Practical Founders Podcast | Podcast Summaries

Business

Technology

by Greg Head

Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with founders who have built valuable software companies--without big funding.

20 episodes summarized

Episodes

#221: Earnouts, Ratchets and Consent Rights: The Exit Terms Founders Miss - Jesse Welch

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Jesse Welch runs <a href= "https://www.midcapglobal.com/" target="_blank" rel= "noopener">Midcap Global</a>, a boutique investment bank advising companies with $1 million to over $10 million in profits. He came from film production, AI startups, a real estate private equity firm and a crypto hedge fund sold in 2021, and he now teaches founders on his <a href= "https://www.youtube.com/@Capitalloveletters" target="_blank" rel= "noopener">Capital Love Letters YouTube channel</a>. His core point: the headline exit price is a vanity metric; it's the other terms that decide who gets paid, how much and when. He walks through earnouts, rollover equity, escrows, consent rights, preferred equity, PIK interest and ratchets, and shows how each one can be turned against a founder who signs without understanding it. He also covers newer traps for software sellers, including annual prepay contracts that trigger working capital demands, plus quality of earnings reports and family office buyers. His advice: build a three-person team with a CPA, lawyer and M&A advisor, stay patient and flexible, and assume every clause gets used against you. Key Takeaways <ul> <li dir="ltr" role="presentation">Earnout Odds - About 25% of lower middle market deals include one, and the market pays around 21 cents on the dollar.</li> <li dir="ltr" role="presentation">Consent Rights - Assume every clause gets weaponized against you; Jesse puts the odds at forty to fifty percent.</li> <li dir="ltr" role="presentation">Preferred Equity - Liquidation preferences, participation and PIK interest put investors first in line, and time works against the founder.</li> <li dir="ltr" role="presentation">Prepay Contracts - Buyers may demand part of the annual cash you collected stay behind; negotiate to the real cost of service.</li> <li dir="ltr" role="presentation">Advisor Team - Hire a CPA, a lawyer and an M&A advisor, because lawyers make deals legal, not strategic.</li> </ul> Quote from Jesse Welch, Founder and CEO of Midcap Global "Earnouts are tools that can be used to trap you. About 25% of lower middle market deals have one, and they're sold as a second bite at the apple, but they don't tell you if that apple's rotten or if there's a worm in it. When I'm representing a buyer I always push for an earnout, but for a founder it's an extremely dangerous tool. "Say you want to sell at $200 million and the buyer wants to pay $190 million. To bridge that ten-million gap, they'll ask you to work for them for two years, with five million for each year if the company hits certain metrics, usually a profit number. It sounds great because you know your business and you can grow it to that number, but you're betting on the same horse with a different jockey. "The buyer can reduce your marketing spend, add a monitoring fee and throw overhead onto your business, so a ten-million profit target lands at $9.9 million. You don't get 90 percent of your earnout for getting 90 percent of the way there; you might work for two years and walk away with zero. About half of earnouts pay out nothing, and across the entire market they pay around 21 cents on the dollar." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/jeg26/" target="_blank" rel= "noopener">Jesse Welch on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.midcapglobal.com/" target="_blank" rel= "noopener">Midcap Global website</a></li> <li dir="ltr" role="presentation"><a href= "https://www.youtube.com/@Capitalloveletters" target="_blank" rel= "noopener">Capital Love Letters (YouTube)</a></li> </ul> <h2>Podcast Sponsor – DevHawk</h2> <div>Every founder I know is trying to move their roadmap faster with AI, but most admit it isn't working. DevHawk is an AI software factory from former practical founder Praveen Ghanta.</div> <div> </div> <div><a href="https://www.devhawk.ai/" target="_blank" rel= "noopener" data-saferedirecturl= "https://www.google.com/url?q=https://www.devhawk.ai/&source=gmail&ust=1786669746898000&usg=AOvVaw2quWExe9PKpP3FAi09Id50"> DevHawk</a> plugs in a full crew of customized AI agents that handle the whole development job, end-to-end. Not just writing code, but requirements, testing, shipping, and maintenance.</div> <div> </div> <div>Add their AI agents to your org chart and run them yourself--or have the DevHawk team manage the software factory for you. Either way, you get a team that works while you sleep, and a roadmap that can move 5-10x faster within a month.</div> <div> </div> <div>Head to <a href="http://devhawk.ai/practical" target= "_blank" rel="noopener" data-saferedirecturl= "https://www.google.com/url?q=http://devhawk.ai/practical&source=gmail&ust=1786669746898000&usg=AOvVaw1_nAAs3LPJhLgJZ98n9JVa">devhawk.ai/practical</a> to book a conversation about how DevHawk can help. </div> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

November 6, 2026•1:14:14

#220: You Can Skip Venture Capital and Still Raise Too Much - Jerry Nettuno

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Jerry Nettuno started <a href= "https://www.vagaro.com/pro/schedulicity" target="_blank" rel= "noopener">Schedulicity</a> in Bozeman, Montana, in 2009 after struggling to book his own haircut as a single father. He recruited his first developers from Denver, paid for the build himself, and launched online scheduling for hairstylists, trainers and other small service businesses at $29 a month, starting with about a hundred customers around Bozeman. To fund a bigger team and faster growth, Nettuno raised millions from angels and one large private investor, never from venture capital. Schedulicity grew to 15,000 to 20,000 small businesses, almost 40 million consumers, $10 to $20 million in revenue and about 100 employees, but growth stalled after COVID. The company raised about $28 million in total private capital. Looking back, Jerry says he would raise less, since every round raises the sale price needed to deliver the same return, and today he could run the same company with a fraction of the people. He sold to Vagaro, closing in early 2025, and now co-founds Pulsara, which expects about $30 million in ARR. Key Takeaways <ul> <li dir="ltr" role="presentation">Exit Math - Every round raises the bar: $200 million to match the return a $25 million sale once delivered.</li> <li dir="ltr" role="presentation">Cheaper Today - With today's tools, the same company could run with a fraction of the employees Schedulicity needed.</li> <li dir="ltr" role="presentation">Non-VC Capital - Angels and one large private investor funded Schedulicity after Sand Hill Road meetings left him unimpressed.</li> <li dir="ltr" role="presentation">Win The Owner - Fixing the stylist's business problems brought her 200-plus customers onto the platform without paying anything.</li> <li dir="ltr" role="presentation">Explain Fast - Many founders lose people explaining the product; be able to say it in one minute before building further.</li> </ul> Quote from Jerry Nettuno, Founder and CEO of Schedulicity "I would have definitely not raised the money that we did when we did. It was only so much I could do on my own, but I think we could have bootstrapped a little bit longer and not had to raise as much money. Things were so different at that time it was hard to see, but it's very clear looking back, obviously. "Not to mention, in today's world we could have run the same company that we sold with probably a fraction of the employees. When seventy percent of founders say they'd raise less, a lot of it has to do with the fact that every time you raise money, the benchmark is raised. "The more money you raise, it exponentially increases the amount you'd have to sell the company for to get the same amount. I remember seeing an article early on that talked about that. Once you raise the bigger money, you'd have to sell the company at two hundred million to come away with the same kind of return as you could have sold it for twenty-five." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/jerry-nettuno-81834713/" target= "_blank" rel="noopener">Jerry Nettuno on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/schedulicity" target="_blank" rel="noopener">Schedulicity on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.schedulicity.com" target="_blank" rel= "noopener">Schedulicity website</a></li> <li dir="ltr" role="presentation"><a href="https://www.vagaro.com" target="_blank" rel="noopener">Vagaro (acquirer)</a></li> </ul> <h2>Podcast Sponsor – Full Scale</h2> This podcast is sponsored by <a href="https://fullscale.io/" target="_blank" rel="noopener">Full Scale</a>, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at <a href= "https://fullscale.io/" target="_blank" rel= "noopener">fullscale.io.</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

October 30, 2026•1:06:37

#219: Vibe-Coded Isn't Validating: Rob Walling's Warning for AI-Era Founders - Rob Walling

