Selling Your Business? The Structure Decision Worth More Than the Offer
For most owners, the business is the largest asset they will ever sell. The deal structure can change the outcome more than negotiating the headline price.
When owners imagine selling, they focus on the number: what will someone pay for the business? It is the wrong place to focus first. Two offers at the same headline price can leave you with dramatically different amounts after tax, depending entirely on how the deal is structured and what you did in the years before it.
The deal you sign is not the money you keep.
An asset sale and a stock sale at the same price can produce very different tax bills. How the purchase price is allocated, how much is ordinary income versus capital gain, whether proceeds are paid at once or over time, these are not footnotes. They are the difference between keeping the proceeds and handing a large share to the IRS. And almost all of it is decided in the structure, not the price.
The years before the sale matter most.
The biggest opportunities close before a buyer is ever at the table. Maximizing retirement and pension contributions in your final high-income years can shelter significant income going into a transaction. Entity structure put in place early can change how the eventual sale is taxed. Clean books and a defensible valuation can lift the offer itself. By the time you have a signed letter of intent, most of the planning leverage is already gone.
Bring the household into it.
The sale is not just a business event. It is the moment your largest asset converts into the capital that has to fund the rest of your life. Coordinating the transaction with your personal tax, investment, and estate plan, before the wire hits, is what turns a windfall into lasting security. That is the work we do alongside owners in our business exit planning.