Founder Exit Tax Planning
Your deal has a timeline. The tax code has a different one.
Most of what decides your after-tax number was fixed years before the term sheet — the date you acquired the stock, whether the company was a C corporation that day, what you did at conversion. The rest is decided in windows measured in days. We model the actual number, find what is still movable, and coordinate with your deal counsel before signing rather than after.
Why founders bring us in before signing
The number that matters is after tax. Nobody models it for you.
Bankers model enterprise value. Counsel models risk. The figure that actually lands in your account is usually the one nobody owns.
We model the after-tax number
Every structure the buyer proposes, run to what you keep. Cash versus stock, rollover equity, an earnout paid over three years — each produces a different answer and they are rarely close together.
Windows that do not reopen
Some elections are measured in days from closing. Miss one and no amount of planning afterwards recovers it, because there is no late election and no extension.
Federal and state, not just federal
A perfect federal exclusion is still a full state tax bill in states that do not conform. Where you live at closing, and where you lived while holding, both matter.
We work alongside your deal counsel
Your attorney runs the deal. We run the tax model underneath it and flag where a drafting choice changes your number, early enough that it can still be changed.
What is included
From the cap table to the wire, modeled before you sign.
An exit engagement covers the whole path, not just the return filed the following April.
Where the real money is decided
Four questions that move seven figures.
These are not exotic. They are the ones most often answered wrong, or answered too late.
What date did you acquire the stock?
Section 1202 changed on July 4 2025, and the rule that applies to your shares is fixed by when you got them, not when you sell. Older stock sits on the earlier tiers and the earlier cap. A cap table built over several years will have more than one answer in it.
Section 1045: sixty days, no extension
Sell qualifying stock before the holding period is met and you can roll the proceeds into new qualifying stock within sixty days of the sale, carrying your original holding period with you. The window is counted from the sale date and there is no relief for missing it.
A perfect federal result, taxed in full at home
Several states do not follow the federal exclusion. A founder with a complete federal exemption can still owe a full state bill on the same gain, which is why residency and timing get modeled rather than assumed.
One exemption, or several
The per-issuer cap applies per taxpayer. Non-grantor trusts funded before a sale have been used to multiply it. The authority is real, the structure is under active Treasury scrutiny, and it only works if it is done well before a deal is in sight.
How we work
Model first. Sign second.
The order is the whole point. Almost everything worth doing has to happen before the deal is signed.
What the rules actually say
The figures your exit is measured against.
Not our results. These are the statutory numbers that decide what an exit keeps, and the reason timing is the whole game.
Keep exploring
Run the numbers yourself — or just talk to us.
Know your after-tax number before you sign, not after.
A 30-minute call. Bring your cap table and the current term sheet — we will tell you which questions are still open, which windows are already running, and what a full model would cover.
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