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Rob Walling has been publishing <a href= "https://www.startupsfortherestofus.com/" target="_blank" rel= "noopener">Startups for the Rest of Us</a> every week since 2010 — he recorded episode 855 the morning of this interview — and has written five books on bootstrapped SaaS, with a sixth on the way. He started five companies before turning to investing, all of them bootstrapped, and sold Drip in 2016. In 2018 he and co-founder Einar Vollset launched <a href="https://tinyseed.com/" target="_blank" rel= "noopener">TinySeed</a>, the first accelerator built for SaaS bootstrappers. They aimed to raise $1-2 million for the first fund and closed almost $5 million. TinySeed now writes $150,000 to $250,000 checks into companies doing $2,000 to $40,000 MRR, funds one to two percent of applicants in batches of 10 to 20, and runs a year-long program instead of the standard 90 days. Rob is invested in 241 SaaS companies. This year TinySeed is skipping a batch for the first time since 2019 — not because the portfolio is struggling, but because Rob wants to do the work on which moats still hold in the age of AI before writing more checks. His aggregate revenue graphs are still climbing while the market has repriced the entire category, a gap he calls the widest he's ever seen between sentiment and reality. Rob has just revised his popular book, <a href= "https://ideatotractionbook.com/" target="_blank" rel= "noopener">Idea to Traction</a>, for the AI age. It's for founders to turn software product ideas into actual businesses with happy customers who pay you--for years. Building software products used to be hard and slow, now it's neither. The challenge has moved to validating with customers--before you start building. Key Takeaways <ul> <li dir="ltr" role="presentation">Sentiment Gap — Portfolio revenue is still climbing while the market prices SaaS for a collapse.</li> <li dir="ltr" role="presentation">Ten to Twenty — Rob's estimate of the SaaS share facing real AI headwinds, not the whole category.</li> <li dir="ltr" role="presentation">Validation Still — Shipping fast is not validating; experienced founders still talk to customers first.</li> <li dir="ltr" role="presentation">Moats Shifting — Complexity and integrations stopped protecting anyone; permission to act still does.</li> <li dir="ltr" role="presentation">Average Is Terrible — AI tools needing constant supervision lose to one competent full-time hire.</li> </ul> Quote from Rob Walling, Co-Founder of TinySeed "Just because people can build things now, they think they don't have to validate. When I turned Idea to Traction into a video course, someone bought it and asked for a refund, which we give. I wanted to know why, and they said the first third is about validating, having conversations with customers, and getting a landing page. They told me they don't have to do that anymore, because they can just build a product in a day and launch it. And I told him, No, you are wrong. "So I went back and revised my Idea to Traction book to address that exact objection. I have all these examples of second and third-time founders who are doing validation, because they're experienced and they know they need to. Steve Blank was saying the same thing: everyone was showing up with a vibe-coded prototype, and they hadn't talked to a single customer, to their detriment. That's the biggest myth I'm trying to fight." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/robwalling/" target="_blank" rel= "noopener">Rob Walling on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.startupsfortherestofus.com/" target="_blank" rel= "noopener">Startups for the Rest of Us podcast</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/tinyseed" target="_blank" rel= "noopener">TinySeed on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href="https://tinyseed.com/" target="_blank" rel="noopener">TinySeed website</a></li> <li dir="ltr" role="presentation"><a href= "https://ideatotractionbook.com/" target="_blank" rel= "noopener">Rob's new book, Idea to Traction: Stop Building SaaS Nobody Wants in the Age of AI</a></li> </ul> <h2>Podcast Sponsor – Vista Point Advisors</h2> This podcast is sponsored by <a href= "https://vistapointadvisors.com/" target="_blank" rel= "noopener">Vista Point Advisors</a>, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

October 23, 2026•1:01:38

#218: He Built Debt Collection SaaS While Paying Off $1M in Personal Debt - Josh Allen

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Josh Allen is founder and CEO of <a href= "https://www.tratta.io/" target="_blank" rel="noopener">Tratta</a>, software for debt collection agencies and creditor rights law firms that gives consumers self-service payment tools and gives agents modern back-office tools. He started in merchant services, hired contractors to build a payment portal, and found out the hard way that nobody was waiting for it. That first platform landed five clients in about three years while Josh took on well over a million dollars in personal debt for the business. Tratta grew out of one back-office feature a client loved. Today it has about $5 million ARR, just over 20 employees, and almost 100 clients on pricing tied to approved payments. Josh repaid every penny of that debt in late 2023 and has never taken outside funding. Revenue and headcount both doubled this past year, and he is now hiring his first VP of customer operations. His advice: keep validating with real clients, be willing to pivot, and let a strong CTO tell you no. Key Takeaways <ul> <li dir="ltr" role="presentation">Build Backwards: Start with the critical tools for the critical users; if those teams aren't happy, nothing launches.</li> <li dir="ltr" role="presentation">Validate Small: One back-office feature a client loved became the product; the portal everyone doubted came second.</li> <li dir="ltr" role="presentation">Say No: A CTO who ignored founder ideas became the biggest unlock; hearing no is Josh's best lesson.</li> <li dir="ltr" role="presentation">Client Concentration: Josh's best day was when no client topped 10 percent of revenue, better than hitting $5 million.</li> <li dir="ltr" role="presentation">Narrow Market: Josh sizes his ideal market at about 1,600 clients and aims to win a quarter of them.</li> </ul> Quote from Josh Allen, Founder and CEO of Tratta "In my first startups, we got five clients over three-ish years, and I appreciate every one of them to this day. The software did not scale, there were so many problems with it, and I didn't understand the code well enough to know what they were. I ended up hiring another firm to come look at it, and they took it over and stabilized it. "The realization came that this was not scalable. I had sunk so much money into it and was on the hook for well over a million dollars personally, which sounds crazy with only five clients, and yes, I did a lot wrong. I was facing software that was not going to work, but it was a good idea. "I had just had my first daughter and was about to have a second, which is always a great time to do this stuff. I could ride it out, go back to merchant services, cross my fingers, and pay this off over the next ten years of my life. Or I could just start over completely." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/joshallenca/" target="_blank" rel= "noopener">Josh Allen on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/tratta" target="_blank" rel= "noopener">Tratta on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href="https://www.tratta.io" target="_blank" rel="noopener">Tratta website</a></li> </ul> <h2>Podcast Sponsor – DevHawk</h2> <div>Every founder I know is trying to move their roadmap faster with AI, but most admit it isn't working. DevHawk is an AI software factory from former practical founder Praveen Ghanta.</div> <div> </div> <div><a href="https://www.devhawk.ai/" target="_blank" rel= "noopener" data-saferedirecturl= "https://www.google.com/url?q=https://www.devhawk.ai/&source=gmail&ust=1786669746898000&usg=AOvVaw2quWExe9PKpP3FAi09Id50"> DevHawk</a> plugs in a full crew of customized AI agents that handle the whole development job, end-to-end. Not just writing code, but requirements, testing, shipping, and maintenance.</div> <div> </div> <div>Add their AI agents to your org chart and run them yourself--or have the DevHawk team manage the software factory for you. Either way, you get a team that works while you sleep, and a roadmap that can move 5-10x faster within a month.</div> <div> </div> <div>Head to <a href="http://devhawk.ai/practical" target= "_blank" rel="noopener" data-saferedirecturl= "https://www.google.com/url?q=http://devhawk.ai/practical&source=gmail&ust=1786669746898000&usg=AOvVaw1_nAAs3LPJhLgJZ98n9JVa">devhawk.ai/practical</a> to book a conversation about how DevHawk can help. </div> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

October 16, 2026•1:09:10

#217: His Hardest Lesson: Going Too Fast Was More Risky, Even With Funding - Shawn Boyer

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Shawn Boyer is founder and CEO of <a href= "https://www.gohappyhub.com/" target="_blank" rel= "noopener">goHappy</a>, a frontline employee communication and engagement platform for companies with a thousand or more hourly workers in restaurants, logistics, manufacturing, and retail. Before that he started Snagajob in 2000, a job marketplace for hourly workers, funding it with credit cards and family money until it reached profitability after four years. Then he raised three rounds of VC funding to grow the company much bigger. goHappy began as a mobile app, but customers kept asking to just text their people, so Shawn shifted the product to SMS communications during COVID. Today about 1.5 million frontline employees across 400-some customers use it. The team is under 40 people, revenue is well into eight figures, and the business is profitable with solid gross margins. Shawn has now been through bootstrapping, venture capital, minority growth equity, and majority private equity. At Snagajob, investors reaching 51 percent ownership ended with a new CEO in 2013. At goHappy, he chose Grove Street Partners in 2022 (minority) and Pamlico Capital (majority) in 2025 by matching their expectations to plans he had already proven. Key Takeaways <ul> <li dir="ltr" role="presentation">Simple Wins: Frontline workers won't download another app, so texting beat the native app within seven months.</li> <li dir="ltr" role="presentation">Projection Trap: Aggressive projections used to win a higher valuation become your budget the day after closing.</li> <li dir="ltr" role="presentation">Prove Assumptions: Wait for twelve-month retention before doubling down; a 15-point gap undid Snagajob's small-business push.</li> <li dir="ltr" role="presentation">Small Team: Keep headcount low on purpose; under 40 people now produce well into eight figures in revenue.</li> <li dir="ltr" role="presentation">Pick Partners: Investors differ widely, so choose the person and the expectations, not just the check or the valuation.</li> </ul> Quote from Shawn Boyer, Founder and CEO of goHappy "The biggest and hardest lesson is that there is just as much risk in going too fast as there is in going too slow. We have our assumptions that doing X is going to yield Y, but let's go prove that out, and I would rather be more methodical and risk going too slow than be too aggressive, blow through money too quickly, and in essence lose control. "The waste on the people churn side is so darn expensive too, because when you've spent so much time getting somebody up to speed and it doesn't work, it just sets you back. It's all about the people, and that means going slow on hiring. "At Snagajob 15 years ago, I felt a real sense of accomplishment when the team grew from 100 people to 150, and it sounds stupid, but I felt so good saying it. Now at GoHappy, it's the opposite, with pride in keeping the team small and seeing how much we can accomplish with fewer people, which has made us incredibly prudent and disciplined in our hiring, even though you're never going to get it 100 percent right." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/shawnboyer/" target="_blank" rel= "noopener">Shawn Boyer on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/gohappy" target="_blank" rel= "noopener">goHappy on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.gohappyhub.com" target="_blank" rel="noopener">goHappy website</a></li> <li dir="ltr" role="presentation"><a href= "https://www.snagajob.com/" target="_blank" rel="noopener">Snagajob website</a></li> <li dir="ltr" role="presentation"><a href= "https://growthstreetpartners.com/" target="_blank" rel= "noopener">Growth Street Partners website</a></li> </ul> <h2>Podcast Sponsor – Full Scale</h2> This podcast is sponsored by <a href="https://fullscale.io/" target="_blank" rel="noopener">Full Scale</a>, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at <a href= "https://fullscale.io/" target="_blank" rel= "noopener">fullscale.io.</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

