I spoke yesterday with an entrepreneur selling his company for around $30 million.

He owns 50%, but after taxes, he figured he’d walk away with less than $10 million.

I showed him how a tax-aware long/short equity strategy could help him keep much more of the proceeds.

He said he’d lower his asking price, knowing he’d keep more after taxes than he originally thought.

If you’re a business broker or work with founders preparing for an exit, this is a game-changer when sellers (rightfully) get hung up on the tax hit.

To make it as effective as possible:

• Start early - fund the account and begin harvesting losses to carry forward before the sale closes

• Timing matters - sales earlier in the year are easier to offset within that tax year

• Use installment sales - splitting proceeds over two years (with a January payment) can smooth recognition and reduce total taxes owed

When you integrate tax-aware investing with liquidity planning, the result isn’t just a higher return - it’s millions more in after-tax wealth.