The aSaaSins Podcast: Recent Episodes
Justin Vandehey
The aSaaSins Podcast helps first time founders build technology startups and take their companies from 0 to 1. You'll hear real stories from founders on their experiences on topics like raising seed capital, finding product-market fit, acquiring customers, building a team, and scaling their businesses. By listening to this podcast, you'll not only become a stronger entrepreneur, you'll also become an aSaaSin.
Most voice AI startups today are thin wrappers on someone else's models. Ayooluwa Odemuyiwa went the opposite direction and built the entire stack.
In this episode, Justin sits down with the CTO and co-founder of Aethex AI, who along with co-founder Mariama is building the voice layer for emerging markets across Africa and the Middle East. This is the AI that banks, call centers, and telcos use to reach the customers a human team never could, and it's already running 17,000 calls a day.
Ayooluwa takes us through her path from Caltech physics to Meta to Stanford to founder, and unpacks the decision that defines the company: in her markets, you aren't competing against other software, you're competing against the cost of human labor. That single reality is why Aethex owns everything from data collection to model serving to deployment, so they can pull every lever on cost and latency.
We also get into why building for the harder market first reveals things a Western-first founder never sees, how the forward deployed engineer became their most valuable role, and why in a market this new, what you're really selling is trust.
A conversation about infrastructure, conviction, and betting on the markets everyone else overlooked.
Catherine Blackmore has spent nearly two decades building the programs that wrap around technology, from the early days of customer success in 2007 to her current role as Group VP of Customer Programs and Employee Success at Oracle. In this episode she sits down with Justin to unpack what the discipline got right, what it got wrong, and what survives the shift to AI.
Catherine makes the case that the high touch model was right all along. It buys a company time to build its moat. But the obsession with the golden record, bridging every data silo, and the red, yellow, green health score was a costly detour, because customers live in their own tools and every account ends up yellow anyway.
From there the conversation turns to the question on everyone's mind. If agents can scale the work, what is left for humans? Catherine's answer is that human connection becomes the scarce, valuable thing, and the next generation of CS leaders will manage teams of agents while doing the relational work no agent can fake. She also reframes customer advocacy as the true end state of customer success, the double funnel where your strongest customers become your most believable salespeople.
She closes with the career advice she is giving her son as he enters a reshaped workforce. Adaptability beats raw talent, the sum of your experiences equals your existence, and you should always watch the game within the game.
What we get into: The high touch model and defending the moat Why the golden record and the red, yellow, green health score never delivered Human connection as the new scarcity model The CSM of the future leading a team of agents Customer advocacy and the double funnel Outcomes over seats and consumption Career advice for the next generation entering an AI-shaped workforce
Guest: Catherine Blackmore, Group Vice President of Customer Programs and Employee Success, Oracle
Andy Mowat has run RevOps at four unicorns, and between every role he's gone out and built something new. His latest is Whispered, an AI platform that helps top GTM execs build their careers through shared insights, warm introductions, and access to the roles that never get posted.
In this episode, Andy and Justin get into why the entire GTM tech stack is heading for a two-year rebuild, what the move to a data-warehouse-first model means for RevOps teams, and why smaller companies are suddenly more nimble than the enterprise. Andy shares hard-won lessons from scaling Culture Amp, including the speed-to-lead system he built around time-critical leads and the market-maturity question he buried in the win-loss forms. They also dig into whether the fractional exec wave is real, why thoughtful gifting and distinctive events still beat automated outbound, and what it actually feels like to run a proactive job search at the VP level for the first time.
A candid conversation between two friends about category strategy, positioning, and building a career in go-to-market when the ground keeps shifting.
Buzzsprout Chapter Markers
00:00 — Intro: how Justin and Andy met around Culture Amp
01:40 — Andy's background: RevOps at four unicorns, and why he keeps building
03:30 — Founders as a hiring profile, and the trap of "ambiguous roles"
05:30 — Rebuilding the GTM tech stack: data warehouse first, the semantic layer, and two years of turmoil
07:00 — The give-to-get ratio and why AI-era outbound still comes down to better emails
08:30 — Strategic gifting, distinctive events, and the Wisconsin business school cold open
11:00 — Podcasts as relationship engines, not just content
11:30 — Inside Culture Amp: 180 events a year and the speed-to-lead system
13:00 — The multi-prospect demo experiment, and the market-maturity question that predicts a category's breakout
14:45 — The fractional exec wave: real shift or euphemism for "between jobs"
16:15 — Why early-stage marketing needs people to "grok what you do" before top of funnel
18:00 — What's next for Whispered: the network, the community, and the roles that get whispered
Justin sits down with Nils Vinje, business growth guide and longtime customer success leader, to talk about the single biggest thing holding most growing companies back: everything still depends on the CEO.
Nils spent the early part of his career on the leading edge of the customer success movement — convincing his first employer to ditch the "account manager" title back in 2011 — and has since coached hundreds of CS and CX leaders through the challenge of making their function legible to the rest of the organization. These days he works with CEOs and their leadership teams using the Pinnacle system, a five-principle framework built around people, purpose, playbooks, performance, and profit.
In this conversation, Nils and Justin get into what running a CX org teaches you about leadership that no other function can, how to read the label from outside the bottle, and why the hardest decisions in any company are usually the ones everyone already knows need to be made.
He also shares what he'd ask anyone standing at a crossroads in their career — and why the answer has nothing to do with money.
Chapters
[00:00] Intro and What Nils Does Now
[01:42] What Leading a CX Org Teaches You About Leadership
[03:30] The Single Biggest Challenge Every CS Leader Faces
[05:01] Who Nils Works With and When to Bring in Outside Help
[07:08] The Pinnacle System — Five Principles for a Well-Oiled Machine
[09:38] Delivering Hard Truths with Grace
[11:00] The People Problem Most CEOs Won't Solve
[13:08] Why Being Inside the Bottle Kills Objectivity
[14:29] The First Question Nils Asks Anyone at a Career Crossroads
[16:25] What's Next for Nils and the Growth Bottleneck Blueprint
[18:34] Never Stop Adding Value
Justin sits down with Sanjay Pal, Worldwide VP of Professional Services at IBM, to explore what it really takes to lead services at global scale and why the role is more strategically important now than ever before.
Sanjay draws on his journey from Cisco to Accenture to IBM to break down what has fundamentally changed about services delivery in the AI era, and what has stayed the same. He shares how IBM thinks about standardizing delivery across 16 global markets without sacrificing client experience, why the forward-deployed engineer model is gaining momentum, and how professional services leaders need to evolve from deployment executors into trusted business advisors.
He also shares a personal story about his father, who wrote 52 books with pen, paper, and a stack of research clippings, and what that means for what's possible now.
Chapters
[00:00] Intro and Sanjay's Path to IBM [02:33] What's Changed in Services, and What Hasn't [05:00] How AI Amplifies Delivery Without Replacing Judgment [08:01] Standardization vs. Customization at Global Scale [10:38] The Evolving Role of the Services Leader [12:44] Forward-Deployed Engineers and Leading with Services [15:02] Breaking Down Silos Across Pre-Sales, Implementation, and Post-Sales [16:05] What's Top of Mind Heading into 2026
Justin sits down with Jessica Chiew, Global Head of GTM Strategy and Operations at Canva, to unpack what it really takes to evolve from a beloved PLG product into a full-fledged enterprise sales machine without breaking what made it great.
Jessica shares how Canva navigates the complexity of multiple handoffs across a PLG-to-SLG journey, why time to value is everyone's job (not just CS), and how she's thinking about marrying product usage data, CRM structure, and conversational intelligence into something actually actionable.
Plus, both Justin and Jessica geek out on the AI and vibe coding moment we're all living through and why it changes everything for revenue teams.
Chapters
[00:00] Intro & Jessica's Path to Canva Justin welcomes Jessica and she traces her journey from Melbourne to San Francisco, through Asana, and into Canva's B2B buildout.
[02:57] Who Owns Onboarding and Time to Value? Jessica breaks down Canva's take on ownership across PLG and enterprise motions — and why success in the first hundred days is a team sport, not a CS problem.
[05:57] Moving Upmarket: What Changes (and What Doesn't) From solo users with credit cards to C-suite transformations with change management — how Canva's onboarding approach shifts dramatically as deal size grows.
[09:40] Using PLG Signals in an Enterprise World The Asana flashback: how rich end-user data and human relationship context can finally live in the same place, and what that unlocks for enterprise sellers.
[11:47] The Tech Stack Behind the Motion CRM alone isn't enough. Jessica walks through how Canva combines structured CRM data, product usage signals, and a full conversational intelligence database to build a real picture of account health.
[14:00] AI, Agents, and the Vibe Coding Moment Justin shares his own revelation using AI agents for GTM workflows, and Jessica drops that she recently vibe coded a weekly forecast interface. Neither of them is going back.
[16:21] What's Ahead for Canva GTM in 2026 Canva Create in LA, platform updates Jessica can't fully share yet, and the team's focus on becoming the gold standard for enterprise go-to-market.
Justin sits down with Allison Skidmore, Chief Customer Officer at Optimizely, the world's first operating system for marketing teams.
Allison brings a rich perspective shaped by stints at Adobe, Stackla, Gigya, and SAP across Asia Pacific before landing in the US to lead customer success at Optimizely. This episode explores how AI is fundamentally reshaping the marketer's daily workflow, what great onboarding looks like in an AI-native world, and what the CCO role must become as organizations race to stay ahead.
Episode Notes & Key Topics
1. Allison's Career Journey
- Started in SEM at a Sydney agency later acquired by Adobe, rode the wave of digital marketing's early SaaS transition.
- Spent six years at Adobe running customer success across Asia Pacific, building offshore teams and subscription services models.
- Moved through Stackla and Gigya (acquired by SAP nine months in), then scaled the CS role across all SAP lines of business in APAC.
- Joined Optimizely two years ago after reconnecting with CEO Alex Atzberger, bringing global enterprise CS experience to a fast-growing martech platform.
2. What Stays the Same in Customer Success
- The sales-to-CS handover friction is timeless: it never goes away regardless of company size or stage.
- Digital-first customer engagement (email, offshore teams, automation) has been a constant scaling challenge for decades.
- The shift from time-and-materials professional services to subscription models remains a dominant trend.
- Tech advancements create the inflection points: AI is today's example.
3. AI and the Marketer's Day-in-the-Life
- Allison paints a vivid picture: by 10 AM, an AI-enabled marketer has completed a full week's worth of work.
- Optimizely's Opal AI product is provisioned across the entire team, enabling agent building, workflow automation, and access to tools like Claude and Gemini.
- The opportunity is not just efficiency, it's the ability to pull forward backlogged work and shrink implementation timelines (e.g., from 12 months to 3).
- The companies moving fastest are the ones blocking calendar time to train their teams on prompting and agent-building, not just giving access.
4. Reimagining Onboarding and the Customer Journey
- Allison's framework: great onboarding is the seamless alignment of three channels, human-to-human touchpoints, email marketing, and in-product experience.
- Customers now expect to self-serve answers (just like asking AI instead of calling a mechanic), human-heavy onboarding alone no longer cuts it.
- Consistency is the key: the message the customer gets in the product, in their inbox, and from their CSM should be identical, no basic repeats, no skipped steps.