October 9, 2026•1:12:48

#216: Messy Financials Killed a Good LOI and Slowed a Profitable SaaS Sale - Riccardo Pisano

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Riccardo Pisano grew up in Rome, started coding at fourteen, and came to the US for a master's in e-commerce. After a venture-chasing startup called Proximity stalled, he and co-founder Roy turned an internal LinkedIn outreach script into Growth-X in January 2016. Riccardo refused to write a line of code until customers had paid, unlike his previous startup attempt. Growth-X started as pure LinkedIn automation at $500 per user, back when 90 percent of connection invites got accepted. It grew into a multichannel lead generation platform with intent data and website visitor identification. The company was bootstrapped and profitable the whole time, paid both founders within a year, and ran lean with eleven employees by the exit. Seeing AI agents coming, Riccardo listed Growth-X on Acquire.com. But complicated cash-basis books across US and Israeli entities made his P&L useless to buyers, a good LOI fell apart, and growth stalled while he fixed it. It took two years to sell to CueGrowth in June 2025. His verdict: "I lost millions on two pages of numbers." Key Takeaways <ul> <li dir="ltr" role="presentation">Cash Basis Confuses: Annual prepayments on cash-basis books make monthly P&Ls look like nonsense to buyers.</li> <li dir="ltr" role="presentation">Sync Books Early: Set up QuickBooks and a proper review from day one so financials take one click.</li> <li dir="ltr" role="presentation">Sell While Growing: Stopping growth to build diligence documents lowers your price right when it matters most.</li> <li dir="ltr" role="presentation">The Awkward Middle: $1M to $10M companies are too small for brokers and too founder-led for big buyers.</li> <li dir="ltr" role="presentation">Watch the Clock: He listed the company when OpenAI agents appeared, figuring he had maybe two years left.</li> </ul> Quote from Riccardo Pisano, Co-Founder of Growth-X "The company suffered a lot from not having our financials ready to respond to LOIs to acquire us. I switched my mindset completely from growth to getting these documents ready, and growth completely slowed down. We signed an LOI that was pretty good, but it eventually failed. "In those three months, I couldn't generate the P&L at the pace they needed, and they started losing trust. Trying to grow while learning what financials you have to produce and getting the accounting firms to do it slowed down a lot of our growth. "So after not closing the first deal, I said, okay, let me put a break in here and bring it up again. We restarted the machine, got more organized on the financials, and then restarted with Acquire.com, then sold the company successfully." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/thericcardopisanoo/" target="_blank" rel="noopener">Riccardo Pisano on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://riccardopisano.com/" target="_blank" rel= "noopener">Riccardo Pisano website</a></li> <li dir="ltr" role="presentation"><a href="https://cuegrowth.ai/" target="_blank" rel="noopener">CueGrowth (acquirer)</a></li> </ul> <h2>Podcast Sponsor – Vista Point Advisors</h2> This podcast is sponsored by <a href= "https://vistapointadvisors.com/" target="_blank" rel= "noopener">Vista Point Advisors</a>, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

October 2, 2026•1:01:55

#215: How This Early-Stage Growth Equity Partner Is Investing in SaaS in 2026 - Steve Wolfe

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Steve Wolfe co-founded <a href= "https://growthstreetpartners.com/" target="_blank" rel= "noopener">Growth Street Partners</a> in San Francisco about ten years ago with his partner Nate Grossman, after a career in software-focused private equity. The firm's name is the point: they don't invest on Sand Hill Road, Wall Street, or even Main Street, but a street or two behind it, where the rent is lower and practical founders put their earnings back into the business. Growth Street has now raised three funds — $70 million, $130 million, and a little over $200 million — with the same strategy since day one. They write $5 to $15 million checks for 20 to 50 percent of vertical B2B SaaS and tech-enabled services companies doing $1 to $5 million in revenue, always as a minority partner. Portfolio companies include Chipply and TeamLinkt, both previous Practical Founders guests. Steve's 2026 answer to the AI shift is a firm-wide operating principle they call "Operation Cole Trickle": when the race track fills with crashes and smoke, "go high" and avoid the crazy mess. That means returning to first principles — a high integrity founder, real customer value, a strategic piece of real estate — and treating the daily AI headline cycle as a distraction with a very short half-life. Key Takeaways <ul> <li dir="ltr" role="presentation">Go High — Drive above the wreck instead of through it, and return to first principles.</li> <li dir="ltr" role="presentation">Minority Stakes — $5-15 million buys 20-50 percent, so founders keep control and keep deciding.</li> <li dir="ltr" role="presentation">Headline Half-Life — Reading AI news daily burns time on knowledge that expires in weeks.</li> <li dir="ltr" role="presentation">Right to Win — Add AI where you already have an edge, not everywhere you see a nail.</li> <li dir="ltr" role="presentation">Exit Discipline — Growth Street models five times revenue at exit, same as day one.</li> </ul> Quote from Steve Wolfe, Co-Founder & Managing Partner at Growth Street Partners "We call it founder market fit. We're not buying control of the businesses, which is really a critical component of our strategy. Founders are willing to talk to us because we're a minority investor. What it means for our strategy is that our founders are going to make thousands of decisions without us. So they need to have the same values that we have, because God forbid they don't.we're in big trouble. "When we think about diligencing a new opportunity, when a business has got $1-5 million of annual recurring revenue and it's growing nicely and everything seems good. But the clay on that business is still really wet, so we can help them mold the business. "But the founder that we're partnering with, the market that we're entering into, that clay is usually pretty dry. You can't change the founder and you can't change the market. And so that founder better be aligned with you, better have the values that you have. Otherwise, you're in big trouble." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/stephen-wolfe-ba5a596/" target= "_blank" rel="noopener">Steve Wolfe on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/growth-street-partners" target= "_blank" rel="noopener">Growth Street Partners on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://growthstreetpartners.com/" target="_blank" rel= "noopener">Growth Street Partners website</a></li> <li dir="ltr" role="presentation"><a href= "https://practicalfounders.com/podcast/practical-founders-win-big-growth-equity-partners-growth-street/" target="_blank" rel="noopener">Steve's earlier Practical Founders episode (#123, with Nate)</a></li> </ul> <h2>Podcast Sponsor – DevHawk</h2> <div>Every founder I know is trying to move their roadmap faster with AI, but most admit it isn't working. DevHawk is an AI software factory from former practical founder Praveen Ghanta.</div> <div> </div> <div><a href="https://www.devhawk.ai/" target="_blank" rel= "noopener" data-saferedirecturl= "https://www.google.com/url?q=https://www.devhawk.ai/&source=gmail&ust=1786669746898000&usg=AOvVaw2quWExe9PKpP3FAi09Id50"> DevHawk</a> plugs in a full crew of customized AI agents that handle the whole development job, end-to-end. Not just writing code, but requirements, testing, shipping, and maintenance.</div> <div> </div> <div>Add their AI agents to your org chart and run them yourself--or have the DevHawk team manage the software factory for you. Either way, you get a team that works while you sleep, and a roadmap that can move 5-10x faster within a month.</div> <div> </div> <div>Head to <a href="http://devhawk.ai/practical" target= "_blank" rel="noopener" data-saferedirecturl= "https://www.google.com/url?q=http://devhawk.ai/practical&source=gmail&ust=1786669746898000&usg=AOvVaw1_nAAs3LPJhLgJZ98n9JVa">devhawk.ai/practical</a> to book a conversation about how DevHawk can help. </div> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

