Bootstrapped Web | For Entrepreneurs Bootstrapping Web Startups | Interviews & Business Case Studies: Recent Episodes
Bootstrapped Web
Bootstrapped Web is for entrepreneurs who are bootstrapping web startups and believe in order to achieve success, we must learn by doing. Interviews with bootstrapped entrepreneurs and case studies in building profitable businesses.
Brian shares the news rebranding ZipMessage to a new name and the transition roadmap ahead... And the new name is...
Jordan and team step away to a conference while go-to-market heats up.
Oh yeah, and recorded on the day the Silicon Valley Bank saga unfolded in realtime... So that was a (and scary) discussion.
Jordan and Brian both feel overworked this week. Putting in more hours than usual, and more importantly, strategizing on which priorities get those hours.
Another week in the chaos that is startup land for Brian and Jordan. Topics include:
- Starting and finishing our day
- Managing focus through daily distractions
- Delegating strategy and teeing up for results
- And other rants… You know the drill
Hit us on Twitter @casjam @jordangal with feedback on what we should talk about next week!
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.
The episode streak continues! Brian’s product design process, Jordan’s annual budget meeting (and takeaways), outbound vs. inbound marketing, and an interesting discussion around the usefulness of projections.
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.
This week, Brian and Jordan yap about:
– Strategic partnerships
– Pricing on transactions
– Communicating company direction (internally)
– Developer-focused content
– …Creatine pills?
We’re running out of ideas! Hit us up on Twitter (@casjam, @jordangal) and tell us what we should talk about.
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.
Back for our weekly founder therapy session, err… podcast episode
Here’s what’s up this week:
– Brian (finally) ships sub-threads in ZipMessage
– Jordan’s hiring an SDR
– Learning from strategic decisions that went wrong
– Product insights with vs without a product in market
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.
We kick off 2023 with a grab bag of topics:
– Jordan’s building in public more
– Brian’s building solo with contractors
– Headless ecom becoming “a thing”
– ChatGPT is firmly in Brian’s coding workflow
Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.
We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on…
Thanks for listening and for sticking with us another year on Bootstrapped Web.
Talking Points:* Viruses, holiday cards, and coming back from vacation * 2022 for ZipMessage and Rally * Lack of product-market fit * Tim Ferriss’ Fear Setting * The Ten-Year Business * Staying “based” and staying true to your vision * Themes and goals for 2023 * Building features specifically for specific markets
Resources:Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.
We asked ChatGPT to suggest some topics for today’s episode but it came up short. So you’ll have to settle for the boring human versions of Brian and Jordan, talking about what’s happening in ZipMessage and Rally. Enjoy.
If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.
“What can this do? How does this change our product? Does this change things significantly enough that we should come off our roadmap?” – Jordan Powered By the Tweet This PluginTweet This*Here are today’s conversation points:** The future of AI and creators * Q4 spreadsheets and budgeting * Updates in Rally and ZipMessage + SEO content + Marketing and sales + Product-led content
“If we’re not working on those growth graphs, I don’t feel comfortable. But, at the same time, I need to work more on the product” – Brian Powered By the Tweet This PluginTweet ThisResources:Brian on Twitter
Jordan on Twitter
ZipMessage
Rally
As always, thanks for tuning in. Head here to leave a review on iTunes.