5. The Evolving Role of the CCO
- The C-suite fundamentals don't change: stay curious, solve problems, skate to where the puck is going.
- Today, the puck is AI. If you can't build an agent, you can't expect your team to.
- Allison is actively realigning roles, KPIs, and commissions around AI-native execution.
- The CCO who can't leverage AI to scale themselves and reimagine their business will become extinct, just like Blockbuster.
- Lego is the positive model: reinvention again and again.
6. What's Top of Mind for 2026
- AI continues to dominate, but the customer journey evolution is a close second.
- Consumers are shifting from Google to ChatGPT and similar tools, which means brands must optimize for GEO (Generative Engine Optimization), not just SEO.
- Personalization is entering a new era: every touchpoint, not just the website.
Brent Krempges, Chief Customer Officer at Gainsight, joins the show to unpack the next evolution of Customer Success in an AI-first world.
After 12+ years at Gainsight, from implementation to global pre-sales to CCO, Brent shares how CS is shifting from seat-based software to outcome-driven operating models. We dive into AI-driven health scores, renewal agents, sentiment analysis, and the looming “retention reckoning” facing AI-native companies.
Key Takeaways (Bullet Summary)* AI will elevate — not eliminate — the importance of services. * Floor-Deployed Engineers (FDEs) signal a return to high-touch value realization. * Health scores are getting smarter, but “watermelon accounts” will always exist. * Sentiment analysis from transcripts and email may replace traditional NPS. * Many AI companies haven’t hit their renewal reality yet. * Retention pressure is coming — especially for growth-at-all-costs AI startups. * Before deploying agents, companies must rebuild foundational lifecycle processes. * Think of agents as “50 interns” — would they know what to do?
In this episode of the Thread Podcast, Justin Vandehey sits down with Elizabeth Herbst-Brady, Chief Revenue Officer of Condé Nast, to explore how one of the world’s most iconic media companies is navigating transformation in the age of AI.
Elizabeth shares lessons from her career spanning media, advertising, and technology, including leadership roles at Yahoo, Snap, and Viacom, and explains why trusted brands, human creativity, and editorial authority are becoming more valuable, not less, as AI accelerates content creation.
The conversation covers how Condé Nast is using AI responsibly to enhance, not replace premium content, how revenue teams are being unified across advertising, commerce, subscriptions, and live events, and what it takes to lead teams through constant transformation with curiosity, accountability, and gratitude.
This episode is a masterclass in modern GTM leadership at the intersection of creativity, technology, and trust.
Chapters
00:00 – Welcome & Elizabeth’s Career Journey
From media and entertainment to technology and back to Condé Nast.
04:40 – Why Condé Nast, Why Now
The opportunity to lead revenue at an iconic, trust-driven brand.
07:30 – AI and the Future of Premium Content
Why AI can’t replace human creativity, taste, and editorial authority.
11:45 – Creation vs. Curation in an AI World
How Condé Nast separates content creation from AI-powered enhancement.
15:30 – Using AI to Improve Consumer Experience
Real examples from Bon Appétit and The New Yorker.
19:30 – Why LLMs Reward Credibility Over Volume
How AI changes the economics of SEO, expertise, and originality.
23:40 – Unifying Revenue Across Silos
Bringing advertising, commerce, subscriptions, and events into one revenue org.
27:50 – Leading Through Transformation
Elizabeth’s leadership framework: curiosity, accountability, and gratitude.
32:30 – What’s Next for Condé Nast & Premium Media
Why trusted brands will accelerate over the next 12–24 months.
Key Highlights & Takeaways
- AI should enhance content, not replace human voice or judgment.
- Trust, credibility, and editorial authority are premium assets in an AI era.
- LLMs reward expertise and originality, not volume or SEO tricks.
- Revenue transformation requires visibility, shared data, and cohesion across teams.
- The best leaders embrace constant change with curiosity and accountability.
- Premium media’s value proposition strengthens as information becomes noisier.
In this episode of the Thread Podcast, host Justin Vandehey sits down with Neal McCoy, VP of Customer Success and Professional Services at BigCommerce, to unpack where customer value most often breaks down after a deal is closed — and how companies can fix it.
Neal shares insights from nearly a decade building CS and PS at BigCommerce, explaining why customers don’t buy software to “solve problems,” but to make or save money. The conversation explores how unclear value realization creates friction during onboarding, why sales-to-CS handoffs fail, and how AI is reshaping customer success through better context, automation, and voice-of-the-customer insights at scale.
Key Takeaways & Highlights
- Customers buy software to make money, save money, or both — not just to solve surface-level problems
- Misalignment on value realization is the #1 reason onboarding and CS struggle post-sale
- Sales teams often assume customers understand value — they usually don’t
- The earlier value is quantified and documented in the sales cycle, the stronger the post-sale execution
- AI can eliminate manual handoff friction by summarizing calls, emails, and deal context automatically
- Traditional CS metrics like surveys and NPS are statistically weak; voice of the customer at scale is the future
- Customer success leaders must act as the primary conduit for customer insight back into product and GTM
- Personalization at scale requires cohort-based learning, not one-size-fits-all onboarding
- Fewer deals with clearer value often outperform higher-volume pipelines long term
- The best salespeople optimize for customer outcomes, not just closed deals
Chapters & Timestamps
00:00 – Welcome & Introduction
Justin introduces Neal McCoy and his background across military, fintech, digital engagement, and ecommerce.
02:00 – Neal’s Career Path & BigCommerce Journey
How Neal helped build CS and professional services as BigCommerce moved upmarket.
04:30 – Where Customer Value Breaks Down Post-Sale
Why customers trade one set of problems for another when value isn’t clearly defined.
06:45 – What CS Wishes Sales Would Hand Off (But Rarely Does)
The missing context that makes or breaks onboarding and adoption.
09:15 – AI’s Role in Fixing the Sales-to-CS Handoff
How AI can summarize deal context and remove the burden from sellers.
11:45 – Voice of the Customer vs. Traditional CS Metrics
Why surveys fail and how AI unlocks insight from unstructured customer data.
14:30 – Personalization at Scale in Ecommerce Onboarding
Using cohort-based success models across industries, regions, and merchant types.
17:15 – The Biggest Misconception Sales Leaders Have About Post-Sale
Why focusing on value may reduce conversions but increase long-term growth.
20:00 – The Future of CS, PS, and AI at BigCommerce
How AI is changing delivery models, expertise, and customer expectations.
22:30 – Closing Thoughts & What’s Next
Neal’s outlook on AI, value delivery, and helping merchants succeed long-term.
In this episode of the Thread Podcast, Justin Vandehey sits down with Jared Myatt, Senior Director of Revenue Operations at Integrate, to explore what it really takes to scale RevOps over time. Jared shares his journey from early employee to RevOps leader, reflecting on key inflection points including acquisitions, private equity ownership, and enterprise growth.
They discuss how the definition of RevOps has evolved, why data must power decision-making (not just dashboards), how culture scales through honesty and curiosity, and why alignment across GTM teams ultimately comes down to communication—not tools. This is a must-listen for anyone building RevOps in a growing SaaS organization.
Key Topics Covered
- Growing with a company from early startup to enterprise
- What RevOps actually is (and what it isn’t)
- Using data to tell real revenue stories
- Scaling culture without over-engineering it
- Career advice for aspiring RevOps leaders
- Why alignment breaks—and how to fix it
- The role of RevOps as GTM problem solvers
Suggested Chapters
00:00 – Welcome + Jared’s background
02:30 – Early ownership and pivotal moments at Integrate
04:30 – How RevOps has evolved over the years
06:00 – Using data to tell the revenue story
07:45 – Preserving culture through growth
10:45 – Career advice for moving into RevOps
13:30 – What alignment really looks like
16:45 – Integrate overview + closing
In this episode of the Thread Podcast, Justin Vandehey interviews Benjamin Roach, Director of Revenue Operations at Optio Incentives, to explore what it takes to build RevOps in the equity compensation and incentives space. Ben shares his “traditional” path from sales into RevOps, why he deliberately took a step back into a junior ops role, and how getting technical became a career unlock.
They dig into the complexities of selling and operating in equity management—where revenue can include ARR, transactional fees, and services, and where buyers span CFOs, CHROs, legal, and finance. Ben also shares his point of view on AI: where it can help participants and admins get fast answers, and why data quality and human oversight still matter. The episode closes with career advice for aspiring RevOps leaders and how to learn the craft.
Key topics covered
- Why Ben moved from sales → RevOps (and why he “took a step back” to level up)
- Equity compensation complexity: strike price, taxes, vesting, global compliance
- How Optio’s GTM motion sells “trusted partner + tech,” not just software
- Measuring growth in equity management beyond traditional ARR
- AI in equity management: where it’s useful today and where it’s risky
- Career advice: become technical, stay curious, build a broader toolbelt
Memorable moments / quotable lines
- “Stock options… were unknown to me. You get handed them and think, maybe one day I’ll make money.”
- “AI is only as good as your data models.”
- “Don’t be scared to take a step backwards.”
- “RevOps wears so many hats—you need a lot of tools on your toolbelt.”
Chapters (suggested)
00:00 – Welcome + Ben’s intro
01:00 – From sales to RevOps (and why he took a step back)
02:10 – Why the equity/incentives space pulled him in
03:30 – Aligning finance, HR, and revenue metrics
04:45 – Why revenue isn’t just ARR in equity management
05:30 – Simplifying a complex story for CFOs/CHROs/legal
06:55 – Global compliance + product readiness constraints
09:00 – AI in equity: what it can and can’t do (yet)
11:05 – Career advice for aspiring RevOps leaders
13:45 – Plug: Optio + how to connect with Ben
In this episode of the Thread Podcast, Justin talks with Tyler Will, VP of GTM Strategy & Ops at Intercom, about how modern revenue organizations are evolving in an era defined by AI, PLG-to-enterprise transitions, and go-to-market speed.
Tyler shares his journey from economic consulting and Bain, to GTM leadership at LinkedIn, to now scaling RevOps at Intercom. He breaks down the key differences between operating at a 20,000-person giant and a high-velocity SaaS company, why balancing PLG and enterprise sales motions requires intentional system and process design, and how Intercom rebuilt its routing, sales assist, and pricing guardrails to accelerate ACVs and bring clarity back to the customer journey.
The conversation digs into how AI is reshaping selling—not by replacing reps, but by giving them time back. From auto-generating QBR decks to enriching data behind the scenes, Tyler explains why AI actually makes sales more human, not less. He also shares why the next generation of RevOps talent will shift from narrow specialists to curious generalists who leverage AI, understand the full GTM workflow, and act as true co-owners of the business.
This is a high-signal episode for anyone thinking about PLG evolution, GTM design, AI-powered sales, and how RevOps must evolve to meet the moment.
Chapters
00:00 — Intro + Tyler’s Background
Justin sets up the episode; Tyler shares his path from consulting and Bain to LinkedIn to Intercom.
02:00 — Early Career Lessons: From Consulting to GTM
How economic consulting and strategy work shaped Tyler’s analytical and leadership approach.
03:30 — Operating at Scale: LinkedIn vs. Intercom
Why large enterprise GTM is committee-driven, and how smaller SaaS companies require speed, adaptability, and influence without authority.
