The people across the table do it every month. They have a team, a process, and a set of plays they have run dozens of times — on people exactly like you.
They are not being dishonest. They are being good at their job.
The problem is that nobody in the room is paid to warn you. Your banker earns at closing. Your lawyer bills the deal. Both want it done.
Five that show up again and again.
The manufactured walk-away. Three months in, the buyer disengages. You panic. They return weeks later with a lower number. It was never a walk-away.
Findings held back. Diligence surfaces an issue in week two. They raise it in week ten, when you have no time, no alternative buyer, and no leverage.
The late retrade. The price moves after you have told your team, your family, and yourself that it is done.
The earnout that never pays. You agree to a number contingent on deliverables and performance. They control the accounting, costs, priorities, and sales. You control none of it.
The TSA squeeze. You are contractually obliged to support the buyer while your own company is dismantled around you. “Reasonable” was never defined.
Most owners think diligence is 'verification'. For an experienced acquirer, it is a value-reduction exercise.
The team is paid to find reasons to pay less — and there is always something to find, because no business is clean under that kind of light.
The question is not whether they will find things.
It is whether you found them first.
In deals of this size, the headline number is not what lands in your account.
The rest sits in holdbacks and earnouts, paid over years, measured by accounting you no longer run.
And the terms that govern it all — the triggers, the definitions, the measurement periods, the TSA scope — are written before close, while everyone is focused on the headline and celebrating.
The money you lose after the deal is lost in the drafting.
A finding two years out is a project.
The same finding two weeks before close is a discount.
Nothing about the business changed. Only when you looked.
Owner dependency. Customer concentration. Contracts that don’t assign. Revenue that doesn’t hold up.
Each one is worth a fraction of a multiple — and on a $20m business, a fraction of a multiple is a house.
Most of it is fixable. Almost none of it is fixable in the deal window.
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