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 Unknown Host, with 213 episodes on record and a Required Pod Score of 80.

Unknown Host hosts Practical Founders Podcast, a business show with 213 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 #215

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

  Sep 25, 20261h 4mS1

  Steve Wolfe co-founded Growth Street Partners 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 Go High — Drive above the wreck instead of through it, and return to first principles. Minority Stakes — $5-15 million buys 20-50 percent, so founders keep control and keep deciding. Headline Half-Life — Reading AI news daily burns time on knowledge that expires in weeks. Right to Win — Add AI where you already have an edge, not everywhere you see a nail. Exit Discipline — Growth Street models five times revenue at exit, same as day one. 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 Steve Wolfe on LinkedIn Growth Street Partners on LinkedIn Growth Street Partners website Steve's earlier Practical Founders episode (#123, with Nate) 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 .

  ListenShow Notes
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  Episode #214

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

  Sep 18, 20261h 10mS1

  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 Affordable Pricing — $30 subscriptions opened a global audience nobody else in cyber training was serving. Revenue Share — Splitting revenue with expert instructors bought quality he could never have afforded to hire. Platform Lock-In — Teachable worked fine at five courses and became a trap at thirty. M&A Advisor — A million dollars in deal costs doubled the offer, and he'd pay it again. Track Data Early — Accrual accounting and a real CRM from day one, not spreadsheets and intuition. 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 Heath Adams on LinkedIn TCM Security on LinkedIn TCM Security website Breach Point (Heath's new company) 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 .

  ListenShow Notes
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  Episode #213

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

  Sep 11, 20261h 7mS1

  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. Chipply 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 Keep Control: The deal preserved control of the product and the board for the founders. Win-Win Pricing: Chipply prices on a percentage of merchandise value, so incentives stay aligned. Scratch Your Own Itch: The best first customer was their own 145-year-old sporting goods business. Just Do It: Trust yourself sooner and take the risk faster. Vertical Depth: Decorated apparel is too complicated for generic tools like Shopify to serve. 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 Chipply on LinkedIn Chipply website Growth Street Partners (growth equity investor) 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 .

  ListenShow Notes
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  Episode #212

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

  Sep 4, 20261h 5mS1

  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. TeamLinkt 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 Aligned incentives - As customer programs grow, TeamLinkt grows, so saving admins time is the growth strategy. VC mismatch - Six months chasing venture capital ended when the one-in-a-hundred exit math stopped adding up. Right capital - Practical growth equity funded leadership hires and discipline, not a land grab; Jay kept board control. Free drives virality - Coaches and parents spread the app club to club, replacing trade show booths they can't afford. 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 Jay Maharaj on LinkedIn TeamLinkt on LinkedIn TeamLinkt website Growth Street Partners 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 .

  ListenShow Notes
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  Episode #211

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

  Aug 28, 20261h 9mS1

  Ajay Gupta founded Stirista 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 One Round: Ten years bootstrapped, then a single $14M round to bring in world-class leadership. Avoid Debt: Nearly every acquisition uses earnouts and cash, not the leveraged PE roll-up playbook. Hire the Pros: Sometimes you spend money on senior talent to elevate how the whole company thinks. Stay Flexible: The people who grow with a startup listen to clients and adapt, not just work hard. Scale as Moat: Privacy regulation now demands enough scale to comply across every state's laws. 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 Ajay Gupta on LinkedIn Stirista on LinkedIn Stirista website Wavecrest Growth Partners (investor) 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 .

  ListenShow Notes

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