06:00 — PLG, Sales-Led, and the Middle Ground
How Intercom balances self-serve PLG customers with enterprise sales—and why a “Sales Assist” motion has become critical.
08:30 — Redesigning Routing, Guardrails & ACV Growth
How simplifying and separating motions helped Intercom lift sales-led logos and drive higher ACVs.
10:45 — AI as an Amplifier, Not a Replacement
Why AI frees reps from low-value tasks (QBR decks, data cleanup) and makes room for more human selling.
13:20 — The Real Risk: Overvaluing Human Busywork
Why reps aren’t losing points for doing things manually—and why AI should elevate the conversation, not eliminate the human.
15:00 — The Future of RevOps Careers
Why RevOps is shifting from specialists to generalists who use AI, understand systems, and act like business owners.
18:00 — What RevOps Leaders Should Learn Next
Tyler’s advice to aspiring operators—how to become more valuable by being curious across the entire GTM ecosystem.
19:30 — Closing Thoughts + Intercom Hiring
Tyler encourages RevOps pros to embrace the field and shape the future; Justin wraps the conversation.
Episode Summary
In this episode of the Thread Podcast, host Justin Vandehey sits down with John Queally, Senior Director of Revenue Operations at Clari, to explore how RevOps is evolving in the age of AI, and what it really means to build a data-driven go-to-market organization.
John’s career spans consulting, analytics at JP Morgan, leadership roles at American Express and Qualtrics, and now Clari — one of the companies that helped define modern RevOps. He shares how his early assumption that tech companies were “amazing at data” turned out to be completely wrong, and why that realization led him to see RevOps as the spinal column and nervous system of every go-to-market organization.
Together, they dive deep into:
- How to unify fractured data systems across sales, marketing, CS, and product
- The difference between “tools” and true data architecture
- Why AI is exposing every fault line in go-to-market organizations
- The human side of RevOps: partnerships, trust, and communication
- What “world-class” looks like for RevOps in 2025 and beyond
- How to balance machine intelligence with human intuition in sales
- And how leaders can prepare for the next generation of revenue operations
Chapters
00:00 – Introduction
Justin introduces John Queally and his path from consulting and banking to RevOps leadership at Clari.
01:10 – From JP Morgan to Clari: The Data Reality Check
John shares how his early experience in finance led him to realize how disorganized data is across tech companies — and how that sparked his RevOps journey.
03:30 – Defining RevOps as the Spinal Column
Why RevOps should serve as the connective nervous system for GTM — ensuring every function operates from the same base of facts.
05:00 – What “World-Class” RevOps Looks Like Today
John explains how the definition of world-class RevOps is shifting toward data ownership, cohesive field experiences, and AI-enabled decision-making.
06:30 – AI vs. Human Intuition
The ongoing tension between automation and human instinct in sales — and why RevOps needs to serve as a checkpoint, not a replacement.
08:15 – The Future of CRM and GTM Systems
A look ahead at how the sales tech stack is evolving beyond monolithic CRMs into a connected ecosystem of specialized tools.
10:00 – Machine Learning and Predicting Customer Behavior
John shares how Clari partnered with data science firm QuadSci to achieve 94% churn prediction accuracy — and how that insight gets surfaced seamlessly to the field.
13:00 – Cross-Functional Alignment at Scale
Why true RevOps alignment comes from people, not tickets — and why John’s team embeds directly within every GTM function.
15:30 – Developing the Next Generation of RevOps Leaders
The skills operators need to thrive in this next era — including data fluency, architectural thinking, and strategic ownership.
18:00 – The AI Wake-Up Call
Why 80% of AI projects fail — and how RevOps leaders can prepare their orgs by fixing data quality and alignment first.
20:00 – Closing Thoughts
John’s reflections on RevOps as a community-driven discipline, the future of collaboration, and why every GTM leader must now own their data story.
In this episode of the Thread Podcast, host Justin Vandehey sits down with Max Mozes, Director of Revenue Operations at Walmart for Business, to unpack what it takes to build a world-class B2B motion inside one of the world’s largest retail organizations.
Before joining Walmart, Max carried a quota as a seller, scaled local business teams at LevelUp (acquired by Grubhub for $400M), and held key operational roles at Amazon Business — giving him a unique perspective on how to connect frontline sales experience with scalable systems and data strategy.
Together, Justin and Max dive into:
- The evolution of RevOps from sales enablement to strategic business architecture
- How Walmart is redefining B2B commerce for 30+ million potential business customers
- What RevOps looks like when you’re serving both local bakeries and Fortune 500s
- The art of structuring and prioritizing massive datasets across millions of prospects
- Why data enrichment and hierarchy matter more than just “more data”
- What’s hype vs. what’s real when it comes to AI and GTM automation
- And the soft skills that separate good operators from great ones: agency, resourcefulness, and ownership
Key Takeaways
- B2B at scale is an architecture problem. Data flows, enrichment, and prioritization define how sales teams actually execute.
- RevOps must translate complexity into clarity. The role is as much about storytelling as it is about systems.
- AI and data are only as powerful as the processes behind them. Automation should amplify human productivity, not replace it.
- Resourcefulness + Agency = Operator Superpowers. The best RevOps leaders identify problems, fix them, and bring solutions already in motion.
Memorable Quotes
“Every business in the U.S. is a potential Walmart customer — from a one-person bakery to a university with a $300M endowment.”
“There’s no sales team big enough to manually reach every account — so data prioritization becomes your growth strategy.”
“RevOps isn’t about the system you use. It’s about how you organize information so sellers can take action.”
“Agency and resourcefulness — that’s the difference between operators who just report problems and those who drive change.”
Chapters
00:00 — Introduction: From Seller to RevOps Leader
02:00 — Lessons from LevelUp and Amazon Business
03:30 — Bridging Sales and Operations
05:00 — Inside Walmart for Business: Scaling B2B at Retail Scale
08:00 — Data Architecture, Enrichment, and Prioritization
11:00 — AI Hype vs. Reality in Enterprise RevOps
14:00 — Building Resourceful Teams and Taking Ownership
17:00 — Walmart for Business: Hiring and Next Steps
Resources & Mentions
- Walmart for Business — https://business.walmart.com
- Grubhub acquires LevelUp — $400M acquisition (TechCrunch, 2021)
- Max Mozes on LinkedIn — https://www.linkedin.com/in/maxwellmozes
About the Guest
Max Mozes is the Director of Revenue Operations at Walmart for Business, where he leads strategy, data, and process optimization for one of the largest B2B commerce initiatives in the U.S. His career spans sales and RevOps roles at Amazon, Grubhub/LevelUp, and high-growth startups, giving him a rare perspective on building go-to-market infrastructure from both startup scrappiness and enterprise scale.
In this episode, Chantel Hirschel, Director of Revenue Operations at Sana, discusses the unique challenges and opportunities in the healthcare industry, particularly in revenue operations.
She shares insights on transitioning from traditional B2B SaaS to healthcare, the importance of HIPAA compliance, and the role of AI in rev ops. Chantel also offers advice for aspiring leaders in the field, emphasizing the importance of communication and strategic thinking.
Chapters
- Introduction to Chantel Hirschel(0:00)
- Transitioning to Healthcare Rev Ops(3:00)
- AI and Automation in Rev Ops(9:00)
- Leadership and Communication in Rev Ops(15:00)
- Future of Sales and Rev Ops(21:00)
In this episode of the Thread Podcast, host Justin Vandehey speaks with Larry Peters, the Chief Revenue Officer of World of Dance.
They discuss Larry's extensive background in sales and marketing within the sports and entertainment industries, emphasizing the importance of understanding customer needs and the role of practice in sales.
Justin and Larry explores the integration of AI in sales strategies, particularly in enhancing team efficiency and customer engagement. Larry shares insights on building effective sales teams and the unique challenges of marketing to Gen Z consumers.
Chapters
00:00 Introduction to Larry Peters and His Background
08:40 Building Revenue Strategies in Entertainment
17:38 The Role of AI in Sales
24:20 Engaging with Gen Z Consumers
Summary
In this episode of the Thread Podcast, host Justin Vandehey speaks with Kara Brown, founder and CRO of Lead Coverage, about her journey in the supply chain industry, the importance of go-to-market strategies, and the impact of AI on sales technology. Kara shares insights from her book, 'The Revenue Engine,' and discusses the challenges faced by women entrepreneurs in achieving significant revenue milestones. The conversation also delves into the intricacies of the supply chain ecosystem and the necessity for companies to adapt to technological advancements.
Takeaways
- Kara Brown emphasizes the importance of owning customer email addresses for effective marketing.
- The supply chain industry has a low bar for go-to-market activities, presenting opportunities for growth.
- Women entrepreneurs face significant challenges in reaching $1 million in revenue.
- Kara's book, 'The Revenue Engine,' serves as a framework for success in the supply chain sector.
- AI is transforming sales tech, but many companies are lagging behind in adoption.
- Understanding the total addressable market (TAM) is crucial for business strategy.
- Kara's agency focuses on companies that physically move freight or have the tech behind it.
- The conversation highlights the tactile nature of logistics and its importance in business.
- Kara's journey includes significant milestones, such as writing an IPO and launching a successful consulting agency.
- The future of sales tech will require companies to adapt to new tools and methodologies.
Chapters
00:00 Introduction to Kara Brown and Her Journey
04:14 The Revenue Engine: Framework and Insights
07:01 Target Audience and Ideal Customer Profile
10:14 The State of CRM in Supply Chain
13:00 AI and the Future of Sales
15:57 Kara's Philosophy on Market Engagement
18:42 Goals and Future Aspirations
In this episode of the Thread Podcast, host Justin Vandehey speaks with Karan Singh, SVP of Go-to-Market Strategy and Operations at LaunchDarkly. They discuss Karan's extensive background in various tech companies, the evolving role of AI in sales, and the importance of human connection in go-to-market strategies.
Karan emphasizes the need for productivity over leanness in sales organizations and highlights the challenges of training and developing sellers in a fast-paced environment. He also shares insights for new revenue operations professionals, stressing the importance of seller readiness and effective onboarding processes.
Takeaways
- Karan Singh has a diverse background in tech, having worked in cybersecurity, data warehousing, and vertical SaaS.
- AI tools should enhance human connections rather than replace them in sales processes.
- Productivity is more important than leanness in sales organizations.
- The average tenure of a seller is around 18 months, highlighting the need for effective training.
- Investing in seller readiness early can lead to long-term success in sales organizations.
- Automation can help sellers focus on meaningful human interactions.
- Sales training should be consistent and comprehensive to ensure seller success.
- Understanding customer needs is crucial for effective sales conversations.
- Karan emphasizes the importance of developing B sellers into A sellers.
The role of Rev Ops is multifaceted, requiring a focus on strategy, systems, and seller enablement. - Chapters
02:26 Karan Singh's Journey in Go-to-Market Strategy
07:15 The Role of AI in Sales and Human Connection
10:36 Productivity vs. Leanness in Sales Organizations
14:13 Challenges in Seller Training and Development
18:53 Key Insights for New Rev Ops Hires
In this episode of the Thread Podcast, host Justin Vandehey introduces his co-founders Jeremy Vandehey and Samuel Kenney as they discuss their journey in building Thread, a company focused on enhancing the go-to-market strategy for sales teams. The conversation explores the challenges of acquiring the first customer, aligning sales operations, and the importance of technology in sales. They delve into the future of sales technology, the role of AI in augmenting seller efficiency, and the competitive landscape of the sales industry. The episode concludes with insights on lessons learned from their experiences and the official launch of Thread.