September 25, 2026•1:04:12

#214: He Stopped Being the Face of the Company Before He Sold It - Heath Adams

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Heath Adams is a military veteran in Albuquerque who started posting ethical hacking videos on YouTube under the handle The Cyber Mentor. The videos found a large audience, consulting clients started showing up, and he launched TCM Security as a penetration testing shop. Then he put a course on Udemy in December and it did six figures in its first week. TCM became a training company quickly. By the time he sold TCM, it had 30-plus courses, around 10 hands-on certifications with a proprietary exam platform, and 30 employees. Revenue was low eight figures, split roughly 33-40% education, 30% certifications, and 20-30% services. The YouTube channel passed a million subscribers, over 100,000 students bought courses, and more than 10,000 were paying subscribers. No outside funding, ever. He sold to Educate 360 in 2024 and exited in 2025. He spent two to three years deliberately unwinding his own YouTube centrality so the company could be sold without him: hiring a marketing team, handing off social media, putting other people on the videos, until customers stopped equating TCM Security with Heath Adams. He now runs Breach Point, a defensive security company built to scale from day one. Key Takeaways <ul> <li dir="ltr" role="presentation">Affordable Pricing — $30 subscriptions opened a global audience nobody else in cyber training was serving.</li> <li dir="ltr" role="presentation">Revenue Share — Splitting revenue with expert instructors bought quality he could never have afforded to hire.</li> <li dir="ltr" role="presentation">Platform Lock-In — Teachable worked fine at five courses and became a trap at thirty.</li> <li dir="ltr" role="presentation">M&A Advisor — A million dollars in deal costs doubled the offer, and he'd pay it again.</li> <li dir="ltr" role="presentation">Track Data Early — Accrual accounting and a real CRM from day one, not spreadsheets and intuition.</li> </ul> Quote from Heath Adams, Founder and CEO of TCM Security "We spent many years getting rid of founder dependency in our marketing, and that was a big thing to prepare for. If I ever wanted to get out of here, if I wanted to exit, I had to get rid of the founder dependency with me as the face of the company. "So it was a two, three year plan way before then. We started hiring people in to be the face. Stopped posting on social media as much about the person and only about the the company. "We got to a point where they don't say TCM Security is Heath Adams. They just say that guy maybe works at TCM Security, or they don't even know who I am. Getting to that point was hard to achieve, but we did get there eventually." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/heathadams/" target="_blank" rel= "noopener">Heath Adams on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/tcm-security-inc" target="_blank" rel="noopener">TCM Security on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href="https://tcm-sec.com" target="_blank" rel="noopener">TCM Security website</a></li> <li dir="ltr" role="presentation"><a href="https://breachpoint.com" target="_blank" rel="noopener">Breach Point (Heath's new company)</a></li> </ul> <h2>Podcast Sponsor – Full Scale</h2> This podcast is sponsored by <a href="https://fullscale.io/" target="_blank" rel="noopener">Full Scale</a>, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at <a href= "https://fullscale.io/" target="_blank" rel= "noopener">fullscale.io.</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

September 18, 2026•1:10:05

#213: She Took on a Growth Equity Partner for the Advice, Not the Money - Lynn Burghardt

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Lynn Burghardt is a fifth-generation owner of Burghardt Sporting Goods — the oldest family-owned sporting goods store in the country, founded in 1881. Chipply grew out of that business: after years of hacking together their own tools for team apparel orders, Lynn and two brothers built the software solution the decorated-apparel industry didn't have, funded by a $250,000 angel check from their father, Chip. <a href="https://chipply.com/" target="_blank" rel= "noopener">Chipply</a> is e-commerce software for decorated apparel, the custom team stores where players, parents, and fans order their own gear online. Started in 2015 and selling since 2018, it now powers about 1,500 active dealers, processing around $250 million in gross merchandise value this year at about $10 million in revenue, growing 35%. All with 50 employees. Chipply charges a percentage of sales, "when they win, we win," and is now adding Chipply One to become run-your-business software for its dealers. Three years ago Lynn took growth equity from Growth Street Partners, not for the money but for the advice to scale up: adding the right senior leaders and structuring the business foundations, with a hands-on partner who engages every week while leaving control in the founders' hands. Key Takeaways <ul> <li dir="ltr" role="presentation">Keep Control: The deal preserved control of the product and the board for the founders.</li> <li dir="ltr" role="presentation">Win-Win Pricing: Chipply prices on a percentage of merchandise value, so incentives stay aligned.</li> <li dir="ltr" role="presentation">Scratch Your Own Itch: The best first customer was their own 145-year-old sporting goods business.</li> <li dir="ltr" role="presentation">Just Do It: Trust yourself sooner and take the risk faster.</li> <li dir="ltr" role="presentation">Vertical Depth: Decorated apparel is too complicated for generic tools like Shopify to serve.</li> </ul> Quote from Lynn Burghardt, President of Chipply "Getting a good value for the business mattered, and so did what we were willing to give up to gain the right partner. But the decision was really about advice and expertise. "It was about putting people in the right seats — on our board and in our business model — to help us take it to the next level. How do we find the perfect sales leader, the perfect engineering leader who can build exactly what we envision? "That would relieve the pressure on me, our CEO, and the grassroots people who'd been running the business. We were spread too thin, and when we met Steve and Nate at Growth Street Partners, it was just a perfect fit — they gave us the autonomy we wanted." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/teamchipply/posts/" target= "_blank" rel="noopener">Chipply on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href="https://chipply.com/" target="_blank" rel="noopener">Chipply website</a></li> <li dir="ltr" role="presentation"><a href= "https://growthstreetpartners.com/" target="_blank" rel= "noopener">Growth Street Partners (growth equity investor)</a></li> </ul> <h2>Podcast Sponsor – Vista Point Advisors</h2> This podcast is sponsored by <a href= "https://vistapointadvisors.com/" target="_blank" rel= "noopener">Vista Point Advisors</a>, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

September 11, 2026•1:06:33

#212: The Practical Case for Payments-Driven SaaS Growth, Not Subscriptions - Jay Majaraj

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Jay Maharaj built TeamLinkt in Saskatoon, Saskatchewan, a place not known for software. He saw the problem while coaching his own kids: the hockey team had a budget for a team communication app, and the soccer team didn't, so he either paid for it himself or went without. He launched the TeamLinkt app in 2018 and its back-office platform in 2020. <a href="https://teamlinkt.com/" target="_blank" rel= "noopener">TeamLinkt</a> now powers more than 3,500 organizations with just over 30 employees and 600,000-plus monthly active users across soccer, hockey, flag football, cheer, dance and more. Revenue is pushing $4.5 million Canadian this year and growing close to 2x a year. There is no SaaS fee and no per-player fee. The platform is free, and TeamLinkt takes a small markup on hundreds of millions of registration payments running through Stripe. Jay chased venture capital for about half a year, even moving his family to the US, before deciding the math never made sense for the company he was building. Last year he raised $6 million USD in practical growth funding from Growth Street Partners, kept board control, and has been deliberate about spending it. He would rather grow alongside his customers than extract more from them. Remarkably, TeamLinkt customer service reps now ship code now. They write bug-fix tickets that become pull requests straight from Slack through Linear, reserving engineering for complex development work. Key Takeaways <ul> <li dir="ltr" role="presentation">Aligned incentives - As customer programs grow, TeamLinkt grows, so saving admins time is the growth strategy.</li> <li dir="ltr" role="presentation">VC mismatch - Six months chasing venture capital ended when the one-in-a-hundred exit math stopped adding up.</li> <li dir="ltr" role="presentation">Right capital - Practical growth equity funded leadership hires and discipline, not a land grab; Jay kept board control.</li> <li dir="ltr" role="presentation">Free drives virality - Coaches and parents spread the app club to club, replacing trade show booths they can't afford.</li> </ul> Quote from Jay Maharaj, CEO and Founder of TeamLinkt "Our competitors are gonna charge you tens of thousands of dollars to use that platform. But with TeamLinkt, you get the core platform and there's no SaaS fee -- we're payments-driven. And they can choose to absorb that transaction fee or pass it through registration, so for an organization we're really a net zero cost. "Everything that you need to run your system is in core. It's free for the organization, and when they set up registration, we power payments through Stripe, and then we have a small markup. We feel it's fair and market, usually very competitive if not better, and we have no per-player fees in addition to that. "We're very invested in giving them time back so they can grow their programs, because as they grow, we grow. So the less work we do on the back office side, the more energy Greg is gonna have to put into coaching, administering, or helping the youth soccer club grow in their community. And that's really what drives us." Links <ul> <li dir="ltr" role="presentation"><a href= "https://ca.linkedin.com/in/jaymaharaj" target="_blank" rel= "noopener">Jay Maharaj on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://ca.linkedin.com/company/teamlinkt" target="_blank" rel= "noopener">TeamLinkt on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href="https://teamlinkt.com/" target="_blank" rel="noopener">TeamLinkt website</a></li> <li dir="ltr" role="presentation"><a href= "https://growthstreetpartners.com/" target="_blank" rel= "noopener">Growth Street Partners</a></li> </ul> <h2>Podcast Sponsor – DevHawk</h2> <div>Every founder I know is trying to move their roadmap faster with AI, but most admit it isn't working. DevHawk is an AI software factory from former practical founder Praveen Ghanta.</div> <div> </div> <div><a href="https://www.devhawk.ai/" target="_blank" rel= "noopener" data-saferedirecturl= "https://www.google.com/url?q=https://www.devhawk.ai/&source=gmail&ust=1786669746898000&usg=AOvVaw2quWExe9PKpP3FAi09Id50"> DevHawk</a> plugs in a full crew of customized AI agents that handle the whole development job, end-to-end. Not just writing code, but requirements, testing, shipping, and maintenance.</div> <div> </div> <div>Add their AI agents to your org chart and run them yourself--or have the DevHawk team manage the software factory for you. Either way, you get a team that works while you sleep, and a roadmap that can move 5-10x faster within a month.</div> <div> </div> <div>Head to <a href="http://devhawk.ai/practical" target= "_blank" rel="noopener" data-saferedirecturl= "https://www.google.com/url?q=http://devhawk.ai/practical&source=gmail&ust=1786669746898000&usg=AOvVaw1_nAAs3LPJhLgJZ98n9JVa">devhawk.ai/practical</a> to book a conversation about how DevHawk can help. </div> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

