Built to Sell Radio

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Ep 487 After the Deal: How the Ultra-Wealthy Invest After Selling Their Business Mar 28, 2025

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What would you do with $20 million?

That's the minimum amount required to join Tiger 21, the exclusive network where ultra-high-net-worth entrepreneurs learn how to preserve and grow their wealth.

Michael Sonnenfeldt founded Tiger 21 after selling two companies and realizing that the skills that made him a successful entrepreneur didn't translate into smart investing. He built the group to help other entrepreneurs avoid costly post-exit mistakes.

Ep 486 Inside the Mind of an Acquirer: The Harvard Playbook for Buying Your Business Mar 21, 2025

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A new generation of buyers trained in Entrepreneurship Through Acquisition (ETA) is looking for businesses like yours. Unlike private equity firms focused on roll-ups, ETA buyers are often searching for a single business to own and operate—making them a legitimate option for certain sellers.

Ep 485 After the Deal: The Psychology of Selling—Kill Criteria, Walkaway Mindset & Why "Telling Your Company's Story" Often Drives Up Your Multiple Mar 14, 2025

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For the first time ever, we recorded a Built to Sell Radio episode in front of a live audience at the Value Builder Summit—a gathering of mission-driven advisors dedicated to helping founders level the playing field as they approach their exit.

Rob Walling has started, built, and sold multiple companies. As an investor and conference organizer, he's seen hundreds of founders exit—some thriving, others struggling. He teamed up with Dr. Sherry Walling, a clinical psychologist specializing in supporting entrepreneurs, to codify what separates a successful exit from one that leaves an owner adrift. Their insights culminated in their new book Exit Strategy.

Ep 484 How to Know When It's Time to Sell Mar 07, 2025

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Kristie Shifflette built a 13-location Orangetheory Fitness empire from scratch—bootstrapping a capital-hungry business, personally guaranteeing leases, and taking on risk most founders wouldn't touch. In the end, it paid off for Kristie and in this episode, you'll discover how to:

Bootstrap a capital-intensive business without giving up control

Reduce your risk when taking on an investor

Attract entrepreneurial employees who will care as much as you do

Think about the $10 million milestone (and why it matters to private equity)

Know when to take some chips off the table—and when to double down

Ace management presentations with an acquirer

Play hard to get (even when you want to sell)

Get an acquirer to bump up their offer

Max out an earn-out payment—even if you don't quite hit your targets

Spot an acquisition offer that's likely to be re-traded

Ep 482 Exit Story: Bob Gilbreath — "The Adult Version of the Marshmallow Test" and How to Capitalize on an Earn-Out Feb 21, 2025

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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.

Ep 481 After the Deal: What 70 Founders Reveal About Generational Wealth, the Achievement Trap & the Happiness Illusion Feb 14, 2025

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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.

Ep 480 Exit Story: The $80M Deception—How Kevin Wagstaff Walked Away and Won Feb 07, 2025

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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.

Ep 479 Exit Story: How to Attract a Fortune 500 Acquirer With Brock Weatherup Jan 31, 2025

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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.

Ep 478 After the Deal: When Can You Afford to Fly Private? with Preston Holland Jan 24, 2025

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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.

Ep 477 Inside the Mind of an Acquirer: Lessons from Analyzing Thousands of Real-Life Transactions Jan 17, 2025

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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.

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