Takeaways
- The consistent challenge for founders is acquiring the first customer.
- Empathy for the seller's experience is crucial in product development.
- Sales is a critical function for every startup, not just a separate department.
- Technology is rapidly changing the sales landscape, making it essential to innovate.
- AI can significantly enhance seller efficiency and effectiveness.
- Understanding the competitive landscape is vital for product positioning.
- Building a product that meets the needs of sellers is key to success.
- The rate of technology adoption is increasing, requiring quick adaptation.
- Founders must navigate noise and chaos in the current market environment.
- Feedback from users is essential for continuous improvement of the product.
Chapters
00:00 Introduction to Thread Podcast and Founders' Journey
05:36 The Importance of Sales Operations and Customer Understanding
08:24 Innovating in the Go-to-Market Space
11:07 Building a Product for Sellers
14:00 Challenges and Rewards of Founding Thread
16:47 The Future of Sales Technology and AI
19:45 Augmenting Seller Efficiency with Technology
22:41 Navigating the Competitive Landscape
24:41 Lessons Learned from Building Thread
27:15 Closing Thoughts and Call to Action
35:51 Introduction and Excitement for the Journey
36:48 Invitation to Join and Future Guests
37:17 Gratitude and Encouragement for Listeners
In this episode of The Bridge, Justin sits down with Jessica Collier, CEO of Spot, and founding partner of All Turtles, to explore her journey from academia to building one of the most thoughtful AI-driven tools in the HR tech space.
Jessica was the first UX writer at Evernote, where she helped shape user experiences through words before it was a recognized craft. She later went on to co-found All Turtles, alongside Phil Libin (former Evernote CEO) and Jon Cifuentes, with a mission to build practical AI applications — long before the current hype cycle.
In this conversation, Jessica shares:
- The early days of bringing AI into product workflows before it was cool
- How Spot is reshaping the case management and incident reporting category with anonymous, AI-powered reporting tools for any case type
- Why “trust” is the foundation of any product solving sensitive problems
- The build vs. partner decision framework when enhancing core functionality
- Lessons from scaling multiple ventures rooted in ethical product design
Whether you're an operator building with AI, a founder evaluating product scope, or someone navigating tough conversations in the workplace — this episode offers tactical insights and big-picture clarity.
Brett Beveridge, Founder & CEO of T-ROC, joins the show to share his journey from bouncer and bartender to building one of the largest retail operators in the U.S.
We dive into:
- How he started selling cell phones out of a van and took Let's Talk Cellular public before selling to Nextel
- What’s fueled his 20+ year run building T-ROC
- His take on when to expand product lines — and when to stay focused
- How to think about funding: bootstrapping vs. venture capital
Tessa Brown, Co-Founder and CEO of Germ Network, joins the show to talk about,
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Tessa's journey from Stanford writing professor to startup founder, the dangers of social platforms designed to maximize exposure, and why privacy should be the default, not the exception.
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How Germ lets users create multiple, compartmentalized identities
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The flaws of phone number–based messaging and the case for link-based connection, and her philosophy on building with integrity in a surveillance-based tech world
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Tessa’s experience fundraising from K5 Global and Mozilla Ventures
Jared Robin, Co founder of RevGenius and Audience Haus, joins the show to talk about
- Jared's first sales job, cold calling office managers at FedEx to building a fashion blog with 10K monthly subscribers.
- The art of audience building, and how a LinkedIn group chat turned into an engaged 50,000 community
- What does it take for a B2B company to successfully build an audience
- Reflecting back on the presidential election and lessons learned in audience building.
- The trends of B2B SaaS companies purchasing media businesses and the future of enterprise content.
Chris Andrew, Co founder and CEO of Scrunch AI, joins the show to talk about
- The evolution of search and consumer shift toward finding answers with AI.
- Building a marketing platform for an AI first customer journey.
- The opportunity for AI and Scrunch to audit search and help brands manage their identities in the era of AI.
- Reflecting on Chris leaving Intuit to work for Clara Shih at Hearsay, and what Chris learned from Clara as employee #3 at Hearsay that made him a better entrepreneur.
- A wild car ride with Gary Vee when Gary first launched Wine Library TV, and pitching Gary Vee a cooking show.
Tatiana Fofanova, CEO and Co Founder of Koda Health, joins the show to talk about
- From pediatrics to entrepreneurship, and Tatiana's experience as a founder in residence at Texas Medical Center (TMC)
- The intersection of the law and health, and building an advanced care planning tool that is patient centric.
- Becoming "patient zero" for Koda Health after being hit by a car and getting diagnosed with kidney cancer, all in the same afternoon.
- Designing Koda's go-to-market strategy in health care, and how Tatiana has thought about building out her team in a healthcare startup.
Conor McCarter, Co founder of Prequel, joins the show to talk about:
- The founding story behind Prequel, the YC experience, and pivoting during the program.
- Market overview on the state of data management and positioning of Prequel.
- The fundraising process for Prequel and importance of not beating yourself up as a founder and staying creative amidst the grind.
Dr. Maheen Mausoof Adamson, CEO and Co founder of Soof Solutions, joins the show to talk about
- The intersection of neuroscience at Stanford and entrepreneurship, and path to founding Soof.
- Building Soof to help her father speak again after experiencing a stroke in 2007.
- The importance of timing and how Apple's advancements in hardware openned up the market for Soof.
- How Dr. Adamson worked with Stanford and the biodesign program to apply research and real patient interacton insights to build their venture.
- How to leverage your investors and advisors to complement your team's strengths.
Megs Shah, CEO and Co founder of Parasol Cooperative, joins the show to talk about:
- Surviving abuse and founding Parasol Cooperative to battle a growing, global, shadow pandemic
- Keeping our kids safe online, and the insights that led Megs to building her two products, SafeConnect and Ruth solutions overview
- Diddy's downfall, the shift toward disconnecting and digital minimalism, and the responsibility of developers to consider safety of your end users up front.
Dr. Jennifer Hintzsche, CEO and Founder of PherDal, joins the show to talk about:
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Dr. Hintzsche's personal story of being defined as "in-fertile", a $10,000 invoice for a solution to a problem that doctor's couldn't define, and how she used her PhD to prove those physician's wrong.
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The process of crowdfunding for PherDal and lessons learned by launching on their platform.
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Market sizing the fertility market, dealing with the FDA, and going from 0 to 1 in biotech.
Daniel Saks, Co founder and CEO of Landbase, joins the show to talk about
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Growing up in an entrepreneurial family in the business of furniture and the insight that led to founding Daniel's first business, AppDirect.
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The importance of establishing "go-to-market credibility" before engaging in sales outreach.
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Daniel's experience fundraising for AppDirect, and most recently Landbase's $12.5M seed round.
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The importance of "founder-market" and "founder-product" fit.
Alex Douzet, CEO and co founder of Pumpkin, joins the show to talk about
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Building his first company Ollie, in the pet food and delivery space, and how doubling down on his experience in pet care and the "humanization of pets" led to founding Pumpkin
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Picking the brand name "Pumpkin" and the importance of building flexibility into what you ultimately call your business.
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The decision to focus on quality of care and alignment with the veterinary community to grow and scale Pumpkin.
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Unpacking the psyche behind a 7 time ironman and a three time founder, embracing the pain cave, and near death experiences in company building
In this episode Justin sits down with Nico Simko, the dynamic CEO and co-founder of Clair, a trailblazing company set on revolutionizing on-demand payroll. Nico shares an inspiring narrative from his beginnings as an economics tutor to spearheading a fintech powerhouse. We uncover how Clair smartly embeds on-demand pay within HR platforms, bypassing the conventional approach of targeting employers or employees directly. Nico also articulates the challenging yet rewarding journey of building Clair into a secure and compliant fintech solution, highlighting the crucial art of maintaining focus and discerning when to say no.
As we explore the intricacies of Earned Wage Access (EWA) services, Nico offers candid insights into navigating the intricate regulatory maze. We dive deep into the significance of foresight in compliance and how strategic partnerships bolster Clair's success amidst evolving financial regulations. Nico's vision stretches beyond the present, painting a picture of a generational fintech company that could redefine employer-linked financial services. This episode is packed with wisdom for entrepreneurs eager to grasp fintech opportunities, and we wrap up with a teaser for our next episode featuring an innovator making strides in the pet tech world.
Tim Fung, Co founder and CEO of Airtasker, joins the show to talk about
- How an apartment move led to the founding of Airtasker.
- How tasking and labor markets differ globally, and what this market looks like in Australia.
- How Airtasker is focusing on localization and community to differentiate from platforms like Fiverr and Upwork.
- Finding product, channel fit, and how Airtasker used regional media outlets to drive awareness in local markets to create local jobs.
Dr. Lewis Bernstein, Co founder of 3G and former executive producer for Sesame Street, joins the show to talk about:
- Dr. Bernstein's early work at Sesame Street, working alongside Jim Henson, and how the mission and message of Sesame Street has evolved over time.
- The founding story of 3G and using multiple generations to help combat loneliness in our youth.
- Current state of children's programming and content. How it has evolved for better and worse.
- The future of early stage childhood education
Tad Milbourn, Founder and CEO of RankedVote, joins the show to talk about
- The momentum that's building around ranked choice voting. What it is, how it works, and why it's a better method of getting consensus.
- Lessons learned from Tad's first company, Payable, the YC experience, and navigating a successful exit and selling to Stripe.
- "Upgrading state and federal elections". An election software market overview and current state of election reform at state and federal levels.
- Eliminating friction in the user experience to build stronger advocates for ranked choice voting.
- Tad's decision to start RankedVote as a solo founder, and the differences in the founder journeys between Payable and RankedVote.
Jon Staenberg, Founder and CEO of Agate Hound Fund joins the show to talk about
- Growing up in Nebraska to Silicon Valley to Microsoft to Venture
- How Venture Capital has changed and the rise of the Search Fund.
- What is a "Search Fund" and the reason behind why it's such a successful asset class.
- The Silver Tsunami and baby boomers without an exit plan.
- The criteria that Jon has established for the successful businesses he backs and the traits that his funds look for in the entrepreneurs they invest in.
- Launching "Hand of God" wines and challenges of building an independent wine brand.
Travis Schoen, Founder of NW Golf Guys joins the show to talk about:
- How Travis moved from scoring free golf to starting a golf league and growing its member base to more than 7,000 members.
- How the game of golf has evolved over the past 20 years, and how NW Golf Guys thinks about their target demographic and approach to member acquisition
- What goes into putting on a great golf tournament, the greatest golf movie of all time
Sahand Dilmaghani, Co founder and CEO of Terra Kaffe, joins the show to talk about
- Building the worlds most beautiful and intelligent espresso machine, and the process that went into prototyping a better coffee experience.
- Balancing development for the software user interface and the human machine interface, and the two journeys people take when brewing their coffee.
- How Terra Kaffe thinks about the competitive landscape in coffee, and how Sahand is approaching partnerships in the coffee category.
- How Sahand and team are helping reduce ecological waste and helping customers "kick the pods", one cup at a time.