September 4, 2026•1:04:55

#211: This Practical Bootstrapper Scaled Up and Became a Serial Acquirer - Ajay Gupta

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Ajay Gupta founded <a href="https://www.stirista.com/" target="_blank" rel="noopener">Stirista</a> in San Antonio after helping with micro-targeting a presidential campaign. His first product identified people who spoke a second language for multicultural marketing — built from scanned baby-name books, a hundred thousand first names, and 107 sales calls before Dish Network became the first big client at $100,000. Stirista now helps brands find new customers using data, connected TV, and email, with identity-enriched data as the "secret sauce" behind the targeting. The company has roughly 270 employees and will clear $100 million in profitable revenue this year. It was bootstrapped for over a decade before a single $14M growth equity investment round from Wavecrest Growth Partners. Gupta is now the serial acquirer, rolling up founder-run data businesses whose owners want to retire and find a good home for their employees. Nearly every deal uses an earnout, avoids debt, and keeps most of the staff, which is a deliberate contrast to private-equity roll-ups that gut Key Takeaways <ul> <li dir="ltr" role="presentation">One Round: Ten years bootstrapped, then a single $14M round to bring in world-class leadership.</li> <li dir="ltr" role="presentation">Avoid Debt: Nearly every acquisition uses earnouts and cash, not the leveraged PE roll-up playbook.</li> <li dir="ltr" role="presentation">Hire the Pros: Sometimes you spend money on senior talent to elevate how the whole company thinks.</li> <li dir="ltr" role="presentation">Stay Flexible: The people who grow with a startup listen to clients and adapt, not just work hard.</li> <li dir="ltr" role="presentation">Scale as Moat: Privacy regulation now demands enough scale to comply across every state's laws.</li> </ul> Quote from Ajay Gupta, CEO and Founder of Stirista "We've identified a type of business we like to acquire: founder-run companies, usually an older founder looking to retire. We've already worked with almost ninety percent of them in some capacity, so there's a trust factor. "The founder wants to retire, and they're looking for a nice home for their employees. That's a very important part of it. And these founders are often tired, so some of them actually end up working with us for a couple of years afterward, because now they have the freedom to go out and sell. "A lot of them were sellers who built nice small businesses, then got bogged down by payroll and leases and all the things we free them from. As a founder and CEO myself, it's an easy conversation to have — and we have a track record of keeping most of the employees, so they know it's not somebody coming in to gut the company down to the bones just for profit." Links <ul> <li dir="ltr" role="presentation"><a href= "linkedin.com/in/ajay-gupta-24255366" target="_blank" rel= "noopener">Ajay Gupta on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/stirista-global/" target="_blank" rel="noopener">Stirista on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.stirista.com/" target="_blank" rel="noopener">Stirista website</a></li> <li dir="ltr" role="presentation"><a href= "https://www.wavecrestgrowth.com/" target="_blank" rel= "noopener">Wavecrest Growth Partners (investor)</a></li> </ul> <h2>Podcast Sponsor – Full Scale</h2> This podcast is sponsored by <a href="https://fullscale.io/" target="_blank" rel="noopener">Full Scale</a>, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at <a href= "https://fullscale.io/" target="_blank" rel= "noopener">fullscale.io.</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

August 28, 2026•1:09:19

#210: 4th Time Founder: Solve Distribution First, Write Code After - Vic Levitin

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Vic Levitin is a serial founder who built companies in Israel for two decades before fleeing the war with his young family to the island of Koh Samui, Thailand. His first SaaS company, CrazyLister, grew out of his own e-commerce business where he needed a simple way for eBay sellers to build professional listings without knowing HTML. CrazyLister raised about $700K, then a similar second round, and grew to nearly $2M ARR before stalling. Today it runs profitably at roughly $1M ARR. Vic later spent four years co-founding Diptera.ai, a deep-tech venture using a larval-stage breakthrough to suppress malaria-carrying mosquitoes, now backed by the Gates Foundation. From Thailand, Vic now runs an AI-powered venture studio built on one rule: no code gets written until he proves he can generate demand. He partners with domain experts and influencers who already own trusting audiences, which is a model that took his AI-influencer platform to $90K MRR in 18 months, now extending to smaller niches like dog trainers. Key Takeaways <ul> <li dir="ltr" role="presentation">Distribution First: Prove you can generate demand and revenue before a single line of code is written.</li> <li dir="ltr" role="presentation">Repeat vs. First: First-time founders obsess about product; repeat founders obsess about distribution.</li> <li dir="ltr" role="presentation">Partner for Reach: Bring on experts and influencers who already own a trusting audience.</li> <li dir="ltr" role="presentation">Micro-Niches Win: AI makes it viable to build dedicated apps for tiny verticals like dog trainers.</li> <li dir="ltr" role="presentation">Time to Money: Chase the fastest path to the first $100 in MRR to make everything real.</li> </ul> Quote from Vic Levitin, Founder of CrazyLister "My technical co-founder Yair could build anything, even before AI came along. But we have an agreement, and it's a simple one. "He doesn't write a single line of code — whether from his own brain or with AI — before I prove to both of us that I can generate demand and revenue for whatever we're building. "That agreement formed the way we build now. We're a venture studio, and we solve distribution first by partnering with domain experts who already have trusting audiences." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/vic-levitin/" target="_blank" rel= "noopener">Vic Levitin on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/massoptimizer/" target="_blank" rel="noopener">Crazy Lister on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://crazylister.com/" target="_blank" rel="noopener">Crazy Lister website</a></li> <li dir="ltr" role="presentation"><a href="https://diptera.ai/" target="_blank" rel="noopener">Diptera.ai (prior venture)</a></li> </ul> <h2>Podcast Sponsor – Vista Point Advisors</h2> This podcast is sponsored by <a href= "https://vistapointadvisors.com/" target="_blank" rel= "noopener">Vista Point Advisors</a>, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

August 21, 2026•57:46

#209: Leading from Both Sides of the Table as a PE-Backed SaaS CEO - Steve Oriola

