform. They eventually raised a small amount of practical outside funding, including a seed funding round of $1.5M and venture debt of $2M.
ClearVoice is now a leading platform for brands to hire industry-savvy experts to write useful content that is branded for their communities and customers. Thousands of brands and over 10,000 industry specialist creators use ClearVoice to drive organic marketing efforts with high-quality content.
In this episode, Joe explains:
- How he had created and sold previous internet marketing agencies and technologies before creating ClearVoice
- The difficult transition of creating and funding the ClearVoice marketplace out of an existing services business
- The acquisition by Fiverr before they went public in 2019 and how they operated as an independent subsidiary after that
- Their practical funding with self-funding from their services business, a little angel funding, a small $1.5M seed investment round, and then venture debt before being acquired
- How he led ClearVoice with a co-CEO and how they worked on all big decisions together
Find all the episodes and resources at practicalfounders.com.
John Francis is a general partner at Stout Street Capital, a venture capital fund based in Denver, Colorado. Stout Street has made 70 small seed and pre-seed investments in software startups outside the big tech centers in North America.
Unlike big Silicon Valley VCs, almost half of Stout Street's investments are in practical startups that have reasonable valuations, sustainable growth models, and won’t need more outside investment before they exit.
In this in-depth interview with a “practical funder,” John explains the ROI math of professional venture investors and reveals how they think about investing. John also has great insights on how founders should think about raising money, or not, in the first place.
In this episode, John explains:
* The basic investment math that a seed-stage venture fund manager needs to deliver the expected return to their “limited partner” investors
- What kind of investment valuation and eventual exit outcomes are required to raise institutional capital
- When a practical founder shouldn’t raise VC funding and how they should be thinking about taking outside investment capital
- How “practical VC investing” is different than traditional moonshot VC investing and why founders need to be clear about which kind of funding they want
- What’s happening in valuation for investment and acquisitions in 2022 compared to 2021
Find all the Practical Founders Podcast episodes at practicalfounders.com.
Zach Moreno was a full-stack developer and coding instructor in Northern California in 2015 when he discovered audio podcasts. There wasn't a remote podcast software for recording high-quality audio over the Internet, so he decided to create one. He and his childhood friend Rock Felder started working on their product and startup idea while they still had full-time jobs, with Zach as the CEO and CTO.
Now Squadcast is one of the leading podcast recording studio platforms used by tens of thousands of audio podcasters all over the world, including me. Squadcast has since added high-quality video recording for YouTubers and other creators to easily generate professional-quality video content without using a professional studio.
With 15 employees and over 10,000 customers, Squadcast is growing steadily and scaling up, but they are still a bootstrapped company with no outside investors. This is unusual in such a fast-growing market like podcasting tools and also because the co-founders live in the heart of big VC funding—Silicon Valley in Northern California.
In this episode, Zach explains:
- How they prototyped their idea and launched their MVP at a podcasting conference before it was really ready
- Why his timing was perfect to solve this problem with the explosion in podcasting and technical changes in browsers
- How he gets advice, support, and insights as a first-time CEO by reading books, meeting with VCs, and participating in a bootstrapped accelerator called TinySeed
- How he thinks about bootstrapping in Silicon Valley and why he hasn't raised outside funding so far
- What he thinks the future looks like for audio and video content creators and how the market will change as it matures
Find other Practical Founders Podcast episodes and get my weekly email at practicalfounders.com.
Karl Swannie was a geographer working in the scenic city of Victoria, British Columbia, Canada, when he started analyzing social media data based on location. He quickly saw there was valuable real-time information that was not being used, so he started Echosec Systems to find a practical use for those insights.
After several years of experiments and hard startup lessons learned, Echosec finally shifted from being an inexpensive news/insights tool to a comprehensive threat intelligence platform for large organizations.
Echosec Systems is now a leading open-source intelligence service (OSINT) that uses publicly available information (PAI) from social media and other sources. They help public and private organizations improve situational awareness and identify threats using geographic insights with real-time data.
