Ep 519 How to Avoid the Unforced Errors That Can Wipe Out Your Equity

Spencer Dennis was an elite golfer whose playing career ended with spine surgery in his teens. He became a tour-level coach, running high-performance programs for juniors, college players, and pros. Managing parents, trainers, and recruiters through texts and email was chaos, so he built CoachNow to guide athletes between sessions.  CoachNow caught on quickly with busy coaches. Then a run of decisions—turning off revenue under "grow fast" advice, stacking convertibles and preferences, and accepting stock-for-stock deals—left Spencer with little to show for a product customers loved. This is a cautionary tale for any owner negotiating with "sophisticated" investors. 

If you're considering your endgame, you're probably looking at private equity. Most PE firms use a familiar formula: buy a majority stake and ask the owner to "roll equity"—re-invest part of the proceeds—into the newco they're building. The downside: you become a minority shareholder in a business you no longer control.   There's another path: growth equity, which lets you take chips off the table via a secondary while maintaining control. That's the business John Ruffolo is in as Founder & Managing Partner at Maverix Private Equity (he also founded OMERS Ventures).

If you've ever noticed those ads inside a mobile game, you have Zain Jaffer to thank. He co-founded Vungle and helped popularize rewarded video ads—the ones that revive your character or hand you in-app currency after you watch.  In this Built to Sell Radio episode, Zain explains how he rode the smartphone wave to a $780M all-cash exit to Blackstone—and why he personally took home more than $100M. Then he gets candid about what came next. 

Most cities have a problem: what to do with cars that get towed and never picked up. They pile up in impound lots—taking up space and tying up cash. Stan Markuze helped solve that problem by co-founding Joyride Auto, an online auction platform where repair shops, scrap dealers, and car enthusiasts can buy those abandoned vehicles directly from the lot.  In this episode, Stan shares how he and his co-founders built a cash-flow-positive business that turned a clunky, paper-based process into a digital marketplace—and sold it to a private-equity firm for seven times revenue in just two years. 

After a 23-year journey building Non-Linear Creations into a marketing giant with more than 120 employees, Randy Woods sold it in 2017 to Valtech. Valtech is a distinguished digital agency offering marketing, digital technology, and business transformation consulting services. Post-sale, Woods now serves as the SVP of Strategic Growth Opportunity at Valtech, a role dedicated to identifying potential acquisitions for the business. In the latest installment of Built to Sell Radio's Inside the Mind of an Acquirer series, we sit down with Woods to discuss how to: Make your company irresistible to an acquirer. Leverage a "put option" to cover your downside. Understand the factors that influence how acquirers value businesses. Target potential acquirers who would see your company as a strategic addition. Avoid deal breakers during negotiations with potential acquirers.

Today's episode of Built to Sell Radio is part of our Inside the Mind of an Acquirer series. John Warrillow interviews Lee McCabe, a former Meta and Alibaba executive turned private equity investor—now an advisor helping PE firms modernize how they create value.  McCabe argues the old model of buying cheap, piling on debt, and hoping for multiple expansion is over. Interest rates are up, LPs are demanding more, and the firms that win will need to act more like operators than bankers. If you're planning to sell, and private equity is your natural buyer, you'll want to hear this. 

Dave Sifry has founded nine companies, including Technorati and Linuxcare, raising more than $170 million along the way. In this episode of Built to Sell Radio, he reveals how he went from being worth more than $100 million on paper to watching that value disappear — and what he'd do differently if he had the chance again.  Despite those scars, Sifry has built an extraordinary career. He has founded nine companies and today is founder and CEO of Warmstart, a platform that helps entrepreneurs turn old contacts into new business. 

In 2006, Tad Fallows and two friends spotted a problem inside Harvard's cancer labs: researchers were spending more time managing freezers, fruit flies, and mice than actually doing research. They built iLab, a SaaS tool for universities and hospitals, bootstrapped it to high–7-figure ARR, and eventually sold to Agilent Technologies for roughly six times revenue.  But the journey wasn't smooth. Cash was often razor-thin with 75 employees on payroll, and an early inbound offer at 3× ARR forced Tad and his partners to decide: take the deal, or gamble on building more value. 

Ronan Berder built Wiredcraft to 140 people, then sold to Publicis for a reported 67 million euros. This Exit Story traces the moment he walked away from Techstars and a product dream to double down on services—and why that decision paid off. 

Most owners want 100% cash at closing. Most acquirers want the opposite—they try to hold back as much as possible and tie it to future results. That tug-of-war defines the negotiation.  In this week's episode of Built to Sell Radio, you discover how to turn common transition structures from potential pitfalls into opportunities for upside.