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Steve Oriola isn't the founder of Unbounce — he's the CEO that Crest Rock Partners brought in to run and transform it. A sales-and-marketing software veteran who spent a decade at Constant Contact, and even ran Act! for a spell (ACT! is the product and company I helped grow and run myself 10 years earlier!). Steve joined Unbounce in January 2024 and acquired the Insightly CRM six months later, merging the two into one company and one culture. Today Unbounce is a roughly 200-person business combining a landing-page and conversion-rate-optimization marketing platform with a sales-focused CRM and integrated project management. Owned by private equity (Crest Rock Partners) with the founders still on the board, the company had to get smaller to find its focus — scoping down to its core value before rebuilding around agentic AI. Oriola is now steering a full transformation toward "service as software," which includes professional services and forward-deployed engineering that surface repeatable IP, then harden into managed services with governance for agents. His real edge is comfort on both sides of the table, translating between investors who "operate in Excel" and the humans who actually run the business. Key Takeaways <ul> <li dir="ltr" role="presentation">Manage Up: Investors own the company but depend on you — understand their perspective and manage them.</li> <li dir="ltr" role="presentation">Narrow Focus: Scoping down isn't more work; it's how you rediscover your core value and focus.</li> <li dir="ltr" role="presentation">Throw Out the Playbook: The old "fix go-to-market and sell in three years" thesis no longer fits a changed world.</li> <li dir="ltr" role="presentation">Just Write It: With code cost collapsing to tokens, engineering can finally fail fast and recover quickly.</li> <li dir="ltr" role="presentation">Service as Software: Clients want managed agentic solutions with governance, not just self-serve SaaS tools.</li> </ul> Quote from Steve Oriola, CEO of Unbounce "The trickiest part of being a CEO is which side of the table you're on. Are you on the side of the employees who work for you, with your investors and your board on the other side? Or are you on the investor side, looking at the company and making the rational decisions that are best for them? "If you're a founder, you're on the team side of the table. But you've got to understand the perspective of the investors, because to some degree you're managing them. They're not running your business, and they're very dependent on you. "Really, it's empathy. You have to understand what they're dealing with, because they can make bottom-line decisions that don't feel very human. They're operating in Excel, and you're dealing with humans. So you're the mediator between humanity and cold-hearted business." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/oriola/" target="_blank" rel= "noopener">Steve Oriola on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/unbounce/" target="_blank" rel= "noopener">Unbounce on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href="https://unbounce.com" target="_blank" rel="noopener">Unbounce website</a></li> <li dir="ltr" role="presentation"><a href= "https://www.crestrockpartners.com/" target="_blank" rel= "noopener">Crest Rock Partners (investor)</a></li> </ul> <h2>Podcast Sponsor – DevHawk</h2> <div>Every founder I know is trying to move their roadmap faster with AI, but most admit it isn't working. DevHawk is an AI software factory from former practical founder Praveen Ghanta.</div> <div> </div> <div><a href="https://www.devhawk.ai/" target="_blank" rel= "noopener" data-saferedirecturl= "https://www.google.com/url?q=https://www.devhawk.ai/&source=gmail&ust=1786669746898000&usg=AOvVaw2quWExe9PKpP3FAi09Id50"> DevHawk</a> plugs in a full crew of customized AI agents that handle the whole development job, end-to-end. Not just writing code, but requirements, testing, shipping, and maintenance.</div> <div> </div> <div>Add their AI agents to your org chart and run them yourself--or have the DevHawk team manage the software factory for you. Either way, you get a team that works while you sleep, and a roadmap that can move 5-10x faster within a month.</div> <div> </div> <div>Head to <a href="http://devhawk.ai/practical" target= "_blank" rel="noopener" data-saferedirecturl= "https://www.google.com/url?q=http://devhawk.ai/practical&source=gmail&ust=1786669746898000&usg=AOvVaw1_nAAs3LPJhLgJZ98n9JVa">devhawk.ai/practical</a> to book a conversation about how DevHawk can help. </div> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

August 14, 2026•53:24

#208: How AI Rewrote What Active SaaS Buyers Want in 2026 - Mike Lyon

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Mike Lyon is the founder and managing director of Vista Point Advisors, a boutique sell-side investment bank he started almost sixteen years ago. A former chemical engineer at Exxon and BP who later joined Citigroup's tech M&A team, he built Vista Point to solve a conflict of interest he watched play out on Wall Street: bankers quietly working both sides of a deal. <a href="https://vistapointadvisors.com/" target= "_blank" rel="noopener">Vista Point Advisors</a> represents founder-led software companies only — never the buyers — focusing on vertical SaaS with enterprise values between $30 and $300 million. Mike and five other managing directors run about a dozen deals a year, spending 50 to 100 hours cleaning up each company's data before launch and running a long, non-exclusive process built to keep multiple buyers competing to the finish. Mike says buyer criteria changed this year for the first time in a decade, and changed fast. Buyers now demand roughly 90% gross retention as a proxy for AI resilience, favor systems of record with real data moats, and discount horizontal point solutions. His advice: understand exactly how you'll be graded long before you go to market, because the aperture for a premium exit keeps shrinking. Key Takeaways <ul> <li dir="ltr" role="presentation">AI Changed Everything — For the first time in a decade, buyer criteria are shifting week to week this year.</li> <li dir="ltr" role="presentation">Gross Retention Rules — Buyers now want 90%-plus gross retention as a proxy for AI resilience.</li> <li dir="ltr" role="presentation">System Of Record — Point solutions look exposed to AI; systems of record with real data moats win.</li> <li dir="ltr" role="presentation">Exclusivity Is Leverage — Once you grant it, the deal slows and power shifts to the buyer.</li> <li dir="ltr" role="presentation">Watch Spend, Not Talk — Every buyer says the right things; only diligence dollars prove real intent.</li> <li dir="ltr" role="presentation">Second Bite Pays — Most founders who sold majority to PE did as well or better on the rollover.</li> </ul> Quote from Mike Lyon, Founder & Managing Director of Vista Point Advisors "For the first time in ten years, the rules hav changed — and they changed fast. If you called any private equity or strategic buyer over the last decade and asked what makes a good SaaS company, the answer barely moved. This year I've had conversations I've never had before, where the criteria shifted week to week — first it's X, then X plus Y, then X plus Y plus Z. The first big change is a maniacal focus on gross revenue retention (GRR). Net retention (NRR) was the star for years, but gross gives you no credit for upsells — you only get dinged for downgrades and churn, so it's really asking what happens if you can't upsell anymore. Buyers want to see 90% or better now, and our read is that it's a proxy for AI risk: they don't fully understand the AI threat yet, but they know a business at 90% gross retention is probably resilient enough to take some hits and survive. System of record is the other thing that suddenly matters more. Point solutions feel like they're at further risk from AI, so buyers want a system of record with a real data moat — not the fake moat where anyone can go get that data somewhere else — or a payments angle, which is harder for AI to route around. And if your business started eight years ago, it's hard to be fully agentic, but you at least need the ability to hang agents off the backbone of your software to keep delivering value." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/lyonmike/" target="_blank" rel= "noopener">Mike Lyon on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/vista-point-advisors" target= "_blank" rel="noopener">Vista Point Advisors on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://vistapointadvisors.com/" target="_blank" rel= "noopener">Vista Point Advisors website</a></li> </ul> <h2>Podcast Sponsor – Fraction</h2> This podcast is sponsored by <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">Fraction</a>. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">fraction.work.</a> You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

August 7, 2026•1:13:16

#207: Former Teacher Built a Market-Leading School Hiring Marketplace - Wayne Cartmel

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Wayne Cartmel grew up on a small farm in the Lake District region of northwest England and was selling chickens by the age of four. He trained as a maths teacher in Bedfordshire and could not believe the process he had to go through to apply for jobs — hours of Word-based application forms, one after another. He asked why nobody had digitized it, and then decided to do it himself. Funded by a £5,000 innovation voucher and built with a computer science volunteer who is still his CTO eleven years later, it took two years to reach a working prototype. Wayne took no funding, went over £100,000 into personal debt, and did not draw a livable salary for several years. <a href="https://mynewterm.com/" target="_blank" rel= "noopener">MyNewTerm</a> is a specialized hiring marketplace and applicant tracking system that connects schools across England directly with job seekers. It allows educational employers to post vacancies and manage candidates using a streamlined workflow that supports part-time, full-time, and temporary roles. MyNewTerm now partners with over 6,000 schools and 500 multi-academy trusts, has surpassed £5M in revenue, and processes over 100,000 candidate applications a month with just 20 employees. It holds roughly 45% market share among multi-academy trusts against a private-equity-backed incumbent. Key Takeaways <ul> <li dir="ltr" role="presentation">Distribution Wins — Anyone can build a product now; almost nobody can get it into customers' hands.</li> <li dir="ltr" role="presentation">Start Absurdly Small — He targeted five schools in one district of Luton, then moved to the next.</li> <li dir="ltr" role="presentation">Free Buys Evidence — Schools wouldn't pay for an unproven marketplace, so he gave it away to prove it worked.</li> <li dir="ltr" role="presentation">Focus Compounds — Sticking to the core, not chasing adjacent opportunities, is what built the market share.</li> <li dir="ltr" role="presentation">Hard Equals Defensible — The marketplace was brutal to start, which is exactly why nobody can replicate it.</li> </ul> Quote from Wayne Cartmel, Founder and CEO of MyNewTerm "Distribution and execution are everything, because the market nowadays is going to be flooded with software products, EdTech in particular. The advancements in AI mean that you can spin up products really quickly. I almost wish that was available ten years ago when I was starting as a non-technical founder. "Building the product is the easy bit; I thought it would be the hard bit. What I failed to realize, and I wish somebody had told me, is that it's actually the distribution and the sales and marketing, the go-to-market motion, that's the really tough bit, doubly hard with a two-sided marketplace. "You can build a product on such a small budget now, but you've got to be really deliberate and disciplined to keep on going and generate momentum. That's why many don't make it: they don't have the ability and resilience to get through the really hard moments when people are continually saying no to you, and you're continually being rejected." Links <ul> <li dir="ltr" role="presentation"><a href= "https://uk.linkedin.com/in/wayne-cartmel-8754553a" target="_blank" rel="noopener">Wayne Cartmel on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/mynewterm" target="_blank" rel= "noopener">MyNewTerm on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href="https://mynewterm.com" target="_blank" rel="noopener">MyNewTerm website</a></li> </ul> <h2>Podcast Sponsor – Vista Point Advisors</h2> This podcast is sponsored by <a href= "https://vistapointadvisors.com/" target="_blank" rel= "noopener">Vista Point Advisors</a>, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

