You don’t feel like you’re rich, but the government thinks you are.

I talk to a lot of people in this band:

$500k – $2M income
$3M – $30M net worth

Here’s what the government sees when they look at you:

• 37% federal income tax
• 3.8% NIIT on investment income
• State income tax (up to ~13% in CA/NY)
• Payroll taxes, property taxes, sales tax layered on top

All-in, it’s not unusual for 50%+ of every incremental dollar to go out the door.

If your plan is to see what the CPA comes back with in April, you’ve already lost.

Tax planning is 90% what you decide during the year, not what gets typed into software after the fact.

The people who keep more of what they make are doing things like:

• Tax-aware hedge funds to reduce income taxes

• Creating tax-free income from real estate investments

• Tax-aware long/short SMAs to avoid capital gains taxes

• Adding cash balance plans to their 401ks so they can defer $400k of income

• Funding DAFs and charitable vehicles in big years - not writing random checks in April

• Borrowing against assets for liquidity instead of constantly selling and triggering gains

None of this happens by accident.

If you’re:

– In the top tax brackets
– Watching half your effort disappear to taxes
– Running a vanilla portfolio and hoping your CPA “finds something”

You’re not being punished by the system.
You’re just not playing the same game the top 0.1% is playing.

You don’t have to feel rich.
But if the government treats you like you are, you should probably plan like it.