What nobody tells you about selling your business for life-changing money is that the hardest part might come after the deal closes.
Adam Rossi built a 250-employee software company serving law enforcement and intelligence agencies — routinely beating Lockheed Martin in head-to-head bids. Then a banker brought back five offers at the “absurd” number you’d think no one would pay. 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 no earn-out.
In this After the Deal episode of Built to Sell Radio, you’ll learn how to:
-
Avoid the post-sale regret that made Adam wish he could “undo the whole sale.”
-
Decide whether to keep equity for a potential second bite of the apple.
-
Handle family members who expect a cut of your sale proceeds.
-
Refuse an earn-out — and what can still keep you tied to the acquirer.
-
Recognize why your first post-sale acquisition might be your worst.
-
Replace the identity of “business owner” with something new.
-
Guard against the guilt that can creep in when you’re no longer working around the clock.
Adam’s story shows why the biggest changes after an exit aren’t always financial — and why they can take years to navigate.
PS. Download The Exit Checklist — a list of things to do to make sure you don’t end up regretting selling your business — free at BuiltToSell.com.
Quote of the Week
I just pulled up a chart of the stock price and thought, this doesn’t really move. I’ll take all cash. If I’d taken even 25% in stock, it would have been a huge second bite of the apple.
Deals
Jolt Software, a provider of digital food safety and operations management tools for restaurants, grocery stores, and healthcare facilities, has been acquired by Digi International Inc. (NASDAQ: DGII) for approximately $145.5 million in cash.
Jolt generated over $20 million in annual recurring revenue (ARR) in fiscal 2025, reflecting a multiple of just over seven times ARR.
