Silly Money • by Ankur Nagpal

If you have been reading this newsletter for more than a few weeks, you may be getting tired of how much I talk about Roth IRAs.

But not without good reason!

A Roth IRA is one of the most phenomenal tax planning tools out there for wealthy professionals.

As a reminder, here’s how a Roth IRA works:

• You do not get a tax break when you contribute to a Roth IRA

• But after that, all growth inside a Roth IRA is tax-free

• When you finally get access to the dollars inside a Roth IRA in retirement, you also owe zero taxes!

No matter how high tax rates go in the future, a Roth IRA protects you with zero taxes in retirement.

A Roth IRA is so powerful at lowering your lifetime tax rate that the IRS originally tried to limit wealthy people from having access to this specific account.

As of 2025, the tax code states that if you earn over $150,000 single or $236,000 married, you cannot directly contribute to a Roth IRA.

But as a reader of this newsletter, you should know that there are 4 separate strategies that allow high income earners to bypass the Roth IRA income limit.

And as of late, this account has become a refuge for wealthy people trying to stash hundreds of millions of dollars in retirement.

In this post, I’m going to take you behind the scenes of four separate individuals that have grown their Roth IRA to extremely large amounts — from hundreds of millions to billions of dollars.

A Roth IRA was never intended by the IRS to get so big.

But since there is no legislation prohibiting it, some of the most sophisticated investors have used the tax code to massively grow these accounts to bypass tens or hundreds of millions of dollars in taxes.

Using fully legal strategies available to you.

But before we dive in, I want to share an important caveat. None of these accounts have been confirmed by the individuals in question.

The data presented here relies on a myriad of sources — official IPO documents, public tax returns when running for office, trusted journalistic sources and more.

But, the individuals here (excluding Ted) have not officially confirmed or denied this.

Let’s dive in:

• The Peter Thiel $5B Roth IRA

• The Mitt Romney $100M SEP IRA

• The Max Levchin $100M Roth IRA

• The Ted Weschler $250M Roth IRA

• How doable is this for a regular, rich person?

The Peter Thiel $5B Roth IRA

Peter Thiel may own the most famous Roth IRA of all time.

It started in 1999 — he was starting Paypal, and under the $110,000 Roth IRA income limit and was able to contribute $2,000 to get his account started.

However, instead of investing it in stocks or ETF’s, he used it to buy his founder shares in Paypal — spending $1,700 to buy 1.7 million shares at $0.001/share.

How was he able to do this?

Before a startup raises outside financing, a brand new company is typically deemed to have a par value of almost nothing… typically a few hundred or few thousand dollars.

Founders can buy their shares at incredibly low values, and when the company raises external financing, the internal or 409a share price goes up.

After that initial contribution, Thiel never had to contribute a single other dollar to his Roth IRA.

When Paypal sold to eBay in 2002, Thiel made $28.5M on the sale — and since the dollars were inside his Roth IRA, he owed zero taxes.

But more importantly, he was now relatively young with tens of millions of dollars in his Roth IRA!

This account then became supercharged tax-free investment vehicle.

From that point on, he used his Roth IRA to invest in all kinds of assets, including founder shares in Palantir (now worth $100B+) and the seed round of Meta (now worth $1T+).

His Roth IRA is now conservatively worth at least $5B and likely substantially more.

And he gets access to all of it with zero taxes in less than 2 years!

Should we try and emulate Thiel?

The IRS has very clear rules limiting “self-dealing” inside retirement accounts.

This effectively means a transaction inside a Roth IRA cannot be deemed to be benefitting you as an individual in any way. As an example, you cannot invest in a house and then also live in it.

If you are caught “self-dealing”, your entire Roth IRA could be rendered invalid so it’s super high risk and worth steering clear of.

While Thiel likely got very good legal advice approving the transaction, my personal understanding is it’s substantially safer to avoid buying shares in a private company where you are also the founder.

There is likely a fair bit of nuance based on exactly how much of the company you own, and Thiel may have been under the limit, but you could potentially be playing with fire.

However, you can likely achieve similar outcomes by buying private startup shares as an early employee, advisor or investor while taking a lot less risk of blowing yourself up.

The Mitt Romney $100M+ SEP IRA

When Mitt Romney ran for president in 2012, it caused quite a stir when it was revealed that his SEP IRA was worth more than a hundred million dollars.

Journalists spent an incredible amount of time trying to investigate the specific tax maneuvers he and other Bain Capital executes were using to grow such a large retirement account.

