5 Post-Sale Mistakes Business Owners Regret
You did it. The deal is signed. The wire hit. Someone brought donuts to the office to celebrate. Life is good, right?
Well… maybe.
Because here’s the thing no one tells you: what happens after the sale can be just as important as what happened before it.
This week we talked about earnouts and how they can be a win-win — if expectations are clear. But not everything after closing goes as smoothly. In fact, we’ve seen smart, successful business owners look back on their exits with one big thought:
“I wish someone had warned me about that.”
So, here’s your warning — delivered with love and just a dash of sarcasm.
1. They Ghost Their Team
Your employees built this company alongside you. Whether they’re staying or going, don’t vanish like a magician at the final staff meeting.
Pro Tip: Make time to share the story, the gratitude, and the plan. A smooth transition is a respectful one.
2. They Don’t Prep for the Tax Hit
There’s nothing like selling your business and then realizing you accidentally invited the IRS to your retirement party. The way your deal was structured (hint: earnout vs lump sum, or stock vs asset sale) can drastically change your tax obligations.
Pro Tip: Talk to your CPA before the next big wire comes through.
3. They Burn the Buyer Bridge
Whether you liked the buyer or merely tolerated them through due diligence, don’t slam the door. Many regret not offering transitional support — especially when a portion of their payout depends on performance. (Earnout flashbacks, anyone?)
Pro Tip: Leave documentation, offer training, and send your buyer a thank-you note — or at least the Wi-Fi password.
4. They Don’t Know What’s Next
One minute you’re the boss, the next minute you’re alphabetizing spices or refreshing Zillow out of boredom. The emotional aftermath of a sale can be rough — especially for founders.
Pro Tip: Make a post-sale life plan before you close. (And yes, “go fishing” counts… for a little while.)
5. They Don’t Understand the Deal They Signed
Okay, this one stings. But some owners nod their way through closing docs without fully grasping whether they sold the business or just its assets. That distinction — stock sale vs. asset sale — can affect everything: taxes, liabilities, and what happens to your team.
Pro Tip: Stay tuned for Monday’s Term of the Week, where we break down Stock Purchase vs. Asset Purchase in plain English. Trust us, it’s worth the read. Or better yet
🎯 Subscribe now and we’ll send you our free Seller’s Negotiation Checklist so you don’t leave money (or peace of mind) on the table.
Because the deal might be done……but your future’s just getting started.
