How to sell your business and NOT overpay the IRS

Most owners think the tax bill on a sale is unavoidable.

You sell for $10M–$50M and 20%–50% disappears to taxes.

But, it doesn’t have to work that way!

Here’s the basic idea:

1) You’re preparing to sell your business

You expect a large capital gain from the transaction.

2) In your taxable accounts, we build a tax-aware portfolio designed to:

• Realize capital losses in certain positions
• While maintaining market exposure and targeting positive overall returns

3) Those losses can offset the capital gain from your business sale

Capital losses realized in the portfolio can be used against the gain from the exit on your tax return.

4) The result

More of the sale proceeds stay invested and compounding for you, instead of going to the IRS.

Example:

If a founder sells their business and realizes a $15M capital gain, harvesting $3M of capital losses beforehand can offset that portion of the gain and materially reduce the tax hit.

The key is timing.

These strategies work best before the sale closes, ideally before you sign a binding LOI, not as a last-minute fix the following April.

If you’re a business owner planning to sell in the next 1–3 years, the timing on this matters.