Jordane Giuly, CEO and Co founder of Defacto, joins the show to talk about
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Jordan'e experience building a Unicorn at Spendesk and the decision to walk away from the successful startup he co-founded.
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The three bets that Jordane and team are making to go big with Defacto.
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Building his startup in Paris vs. Silicon Valley, and the benefits of building outside of the US.
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Lessons learned from fundraising for Defacto vs. Spendesk, the importance of balancing transparency and confidence when going through challenging times, as well as the importance of remembering to find joy in what you're building.
Martin Pannier, Co founder and CEO of Primo joins the show to talk about
- Lessons learned building product at Gusto that led to solving for the "accidental IT Manager"
- The decision to launch a free product SKU, PLG, and considerations to make before launching a free product
- The pros and cons of building your startup pitch with your VCs.
Parker Gilbert, Co founder and CEO of Numeric, joins the show to talk about
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How going through a challenging financial audit led to the insight of founding Numeric.
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The character traits that Parker looked for in his co founders for Numeric.
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Parker's experience closing is $10M Series A and what it took to close a round from Founders Fund, Menlo Ventures and how he iterated to build a pitch that ultimately landed.
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Signing customers that can help Numeric accelerate partner growth, and the "why now" answered for Numeric.
Carin Luna-Ostaseski, Founder of SIA Scotch Whisky, joins the show to talk about
- The process Carin went through to kickstart the SIA brand, and being the first hispanic woman to found a Scotch brand.
- The state of the spirits industry and how SIA positions itself and competes with other liquor brands in the beverage category.
- The "bonsai tree" method of building your company, and the importance of "starting in your own backyard" when launching a brand.
Adam Katz, CEO of Sightly, joins the show to talk about
- Adam's journey from IC to becoming the CEO at Sightly and leading from the front
- The evolution of the marketing tech category and generating an authentic brand voice in the era of AI.
- How Kobe Bryant inspired Sightly's Brand Mentality vision and narrative.
- Caitlin Clark and the future of the WNBA brand and women's sports.
- Defining your brand through what you say AND what you do.
Andrew Firestone, CEO of Mermaid Chart, joins the show to talk about:
- The venture studio model and building Mermaid Chart out of Open Core Venture Studio.
- Stepping into the CEO role at Mermaid and building an open-sourced approach to the diagramming and creator tools industry.
- Unlocking go-to-market and investing in channels that create accumulating advantages for Mermaid.
- Lessons learned from raising capital and taking 300 meetings in four months for Mermaid Chart (and eventually closing a round with Sequoia, Microsoft and OCV)
Matt Wadiak, Co founder and former COO Of Blue Apron, and CEO and Co founder of CleanUp joins the show to talk about
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Founding Blue Apron and being one of the first movers in meal planning and e-commerce ingredient market.
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The importance of capital planning and cash flow and the importance of picking markets.
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Key ingredients to succeed as an entrepreneur in the food space.
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How customer acquisition has evolved in the D2C space and what founders can do to ensure the cream rises to the top.
Harry Tannenbaum, Co founder of Mill, joins the show to talk about.
- Harry's experience at Nest and building products that are really good for that planet.
- The Mill process of finding PM fit as a hardware startup.
- Harry's decision to go DTC, "core vs. context", and how he thinks about evaluating BD and partnership collaboration opportunities
- Lessons learned from Harry as a first time founder and the importance of ideating tactfully.
Joel Pollick, Co founder and CEO of Percent Pledge, joins the show to talk about
- The three main challenges that consumers wrestle with when it comes to giving back.
- Building a culture of giving, shifting from paycheck to purpose, and a generation that gives more
- The importance of reinforcing your mission...over, and over again.
David Sauers, Co founder of Royal Restrooms, joins the show to talk about:
- A porta potty mishap that led to building one of the largest and most successful portable sanitation companies.
- The explosion of the sanitation market post-COVID, and the market opportunity in public restrooms.
- Maintaining a high level of professioal services while scaling Royal Restrooms.
- Royal Restrooms franchise model and what David looks for in business partners to expand the company's footprint.
David Meltzer, author, coach, speaker and co founder of Sports 1 Marketing joins the show to talk about:
- Growing up in a family with "not-enough" to a $3.5B exit and building the most successful sports agency in the world.
- Losing everything (>$100M) and having to rebuild a sense of purpose in the founders' journey.
- Dave's model for prioritization and time management, as well as ways to create a better working relationship and deeper connection with your partner/spouse.
Chris "Tito" Sestito, CEO and Co founder of HiddenLayer, joins the show to talk about
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How prepared (or unprepared) companies and our government is for the evolution of AI
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Raising a $50M round from Microsoft, Booz Allen Hamilton, IBM, and Capital One, and Chris' thoughts around building a business with strategic capital and partnerships.
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How Tito and team think about prioritizing what HiddenLayer works on when the total addressable market is HUGE and customers want it all, now.
Tom McLeod, Founder and Executive Director of Arkive, joins the show to talk about:
- Re-imagining the art museum and the founding story behind Arkive.
- Breaking down the collectibles space and the evolution of NFT's and digital creative works.
- Lessons learned from shipping 17 iPhone apps, and measuring "speed to learning" as Tom's ultimate KPI
- Why the wave of Gen AI apps is very different than the rise of mobile apps.
- Keeping love, passion, and business separate.
Guy Kawasaki, evangelist and author, joins the show to talk about
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From Kalihi Valley to Apple. The first bridge that Guy took to success that started in the 6th grade.
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What is a product evangelist and how should early stage founders be thinking about evangelism?
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Guy's definition of what it takes to be remarkable (and what it isn't), what it was like working for Steve Jobs, and how Steve Jobs showed him what being Remarkable looked like.
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Guy's Golden Touch, what "golden looks like", and how Guy decides to get involved in the projects he works on.
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The keys to being a successful nonfiction author and when to borrow and/or steal.
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Growth, Grit, and Grace - and his book "Think Remarkable"
Ariel Renous, Co founder and CEO of Augment joins the show to talk about
- How Augment is disrupting the traditional MBA program.
- Fundraising for Augment and $6M from RTP Global.
- The future of executive education, and the importance of learning and raising money from people that have actually done the thing.
Baron Davis, Founder and CEO of B.I.G (Business Inside the Game), joins the show to talk about:
- Baron's "renegade approach" in transitioning from NBA All-Star to entrepreneurship.
- The importance of investing in "multi-hyphenates", and how B.I.G is building its network around creators with these super powers.
- Who were some of Baron's early mentors and advisors as an entrepreneur, and what entrepreneurs should be looking for in mentorship.
- Baron's perspective on the future of the business of basketball, where we're at in terms of the quality of the game, and what he wishes he would have known as a rookie before entering the NBA and entrepreneurship.
Eve Halimi and Anam Lakhani, Co founders of Alinea, join the show to talk about:
- The challenges of managing money out of college & founding Alinea.
- Taking Alinea to profitability before their seed round.
- Slackers vs. trackers and how Gen Z compares to prior generations of money managers
- Ways to teach my kids how to be financially literate.
- The role of co-CEO and how Eve and Anam divide and conquer.
Kamakshi Sivaramakrishnan, CEO and Co founder of Samooha (acq'd by Snowflake), joins the show to talk about
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how she built two companies that helped customers "bring data to life", selling DrawBridge to LinkedIn and Samooha to Snowflake.
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Kamakshi's advantages as a second time founder.
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How Kamakshi knew it was the right time to sell Samooha and the process she went through in the acquisition with Snowflake.
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Leadership differences between the leaders of the companies that Kamakshi sold to, most notably, Satya Nadella (Microsoft) and Frank Slootman (Snowflake)
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Betting on the Snowflake platform, the importance of partnerships and dating before marriage, and the pros and cons of a single platform approach.
Albert Gozzi, CEO and Co founder of Aleph joins the show to talk about.
- The insight Albert got from his time in consulting at Bain, specifically the pain in and around FP&A (Financial Planning & Analysis), that led him to founding Aleph.
- How CEOs should be thinking about balancing "relationship building" with VCs vs. building the business.
- The mentality of company building after closing a Series A, and balancing resource allocation across product development and growth.
Nora Jones, CEO and Co founder of Jeli, joins the show to talk about
- How Nora's experience at Jet, Netflix, and Slack led her to founding Jeli.
- Chaos engineering, quantifying the impact of burnout in an "always on" economy, and the human side of incident management.
- Selling Jeli to PagerDuty and the process Nora went through to sell the company (when to bring in outside help)
Tracy Young, CEO and Co founder of TigerEye, joins the show to talk about
- Building Tracy's first successful company, PlanGrid, and how the Autodesk acquisition of PlanGrid led to Tracy uncovering the opportunity for her current venture, TigerEye (launching this year in 2024!)
- Tracy's decision to start another company and how she evaluated her options after her time at AutoDesk.
- Balancing family and founder responsibilities, the efficiencies gained when time is in limited supply.
- Scaling beyond boundaries, and the cost v. benefit of building a team that is in-person v. remote.
- Heightened expectations as a second time founder, learning to listen more, and a better way to build and forecast revenue.
Anna Believantseva, COO and Co founder of Esper Bionics joins the show to talk about
- Human augmentation and using bionics and technology to extend our human potential.
- The human technology stack, and the potential of embedded hardware in humans.
- The role of a COO at an early stage startup, B2B2C business model challenges and fundraising for a bionics, robotics, and hardware startup.
Hedda Båverud Olsson, CEO and Co founder of Lassie, joins the show to talk about
- The Pet insurance and pet ownership space, the major insurance incumbents, and Lassie's focus on preventative veterinary practices.
- Chicken problems and how different cultures view pet ownership.
- Hedda's experience closing out her €23M Series B round from Balderton Capital, and best practices on how to close your round efficiently.
- Hedda's experience in the music business, and how it helped her become a stronger entrepreneur.
Rachel Blank, CEO and Co founder of Allara Health, joins the show to talk about
- The evolution of women's health care and how improvements are being made through digital health.
- The importance and advantages of a "direct to consumer" health care model.
- Raising $10M from Google Ventures, balancing cash conservation with growth, and how Rachel is thinking about scaling quality of care as she grows her team.
Mike Weiland, Co founder and CEO of Govly, joins the show to talk about
- Why selling to the government is really hard and how Govly makes that easier for businesses contracting with the government.
- Raising $9.5M Series A from Insight, fundraising for a government tech startup, and the advantages of picking a more unique venture vertical that is recession proof.
- Raising the bar and challenging employees to achieve more, and how Govly did that to hit their revenue milestones ahead of raising their Series A.
- Founder/VC fit, and some of the proof points that validated that Insight was the right partner to help Govly scale its company.
Navneet Dalal, CEO and Co founder of Matic joins the show to talk about
- Being an early mover and pioneer in computer vision and deep learning.
- Moving beyond an interface and a good product to build a lasting, sustainable business.
- Being acquired by Google, working for Tony Fadell and with the Nest team, and the insight that led to Matic.
- The "human sensor stack" and how it intersects with the "robot sensor stack", and why Matic started with cleaning the floors.
- Picking an existing market and the importance of building a "minimum loveable product".
Sam Chaudhary, Co founder and CEO of ClassDojo, joins the show to talk about
- Where early stage education is falling short, and Sam's experience building the largest community for teachers, parents, and kids to thrive in the educational system.