Echosec was partially sold to a "search fund" called The Tusker Fund in 2020 and Jeff Oldenburg came in as CEO to scale the company, which he did. In 2022, Flashpoint acquired Echosec completely and the business continues to grow.
In this episode, Karl explains:
- How they started as an inexpensive B2C solution and then pivoted to large B2B deals with big organizations
- What it's like to be a Canadian software company selling a threat detection service to large organizations around the world
- How they finally started to scale when they focused on the largest customers with the biggest needs
- How he worked with a private investor to start the company but used venture debt to grow it when they were profitable
- What a "search fund" is and why this was a great fit to partially acquire the company and bring in an experienced CEO
- What it was like to sell the company and not be the CEO-in-charge any more
- What he learned about himself in this journey that he is applying to his next venture
Find out more at practicalfounders.com.
Brad Redding calls his first startup a "successful failure." It didn't end well, but he learned several very important lessons that helped him be more successful with his second startup, Elevar. Now the bootstrapped SaaS company is growing steadily with 45 remote employees. And Brad is learning fast to be a capable CEO of a larger SaaS software company.
Brad's deep experience with e-commerce advertising data and conversation tracking analytics helped him find a problem to solve. He and his cofounder funded the development of the first product by providing consulting services to the same customers they were trying to serve with their new software product.
It took three years before they found product-market fit and started to grow steadily and profitably. Now Elevar is a growing SaaS business that helps 6,500 e-commerce and direct-to-consumer brands that use Shopify to ensure the accuracy of their conversion tracking data and analytics. Brad has never raised outside funding and he has no intention of raising money or selling the company.
"I am certainly evolving as a leader through reading. Leaders are readers. And through coaching and through surrounding myself with other leaders who have grown companies to the size we are growing into.
"The way I look at is that no longer can I just assume that I'm going to figure it out on my own. I need to invest in myself, invest in my leaders, invest in my brain and my habits, and improve everything. Not necessarily all at once, but over time.
"It's all about the team. You build the people and bring in the right team and the team is going to build the business and that business is going to evolve. If you just stay in the game long enough and have the right team and the right people leading, you'll follow the customers and solve their problems."
In this episode, Brad explains:
- The painful lessons of his first startup that he was able to apply and do differently with Elevar, his second startup
- Why he bootstrapped Elevar instead of raising VC funding
- Why he doesn't think of products and services as two different things when solving customers' problems
- How he is intentionally investing in self-development to learn to be the CEO he needs to be to continue to grow the company
- Why it took three years to find product-market fit despite being a domain expert in his industry
Learn more at practicalfounders.com.
Daniel Yuabov was a 22-year-old IT manager in New York who wanted to buy a new car. He was so frustrated with the buying experience that he started a software company called Carvoy to make it easy for car buyers to find, buy, and finance a new car online. He grew the company for 5 years—without VC funding—and sold it to a giant Fortune 500 company in 2020.
Daniel quit his job in 2015 to build Carvoy's first product using developers in Ukraine. It allowed consumers to choose a new car online and then buy it easily from a dealer. Their first version was interesting to consumers but resisted by most car dealers. Their second solution had them manually arranging the car purchases behind the scenes for their growing crowd of online buyers.
It wasn't until they started automating every step in the car buying process, including choosing a car, getting a confirmed best price from dealers, pre-approved lending, and delivery that they started to sell thousands of cars. They pivoted from a marketplace with transaction revenue to selling it as a SaaS product to car dealers. They grew faster and were acquired by a major car-financing lender for an undisclosed sum in 2020.
