An earn-out is a deal structure where part of the sale price is contingent on the business hitting future performance goals. For many owners, it feels like a gamble—where the payout is uncertain, and the risks are high. 

But Bob Gilbreath flipped the script. 

He navigated two complex earn-outs across two service businesses and turned both into massive financial wins. In this episode of Built to Sell Radio, Bob shares how he turned the dreaded earn-out into his greatest asset. 

Most founders focus all their energy on getting to an exit, but few stop to consider what comes next. In this episode of Built to Sell Radio, John Rood shares what he learned after selling Next Step Test Prep to private equity—and why he decided to write Beyond the Exit. 

When Kevin Wagstaff and his brother bootstrapped Spectora, a SaaS platform for home inspectors, with just $2,500 each, they never expected to one day face an $80 million acquisition offer. Spectora transformed the home inspection industry by replacing outdated paper reports with a digital platform that streamlined workflows, saved inspectors time, and enhanced the client experience. 

But when an acquirer attempted to re-trade the deal at the last minute—adding a $25 million seller’s note, a $10 million earn-out, and a 36-month call option—Kevin learned a hard lesson: just because an offer is on the table doesn’t mean the deal is done. 

The acquirer assumed Kevin and his brother would be too invested in the deal to walk away. But thanks to their advisor’s guidance, they stood firm. The result? The acquirer backtracked, offering the original terms. Kevin and his brother still walked, ultimately selling a majority stake at a $90 million valuation to a better partner. 

Selling your business to a Fortune 500 company is a dream for many founders. Strategic acquirers often pay the most because they can integrate your business into their larger ecosystem. It’s rare to pull off even once—Brock Weatherup has done it three times. 

In this episode of Built to Sell Radio, Brock reveals the strategies that helped him attract Fortune 500 buyers like PetSmart and Petco. This episode is a roadmap for anyone who wants to sell their business to a strategic acquirer. 

That’s why we created the After the Deal series on Built to Sell Radio. This series explores life after selling a business—delving into the personal, financial, and emotional transitions that come when work becomes a choice, not a requirement. 

In this episode, we speak with Preston Holland, author of Private Jet Insider and an expert in private aviation. Preston shares why private jet travel isn’t just for celebrities and explains how business owners use private aviation to buy back their most valuable asset: time. 

This week on Built to Sell Radio, John Warrillow interviews Blake Hutchison, CEO of Flippa, the world’s largest marketplace for buying and selling digital businesses. With experience overseeing thousands of real transactions, Blake offers a unique window into the minds of today’s acquirers. 

Ben Landers built Blue Corona, an 8-figure digital marketing agency focused on home service businesses, into a data-driven powerhouse. When it came time to sell, Ben achieved something extraordinary: a clean exit with no earn-outs, a rare feat in the service business world where earn-outs are practically the norm.

Adam Kerrigan started as the owner of a managed service provider (MSP) business, which he built and eventually sold. After his exit, he joined the acquiring company to lead its M&A group, where he completed 16 deals and helped build a private equity-backed organization. 

In this episode of Built to Sell Radio, Adam pulls back the curtain on how acquirers often push for cashless deals, offering equity instead of cash—and how sellers can negotiate to ensure they get the deal they deserve. 

As we gear up for 2025, I wanted to highlight the top strategies covered this past year on Built to Sell Radio. These insights are designed to help you increase the value of your business and position yourself for a successful exit.

Imagine personally guaranteeing millions in debt to fill a $28M order—only to have it yanked at the last minute. It nearly bankrupted founder Adi Gullia as well as Grace & Stella. Yet he overcame it all and sold at a 5.8x EBITDA multiple.