Our obligatory take on Twitter in the Elon era. Also: SEO, board meetings, and growth targets. What are your thoughts on Twitter in the time of Elon? How do you run your board meetings? When it comes to growth targets, where do you focus your energy? If you have any questions, comments, or topic ideas … Continue reading Twitter Takes (and Some Business Talk)
Jordan talks defining their category and stepping back into the sales demo seat. Brian launched a community strategy while big product plans are underway in Q4. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. Here are today’s conversation points: NoSnowTinyConf Recap Residual issues that arise after … Continue reading Q4 Energy
What tools do you use for sales and support? Which tools work best for project management? How do you know who to hire first if you’re a bootstrapped company? Brian and Jordan asked for your questions and Twitter delivered. Today, they are answering Twitter’s questions about what tools they use, and who to hire, and … Continue reading Tools & People
Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most random Bootstrapped Web episode yet? How do you navigate the Catch-22 that is operations versus growth? If you were to jump into a completely different niche or … Continue reading What We’d Build (If Not This)
What are the rocks in your life right now? How do you balance work and life? What are some good compartmentalizing tactics, so you can leave work at work? What are routines and habits that work for your schedule and team? Today, Brian and Jordan are talking about their daily routines and how they plan … Continue reading Work-Life (Hour-by-Hour), Explained
How do you figure out the next iteration of your business? What keeps you unemployable? Does your environment change your outlook on personal and professional goals? After a short but busy couple of weeks, Brian and Jordan are back to talk about updates in their businesses and their lives. Jordan is starting to settle into … Continue reading Research, Roadmaps, People, and Product
How do you get rid of post-illness brain fog? How do you build company culture when you’re absent? What are your steps to shipping out features? There have been plenty of changes with Brian and Jordan since the last episode: moving and changing environments, changing energies, and changing up routines. Today, Brian and Jordan are … Continue reading Company as a Product
What has happened in the venture funding world in the past couple of months? How do you handle repositioning? Can you lean too heavily on your product, features, and roadmaps? What do you do when one of your features falls flat? It’s the middle of the summer edition of Bootstrapped Web. Brian and Jordan are … Continue reading Product vs. Pipeline
How do you avoid consistent churn with new products? What tools do you use to learn about your market? What influences the changes in your products? It has been a while but Brian and Jordan are back, and they’ve brought updates with Rally and ZipMessage. Jordan talks about his fundraising efforts. Brian talks about his … Continue reading Talking to Customers
Brian and Jordan are both in flux between school, stressing over work, selling houses, and MicroConf. They summarize their chaotic couple of weeks and then do a deep dive on what content marketing will look like in 2022. Recently Aaron Francis (Tuple’s first marketer) talked about their $200,000 loan from Stripe and how he plans … Continue reading Marketing in 2022
What do you get out of conferences? Do you mute competitors on Twitter? How to you utilize Twitter as a budding SaaS entrepreneur? After a brief hiatus, Brian and Jordan are back with some big news: Carthook was officially acquired! Jordan shares what details he can about the acquisition as well as the process and … Continue reading CartHook Acquired!
How do you decide what features you should work on now? How do you stay unplugged during a vacation? What are the milestones and progress markers that tell you if you are on the right path? As Brian comes back from a vacation and conference (and before Jordan leaves for his own), we’re catching up … Continue reading Traction… Then what?
We have some big news to share before we go on a (much needed) two-week hiatus. Brian talks about his sale of Productize, in addition to nearly every other business he has owned. Jordan talks about his latest tweet thread, responding to Moiz Ali’s criticisms of Shopify. We also talk about the power of audio, … Continue reading Everything Must Go
How are you and your company changing with the times? Are you considering tokenizing your software company? Have you begun adopting web3 technology? Today, we’re talking about marketing, hiring developers and writers during “The Great Resignation,” and tokenizing. Token-based economics is the future of SaaS. Web3 tech isn’t just in the future, it’s happening right … Continue reading Tokenizing
Brian and Jordan are having a great time as they ride good days, give great updates, and look forward to some exciting things in the near and far future. In today’s unscripted and random episode, Brian and Jordan give us some great news in terms of business updates. They also talk about one of the … Continue reading So Meta
Brian has sold ProcessKit! He explains the surprisingly stress-free and smooth process. Jordan talks about his upcoming move to Chicago. Meanwhile, they also give updates on Rally’s marking and sales funnels, and prioritization at ZipMessage. Today’s episode is filled with business updates, optimism, and great outlooks for 2022. Don’t forget to check out ZipMessage on … Continue reading Wheels Are Turning
Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th 🚀 Your comments and feedback on Product Hunt would go a long way today 🙂 To kick off the new year, Brian and Jordan share their 2021 reflections and 2022 goals (or whatever you want to call these … Continue reading 2021/2022 New Year reflections
What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phases of product/market fit. Jordan dives into the different and unique ways Rally is marketing. Brian updates us on ZipMessage momentum: website updates, premium enrollment, and crossing a customer milestone. Today’s episode … Continue reading Define Traction
Does experimentation affect your business and cause more stress within your leadership team? How are the communication levels within your team? How do you reach a niche market? Jordan and Brian talk about these questions and more on this episode of Bootstrapped Web. Jordan talks about his hangups and why his need for idea exploration … Continue reading The Chaos
When launching a new SaaS business, what comes first? What features do you focus on? How do you keep an eye on your key metrics early on? How do you handle onboarding when you’re shuffling team members’ priorities? Brian and Jordan talk all about the newest updates with ZipMessage and Rally. From experimenting with free … Continue reading Chicken or Egg Development
Jordan shares some big news, 5.8 million dollars worth of news. At the feet of the news of Rally’s seed funding announcement, Brian and Jordan talk all about raising money for businesses. What are the mechanics of starting the funding journey? Which funding path should you take? What does it mean for a fund to … Continue reading How to Fund a Startup
What is the difference between going to market and marketing? What mindset do you need to be in to accomplish your goals for both of these stages of business? In addition to answering these questions, Brian and Jordan dive into their marketing goals, content strategists, and updates on where they are with their Rally and … Continue reading Go to Market vs. Marketing
Bootstrapped Web is no longer bootstrapped, on either side! Jordan starts off this episode with his “coming out” strategy, which all starts with his initial three-post series on Rally. He also dives into Rally updates, comparing your start-up businesses, and the importance of developing a unique view of the market. Brian takes funding from Calm … Continue reading Should We Rename the Podcast?