In this episode, Daniel explains:
- Why did he quit his job to build an online solution after having a frustrating car buying experience
- How many "gruesome" pivots and experiments they tried in three years before they finally created an amazing online car-buying solution that dealers were excited to pay for
- How he financed the startup phase with his savings, a loan from his father, and credit card debt
- Why he chose to sell his startup to a big industry player rather than get venture funding
- How he dealt with the long process of selling to a large financial lending company and what it's like to work there now
- What it felt like to sell his company for life-changing wealth and then realize the money wasn't the biggest prize
Melissa Kwan created her first software company in 2014 and then sold it in 2019. It was extremely difficult to start and even harder to grow, but it's how she learned what not to do in her next startup and what was really "non-negotiable" in her life. Now she's a nomadic world traveler and the founder of a growing software business.
Melissa started Spacio to provide a technology solution to high-end residential real estate agents to capture visitor names electronically at open houses. It took years to find the right features that someone would pay for while tapping out her savings--and her family support. She sold the business in frustration to find a better business idea and to stop sacrificing everything for her business.
Melissa started her second software business, eWebinar, to solve a painful problem she faced while selling and supporting software. eWebinar is an automated webinar platform that provides interactivity and real-time chat support for software companies. Her business also supports her personal priorities, including traveling around the world and working from anywhere.
In this episode, Melissa explains:
- The hardest lessons she learned from her first software company which helped her design her second startup in a different way
- Why she was frustrated selling to the real estate market and why she chose to serve software companies with eWebinar
- The pervasive myth of big funding, unicorn exits, and ego-driven ecosystems that ultimately rob founders of their own freedom and control
- What success means to her and how she is creating her business to support her version of happiness
- How she bootstrapped eWebinar with small investments from friends and how she is growing it profitably each month
- Why a "5% better" product design and customer experience "that just works beautifully" is their key competitive advantage
- Why nobody wants to talk to a salesperson just to get a demo of a business software product
Learn more about Practical Founders at https://practicalfounders.com.
Seth Radman created, grew, and sold two music app startups in his twenties. A saxophone player in his college marching band, Seth was passionate about helping musicians and school band directors to improve how they learn music using technology.
Seth was the founder and CEO of Crescendo, an interactive music trainer that provides real-time performance assessment feedback using acoustic pitch detection and machine learning as a mobile app. With a little angel funding, Crescendo grew to over 1M users and 7,000 schools before being acquired by Ultimate Guitar in 2018.
He was also co-founder and CEO of Upbeat, a bootstrapped startup providing a virtual music collaboration platform for school music departments. When schools shut down during COVID, Upbeat allowed musicians to rehearse and perform music virtually with others in real-time without sound delays. Upbeat grew to over 200,000 users in 12 months and was purchased by 5,000 schools before being acquired in 2021 by MakeMusic.
"Having a company acquired seemed like this big elusive goal that every founder wants to achieve. And then I did it. And then I wasn't sure what to do next at all, I was completely shocked on the first day," Seth says.
"I say it was one of the happiest days of my life when I saw the money hit the bank. And then the day after, that was probably one of the most depressing days of my life, because I was like, whoa, what do I do now? I definitely thought there was a little bit of loss of identity for me going through that.
"And I spent the next several months kind of doing nothing. I was honestly just depressed. I just felt super lost and was not sure what to do. And that was a really tough period. "
In this episode, Seth explains:
- How he had hundreds of product ideas, did hundreds of customer interviews, and ran dozens of experiments to eventually find problems that customers would actually pay to solve
- What product-market fit really means to him and why it's so important to experiment before you invest lots of time and money
- Why he felt that he wasn't the right person to scale up his first company and the deep anxiety he felt when he successfully sold it
- How he's managing the emotional ups and downs of being an entrepreneur now after experiencing mental health challenges
- How he leveraged an existing customer base and channel to rapidly grow his second startup as COVID lockdowns created an acute problem in the music teaching industry
- How he developed a strong persistence habit as a musician that helped him do hard things every day that he didn't want to do
Dougal Cameron created Golden Section to provide support and practical funding to SaaS founders with deep experience in select vertical markets. Their founder-first approach is different than the traditional VC or private equity investment model which often doesn't work out well for founders in the end.