- The process Sam and his co founder Liam went through to unlock PM fit for ClassDojo.
- The jobs left to be solved in education, reflecting on the COVID home school experience, and how ClassDojo is expanding into the Virtual Learning Experience to solve the jobs that the classroom won't (or can't do well).
Siva Namasivayam, Co founder and CEO of Cohere Health, joins the show to talk about
- Starting companies in chaos and a family full of MDs.
- The inefficiencies that exist in the operational side of Health Care.
- Identifying early adopters and the nuances of doing that in a more conservative market like Health Care.
- Raising capital in health care and the traction you need and expectations you need to set before going out to raise capital in Health Care.
Mallory Greene, Co founder and CEO of Eirene Cremations, joins the show to talk about
- "Death tech" and growing up in a family business centered on death.
- Why death is a great business, and the metrics that matter when raising capital in the Death Tech space
- Building an "honor based" mindset to servicing the families who have lost loved ones.
Tony Jamous, Co founder and CEO of Oyster, joins the show to talk about
- Globe trotting from Lebanon to France to Cyprus, and the pains of starting a globally distributed business and the founding story of Oyster.
- The assumptions and excuses of an in-person office culture
- A purpose driven approach to company building, and why Tony built Oyster as a B Corp.
- Hiring the right people for the C-suite, and how Tony has approached executive hiring at Oyster.
Farzad Rashidi, Co founder of Respona, joins the show to talk about:
- The process Farzad went through to calculate customer acquisition costs and find the channel that ultimately led to founding Respona.
- A brief history of SEO, and a few hacks that founders can apply to grow their business.
- Tactics for podcasters to grow their own listener base + how Farzad landed an interview on this show.
- Balancing speed with quality, and when is "too early" to ship your product?
Daniel Yanisse, Co founder and CEO of Checkr, joins the show to talk about
- The insight from building a startup in the gig economy to founding Checkr.
- Eliminating bias in the hiring process to help prospective hires live the dream.
- How founders should evaluate M&A opportunities and when it makes sense to acquire another company.
- Going up market into selling to larger enterprise with your product
- Flying high and flying low. When and how a founder should get "in the weeds" when running their company.
Sukhinder Singh Cassidy, CEO of Xero, joins the show to talk about
- Her first exposure to entrepreneurship running the books for her father's business
- How Sukhinder has thought about evaluating the entrepreneurial ventures she has taken on, and how she evaluates the importance of the market/opportunity, and team she's building.
- How Xero is using AI to help support small businesses, and opportunities that Sukhinder sees for small business to save time and money.
Arjun Sethi, Founder of Tribe Capital, joins the show to talk about
- The founding story and investment thesis behind Tribe Capital
- From being kicked out of high school, to joining the army and founding startups.
- Transitioning from Social Capital to Tribe, and "bottoms up" approach to investing.
- Arjun's experience gaining leverage through bootstrapping, and differences between raising capital for your startup and raising for your investment fund.
- The humbling experience of raising capital for Tribe, building the firm from the ground up, and a quantitative approach to demonstrating firm performance.
- Arjun's perspective on the current state of crypto.
Job van der Voort, Founder and CEO of Remote, joins the show to talk about
- The pain of hiring and onboarding remote employees, and the insight from GitLab that led to founding Remote.com.
- The "superpowers" that AI is going to give employees in this new era of work.
- Whether or not remote employees are as productive as their in-person colleagues.
- Job's reflections on the company he started before Remote
Super Bowl champion and New England Patriot, JuJu Smith-Schuster and CEO of World Champion Fantasy, Mike Vela, join the show to talk about:
- JuJu and Mike's perspective on the future of eGaming and Fantasy Sports
- How JuJu, Mike and team at WCF are reimagining the Fantasy Sports experience with the PlayerX Portal.
- The evolution of player empowerment and player ownership in ventures on and off the field.
- JuJu's mentality around the business and game of football and player brand.
Josh Reeves, Co founder and CEO of Gusto, joins the show to talk about
- Using Word of Mouth growth to over 300,000 business customers
- Battling against payroll giants like Intuit and ADP to build a category leader, and how much attention Josh pays to competitors
- How payroll is evolving, and how Gusto is innovating to support small business on a global scale.
- The advice Josh gives founders building their first company from his first startup prior to Gusto.
Christina Cacioppo, Co founder and CEO of Vanta, joins the show to talk about
- How Christina's experience as a PM at Dropbox gave her the insight to starting Vanta.
- Current state of the security and compliance industry and why it's primed to explode.
- The impact that AI will have on security.
- Should founders raise strategic capital? And at what stage does it make sense to do so?
- Your startup is special, but not THAT special, and the hiring plan to support it.
Joe Thomas, CEO and Co founder of Loom, joins the show to talk about
- How Joe and team have scaled Loom to +21M active users
- The decision to hold on monetizing Loom until Year 3 of the company, and why founders should use activation as a success metric.
- The "earned insight" that led the Loom team to build a horizontal application vs. vertical application
- How Loom is planning to use Generative AI to improve collaboration and leapfrog its competitors.
Bill Smith, Founder and CEO of Landing and Shipt (acquired by Target), joins the show to talk about
- Moving from Birmingham to San Francisco, the insight that led to Landing, and re-imagining how we rent homes.
- The remote work debate. Which hires should be in person and which hires can thrive remotely.
- Founder insights from building and selling Shipt to Target for $550M, and the differences between founding Shipt and Landing.
- The future of home rentals and how AI will impact the real estate category.
Rahul Vohra, Co founder and CEO of Superhuman, joins the show to talk about
- Founding Rapportive, selling to Linkedin, and the insight that came from filtering every idea through the lens of our most valuable asset. Our time.
- The Superhuman Product Market Fit Engine and Rahul's method of quantifying whether or not you've found PM fit.
- A vision driven approach vs. a metrics driven approach to building your company, and the importance of balancing the two.
- The lattice model of virality, the desire to be more like our bosses, targeting the leadership layer, and how to unlock vertical and horizontal virality.
- At what point can (and should) a startup afford to compromise on talent.
- Superhuman AI and rewriting the future of email.
Max Lytvyn, Co founder of Grammarly, joins the show to talk about
- Pivoting from plagiarism detection to building Grammarly, the 10th most valuable startup in the US.
- A 16 year "overnight" success story. Building a and innovating when your vision is ahead of what's technically possible.
- Direct to consumer or B2B? How founders should evaluate building a direct-to-consumer vs. B2B, and how Max and team did both successfully.
NBA Champion, investor, and hoops analytics guru, Shane Battier joins the pod to talk about
- The transition from playing alongside Lebron, D Wade, and Chris Bosh to the front office leading analytics for the Miami Heat.
- "Burning the ships". Shane's decision to go "all-in" on basketball and the parallels to founding a company.
- The impact that generative AI will have on the business and game of basketball
- Player ownership and the evolution of player empowerment in professional sports.
Kaveh Khorram, CEO of Usage.ai, joins the show to talk about:
- Eliminating "cloud waste", creating a new category in the midst of the cloud wars, and the importance of timing when creating Usage.ai.
- Kaveh's experience taking Usage from 0 to 1 and learnings from the scale and growth phase of his company
- Diversifying and de-risking partner and platform risk, and predictions on where the future of the cloud is headed.
Edith Harbaugh, Co founder and Executive Chair at LaunchDarkly, joins the show to talk about
- The process LaunchDarkly went through to validate PM fit and create the category for feature management.
- LaunchDarkly's target customer profile when finding PM fit and how their target customer profile has evolved as their category and company has scaled.
- At what stage in a company's growth should a founder invest in Dev Ops.
- The evolution of DevOps landscape over the next 3-5 years.
CEO Succession draft! My co founder and brother Jeremy joins the show to analyze the top 10 CEO successors of the past two decades
Kurt Davis, Co founder/CEO of Biteline and author of "Navigate the Lighthouse" and the BD aSaaSin, joins the show to talk about:
- International deal making and how Kurt approached doing large carrier BD deals in the early days at Boku.
- The process of crossing the second "chasm". What is the second chasm and how founders should approach it.
- Navigating the lighthouse and when a company should make their first BD hire.
Scott Kacyn, Co founder and CTO of Hunt Club, joins the show to talk about:
- Hunt Club's process of finding PM fit, startup life before and after raising $40M, and creating the category of Network Relationship Management in the process.
- The impact that generative AI will have on the hiring space.
- How Scott is using Copilot to support his engineering team in building Hunt Club
- Creating a startup in Chicago, Jay Cutler love, and the outlook on the Chicago Bears in 2023.
Suze Dowling, Co founder and Chief Business Officer of Pattern Brands, joins the show to talk about
- Unlocking direct to consumer businesses and creating a successful multi-brand model.
- The value in developing a brand that resonates with your personal stage of life, and how to define successful brand and buying personas.
- The differences between operating an agency and operating a startup.
- Direct WITH consumer vs. Direct TO Consumer and creating with your customer.
- Suze's evaluation framework for M&A and the brands that Pattern acquires.
- When it does and doesn't make sense for a brand to open up a brick and mortar location.
- The secret sauce to finding an underserved category for DTC disruption.
Terry Rice, Host of Entrepreneur's "Launch Your Business" podcast and author for Entrepreneur Media joins the show to talk about:
- How Terry got on Jason Feifer's radar (Editor in Chief at Entrepreneur Media), and how he turned that interaction into his dream job.
- Terry's process for launching his own consulting practice, finding your zone of genius, and tactics to take your consulting practice from 0 to 1.
- Going solo and making it as a solopreneur, the "10 questions" framework, and where Terry gets the inspiration for the content he creates for Entrepreneur.
- An awkward afternoon with the Rapper TI.
- Launching the "Launch Your Business" podcast and landing the right guests for your show.
- The two biggest mistakes that Terry sees solopreneurs making and how to fix them.
Miguel McKelvey, Co founder of WeWork, Proto, and Nayah joins the show to talk about
- How Miguel got the inspiration for founding WeWork and how he and Adam approached finding PM fit.
- The cultural challenges WeWork faced in the early days as the company scaled, and creating WeWork's Culture OS (Operating System) to scale culture.
- Founding Proto and building a more inclusive brand of footwear.
- Supporting our elders and building a better community for our aging population with NAYAH.
- Pick up hoops and the venture that Miguel wishes someone would start!
Ann Miura-Ko, Founding Partner at Floodgate joins the show to talk about
- Founding a Venture Capital firm in the midst of a financial crisis.
- How founders should be thinking about their business and communicating to VCs at the pre-seed, seed, and Series A stages of company building.
- Why VCs say no and why Floodgate said no to Disco.
- What VCs actually mean when they say they're "investing in the founder, not the idea".
- The company that Ann wishes someone would start.
Jake Gibson, Co Founder of NerdWallet and Founding Partner at Better Tomorrow Ventures, joins the show to talk about
- Founding NerdWallet, building a public company, and pioneering in the early days of financial services on the internet.
- The right time to replace yourself in order to help your company scale.
- Investing in the future of FinTech, embedded FinTech and rethinking the interface of Financial Services.
Chris Buttenham, CEO and Co Founder of Obie (acquired by Seismic), joins the show to talk about
- How Chris' experience installing security cameras that led to the customer insight behind founding Obie
- Creating and falling into startup categories
- The process Chris took to successfully sell Obie to Lessonly and Seismic.