Some news! Brian has sold his business, Audience Ops, to JD Graffam! And what better way to announce this transition than to bring JD on the show! Jordan leads the way as Brian and JD talk through how this deal came together, the process from each of their perspectives, and the successful close and transition that’s now … Continue reading Audience Ops Changes Hands
Introduction: Do you work with a full-service accounting and admin company? How do you create markers on your business’s path to success? What unique marketing platforms and ideas do you use? Brian and Jordan are back behind the mic, during this horrendous heatwave. Today’s topics range from admin and accounting tasks they would rather avoid, … Continue reading Marketing ideas
After a month hiatus, Brian and Jordan are back with stories about trips, waking up in pain, and prepping for competition. They also talk about growth in terms of profitability versus milestones, the newest developments with ZipMessage, and introducing “common, everyday tools” to people outside of the SaaS community. If you have any questions, comments, … Continue reading Back and Running
Brian and Jordan are back to back-to-back weeks before vacation and travel plans kick in because… It’s summertime! While Jordan deals with a minor lacrosse injury, they both gush over Matt Medeiros, and give updates on their latest business endeavors. They talk about the progress on the search for a media creator for both Rally … Continue reading Metrics & Hiring Funnels
Brian and Jordan are back with updates about diving headfirst into team sports with an “old man lacrosse leagues,” to celebrating 10-year wedding anniversaries, job postings, and creating messages that resonate with customers. They’re covering a little bit of everything today. Brian shares a couple of interesting job openings based on ZipMessage: a media creator … Continue reading Hiring Media Creators
Brian and Jordan are back with no excuses and plenty of updates for both Rally and ZipMessage. Today’s topics are all about roadmaps, leading tech teams, and ecommerce marketing. While ecommerce has been around for a while, SaaS is evolving in the way it is marketed and sold. What are your thoughts on SaaS marketing … Continue reading Raising The Bar
It’s a big day here at Bootstrapped Web now that Jordan can talk more openly about his newest endeavor: Rally. Brian and Jordan talk about what Rally is, breakdown Rally’s elevator pitch, as well as the steps Jordan has taken up to this point. They also get into a few updates with ZipMessage. Brian talks … Continue reading Rally On
Brian and Jordan are back behind the mic for the second week in a row. Today they’re focusing on bugs over customers, or should it be the other way around? After some project and business updates, they talk about the early stages of development and launch for a new product. How do you decide if … Continue reading Bugs vs. Customers
Brian and Jordan are back with big news about both of their newest projects. Today they’re doing a deep dive into some of the mental struggles when you start something new. Some touchy-feely topics, some logistics, and back to touchy-feely topics: a typical Bootstrapped Web episode. If you have any questions, comments, or topic ideas … Continue reading Staying positive
Brian and Jordan are back before Brian leaves to scratch his travel itch. Today, they are talking about the things they can control (launching ZipMessage and Jordan’s new company), while also touching on a couple things they can’t control (vaccines and concerts). They also spend a little time talking about Josh Pigford’s amazing public journey, … Continue reading Never Fast Enough
Will this be the week that Jordan finally gets to talk about crypto? In this episode of Bootstrapped Web, Brian and Jordan give us some updates on their businesses. Is Brian running late with ZipMessage? What has been going on behind the scenes of Jordan’s secret project? They also talk indepth about discipline and productivity. … Continue reading Know Thyself
This is two weeks in a row for Brian and Jordan. In today’s episode they’re talking about new toys and tools, Twitter drama, and business talk, specifically Jordan’s newest team member and Brian’s newest product. April 5th is going to be a big week for both Brian and Jordan when it comes to business news. They also successfully avoid having Jordan talk about crypto for another episode. How long will they be able to go without talking about it?
“It’s like part fundraise, part marketing.” – Brian, about the Sahil’s 7,000 investors which helped raise 5 million dollars Gumroad Powered By the Tweet This PluginTweet This Here are today’s conversation points:
- Regulation crowdfunding ceilings
- SaaS and tech people and temperaments on Twitter
- Updates on ZipMessage
- Nine simple reasons why Brian loves and is launching ZipMessage
- It’s sharable and boastable
- Brainstorming ideas for a viral launch
- Arrows.to’s launch strategy
- Jordan’s new chief-of-staff started, which has led to a productive week
- Easier to do things when you’re being held accountable
- Writing content, then handing it over to a copyeditor to tighten the drafts
- Rearranging the sequence of rollout
“People have money to invest. If you just let people in, there are a lot more people than you’d expect, who want to get involved.” – Jordan Powered By the Tweet This PluginTweet This Resources
ZipMessage
SunriseKPI
Productize
AudienceOps
ProcessKit
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.
