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Reserve your spot for our next webinar →Before, during, or just after the sale
You ran a P&L for twenty years and you know how to read a deal. What almost nobody gets a second attempt at is the tax and structure work around a sale, most of which has to happen before the close, and all of which is judged afterward.
If this sounds familiar
Nothing below is a diagnosis. It is the list of things people in your position say out loud once they stop performing confidence about it.
You spent decades building one asset, and you are about to hold the proceeds of it in a form you have never managed before.
The deal has lawyers and an accountant. Nobody in the room is being paid to think about your retirement.
You suspect the tax side could have been handled better, and you will find out for certain in April.
The business was the plan. Without it you do not have one, and nobody has asked you what it is.
You are being pitched by people who found out about the sale before you told them.
Where it usually goes wrong
Each of these is a way the instruments actually behave. None of them requires anybody to have done anything stupid, which is exactly why they are so common.
01
Most of what can be done about the tax treatment of a sale (entity structure, the allocation of purchase price, charitable and trust vehicles, installment treatment) has to be in place before the deal closes. Afterward you are filing, not planning.
02
A sale year is an unusual tax year, and unusual tax years are the ones where deliberate action is worth the most. Treated as a windfall to be reported rather than a year to be planned, it is the single most expensive missed opportunity most owners have.
03
The business was one asset carrying everything. Proceeds parked in whatever the deal produced can be the same problem wearing different clothes, and the risk tolerance that was correct while you controlled the asset is not the one that fits now.
04
Buy-sell agreements, entity-owned insurance, succession provisions and trust funding were all drafted around an operating business. After a sale, several of those documents describe something that no longer exists.
What we would actually do
Every plan runs through all five layers of PILOT, in the same order, every time. What changes by audience is what each layer is actually looking for.
Turn proceeds into something that produces the income the business used to, at a risk level that fits not controlling it any more.
Model the sale year and the years after it together, and identify what has to be decided before signing rather than after.
Test the plan against the deal changing shape (a lower price, an earnout that underperforms, a buyer who walks), because a plan built on one number is a plan built on a number you do not control.
Review the structure and the documents against what you will actually own after the close and, if you are early enough, before it.
Retire the protection the business needed and put in place the protection a household with no payroll needs.
Plain answers
For some of it, yes, and being told so plainly is more use than being told otherwise. Purchase-price allocation and entity structure are settled at close. What remains open is often substantial: how the proceeds are positioned, multi-year tax sequencing from here, the estate documents that still describe a company you no longer own, and installment or earn-out payments still to come.
The earlier the better, and a year before a target close is not unusual. The work that saves the most has to exist before the deal does.
Transaction counsel gets the deal done and your CPA files the result. Both are necessary and neither is being paid to answer what the proceeds have to do for the next thirty years, or what happens to them when you are gone. That is a different question, and it is the one this firm exists to hold.
Start here
A Clarity Map Session is 30 minutes, costs nothing, and produces a written picture of your income, your future tax bill and your estate documents. Whether you hire us afterward is a separate conversation.
30 minutes · No cost · No obligation
