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.