Built to Sell Radio 1b353y

When Doug Lowenthal discovered that $1 million in EBITDA was the minimum threshold acquirers looked for in his industry, he had a goal. Then he learned that managed service providers—businesses that offer outsourced IT —were trading for 6–8× EBITDA. That’s when he realized he was building something truly valuable.  But getting there required more than just strong financials. Doug had to rethink how he led his team, structured his business, and prepared for life after the deal. 

Chang Kim—friends call him CK—sold his company Tapas for more than $500 million and walked away without an earn-out. Instead of jumping into his next venture, he did something few founders have the nerve to do: he took a year off.  In this episode of Built to Sell Radio, CK opens up about what life looks like when work becomes a choice, not a requirement. From cross-continental travel to difficult conversations with his kids about wealth, this is a rare, candid look at what happens after the wire hits. 

Ep 494 Exit Story: Building News Sets for TV Stars—and a Business Worth Millions

Most stories we cover involve eye-popping multiples or headline-making exits. They’re fun—but not always realistic.    Jeff DeGarmo’s story is different. No private equity windfall. No tech hockey stick. Just a well-run, 20-person service business built over 16 years and sold for a solid 5.5x EBITDA. 

Greg Alexander sold SBI, his 30-person consulting firm, for $162 million. Since then, he’s had a front-row seat to 50 other service firm exits through his peer group, Collective 54. In this episode of Built to Sell Radio, Greg breaks down what separates firms that sell from those that stall.  This is a Mastering the Deal episode of Built to Sell Radio—designed to help you punch above your weight in a negotiation to sell your business. 

What makes someone want to buy an “unsexy” business?  Jon Pole has acquired 19 traditional radio stations. On paper, it’s an industry many assume is in decline. But for an experienced buyer like Pole, these deals are less about media trends and more about community, cash flow, and culture. 

Sean McAuliffe didn’t invent anything. He was a distributor.  If you lost your car keys and went to a locksmith to cut a new set, chances are your locksmith got the replacement key from Sean’s business. He bought cheap keys from Asia and sold them to locksmiths. Nothing fancy. Like so many businesses, Sean was a middleman. He'd never really thought about selling—didn't think anyone would want to buy it—but when a private equity group offered him millions, Sean realized he was sitting on a potential goldmine. 

What do acquirers really want?  Sequoya Borgman has acquired 19 companies and exited two. He’s raised capital on a deal-by-deal basis, working outside the traditional private equity model. In this episode of Built to Sell Radio, Borgman explains how “independent sponsors” operate—and why more wealthy individuals are now pooling money to buy lower middle-market businesses.  You discover how to: 

When Garren Hilow helped start Abveris, he didn’t have much—just a background in sales, a co-founder with a Harvard PhD, and a stock option representing 16% of the company.  Eight years later, he bought out his co-founder, bootstrapped the company with bank debt (collateralized by his house), and sold it in a stock deal that peaked at $190 million. 

What would you do with $20 million?  That’s the minimum amount required to 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. 

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. 

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 ing entrepreneurs, to codify what separates a successful exit from one that leaves an owner adrift. Their insights culminated in their new book Exit Strategy. 

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 

When Frank Shultz co-founded Infinite Blue, he and his partner split ownership 50/50. The business thrived, but their working relationship soured. Frank wanted to buy out his co-founder, but with a valuation in the eight figures, he faced a daunting question: where would he get the cash? 

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 . 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 roap 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.