Practical Founders Podcast

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Aug 2026

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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.

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August 21, 2026Episode 21057 min

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

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 Distribution First: Prove you can generate demand and revenue before a single line of code is written. Repeat vs. First: First-time founders obsess about product; repeat founders obsess about distribution. Partner for Reach: Bring on experts and influencers who already own a trusting audience. Micro-Niches Win: AI makes it viable to build dedicated apps for tiny verticals like dog trainers. Time to Money: Chase the fastest path to the first $100 in MRR to make everything real. 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 Vic Levitin on LinkedIn Crazy Lister on LinkedIn Crazy Lister website Diptera.ai (prior venture) 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 .

August 14, 2026Episode 20953 min

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

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 .

August 7, 2026Episode 2081 hr 13 min

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

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 .

July 31, 2026Episode 2071 hr 4 min

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

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 .

July 24, 2026Episode 2061 hr 15 min

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

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 .

July 17, 2026Episode 2051 hr 11 min

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

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 .

July 10, 2026Episode 2041 hr 7 min

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

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

July 3, 2026Episode 2031 hr 2 min

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

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

June 26, 2026Episode 20256 min

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

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

June 19, 2026Episode 2011 hr 0 min

#201: Creating a New Category in SaaS for Key Account Managers - Jerry Alderman

Jerry Alderman is the co-founder and CEO of Valkre Solutions , a SaaS platform built specifically for key account managers who oversee the largest and most strategic customers in global B2B companies. After careers in engineering, sales, leadership, entrepreneurship, and customer value consulting, Jerry discovered that key account managers were still managing critical customer relationships with spreadsheets and PowerPoint. That insight led to Valkre, which helps large companies build account plans, coordinate teams, identify growth opportunities, and manage strategic customer relationships. Today Valkre serves major enterprise customers, has grown beyond $4 million ARR, and helps organizations move key account management from disconnected documents into a structured system that can leverage AI and organizational knowledge. In this conversation, Jerry explains why key account management may be the last major sales role that remains deeply human in the AI era. He shares lessons from building a new software category, finding product-market fit after several pivots, raising more than $5 million in practical funding from Golden Section, and why the biggest opportunities often hide inside markets that look small from the outside. Based on the transcript discussion of Valkre's growth, funding, and AI-driven market shift. Key Takeaways PowerPoint Problem - Hundreds of thousands of key account managers still run critical customer relationships in spreadsheets and PowerPoint. Human Workflow - Key account management depends on trust, judgment, negotiation, creativity, and relationships that AI cannot easily replace. AI Catalyst - AI isn't replacing account managers; it's finally forcing companies to digitize strategic account management processes. Category Creation - Building a new software category takes longer than expected, even with strong customers and product quality. Practical Funding - Raising minority growth capital helped accelerate sales and technology investments without sacrificing founder control. Product-Market Fit - The biggest startup challenge is getting product-market fit right and finding the right feedback sources. Quote from Jerry Alderman, Co-founder and CEO of Valkre Solutions "AI is automating a lot of processes now. I think that key account management will be the last sales role standing. I really do. I used Claude to investigate. Can AI take over key account management sales and disrupt Valkre? And here's what it says. 'No, because key account management is very relationship and trust dependent. "It requires this trust of people and relationships in order to get this done. It can't replace that. It says real-world coordination, meaning teamwork. It involves having this team of people coordinated together. This is a very human role and it requires the human to be creative and think forward. AI is very much an accelerator. And so you did this job. Building an account plan and doing SWOT analysis and doing white space analysis, that stuff takes time. With AI in Valkre, you can do those things so much more efficiently and effectively." Links Jerry Alderman on LinkedIn Valkre Solutions on LinkedIn Valkre Solutions website Winning Customers book by Jerry Alderman Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital . In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors. Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period. Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head .