Officially a year after the pandemic started, Brian and Jordan do a bit of reminiscing and chatting about vaccine news before diving into updates about work. Not to mention, Jordan gets his first real haircut of the year.
On the business front, things are moving (slow and steady) for Brian. ProcessKit has accumulated a decent amount of data which means that he can start making data-driven decisions for the business. While ZipMessage is still new and in the early stages of the process. Jordan talks about the change in his mindset from Carthook to his new project. Meanwhile, Brian talks about delegating tasks, what it means to “hire to collaborate,” and the things he’s doing in order to build his rhythm with ProcessKit and see progress.
“The more tight you can be, the more narrowly-targeted, niched-down you can be, the better off you are. The easier you are to market. Easier to sell that value proposition.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points:
- The shift in temperance about the ongoing pandemic
- Vaccines and vacations
- Changing your mindset: going from bootstrap to VC
- How that affects your appetite for risk
- Delegating tasks to people now and hiring to collaborate
- Hiring freelancers
- Finding talented people who don’t want to be full time employees
- Stories (success and otherwise) with freelancers
- New trends with sales since Jordan started Carthook
- What do you do with marketing, prelaunch?
- ProcessKit updates
- In-app onboarding flow is helping self-conversion
- Is patience the key?
- Home page content about customer on-boarding and niches
- Testing headlines and swapping out pages to test data and changes in customer trends
- The possibility of launching a new version versus launching new features
“When you get used to that for a few years, and that gets ingrained into your mindset, it has an effect on a lot of different things. Not only your cash management and your willingness to hire and your willingness to spend and who you work with… All that stuff, it also trickles down into your appetite for risk and that has a big impact on the product itself.” – Jordan Powered By the Tweet This PluginTweet This Resources
ZipMessage
ProcessKit
AudienceOps
Productize
SunriseKPI
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.
Today, Brian and Jordan are talking about what it’s like in no man’s land and their struggles with imposter’s syndrome. Brian shares more details about his newest venture. Jordan talks about his need for structure. They do a deep dive into the launch process and various launch strategies as well as updates on their various projects, their opinions on Clubhouse, and how they avoid feeling overwhelmed with new ideas.
“Just stick the flag in the group and make the case. In the end, either they strongly agree with it or the strongly disagree with it..” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points:
- Launching a brand new product… with no product yet
- What to do when you’re in no man’s land:
- Jordan’s three goals each week
- How Brian uses the Day One app
- Zipmessage updates
- Launch strategies
- Content and web copy versus product
- Does nobody read anymore?
- What format works?
- Clubhouse and Twitter
- The “I’d rather do X” conundrum
- Live broadcasts
- Jordan’s new chief-of-staff
- AudienceOps updates
- Delegating duties
“Our product is extremely opinionated. It’s not for everyone. I think the best thing that we can do is put out our philosophy and our thinking, along with the product. And use that as a beacon.” – Jordan Powered By the Tweet This PluginTweet This Resources
Day One
ZipMessage
ProcessKit
AudienceOps
Productize
SunriseKPI
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.
Brian and Jordan are back after a short break. Today’s topics involve new developments with Brian, Twitter conversations, and market research for new and current projects. Brian gives us a sneak peak into a new project. Jordan brings his opinions on Twitter and how companies are using their social media profiles for marketing. They briefly talk about the pros and cons of Clubhouse. Lastly they dive into networking and e-commerce.
“Zoom fatigue is real.”- Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points:
- Zipmessage: sharable conversation pages
- Intention, goals, and vision for this new product
- Different landing pages for different niches
- Risk and innovation
- Figuring out pricing
- Price based on usage
- Clubhouse
- Waiting for value
- Tuning in during the workday or after
- Live versus podcasts and recorded media
- Ruben Gamez’ Twitter conversation about personal brands and bragging on Twitter
- The dangers of Twitter
- Networking and ecommerce
- Reaching out past your comfort zone
- “Not knowing what you don’t know” when it comes to untapped opportunities outside your field of vision
“My feelings for Twitter have been much more negative in the past few weeks.” – Jordan Powered By the Tweet This PluginTweet This Resources
ZipMessage
Ruben Gamez’ Twitter Convo
ProcessKit
AudienceOps
Productize
SunriseKPI
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.