The deal almost closed. Then the risk changed

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Birds Fly, Fish Swim and Deals…

Hey friends,

Quick update from the trenches of buying a business — because this week was a good reminder of why discipline matters more than momentum.

The business we really liked and had an offer accepted back in August. Strong reputation. Solid revenue. Clear upside.

Then something shifted.

Key roles were no longer in place. The operational load quietly slid back to the owner. What was previously a business with leverage started to look a lot more like a job again.

That changed the risk profile.

So I did what buyers have to do (even when it’s uncomfortable):
I re-worked the offer.

I put three options on the table — all fair, all executable, all designed to reflect the new reality:

• A clean, all-cash deal with a defined transition
• A lower-risk structure with extended involvement to stabilize ops
• A performance-based option that rewarded outcomes, not promises

The owner called me shortly after and said they’d be relisting the business.

And honestly? That’s okay.

This is the part of buying businesses no one posts about on Twitter:

Deals don’t fall apart because people are irrational.
They fall apart because buyers and sellers see risk differently.

Sellers price the business they remember.
Buyers price the business they’re about to inherit.

When those two versions drift too far apart, walking away isn’t failure — it’s the job.

What I’m doing next

1. Staying patient

2. Continuing off-market conversations

3. Doubling down on businesses where the team and systems stay intact

4. Treating every “no” as signal, not setback

There will be another deal. Probably a better one.

If you’re thinking about buying a business, here’s the real takeaway:

Momentum is dangerous. Discipline is protective.

On to the next one.

— Matt