- Suggestions on how to grow the aSaaSins podcast
Gretchen Salyer, CEO and Founder of June Care, joins the show to talk about
- The childcare crisis in the US, and parenting and homeschooling in a global pandemic.
- Building a MVP for a better way to child care through community.
- How June Care's service model and product has evolved as they've received customer feedback from Moms on the network.
- The time I almost had my wife accidentally arrested.
Lauren Peate, CEO and Founder of Multitudes, joins the show to talk about
- The future of engineering and how teams use DORA metrics to measure engineering effectiveness.
- The importance of focusing on team outcomes and goals as an engineering leadership team.
- The impact that Generative AI will have on engineering team performance and productivity
- Ethics in AI and how entrepreneurs should respond to build to a higher standard.
Nichole Powell, CEO and Founder of Kinfield, joins the show to talk about
- Nichole's decision to make a professional pivot out of big tech to building clean, sustainable,consumer products for the outdoors.
- Nichole's experience appearing on Shark Tank, swimming with the sharks and receiving four different offers from investors to build Kinfield.
- How Kinfield has approached building product in a way that aligns with its core values and commitment to consumer health and sustainability.
- How Nichole and team have approached product segmentation for their various product lines and Kinfield's positioning strategy in retail.
Joe Pompliano, Co founder and CEO of Huddle Up, joins the show to talk about
- Two Billion social impressions, 25M YouTube views, and the journey to building one of the most successful content platforms for the business of sports.
- How Joe landed podcast guests like Ice Cube, Troy Aikman, Lance Armstrong, and others.
- How Joe evaluates the companies he invests in, and his perspective on working with his brothers and winning as a family.
Henry Shi, Co founder of Super, joins the show to talk about
- Democratizing the miles, points and rewards space, and Super's approach to customer segmentation.
- Henry and Hussein's approach to finding product market fit for their consumer focused startup, and Henry's thoughts on how this differs from finding PM fit in building a B2B company.
- Super's initial focus on the travel vertical, and what they learned in the process of shipping their first product that accelerated their business growth and expansion into other product verticals.
- How Super has secured $100M+ in financing and landed the real baby faced assassin Steph Curry, as an investor in the business.
- The product market model channel (PMMC) fit and getting all four right to build a hundred million dollar plus business.
Jacob Jaber, Chairman and Co founder of Philz Coffee joins the show to talk about:
- The founder's story behind building one of the industry's most successful specialty coffee brands.
- Creating a culture of "Grandma's house hospitality" and a personalized approach to building product and delivering service to customers, one cup of coffee at a time.
- How Philz harnessed initial customer fandom and built the flywheel around the Phil's brand.
- The role of the Philz barista, finding and empowering great people to extend the culture you're creating.
- Competing against global coffee brands like Starbucks and Peets, disrupting the coffee space, and thinking big but acting small
- How a lost bag at an airport resulted in a game changing distribution deal with Virgin America.
- Jacob's focus as an investor and building companies and products that people have a personal relationship with.
Justin rounds out the week with a quick recap from the MIT Sloan Sports Analytics Conference and talks about
- The future of fan engagement and personalization in sports.
- The evolution of the athlete, player empowerment, and the "look at me" generation
- Leadership lessons from WNBA legend, Sue Bird, Miami Heat VP of Analytics, Shane Battier, and Celtics GM Brad Stevens.
David Booth, CEO of On Deck, joins the show to talk about:
- How On Deck helps founders get leverage on their time and lean into community to build exceptional companies, as well as how On Deck differs from traditional accelerators like YC and 500 Startups.
- David's "three edges" framework to evaluate On Deck's founder candidates, and evaluating the mindset that many founders have before taking the leap to start their companies
- The importance of building founder relationships and communities in-person, and the evolution of the "Sand Hill Road" entrepreneur.
- David's advice to founders and companies operating in our current market conditions, and who has the better job, founders or investors?
Ben Emmrich, CEO and Co founder of Tusk joins the show to talk about:
- Disrupting FedEx and UPS with a better way to ship.
- The process Ben went through to sell and establish Tusk's first network partners.
- Diagnosing customer pain by checking the labels on the purchases we make every day.
- Ben's hustle selling dry ice and his approach to constructing monopolies.
Jesse Lipson, CEO and Co founder of Levitate and ShareFile, joins the show to talk about
- Bootstrapping his SaaS company, ShareFile, to a $93M acquisition by Citrix.
- What the acquisition process looked like during the sale of ShareFile to Citrix.
- The keys to building successful companies with and without venture capital.
- Becoming the diagonal aSaaSin and dominating in categories that cut across verticals.
- Building really big businesses in the Raleigh tech scene.
Stephanie Bowker, Co Founder and CMO of Ourspace, joins the show to talk about
- The "people puzzle problem", and the biggest challenge individual contributors face as they transition to managers of people.
- The rise of the marketing aSaaSin and why marketers make great founders.
- Brand building and positioning during the stage of going from 0 to 1.
- The growth of the international tech scene and founding a company from Paris.
Bryant Chou, Co founder and CTO of Webflow, joins the show to talk about
- Bryant, Sergie and Vlad's journey to building a unicorn, and the three signals that gave Bryant conviction they were on to something really big with Webflow
- Bryant's suggestions for entrepreneurs looking for a technical co founder and traits of what makes an exceptional founding CTO
- Webflow's origins as a self-service business and how the company has matured into an enterprise grade solution
Bryan Tublin, Owner and Co Founder of Kitava, joins the show to talk about
- Taking the leap to leave a stable tech job to start a restaurant.
- How Bryan validated the concept for his restaurant by bringing soup to house parties.
- His process for gathering customer and employee feedback to inform his menu and dining experience
- Bryan's decision to expand Kitava to multiple locations and how he used partnerships to test new markets before going all-in.
- Gourmet PB&Js and growth hacking through pop-up stands and food trucks.
Howard Lerman, CEO and Co founder of Roam and Yext joins the show to talk about
- Building Yext, pivoting after $20M in ARR, and replacing the Yellow Pages
- Whether or not remote work is here to stay, the impact of the Zoom meeting boom, and the death of the recurring meeting with Roam.
- The importance of founder stock and making employees founders.
Rajat Suri, CEO and Co founder of Presto and previous Co founder of Lyft joins the show to talk about:
- The customer insight that led to starting Zimride (aka Lyft)
- "Fork in the road" moments that have defined Raj's career as an entrepreneur.
- The thought process that led Raj to drop out of MIT to wait tables in a restaurant, and ultimately found Presto.
- Raj's decision to take Presto public and what that process looked like.
- Presto's position as an anti-metaverse idea and opportunities for automation in the physical world.
Roger Obando, CTO at Loyalsnap and Co founder of Baker Technologies (acquired by TILT Holdings), joins the show to talk about
- The evolution of the cannabis space, customer segmentation in weed, and the customer profile of the Chardonnay mom!
- Roger and team's experience raising capital for Baker, and his experience authoring his book, "The Highest Common Denominator",
- The differences of being a CTO that takes a company from 0 to 1 and a CTO that takes a company from 1 to 100 (and beyond).
Bill Clerico, Founder and Managing Partner at Convective Capital, and Co founder and CEO of WePay, joins the show to talk about
- Building companies in a recession and Bill's model for evaluating investment opportunities.
- How Bill and his team uncovered PM fit for WePay, and the signals that helped WePay make the transition from a consumer to B2B company.
- Current state of the payments industry and picking categories that are less evolved for disruption.
- Hiring the right profile of employee for the right stage of your venture.
- Bill's advice for navigating the fundraising market over the next 18 months as a startup founder, and why more founders should be building in climate, and more specifically, fire tech.
Brian Wang, founder and executive coach at Dashing Leadership joins the show to talk about:
- The similarities and differences of starting a venture backed startup and a coaching and services business.
- How early stage startup founders and leaders can get the best out of their people, specifically creating an environment that encourages risk taking and setting a clear short term AND long term vision.
- How founders can build more successful relationships with their investors and the importance of pushing back and embracing difficult conversations with your investors.
Cam Doody, Co founder and GP of the Brickyard, joins the show to talk about:
- Cam's first successful venture, Bellhop, and how he scaled one of the fastest growing companies in the moving industry.
- Brickyard's approach to accelerating and "insulating" great companies
- The benefit of relocating your early team to an island and the importance of physically working together in the early stages of building your culture and company.
- The best advice I've heard someone offer a founder when going through the grind, courtesy of Mr. Doody Sr.
AJ Forsythe and Jordan Barnes, Co founders of Coop, join the show to talk about
- Building the world's largest decentralized food network.
- The future of AgTech and putting automated agriculture systems on the moon.
- Pros and Cons of raising (and then being asked to spend) Venture Capital.
- Most importantly, unpacking what a cheese factory is all about.
Stefan Seltz-Axmacher, CEO and Co founder of Polymath Robotics, joins the show to talk about
- The importance of timing when tackling an emerging category.
- How Polymath thinks about customer segmentation and the customer profile(s) it's solving for.
- Finding the right technical co founder and building a strong engineering team.
- Opportunities for automation in specific verticals and the future and role of robots over the next 50 years.
Troy Vosseller, Co founder of the Gener8tor accelerator and Co founder of Sconnie Nation joins the show to talk about
- Troy's experience founding a startup accelerator, and the similarities and differences of being an entrepreneur and investor.
- The story behind Sconnie Nation and how Troy established a meaningful and lasting brand.
- How Troy got into the business of selling his own brand of beer, and how he thinks about category expansion.
Alan d'Escragnolle, CEO and Co Founder of Filmhub, joins the show to talk about
- How Filmhub approached the BD and enterprise sales process to secure distrubtion deals with incredible partners like Amazon Prime Video, Tubi, and The Roku Channel.
- The importance of focusing on partners that have high growth potential, versus only focusing on partners with the greatest market share.
- The future of the film and entertainment industry, democratizing film production, and spitballing ideas for TV series that could be huge (or fail miserably)
Anu Shukla, Co founder and Executive Chairman of Botco.ai, joins the show to talk about:
- The keys to finding product market fit as an entrepreneur, and her experience finding product market fit, multiple times, in various market conditions.
- Anu's experiences as a pioneer in the marketing automation space, as well as the ups and downs of building on someone else's platform.
- Anu's evolution as an entrepreneur from a specialist to a portfolio aSaaSin.
Matt Danna, CEO and Co Founder of Boulevard, joins the show to talk about:
- How Matt uncovered product-market fit in the salon category
- Boulevard's approach to customer segmentation and targeting, and the company's decision to build a vertical SaaS business versus horizontal SaaS business.
- Matt's approach to fundraising, and how he closed a 70M Series C during one of the most difficult times to fundraise.
- The best and the worst haircuts we've ever received.
Rob May, Serial entrepreneur and CTO and Cofounder of Dianthus joins the aSaaSins Podcast to discuss:
- His decision to start a company that wasn't SaaS first, and how Rob and his team are disrupting eCommerce.
- The evolution of AI and automation in the workplace, and what's missing for the space to really take off.
- Industries that are ripe for disruption through practical applications of automation, and the three criteria that make them candidates to target.
Jen Abel, CEO and Cofounder of JJELLYFISH joins the show to talk about:
- The importance of having the founder involved in the sales process when going from 0 to 1.
