03/12/2026
A business owner once told me:
"I'll deal with the tax side once I have an offer."
The problem is… by then it’s often too late to do the planning that actually saves money.
One example.
An owner preparing to sell his company expected the transaction to generate roughly $3M in proceeds.
When we started reviewing the deal structure and his broader financial picture, we realized something:
With no planning, a significant portion of the gain would land in the highest capital gains bracket and trigger additional taxes.
But because he started planning before the deal closed, we had options.
Things like:
• Structuring parts of the transaction differently
• Coordinating timing with other income
• Reviewing charitable strategies
• Evaluating ways to manage how gains were recognized
None of those strategies exist after the closing documents are signed.
Tax planning around a sale isn’t about avoiding taxes completely.
It’s about controlling timing and structure so you don’t give up more than necessary.
And many of the most valuable strategies require planning years before the exit, not weeks.
If selling your business might be on the horizon someday, one of the most valuable questions you can ask is:
How much of the eventual sale price will I actually keep?