Dougal's family had been investing in software companies for over 20 years through their Houston-based family office. Now Golden Section includes a founders studio for venture development, a world-class software product development service, and optional equity funding for B2B SaaS founders with deep domain experience in their industries.
This is an example of one of many possible ways that funding can be practical and helpful for founders who want to accelerate growth but don't want to play the unicorn-hunting grow-or-die game required by most venture capital investors.
"Our capital needs to look very different than the traditional venture capital side, where 66% of the time venture-backed founders make nothing when their company sells. And that's companies that get to an exit," says Dougal.
"I think that's a horrible statistic that really reveals some of the problems in the venture capital industry. It doesn't make a ton of sense for founders who see a clear problem that they know very well and they know people are going to buy their solution."
In this episode, Dougal explains:
- Why traditional venture capital investment is not a good fit for certain kinds of software businesses
- The hard lessons he has learned from years of investing in software companies and running software companies himself
- How they have designed their investment model to support founder-friendly exits where everyone can win: founders, investors, employees, vendors, and customers
- How they provide deep support for the founders they partner with, including software development services, growth advisory, and execution advice in every aspect of the company
- What Golden Section does to support the brutally hard emotional journey that all founders go through as they grow their companies
Find the show notes for this episode at practicalfounders.com.
Sean Meister was a sales professional and leader with a successful career selling hospital and medical supplies before he left to join his long-time friend who had a vision for a new software company serving smaller trucking fleets with simple GPS-tracking fleet management software.
Sean was a co-founder and COO of M2M in Motion, a self-funded software company based in the Chicago area. Sean wasn't the trucking industry expert, the crazy entrepreneur, or the visionary salesperson. He provided the savvy help to get the company started and the operational leadership to build a scalable sales team, reliable product development, and quality customer operations.
M2M in Motion was bootstrapped with founder funding, then customer funding (revenue), to grow to over $5M in revenues before being acquired in 2021 by a larger vehicle telematics company, AAMP Global. M2M in Motion allowed small and mid-sized fleets to track their vehicles with a simple software solution and GPS-tracking devices.
"I think another reason we were successful is that we identified our ideal customer profile early, and we owned it, and then we really targeted that. In the beginning, you're just so desperate for anything, that you don't realize you're actually hurting yourself," Sean says.
"I think that was a big lesson for us. When you can start saying NO is when your trajectory starts taking off."
In this episode, Sean explains:
- Why he quit his successful sales career to join his long-time friend who had an idea for a software startup in the transportation technology industry
- How long it took to get to breakeven revenue after spending their personal savings to get the company started
- How the US "ELD" government trucking safety mandate helped them grow fast
- How they introduced device financing to bundle the GPS-tracking hardware and software for a simple monthly fee
- How they successfully competed in a very active, well-funded industry as a small, bootstrapped company by keeping things simple and narrowing their focus
- How their multi-channel growth strategy included "white-labeling" their software to strategic reseller partners and how one of those relationships led to their acquisition
Check out the show notes and links for this episode at practicalfounders.com.
Thomas Brown creatively bootstrapped his software company and ran it as a very small "lifestyle" business before committing to growing his SaaS business with a larger team.
Thomas was an independent insurance claims adjuster in the 1990s in New Orleans, Louisiana before quitting his job to start one of the first insurance claims management software companies called ClickClaims. It grew slowly and profitably as a very small company for over 10 years before Thomas sought help from advisors to see how he could grow to the next level and learn to be a real CEO of a bigger SaaS company.
E-Claim is now a steadily growing vertical SaaS business with 18 employees and over $4 million in ARR. They have helped independent insurance adjusters and insurance carriers process over 2 million claims with their ClickClaims product since he started the company in 1999.
"I know this sounds cliche, but I didn't get into this for the money. I got into it because I'm a guy from South Louisiana who's been through a bunch of hurricanes and knows the horrors that people go through. And I wanted to make it better. So you reach a point in the business where you start to think about not what it means for you, but what it means for others. What can you do for your employees and their careers? What other charities can I go and support with this money someday? And then you think about it, and you say, you know, hell, I want to double it, because I could do a lot of good with a lot more money."
