Practical Founders Podcast

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.

Practical Founders Podcast is a business podcast hosted by Greg Head, with 208 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Greg Head hosts Practical Founders Podcast, a business show with 208 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #209

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

  Aug 14, 202653 minS1

  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 Manage Up: Investors own the company but depend on you — understand their perspective and manage them. Narrow Focus: Scoping down isn't more work; it's how you rediscover your core value and focus. Throw Out the Playbook: The old "fix go-to-market and sell in three years" thesis no longer fits a changed world. Just Write It: With code cost collapsing to tokens, engineering can finally fail fast and recover quickly. Service as Software: Clients want managed agentic solutions with governance, not just self-serve SaaS tools. 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 Steve Oriola on LinkedIn Unbounce on LinkedIn Unbounce website Crest Rock Partners (investor) Podcast Sponsor – DevHawk 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. DevHawk 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. 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. Head to devhawk.ai/practical to book a conversation about how DevHawk can help. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head .

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  Episode #208

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

  Aug 7, 20261h 13mS1

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

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  Episode #207

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

  Jul 31, 20261h 4mS1

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

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  Episode #206

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

  Jul 24, 20261h 16mS1

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

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  Episode #205

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

  Jul 17, 20261h 11mS1

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

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