What Kills a Deal Is Bad News That Arrives Late
Frank Williamson runs Oaklyn Consulting, an M&A advisory firm. Asked the number one reason deals fall apart, his answer was a buyer's assumption that turns out wrong. His fix is for the seller to raise the deal killer early.
September 25, 2026
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1 min read
The example he gave was from the buy side. His team was acquiring a money-losing company and had everything it needed except the tax returns. Frank argued they could close without them. How bad could it be? The CEO said no and made everyone wait.
It took a long time. The returns had never been filed, and the company had collected sales tax it never paid over. That repriced the deal. By then it was the only issue left on the table, so it hit everything.
Do it that way, he says, and the negotiation holds up all the way to close.
Why it matters to you.
Most founders would hold it back. You're months from a deal you want, the buyer is excited, and the problem might never come up. Waiting feels smart. It's the expensive choice. In week 1 the buyer has spent very little and is still deciding whether they want the firm. They price the problem in or walk away, and either is cheap for you. In month 8 they've paid fees, they're invested, and your problem is the only open item. It reprices everything around it. This applies to anything a buyer will find anyway: a missed filing, a liability, a client who's about to leave. Know yours before anyone calls. Frank's other rule helps here: your strongest position is being willing to walk away.
“We tell them, look, if something's going to kill the deal in the end, it's going to kill the deal in the beginning. And so why don't you just save everybody time and heartache and tell them the ugly thing up front. If they're still interested, great, you've got a deal. - Frank Williamson, founder and CEO, Oaklyn Consulting”
Your one thing.
Write down the one thing you'd least want a buyer to find. Then pick one: fix it this year, or plan to raise it early. Don't leave it for diligence.
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