- The point at which founders should hire their first full-time sales person.
- The signals that companies and founders should be looking for to know when they've hit Product-Market fit.
- Using customer feedback to inform how your customers want to buy from you and how much your customers want to pay you.
"There's nothing scaleable about uncovering an earned insight." - Jen Abel, CEO and Co Founder of JJELLYFISH
Nate and Dave Evans, brothers and co founders of Fictiv join Jeremy and me on the show to talk about
- How Nate and Dave combined their unique interests and strengths as kids to build Fictiv. Dave's ability to break things and Nate's ability to think strategically.
- The process that Nate and Dave work through to make critical business decisions, and avoiding the 'Mom and Dad Syndrome'.
- The importance of not having the 'sibling debates' in public or in front of other work colleagues, and advantages of having an established baseline of trust over other co founders.
- How Nate and Dave have prioritized building a diverse team as they've grown and scaled Fictiv.
- The most important founder sibling questions: Who has a better jump shot? Who would win in a head-to-head wrestling match? Who is smarter?
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Puttshack, an upscale, tech-infused, mini golf experience. He analyzes their $150M growth round from BlackRock to takeover the indoor entertainment market.
Federico Baradello, CEO and Co founder of Finalis, joins the show to talk about
- The evolution of the investment banking space and the opportunities to innovate in the back office of the financial services space.
- Finalis' 'five year overnight success story' and finding product go-to-market fit through 200 failed sales calls.
- Key insights and recommendations for first time founders building products in FinTech.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Tumble, a smart laundry technology platform for property managers and renters. He unfolds their $7M Series A and the opportunity that Tumble is going after in the laundry industry.
Legendary educator and the Godmother of Silicon Valley, Esther Wojcicki, and her co Founder and CEO of Tract, Ari Memar, join the show to talk about:
- Esther's approach to empowering kids to be successful and how to raise successful kids.
- How Ari and Esther are disrupting early stage education with collaborative, peer to peer learning.
- Esther's experience working with her daughters, Anne (CEO of 23andMe) and Susan (CEO of YouTube) as her investors, and the dynamic of mixing family and business.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Artly Coffee, an AI-powered machine that makes a perfect cup of coffee every time. He unpacks their $8M Series A and the opportunity that Artly has in the coffee industry.
Kristen Berman, Co founder of Irrational Labs joins the show to talk about:
- When companies should look to behavioral science to help answer critical questions about their businesses.
- Practical examples and applications of behavioral science that founders can use to drive better outcomes for their startups.
- The three B model of behavioral change and the irony and importance of adding friction to drive better results around onboarding and sign-up flows.
- The importance of asking for help when making friends.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Pano AI, a hardware and software platform that helps fire professionals detect threats and respond to fire emergencies faster. He unpacks their $20M Series A and the opportunity that Pano has to help fight wildfires.
Laura McGee, CEO and Co founder of Diversio joins the show to talk about
- Laura's experience raising capital for Diversio.
- How she bootstrapped the company to profitability before raising capital.
- The current state of the technology industry as it pertains to diversity, equity, and inclusion.
On the aSaaSins 'Money Morning Quarterback' segment, our hosts Justin Vandehey and Chris Yeh break down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin and Chris play 'Money Morning Quarterback' with Verkada, an enterprise building security company, and Tract, a community and content marketplace for student-directed learning. They unpack Verkada's $205M round and Tract's $7M round.
Christine Tao, CEO and Cofounder of SoundingBoard joins the aSaaSins Podcast to discuss:
- The future of executive coaching and disrupting a category that has traditionally been limited to the highest earners in society.
- The challenges she faced when raising her seed round and additional challenges that female founders face when raising venture capital.
- The differences between raising SoundingBoard's Series B vs. their Seed and Series A.
- How Christine built SoundingBoard's initial network of leadership coaches, and importance of experience quality when building out the hard side of their network.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Muck Rack, a Public Relations Management platform. He unpacks their $180M growth equity round and analyzes the opportunity in the media intelligence and PR space.
Dan Reich, Co founder and CEO of Troops.ai joins the show to talk about:
- The story behind founding Troops and the sale of Troops to Slack.
- The story behind founding TULA, an industry leader in the skincare business, and the sale of TULA to P&G.
- The biggest differences and surprising similarities of running an enterprise SaaS business and D2C skincare company (and how to apply best practices across both business types to one another)
- His perspective on managing stress and pressure as an entrepreneur, and the importance of "thinking bigger" when building your business.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Yesler, a lumber and building materials marketplace. He unpacks their $5M round and analyzes the opportunity in the lumber management space.
Marvin Liao, Founder and Partner of Diaspora Ventures and formerly a General Partner at 500 Startups joins the aSaaSins podcast to talk about.
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What are Marvin's assessment criteria for investing in pre-seed and seed stage companies.
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How long after a company joined 500 Startups did he know if a company was going to make it or not, and what differentiated those that made it from those that didn't.
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How the incubator model is changing and evolving, and what this means for the future of seed stage companies going through incubator programs.
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How to improve your odds at getting accepted into an early stage accelerator, and alternative approaches and options founders can take to get support to go from zero to one.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with CurbWaste, a waste management and business operations platform for physical waste haulers. He unpacks their $6M seed round and analyzes the opportunity in the waste management space.
Jon Fasoli, Chief Product Officer of Mailchimp, joins the aSaaSins podcast to talk about.
- How he assesses the professional opportunities and projects that he invests his time and energy into.
- His experience running the product strategy for Intuit's $12B acquisition of Mailchimp.
- Future growth drivers and industries of interest for Intuit.
- Intuit's framework of 'horizon planning' and how early stage founders can use this framework to evaluate the progress they're making with their venture.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Incredible Health, a medical and health platform that connects health systems with nurses. He unpacks their $80M Series B round and analyzes the healthcare technology industry's first health talent unicorn.
Daniel James, CEO of Zen, joins the aSaaSins podcast to discuss:
- How Daniel's experience transitioning from being a Division 1 collegiate athlete to a working professional led to the opportunity around improving posture at work.
- How Daniel and his team have navigated questions and concerns around privacy while building a solution that's providing real customer value.
- Daniel's focus around building an experience that meets employees where they work.
On the aSaaSins 'Money Morning Quarterback' segment, our hosts Justin Vandehey and special guest host Chris Yeh break down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin and Chris play 'Money Morning Quarterback' with Boulevard, a platform that helps appointment based businesses (like Spas and Salons) streamline their operations, and Ben, an employee benefits and rewards platform. They unpack Boulevard's $70M Series C and Ben's $16M Series A.
BJ Schaknowski, CEO of symplr joins the aSaaSins pod to talk about:
- How BJ helped me "flip the switch" from being a disengaged poor performer to becoming a top performer at Intuit.
- BJ's guidance on effective leadership and the importance of balancing the "what" (work output) with the "how" (how we accomplish those objectives).
- The importance of being direct and helping your teammates understand the "why" behind your actions.
- The value and importance of bringing your authentic self to work, maintaining a learning mindset, and building a diverse and balanced team.
- BJ's decision to join and lead symplr, his noble purpose, and the opportunity to achieve better health outcomes through the business he's building.
- What should first time founders be thinking about if they want to start a venture in healthcare.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Arena, a platform that helps large enterprises make high frequency decisions (like pricing and inventory) fully autonomously. He unpacks their $32M Series A round and analyzes the market opportunity in the Big Data and Business Analytics space..
Ram Jambunathan, SVP and GM of SAP.io (SAP's strategic investment and incubation arm) joins the aSaaSins Podcast to discuss:
- Ram's experience as a founder, advisor and investor, and how those experiences have shaped his approach to supporting early stage founders.
- What founders should think about when raising capital from strategic or corporate investors.
- The real incentives behind corporate strategic investment.
- How corporate development and M&A really work inside of a large enterprise software company.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Sage, a platform that helps improve care with better caregiver tools that ensures older adults receive individual care. He unpacks their $9M Seed round and analyzes the market opportunity to improve the caregiver and resident experience inside assisted living facilities.
Jay Srinivasan, CEO of Spoke, joins the aSaaSins podcast to talk about.
- Going after large incumbents like ServiceNow, SAP, and Salesforce, and how he landed on the problem space for Spoke.
- The differences between being a second time aSaaSin vs. a first time aSaaSin, and what has been easier and harder about each venture.
- Advice he WOULDN'T offer to first time founders and when is the right time to sell your startup.
- The importance of product, go-to-market fit when scaling, and why this is more important than product-market fit.
- Walking through the acquisition process for Jay's two startups, Appurify (Google) and Spoke (Okta).
Summary:
- Ben shares how Octane thought about early traction channels and platform partners when launching their business. Specifically their partnership with Shopify.
- He discusses the process he went through in writing and authoring his book, "Captivology".
- Ben provides suggestions on how entrepreneurs can tap into 7 different triggers to get above the noise and captivate audiences to grow their startups.
- How Ben got Rick Ross and DJ Khaled's attention.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with FairPlay, the world's first Fairness-as-a-Service company, to unpack their $10M Series A round and analyzes the market opportunity to make applying for a mortgage a more fair and transparent process.
Cody Candee, CEO of Bounce joins us to talk about:
- How global travel unlocked his insight to found Bounce, and how he convinced total strangers to hand over and store their things with him for cash.
- Cody's experience building a company that was dependent on travel in the midst of global travel lockdowns, and how his team persevered through that.
- The signals that gave Cody and his team conviction to keep going, and how taking a 'helpful' approach to building solutions for their SMB customers unlocked new opportunities.
- Tactics on establishing and maintaining network effects at the earliest stages of founding your company.
Jassim Latif, Cofounder of Zipper and formerly Slack's first Platform and BD hire, joins the pod to talk about.
- Reflecting on the early days at Slack.
- Building an early ecosystem and raising capital on someone else's platform.
- Gathering insights to build Zipper and unlock cross functional teams.
- The boldest things founders have done to get on Jassim's radar and hacks to get on larger platforms' radars.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with Aquabyte, an AI Aquaculture company, to unpack their $25M Series B round and analyzes the market opportunity that technology has in the commercial fishing industry.
Veronica Belmont, Product & Evangelism leader at Adobe (and Disco's first hire!) joins the show to share some insight into:
- How we convinced her to join as our first product hire.
- How values, culture, and company mission played into her selection criteria when joining our startup.
- The value of onboarding employees through the lens of customer support to gain empathy
- Recommendations on how to build and foster community at the earliest stages.
On the aSaaSins 'Money Morning Quarterback' segment, our host Justin Vandehey breaks down the companies that raised their Seed, Series A, or Series B round of funding the prior week.
This week, Justin plays 'Money Morning Quarterback' with StyleScan, a virtual dressing room, to unpack their $1M seed round and analyzes the market opportunity in fashion tech to decide whether or not he'd invest.
This episode features cofounder of strongDM, Schuyler Brown as he shares his story on how strongDM raised its first round of financing BEFORE building their product. He also talks about turning down his offer to join YC, the time they almost gave away a car to build hype, and how to run a fundraising process that maximizes your startup value.
This episode features legendary 500 Startups pitch coach and founder of sexual wellness company, O.school, Andrea Barrica where we talk about
- The psychology behind the founder's pitch
- How timing and hype cycles influence pitch strategy.
- The similarities behind selling money and sex