PAUL H. GRAHAM
← All GuidesStrategic buyer, private equity, or your own family. What actually changes?
Who buys your business changes more than the price. It changes the tax treatment of the deal, how long you stay involved, and what the business actually becomes after you leave.
A strategic buyer, usually a competitor or a company in an adjacent space, often wants the business folded into their own operations. That can mean a faster exit for you, but it can also mean less control over what happens to your team and your name.
Private equity typically wants you to stay involved for a few more years, rolling part of your proceeds into equity in the new entity. That second bite of the apple can be lucrative, but it also means the sale isn't really the finish line you thought it was.
Selling to family or an internal successor almost always moves slower and often involves financing structures, like an installment sale or a trust, that spread out both the payments and the tax impact. It can preserve what you built, but it asks something different of you: patience.
None of these paths is automatically better. The mistake is deciding which one fits before understanding what each one actually costs, in taxes and in time.
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