In this episode, Thomas explains:
- How he started his company and built a software solution after experiencing a massive industry problem himself
- How he grew a $4M+ ARR SaaS company without funding with just 50 customers
- Which creative side businesses he started to generate enough cash to build and start his software company
- How trusted business advisors helped him gain the knowledge and the confidence to be the SaaS CEO and team leader required to keep growing his company
- Why he is inspired to make a bigger impact with his employees and in his community by continuing to grow his business
Nick Santora bootstrapped Curricula for 4 years with his co-founders before raising $3M in practical funding and then getting acquired in 2022 for $22 million.
Nick and his co-founders quit their jobs to build innovative story-based education courses and a single-purpose learning platform for cybersecurity security awareness training. Nick had found a big hole in the cybersecurity market while working as a cybersecurity trainer in the electric utility industry.
Curricula features fun and engaging training content, which was the opposite of the typical "death by Powerpoint" training that users ignored. Now Curricula is a powerful platform that allows companies to create their own engaging content and then measure custom training results.
When they almost ran out of cash before revenues grew, Nick says. "I would do anything I could do to keep this heartbeat going instead of getting an investor to run our future. Once that starts happening, I knew it was going to start cascading into desperation. And I wanted to hold the cards in our hands as long as we could."
In this episode, Nick explains:
- How he saw this problem as a cybersecurity trainer in the electric utility industry
- How he and his cofounders quit their jobs to build this platform while living on savings and no salary
- What happened when they ran out of money three times while pivoting and experimenting to find their growth path
- How they used freemium PLG tactics to compete with an aggressive competitor who had raised $80 million in VC funding
- How his last-ditch promotion test with LinkedIn advertising created their primary efficient customer acquisition tactic
- Why he didn't raise money from VCs but instead raised from a practical investor who had grown and sold a bootstrapped company
Check out all our podcast episodes at https://practicalfounders.com.
Jeremy Clarke created, grew, and sold his software company in a most unusual and successful way:
He grew WebMerge to $4M revenue by just himself in 6 years before hiring his first and only employee, a strategic sales rep. It's an incredible "bootstrapped unicorn" success story that ultimately was worth $100M when he sold WebMerge in 2019.
WebMerge was an online service that automates document creation to automatically fill in any documents with merged data from any source. WebMerge automatically generates PDF and Microsoft Word documents. Think of it as "mail merge for the web."
Jeremy's first employer, Formstack, ultimately acquired WebMerge to bring Jeremy back to the Formstack team and renamed the product to Formstack Documents.
In this episode, Jeremy explains:
- How he came up with the idea and pitched it to his employer before building it on his own
- How he grew revenues to $1M ARR before he quit his day job as a full-time software programmer
- What it was like to grow a $5M+ ARR SaaS business without any other employees or Slack groups or constant meetings
- How many years in a row he raised prices before he found the right price
- How he grew awareness and conversion efficiently by integrating with other apps and appearing in their add-on marketplaces
- What it was like to sell his company to a private equity (PE) buyer in two phases
Check out all our episodes and articles at https://practicalfounders.com.
Luke Hohmann was an engineering and product management leader at Silicon Valley startups before he became an acclaimed author and speaker in the enterprise software development world. He used funding from his consulting business—plus revenue from his first big customers—to build a new software product called Conteneo.
Conteneo was enterprise collaboration software that enabled the biggest companies to engage their leaders in new ways to make much better decisions about product portfolio investments. Started in 2010, this idea came out of several of the gamified collaboration exercises Luke used in his consulting business. Conteneo software customers include Adobe Systems, Cisco, Emerson, HP, Rackspace, and Reed Elsevier.
As the Conteneo software business grew, their consulting business shrank. Eventually, Conteneo was acquired by a strategic partner who was also a leader in enterprise software development and innovation, Scaled Agile. Conteneo was rebranded as SAFe Collaborate.
