A $20M net worth software exec was told this by his broker:

“You should be happy you’re paying taxes, it means we’re making you money.”

He had asked why his portfolio had created such a large tax bill and what tax planning ideas they had for him.

He’d been following my content and felt like he was missing something.

He was right.

We HAVE to get away from this mindset in the industry.

Your after‑tax return IS your return.

Your pre‑tax return means absolutely nothing.

The good news for him is there’s a lot of room to improve:

• Real estate + REPS

His spouse is working toward Real Estate Professional Status, so we can use large depreciation from their real estate investments to offset his ordinary income.

• Tax‑aware public equity

Instead of just sitting in “blue‑chip growth stocks,” we can overlay his stocks with tax‑aware long/short extensions to harvest losses now and prepare for future capital gains from a business sale.

• Smarter use of his IRA

Using his IRA to access hundreds of private companies where taxes and liquidity needs are different than the brokerage account.

• Roth conversions

Already mapping out how to pair future real estate depreciation with Roth conversions if he takes time off after an exit.

• Cheaper, more flexible financing

Exploring box spread loans for lower‑cost financing than what his current firm offers, so he doesn’t have to sell assets just to raise cash.

We want to optimize for after‑tax, real‑world results instead of pre‑tax nonsense.

If you’re north of $10M and your advisor’s answer to a big tax bill is, “that just means we’re making you money,” it might be time for a second opinion.