Adam Rossi built a 250-employee software company serving law enforcement and intelligence agencies. They routinely beat Lockheed Martin in head-to-head bids.

Then a banker came back with five acquisition offers — each at the “absurd” number Adam and his wife had thrown out as a hypothetical. The winning bid came from SRA International, a publicly traded defense contractor, for a price that created generational wealth for his family. Adam took all cash and walked away with no earn-out.

But as Adam discovered, the hard part wasn’t negotiating the deal — it was figuring out what to do after it closed.

Unlike most tech founders, Josh Payne never dreamed of a billion-dollar valuation.

His goal was simpler—and harder. He wanted his equity stake to be worth $50 million.

To get there, he skipped the usual playbook. No blitzscaling. No VC treadmill. He raised a small seed round, built a profitable company, and avoided dilution. By the time he sold StackCommerce, Payne still owned 75%—and hit his number.

Most founders measure success by the price they get for their company.

David Hauser did that—he built Grasshopper to $30M Annual Recurring Revenue (ARR) and sold it for $175M – almost 6 times revenue. He and his partner owned the majority of the shares so the deal was life-changing for Hauser. But what makes this interview different is what Hauser did next: he crossed the table to become an investor and now acquires businesses through Durable Capital.

It’s a study in contrasts. As a founder, Hauser chased growth. As an investor, he’s ruthlessly disciplined. He mocks the PE herd chasing home services roll-ups and avoids auction-driven deals. Drawing on his experience founding Grasshopper and Mark Cuban-backed Chargify, he outmaneuvers ETA buyers and first-time acquirers with quiet, direct, close-ready offers. This is a rare window into how someone who’s built and sold a business thinks about buying one—and what makes a deal attractive from the other side.

After selling When Rich Galgano was 25, he left a sales job in wire distribution to start Windy City Wire. Within nine months, he was doing over $1 million in sales—while fighting a lawsuit from his former employer. Fast forward 30 years, and Galgano had built the dominant low-voltage cable distributor in the U.S., sold it for just under half a billion dollars, and stayed on as CEO.

When Ryan Atkinson sold CORE Resources to 24 Seven, it wasn’t his first exit. After selling Redwood Global in 2014, Ryan played a different role in his next venture—injecting $2 million of his own capital while his partner ran the business day-to-day.

The model worked. They grew CORE Resources into a go-to firm for specialized technology talent solutions and ultimately sold the company to 24 Seven—one of the largest privately held marketing, creative, and digital talent firms in North America—in an eight-figure exit.

In this week’s episode of Built to Sell Radio, Ryan shares how they structured the deal, avoided resentment, and nearly lost the sale in the final hours.

Negotiating the sale of your company may be the highest-stakes conversation of your life. In this episode of Built to Sell Radio, part of our Mastering the Deal series, you'll learn how to stay composed when everything you’ve built is on the table.

Christopher Hadnagy, author of Human Hacking, teaches elite military units and Fortune 500 companies how to negotiate using psychological insights. In this conversation, he shares how founders can use the same tools to level the playing field with sophisticated buyers.

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.