"One of the important lessons for any practical founder is this: Instead of thinking of investors as your first source of funding, look to your first customers," Luke says.
In this episode, Luke explains:
- How his biggest consulting client asked him to build their proven collaboration process into a SaaS software product.
- How he funded the initial development and subsequent features with creative customer contract commitments.
- Why his little, bootstrapped company was successful in selling to the largest software companies in the world in the heart of Silicon Valley.
- The bet he won with a funded founder friend about who would end up with the biggest prize when they sold their companies.
- The crazy story of how a well-known business author offered to invest in his company over a handshake at a conference.
- Why he thinks founders should have a structured advisory board and pay them instead of just having informal advisors.
Check out all our episodes and articles at https://practicalfounders.com.
Steve Gelley created two successful businesses and learned important lessons before he and a cofounder self-funded a third startup that was acquired in only 18 months for a big prize.
Steve started his entrepreneurial journey by buying, improving, and then selling CPA accounting services firms in the Eastern U.S. Then he grew his first VC-funded tech startup, Xendoo, to innovate in the small business accounting services space.
He exited Xendoo and worked with a partner to fund and create a new startup called wemlo to automate the manual process of processing mortgage loans for mortgage brokers. Only 18 months from starting, including four strategic pivots, Steve and his cofounder, David Rogove, sold wemlo to a strategic buyer owned by RE/MAX.
Steve says, "Nobody tells you that founders end up spending so much time on funding and the optics of the dog and pony show that no one's running the business. It's actually counterproductive."
In this episode, Steve explains:
- Why he sold his interest in his first startup when the company achieved its first VC funding
- How he and his cofounder built a market-leading solution for a massive industry with a small team
- What the true opportunity cost of raising VC funding is for founders growing vertical software companies
- The simple math that showed him raising big funding would not be better for the founders
- What it takes to design revolutionary software with automated processes that revolutions
- Why he says "timing is the luck factor in a business," especially when you exit a business
- Why money from investors won't solve all your problems and often make things worse
Check out all our episodes and articles at https://practicalfounders.com.
Hamid Shojaee is a technical founder and serial entrepreneur who created several software companies and dozens of products in the last 25 years. He sold his two software companies in 2021—Axosoft and Pure Chat—and now is an active investor and has a new startup to keep him busy.
Axosoft was popular project management and bug-tracking software for developers that he bootstrapped to launch in 2002. It grew profitably for years until it met stiff competition despite active efforts to grow. Dozens of product experiments finally produced a hit, the popular software GitKraken.
In this episode, Hamid shares some hard lessons learned:
- How he and his team experimented to test new product ideas and don’t invest until they prove real user traction (DAUs)
- The challenges of raising money from investors who want faster revenue traction too early in the product-led growth cycle
- The challenges of not being the dominant leader in your market in the long-run
- Selling one business to a strategic buyer without help: selling the other business to a financial buyer using M&A investment bankers
- The modest changes in his life after selling two companies for life-changing wealth in 2021
- Why he’s starting and building another software company
Check out all our episodes and articles at https://practicalfounders.com.
Dan Jaffe is the founder and CEO of LawLytics, a popular website marketing platform for small law firms. Dan was a practicing lawyer before he became an internet entrepreneur with his first venture, which he sold before he started LawLytics in 2012. LawLytics was acquired by the Australia-based Smokeball-LEAP-InfoTrack Group in 2021. Dan is still growing LawLytics as its leader of the acquired company.
LawLytics is a website platform for small law firms who want a successful website but don’t want to overpay an agency or struggle with software that isn’t built for them. LawLytics has templates, designs, and lead-generation tools specifically designed for lawyers to generate business efficiently.
