#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 …
#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 profes…
#211: This Practical Bootstrapper Scaled Up and Became a Serial Acquirer - Ajay Gupta
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 Ne…
#212: The Practical Case for Payments-Driven SaaS Growth, Not Subscriptions - Jay Majaraj
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 …
#213: She Took on a Growth Equity Partner for the Advice, Not the Money - Lynn Burghardt
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…
44 | How Bootstrapped Software Founders Build a Company Worth Buying (with Greg Head of Practical Founders)
For founders who built a software company without big venture rounds, the exit playbook looks different. Raising little or nothing keeps your options open, but it also means you have to build a company worth buying without the fuel VC-backed peers spend on sales, marketing, and product. In this epi…
#214: He Stopped Being the Face of the Company Before He Sold It - Heath Adams
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 Ude…
#215: How This Early-Stage Growth Equity Partner Is Investing in SaaS in 2026 - Steve Wolfe
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, w…
#216: Messy Financials Killed a Good LOI and Slowed a Profitable SaaS Sale - Riccardo Pisano
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 o…
#217: His Hardest Lesson: Going Too Fast Was More Risky, Even With Funding - Shawn Boyer
Shawn Boyer is founder and CEO of goHappy, 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 …
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