Ep 499 After the Deal: The Hidden Cost of Generational Wealth

When Ben Leonard sold Beast Gear—a strength and conditioning equipment brand he built from his spare room into a business generating $6 million in revenue—he thought he’d made the deal of a lifetime.  He got 80% of the proceeds up front, agreed to a small earn-out, and became the face of Thrasio, the acquirer.  Then things started to go sideways. 

You’ve built a valuable company. Maybe you’re even thinking about selling. But what happens after the wire hits?  In this episode of Built to Sell Radio, Alex Bean, co-founder of Divvy, shares what it felt like to sell his company for $2.5 billion—and why the real challenges began after the deal closed.  This conversation will help you think more strategically about what you’re really building—and how to avoid the regrets that often follow a big payday.

Most acquirers want you to stick around. Roll equity. Hit targets. Train your replacement.  But there’s a different kind of buyer out there. One who wires 100% of the money at closing—and lets you walk.  Dan Mytels represents this type of buyer. Through his firm, Salt Creek, he’s acquired 100 businesses—most of them mature, profitable, niche companies where the owner was ready to move on. They don’t always offer the highest multiple, but they do offer something many founders value more: a clean break. 

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 support—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. 

Private equity firms are the most likely buyers for your business—and some do a fine job preserving what makes a company great. But many are financial engineers. They offer a generous multiple, then lever up the business, cut costs, and flip it within a few years. Longtime employees get let go. Culture erodes. You walk away with a check, but it can feel like selling out. 

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.