In this episode, you’ll hear how Dan:
- Transitioned from being a practicing trial attorney to an internet entrepreneur and SaaS founder
- Created and sold his first business, an online law firm directory
- Self-funded LawLytics then added small investments from angels and a local seed fund
- Found a technical co-founder by networking in San Francisco
- Competed with bigger competitors to deliver a successful website marketing platform for attorneys
- Grew to over 30 employees and contractors, then successfully sold the business in 2021 with the help of an M&A investment banking firm
Check out all our episodes and articles at https://practicalfounders.com.
Rafael Zimberoff was CEO of ShipRush, a software company he founded in 2001, then grew, and eventually sold in 2017 to Descartes Systems Group for $17 million. Rafael started ShipRush as an add-on product for popular CRM and accounting software and was a pioneer in shipping technology for small businesses.
ShipRush is now a comprehensive shipping platform for small ecommerce providers so they can easily process shipment orders and carrier labels for USPS, Fedex, and UPS. ShipRush integrates with popular ecommerce and accounting platforms, including Shopify, Amazon, eBay, Quickbooks, and more.
In this episode, you'll hear how Rafael:
- Boostrapped his tech services company to fund their first software product then grew without outside investors
- Created a popular add-on software product for bigger software ecosystems as an efficient way to find customers and grow revenues quickly
- Managed complexities of being an early pioneer in shipping technology working with large carriers like Fedex, USPS, and UPS
- Ran a profitable software company for more than 15 years with a small and amazing team
- Learn hard lessons then succeeded in working with M&A investment bankers to sell his company
Check out all our episodes, articles, and resources at https://practicalfounders.com.
Jonathan Cronstedt, also known as JCron, was the president of Kajabi software from 2016 through 2021 as he helped the company grow past the early startup years. JCron is a savvy entrepreneur, digital marketer, and sales leader who shares the story of the bootstrap founding of Kajabi through getting $550M in venture capital funding in 2021.
Kajabi is a leading "knowledge commerce" platform for experts and entrepreneurs to market and sell their expertise as online content. Started in 2010 to help early internet marketers and small business experts deliver videos and training, Kajabi has helped over 30,000 creators to sell their expertise and expand their businesses.
In this episode, you'll hear how Kajabi:
- Had $1M+ annual recurring revenue the moment the product launched after coding on nights and weekends for a year to create the first product
- Founder and CEO Kenny Rueter grew revenues ahead of expenses to stay profitable from day 1 to over $50M in revenue 10 years later
- Grew as a modest software business for the first 5 years, then rebuilt the product to grow the business much bigger as the market eventually grew up in the next 5 years
- Kept a fanatic focus on their target customer (called “Kajabi heroes”), a powerful and easy-to-use product, and a well-defined culture
- More than doubled in size in 12 months during the COVID crisis when online courses and content became a global focus
- Waited 10 years to take any outside investment in 2020 that helped bring the expertise to scale, then raised $550M at a $2B valuation from VC investors in 2021.
Check out all our episodes, articles, and resources at https://practicalfounders.com.
Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started as a videographer before joining a friend in 2006 to create a scrappy software business that made inexpensive photo-presenting and sharing tools for photographers.
The Showit company was created when Todd took one of their two products and half the small team in 2010 to spin off Showit as an independent business. The small revenue from the small customer base and his own savings allowed them to rewrite Showit for the cloud and then continue their fanatic customer focus to keep growing every year.
Now Showit is used by 35,000 designers, photographers, and small businesses as their website platform using its elegant “Photoshop-like” no-code visual builder. The Showit company is growing quickly every year and is profitable, yet Todd has no interest in taking outside funding or selling his beloved company.
In this episode, you’ll hear how Todd and the Showit team:
- Spun off Showit from a small software company, then rewrote the software from old Flash technology to new cloud software
- Serve and love their customers to create a fanatically loyal community that is expanding quickly without expensive marketing
- Recruit, engage, and empower their employees in creative ways that no funded software company ever would
- Never think about external funding or selling the company despite the company’s extraordinary value and potential
- Started with a fanatic niche focus on an underserved community and then expanded its market as the community grew
Check out all our episodes, articles, and resources at https://practicalfounders.com.