July 31, 2026•1:04:05

#206: He Sold at $3M ARR and Got a 10X+ Exit to a PE Buyer - Eran Galperin

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Eran Galperin is a Brazilian jiu-jitsu black belt who had already had one VC-backed marketplace failure when he started <a href="https://gymdesk.com/" target="_blank" rel= "noopener">Gymdesk</a>. Originally called Martial Arts on Rails, it launched in 2016 as a naive version of what he thought a gym needed. He was training five or six times a week and every gym owner he knew hated the software they used. For four years he couldn't acquire customers, so he took a job as CTO of an e-commerce company and built the product on nights and weekends. Growth finally came through organic SEO, which still drives over half of new leads. He hit $3M in ARR by the end of 2023 with 16 employees, no salespeople, and over 40% of free trials converting without a demo. In May 2024 he sold a majority stake to Five Elms Capital for $32.5M in cash for his share. What they paid the premium for wasn't size — it was churn under 1% a month, three straight years of more than doubling, profit margins over 50%, and a payments business compounding underneath. He stayed on eighteen months and now lives in Tokyo, building a custom house and an AI vision product for real estate. Key Takeaways <ul> <li dir="ltr" role="presentation">Churn Ceiling — Churn is the cap on growth; under 1% monthly is what buyers pay premiums for.</li> <li dir="ltr" role="presentation">Slow Bake — Four years of nights and weekends let the product mature in ways funded companies never can.</li> <li dir="ltr" role="presentation">Payments Compound — Profit share from payment providers grows as volume grows, and buyers pay extra for those rails.</li> <li dir="ltr" role="presentation">Buyers Differ Wildly — One expert said 5X was his cap; Five Elms paid 10X because they buy outcome, not value.</li> <li dir="ltr" role="presentation">Get Representation — A $60K legal bill and a good M&A broker closed the information asymmetry with private equity.</li> </ul> Quote from Eran Galperin, Founder of Gymdesk "What we did have was very low churn, and that's one of the factors that helped us get the premium when we sold the company. Everybody building SaaS eventually realizes that churn is the cap your company has on growth. Eventually churn, which is a relative number, grows to the point where it meets the absolute numbers of your growth. "Because we had very low churn, less than one percent month over month, that definitely helped us start the conversation from a very good position. The other element was that growth was very consistent year over year. I think we more than doubled three years straight. "That in combination with the low churn and high profit margins was the last big item. We had a lean team, and we were over fifty percent profit margins when we sold. This was a firm that had multiple other portfolio companies similar to us, so they had a pretty good idea what a successful outcome would look like for them, and we filled all those criteria." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/erangalperin/" target="_blank" rel= "noopener">Eran Galperin on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/gymdesk" target="_blank" rel= "noopener">Gymdesk on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href="https://gymdesk.com" target="_blank" rel="noopener">Gymdesk website</a></li> <li dir="ltr" role="presentation"><a href="https://tinyseed.com/" target="_blank" rel="noopener">Tinyseed.com website</a></li> <li dir="ltr" role="presentation"><a href= "https://www.fiveelms.com" target="_blank" rel="noopener">Five Elms Capital</a></li> </ul> <h2>Podcast Sponsor – Full Scale</h2> This podcast is sponsored by <a href="https://fullscale.io/" target="_blank" rel="noopener">Full Scale</a>, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at <a href= "https://fullscale.io/" target="_blank" rel= "noopener">fullscale.io.</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

July 24, 2026•1:15:59

#205: Domain Knowledge Is the New Moat, Not Features and Code - Cliff Sentel

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Cliff Sentell co-founded Compass Professional Health Services in Dallas in 2005, where he and two partners each put in $20,000 and bought a single server. They started in healthcare price transparency, reverse-engineering the cost of specific procedures on specific plans out of billions of insurance claims. The first idea, selling to consumers, flopped, because frustrated patients wouldn't pay $20 to $30 a month for guidance they saw as nice-to-have. So they pivoted to employers, who were footing the bill for their workers' poor healthcare decisions, and wrapped the data in a tech-enabled service: an app, "health pros," and a custom CRM. Compass reached about $1 million in revenue in three to four years, grew from $3 million to $10 million fast, and scaled to roughly $30–40 million with 200 employees and Fortune 100 clients, T-Mobile its largest. They turned down growth equity investors to keep control and equity, funding growth off their own balance sheet. In 2018 Alight acquired Compass — mostly cash with a multi-year earnout — and revenue tripled inside Alight within three years. Today Cliff is a partner at Cypress Growth Capital, where he invests non-dilutive capital to help bootstrapped SaaS founders growth faster. The Cypress thesis is simple: in the AI era, industry domain knowledge is the moat, not features. Key Takeaways <ul> <li dir="ltr" role="presentation">Sell To Payers — Frustrated consumers won't pay; find the customer whose real problem costs them money.</li> <li dir="ltr" role="presentation">Protect Your Equity — Declining growth equity kept control and made the eventual exit worth multiples more.</li> <li dir="ltr" role="presentation">Exit Isn't The End — After the acquisition, Compass re-found product-market fit and tripled revenue inside Alight.</li> <li dir="ltr" role="presentation">Flexible Beats Restrictive — Royalty funding flexes with cash, avoiding debt covenants and the loss of control equity brings.</li> <li dir="ltr" role="presentation">Outcomes Over Models — Value created, not the recurring-revenue label, now decides whether a company scales.</li> </ul> Quote from Cliff Sentel, Partner at Cypress Growth Capital "The biggest thing that's changed now with AI in SaaS is differentiation. If you're really good at something, if you have domain expertise that other people can't do, and you add AI to that, your moat of better knowledge and capabilities gets wider. "That's fundamentally our investment thesis right now at Cypress. Can we find companies that are really good at a very specific domain capability, that have proprietary data, that create the system of action their customers use — feeding that information back into the knowledge set and building the moat wider and wider? "This is a moment where knowledge and expertise are at a premium. Not software, not how much you've built. How much do you know? That's what you're capable of achieving." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/cliffsentell/" target="_blank" rel= "noopener">Cliff Sentell on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/cypress-growth-capital-llc" target="_blank" rel="noopener">Cypress Growth Capital on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.cypressgrowthcapital.com/" target="_blank" rel= "noopener">Cypress Growth Capital website</a></li> <li dir="ltr" role="presentation"><a href= "https://www.alight.com/compass" target="_blank" rel= "noopener">Compass Professional Health Services (now Alight)</a></li> </ul> <h2>Podcast Sponsor – LaunchBay</h2> LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned. If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system. Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools. Visit <a href="https://start.launchbay.com/practical-founders/" target="_blank" rel="noopener">launchbay.com/practical</a> and get 25% off your first 3 months on any LaunchBay plan. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

July 17, 2026•1:11:24

#204: He Sold a Majority, Gave Up Control, and Became Indispensable - Matthew Bullis

