STOP PAYING THE IRS MORE THAN YOU PAY YOURSELF

What the Aspire Tour reminded me about building wealth the IRS can never touch.

Last week I was at the Aspire Tour — a wealth creation event that brought together some of the sharpest minds in personal finance, tax strategy, and alternative investing. I wasn't there to be inspired. I was there to learn something I could apply.

I walked away with one thought that I haven't been able to shake:

Most people spend their entire lives optimizing what they earn. Almost nobody optimizes what they keep.

That gap — between what you earn and what you actually keep after taxes — is where the wealthiest people in the world operate. And the tool they use isn't complicated. It's just rarely talked about in a way that makes it actionable.

So this week I want to share what I learned, what I've been working through in my own planning, and the framework I'm now using to make sure I'm paying my future self as aggressively as I pay my taxes.

THE UNCOMFORTABLE TRUTH ABOUT TAXES AND WEALTH

Here's the thing nobody tells you when you start earning real money: the tax code was never designed to help you build wealth. It was designed to fund a government. Which means every dollar you earn in a taxable account, every gain you realize, every piece of rental income you collect — the IRS gets a seat at the table before you do.

For most people that's just accepted as the cost of doing business. But the wealthiest families in America — people like Peter Thiel and Mitt Romney — figured out something different. They used the existing tax code not to evade taxes, but to legally remove certain assets from the IRS's reach permanently.

Thiel famously built a Roth IRA from roughly $2,000 into over $5 billion — completely tax free. Romney reportedly grew a similar account from $2 million to over $100 million. Same principle, different scale.

The vehicle wasn't exotic. It wasn't illegal. It was just a retirement account — used intentionally.

THE FOUR ACCOUNTS TRULY WEALTHY PEOPLE USE

The Aspire Tour reinforced something I've been thinking about for a while now: there are four specific tax-advantaged accounts that sophisticated wealth builders use, and most people either don't know they exist or don't know how to use them beyond just holding mutual funds.

Here's the stack:

1. The Roth Solo 401(k)

This is the most powerful wealth-building account available to entrepreneurs and business owners. In 2026, you can contribute up to $72,000 per year as both the employee and employer of your own business. The Roth version means contributions are after-tax — but every dollar of growth, every piece of interest income, every capital gain that accumulates inside that account comes out completely tax free in retirement. No exceptions.

The key most people miss: a self-directed Solo 401(k) isn't limited to stocks and mutual funds. You can use it to invest in real estate, private lending, syndications, and private businesses — all compounding inside the account with zero tax drag.

2. The Self-Directed Roth IRA

Lower contribution limits ($7,500/year in 2026) but this is where the Thiel and Romney plays lived. The strategy is getting high-upside assets — early-stage companies, private equity stakes, alternative investments — into the account while their valuation is low. When those assets appreciate, the gain is permanently tax free. The earlier you start, the more time the account has to compound without the IRS taking a cut.

3. The HSA — The Triple Tax Account

The HSA is arguably the most tax-efficient account in the entire tax code. Contributions go in pre-tax (reducing your taxable income today). Growth is tax free. Withdrawals for qualified medical expenses are completely tax free. That's three tax benefits in one account. The sophisticated play is to invest the HSA in alternative assets, pay medical expenses out of pocket in the short term, and let the HSA compound untouched for decades. After 65 it functions like a traditional IRA for any expense.

4. The CESA — Coverdell Education Savings Account

$2,000 per child per year. After-tax contributions, tax-free growth, tax-free withdrawals for qualified education expenses from kindergarten through college. For my daughters, starting this now at 10-12% returns inside a self-directed account means potentially $80-100K+ each waiting for them at 18 — completely tax free.

The IRS doesn't penalize you for being wealthy. It penalizes you for being unintentional about where your wealth lives.

WHAT SELF-DIRECTED ACTUALLY MEANS

Most retirement accounts at Fidelity, Schwab, or Vanguard limit you to publicly traded stocks, bonds, and mutual funds. That's fine for passive investors. But if you have expertise in real estate, private lending, or alternative assets — why would you let your retirement account settle for index fund returns when you could be deploying that same capital into what you actually know?

A self-directed retirement account — whether it's an IRA or Solo 401(k) — allows you to invest in:

•    Real estate — residential, commercial, rentals, raw land

•    Private lending — making loans secured by real property

•    Real estate syndications — LP positions in professionally managed deals

•    Private businesses — C-Corps, LLCs, startups, private equity

•    Tax liens, notes, and other alternative instruments

The rules are specific — you can't invest in companies you control, and transactions with close family members are prohibited. But the asset class options are far broader than most people realize.

The question isn't whether these accounts can hold alternative assets. They can. The question is whether you're using them that way — or whether you're leaving decades of tax-free compounding on the table inside a target-date fund.

THE MATH THAT SHOULD BOTHER YOU

Let me make this concrete. Imagine two investors, both 34 years old, both deploying capital at 12% annual returns:

Investor A deploys in taxable accounts. Each year, 30-37% of income is taxed. Compounding is interrupted annually by the tax bill. After 25 years, let's say they've built $8 million.

Investor B does everything the same — same returns, same amounts — but routes as much as legally possible through Roth tax-advantaged accounts. Compounding is uninterrupted. Zero tax drag. After 25 years, the same inputs produce roughly $11-12 million — and all of it comes out tax free.

The difference between Investor A and Investor B isn't intelligence. It isn't access to better deals. It's intentionality about where the money lives while it compounds.

That $3-4 million gap is the IRS's cut — taken not through any single transaction, but slowly, year by year, through the friction of taxes on compounding growth.

WHAT I'M DOING ABOUT IT

The Aspire Tour didn't teach me anything I didn't intellectually know. But it forced me to confront whether I was actually acting on what I know — or just nodding at the concept.

The honest answer: I have NFL retirement accounts that have been sitting in standard investments for years, doing nothing exceptional tax-wise. I have annual earning capacity I haven't been maximizing through the Solo 401(k). And I have two daughters who don't have CESA accounts yet.

That changes this year. The goal is simple:

•    Establish a self-directed Roth Solo 401(k) with checkbook control

•    Evaluate NFL account rollover eligibility — and whether a Roth conversion makes sense given my tax picture

•    Open CESA accounts for both girls and start investing immediately

•    Route new alternative investment capital through the tax-advantaged structure where possible

None of this is complex. All of it is legal. Most of it is just the discipline to do what you already know you should do.

THE TAKEAWAY

Wealth building has two sides: what you earn and what you keep. Most people spend 90% of their energy on the first and almost none on the second.

The tax code isn't going to change in your favor. The IRS isn't going to start rooting for you. But the tools to legally protect your compounding wealth from unnecessary taxation exist right now — and they've been used by the most sophisticated wealth builders in the world for decades.

The question isn't whether these accounts work. They do. The question is whether you're using them — or whether you're still paying the IRS more than you're paying your future self.

That's the question the Aspire Tour left me sitting with. I hope it does the same for you.

Want to continue this conversation?

If this topic resonates with you — or you have questions about how tax-advantaged accounts fit into a broader capital allocation strategy — reply to this email or reach out directly. These are the kinds of conversations I have one-on-one with the people in this community.

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