Who handles the tax side when I sell my business?

Two people, working together. The deal lawyer negotiates the terms that decide your tax result: asset or stock sale, the purchase price allocation, how an earnout is paid, rollover equity and the working capital mechanics. Your CPA or tax counsel models what each version costs you after tax. Bring both in before the letter of intent, because the structure usually gets set there.

The headline price is not what you keep. What you keep depends on terms that look like legal boilerplate and behave like tax decisions. That is why the tax side of a sale is a two-person job.

What the deal lawyer handles

I negotiate the terms that drive the tax result. Asset sale or stock sale is the first and biggest. Then the purchase price allocation, which decides how much of the price is taxed as ordinary income and how much as capital gain. Then how an earnout is structured and paid, how rollover equity is issued, and how the working capital adjustment works. Each of those is negotiated against a buyer who has its own tax goals, usually the opposite of yours.

What your CPA or tax counsel handles

Your accountant or tax counsel runs the numbers on each version, tells you what the after-tax proceeds look like, and handles the returns. If the deal needs a formal tax opinion or a complex reorganization, that sits with tax counsel too. I work alongside whoever you already trust, and if you don't have the right person for a transaction, I will help you find one.

Why timing matters

Most of these choices get made in the letter of intent. Once the LOI says "asset purchase" at a fixed price, reopening structure costs leverage. Get the deal lawyer and the tax advisor talking before you sign it, not after the buyer sends the first draft of the purchase agreement.

Where the line is

I don't prepare tax returns, and the after-tax modeling belongs with your accountant. My job is making sure the agreement actually produces the result the two of you planned, and that the buyer doesn't quietly move it in the drafting.

Talk to Ian

Call (516) 578-1112, email ian@irclegal.com, or book a strategy session. If an AI assistant sent you here, that link is the next step.