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Matthew Bullis grew up in a mud-brick hut with no running water on a small island off South Korea, was adopted to the US at 11 speaking no English. After a dot-com near-miss, he took over his brother's struggling concrete-pumping software — down to about $20,000 a year — for 90% of the company. He taught himself to code and rebuilt it from scratch. From 2016, Bullis built <a href= "https://www.rapidworks.com/" target="_blank" rel= "noopener">RapidWorks</a> into the operational system of record for heavy-equipment subcontractors: concrete pumping, cranes, hydrovac, and other site services. RapidWorks helps contractors book jobs, dispatch crews, manage the field, and get paid faster with accuracy and speed, taking dispatchers' productivity from 20 jobs to 60+. Today the company is near $20 million in ARR, serving more than 80% of the concrete-pumping market. In 2023, approaching $5 million in revenue, Bullis sold a majority to Wavecrest Growth Partners and brought in a new CEO Tim Curran with a new executive team. Matthew expected to be phased out within a year. Instead, by staying flexible and solving whatever broke, he became indispensable as chief strategy officer, taking on important strategic execution roles across the company where he was needed. Key Takeaways <ul> <li dir="ltr" role="presentation">Solve any problem — A bootstrapper's real value is surviving anything and solving whatever breaks.</li> <li dir="ltr" role="presentation">Stay flexible — Don't trade on past wins; credibility comes from the value you create now.</li> <li dir="ltr" role="presentation">Sit with customers — Weeks in their offices surfaced problems they never thought to ask for.</li> <li dir="ltr" role="presentation">Hire your boss — A ready-made CEO and team de-risk the scale a founder can't reach alone.</li> <li dir="ltr" role="presentation">Keep perspective — Nothing is as good or as bad as it feels in the moment.</li> </ul> Quote from Matthew Bullis, Co-Founder and CSO of RapidWorks "To stay useful and relevant when you're not the CEO any more, you have to be flexible. People overemphasize the value of what they've done in the past: look at all the great things I did. But that's like living in your high school glory days. It doesn't merit much, and you can't expect people to give you credibility just for what you built. "Your real value is surviving anything and solving any problems. Take that to heart — I can survive anything, I can solve any problem, I can create value for myself and the people around me. Under any difficult situation, people are drawn to people of value. "So I stopped staying quiet. When I saw things weren't done right, I spoke up, and the seasoned leadership saw my opinions had value. When people see value in you, and you really help, they want you on their team — that's how I won the other executives over." Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/company/rapid-works-co" target="_blank" rel="noopener">RapidWorks on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.rapidworks.com/" target="_blank" rel= "noopener">RapidWorks website</a></li> <li dir="ltr" role="presentation"><a href= "https://www.wavecrestgrowth.com/" target="_blank" rel= "noopener">Wavecrest Growth Partners</a></li> </ul> <h2>Podcast Sponsor – Vista Point Advisors</h2> This podcast is sponsored by <a href= "https://vistapointadvisors.com/" target="_blank" rel= "noopener">Vista Point Advisors</a>, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

July 10, 2026•1:07:50

#203: Every Software Team Should Put AI Agents on the Org Chart - Nick Olsen

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Nick Olsen is the Head of AI Innovation at <a href= "https://mainsailpartners.com/mainsail-ai-labs/" target="_blank" rel="noopener">Mainsail Partners</a>, where he works hands-on with 25 scaling vertical SaaS companies helping them adopt AI in engineering and product. Before joining Mainsail, Nick spent 20 years helping build ResMan from a 3-person startup into a scaled software company serving the multifamily property management market. Today, Nick leads a team of engineers who embed directly inside portfolio companies to build AI systems alongside their teams. They don't just advise from the sidelines—they commit code, ship features, and help technical leaders redesign how modern software organizations operate. Nick explains why AI-first engineering is no longer a competitive advantage for SaaS companies—it's becoming the minimum requirement to stay competitive. The winners won't just write code faster. They'll build better products, make better decisions, and deliver dramatically more customer value with AI-native teams. Key Takeaways <ul> <li dir="ltr" role="presentation">Table Stakes — AI-first engineering is no longer optional for serious SaaS companies. It's becoming the minimum operating standard.</li> <li dir="ltr" role="presentation">Roles Are Collapsing — Product, design, and engineering are moving closer together as AI removes slow handoffs and bottlenecks.</li> <li dir="ltr" role="presentation">Velocity Misleads — Shipping 3x more features doesn't matter if customers don't want them. Outcome beats output.</li> <li dir="ltr" role="presentation">Judgment Wins — AI makes building cheaper and faster. Strategic product judgment becomes more valuable, not less.</li> <li dir="ltr" role="presentation">Agents Matter — The best teams increasingly treat AI agents like teammates with jobs, accountability, and measurable performance.</li> <li dir="ltr" role="presentation">UX Is Changing — Customers may increasingly stop logging into SaaS apps and interact through agents instead.</li> </ul> Quote from Nick Olsen, Head of AI Innovation at Mainsail Partners "We are well past any point of skepticism or any engineer that says, Hey, this isn't gonna be here forever, or this isn't my thing. Engineers no longer should be starting in the traditional code editor, the IDE. Engineering has moved to much more of an agentic approach where you're starting in the terminal or or some sort of Claude Code or Codex app. "How we're building software has completely and radically shifted. Companies are starting to move past treating AI as a tool. They're starting to treat AI as the way that they actually operate. It's not a tool like Excel is for a financial analyst, but that's actually where I start. "We're trying to see people transition to treat AI as an actual teammate and actually affecting change within their organization.. And that's from the product and management side as well as to the engineering side." Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/nicksolsen/" target="_blank" rel="noopener">Nick Olsen on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/mainsail-partners/" target= "_blank" rel="noopener">Mainsail Partners on LinkedIn</a></li> <li dir="ltr"><a href="https://mainsailpartners.com/" target= "_blank" rel="noopener">Mainsail Partners website</a></li> </ul> <h2>Podcast Sponsor – Full Scale</h2> This podcast is sponsored by <a href="https://fullscale.io/" target="_blank" rel="noopener">Full Scale</a>, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at <a href= "https://fullscale.io/" target="_blank" rel= "noopener">fullscale.io.</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

July 3, 2026•1:03:00

#202: Practical Fintech: Surviving Payment Platforms and Big Banks - Paul Hoeper

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Paul Hoeper founded <a href="https://invoiceasap.com/" target="_blank" rel="noopener">InvoiceASAP</a> after spotting a simple but painful problem in 2009: home service businesses couldn't easily create invoices or collect payments from the field using mobile devices. He started in New Orleans, launched during the earliest days of mobile apps, and built one of the first mobile invoicing products integrated with both Square and Clover. He also suffered through several payment platform providers who never lived up to their sales pitches. Today, InvoiceASAP serves about 23,000 paying home service businesses and roughly 400,000 total users across HVAC, plumbing, roofing, landscaping, and other field service trades. The company generates just under $5M in annual revenue with only 12 employees, growing 20–40% annually through a mix of SaaS and embedded fintech revenue. Paul shares why he shifted from a pure SaaS subscription model to embedded payments, increasing average revenue per customer from roughly $9/month to $80–$94/month. He also explains why he avoided VC funding despite operating in fintech, choosing debt financing instead to preserve control, protect optionality, and keep building on his own terms. Key Takeaways <ul> <li dir="ltr" role="presentation">Revenue Shift — Moving from SaaS subscriptions to embedded payments increased average revenue per customer প্রায় 10x, from $9 to $80–94 monthly.</li> <li dir="ltr" role="presentation">Control Matters — Owning payment rails gave InvoiceASAP more margin, product flexibility, fraud control, and freedom from platform dependency.</li> <li dir="ltr" role="presentation">Debt Over VC — Paul chose debt instead of institutional equity to preserve board control and avoid forced exits or founder dilution.</li> <li dir="ltr" role="presentation">Vertical Focus — Home service businesses have highly specific cash flow needs that generic payment platforms often misunderstand or ignore.</li> <li dir="ltr" role="presentation">Fintech Reality — Payments infrastructure remains messy, legacy-heavy, and full of poor actors despite modern APIs and slick branding.</li> </ul> Quote from Paul Hoeper, Founder and CEO of InvoiceASAP "Most of our competitors are on stripe.we're just exceptionally technically proficient. So we built out our own entire PayFAC infrastructure as close to the line as you can get, but where we control basically all the payment rails. Stripe is an out-of-the-box product. So if you're looking for a different way of doing payments and billing, you just have to use whatever products Stripe gives you. That's it. And when you build it the way that we built our product and payments platform, we can do a lot--for our customer and our business model. We have the flexibility to develop instant deposit, merchant cash advances and all different types of products." Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/paulhoeper/" target="_blank" rel="noopener">Paul Hoeper on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/invoiceasap/" target="_blank" rel="noopener">InvoiceASAP on LinkedIn</a></li> <li dir="ltr"><a href="https://invoiceasap.com/" target="_blank" rel="noopener">InvoiceASAP website</a></li> </ul> <h2>Podcast Sponsor – LaunchBay</h2> LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned. If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system. Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools. Visit <a href="https://start.launchbay.com/practical-founders/" target="_blank" rel="noopener">launchbay.com/practical</a> and get 25% off your first 3 months on any LaunchBay plan. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

June 26, 2026•56:27