After a lot of research, it was determined to be likely that he employed a combination of these three strategies:

Strategy 1: Using a SEP IRA

If you are self-employed or have any self-employment income, you can use a SEP IRA or (even better) a Solo 401k to contribute 10 times more than a regular IRA.

In 2025, you can contribute $7K to a Traditional or Roth IRA and $70K to a Solo 401k or SEP IRA.

You can also combine the two!

You can use a Solo 401k with the mega backdoor Roth feature and a Roth IRA to contribute a combined $77K in 2025 if you are under the age of 50.

If you are over 50, you get a combined $85,500 and between 60-63, you get a combined $89,250.

You and your spouse both get their own limits so as a family, you can get multiply your limits and get twice as much into these accounts.

Romney used his SEP IRA to contribute large amounts to load a greater amount of tax-advantaged principal into the account.

Strategy 2: Buying private equity interests at low prices

While running a private equity fund (Bain Capital), Romney and his associates frequently found investments with asymmetric upside.

They had access to investment opportunities regular people never did — and critically, deployed their Roth IRA to individually cherry pick and invest their retirement accounts in some particularly distressed assets.

When these assets with low basis eventually grew, the upside was contained inside the retirement account and thus tax-deferred.

Strategy 3: Buying his management company interest from his IRA

This is equal parts genius and sketchy.

When you run a fund with third-party investors, you are typically require to commit a small percentage of capital as a General Partner.

Additionally, you earn management fees for managing the dollars and a share of “carried interest” or carry for short — this carried interest is typically 20% of the profits generated across the entire fund.

It was reported that Romney made his contribution as a general partner from his IRA, which in turn allowed him to pay the carry (or share of profits generated from the fund) into his retirement account.

If legal, this dramatically increases the leverage on a relatively small amount of dollars — you can make a smaller GP commit, and then earn carried interest on a much larger pool of dollars.

If this is both accurate and legal, it opens up a lot of opportunities for investment professionals to grow a massive Roth IRA.

The Max Levchin $100M Roth IRA

While Peter Thiel was running Paypal, he may have also been giving his cofounders a tax masterclass on the side.

Max Levchin — the other cofounder of Paypal steered clear of self-dealing rules by not buying his Paypal founder shares from his Roth IRA.

However, he was the first and most significant investor in Yelp — and decided to make a material part of his investment from his Roth IRA.

When Yelp went public and had to list their largest shareholders, it was revealed in the Yelp S-1 that Levchin’s Roth IRA owned 13,258,588 shares!

Yelp IPO’d at $15 which means the stake in his Roth IRA was worth comfortably more than $100M at the time.

I’m not sure if he still held onto his shares… but if he did, at today’s market value that would be close to half a billion dollars!

The Ted Weschler $250M Roth IRA

Ted Weschler, the investment manager at Berkshire Hathaway started saving for retirement all the way back in 1984.

He started contributing to his 401k plan at work so that he could get the full match from his employer.

Eventually, he transferred those assets into a self-directed IRA so that he could decide exactly which stocks to invest in.

After that, he went on a legendary run for the next 15+ years averaging an IRR of 22% in that time period. And impressively, he did this only investing in public market stocks that are theoretically available to all of us.

However, that’s not even the most remarkable part of his story.

In 2012, when his Roth IRA was worth over $100M, he decided to do a taxable conversion of the entire amount to Roth.

A taxable conversion allows you to convert a pre-tax IRA to a Roth IRA, with the entire converted amount taxed as income in the year of conversion.

But after that, the dollars in your IRA are fully tax-free. And 5 years after a conversion, you can withdraw the converted amount even before you hit retirement age.

This left Ted with a 2012 tax bill of more than $28 million!

But after that the dollars in his Roth IRA were fully tax-free.

He’s since continued to grow the account to over $250M+… which makes the conversion look like a shrewd move in retrospect.

How doable is this for a regular rich person?

I know what you are thinking… if you don’t have access to Thiel or Levchin’s dealfow or have Ted Weschler’s investing prowess, how doable is building a massively large Roth IRA for a regular wealthy person?

I built an incredibly simple model to test this out.

Here were my assumptions:

• You start making contributions to a Roth IRA by age 19, and start maxing it out by age 23.

• You started making 401k contributions using the mega backdoor loophole by age 23 and max it out by age 30.

• The maximum contribution limits stay where they are today and I plugged in the 100-year average return for the S&P 500 including dividends.

You still end up with a Roth IRA worth $25M by age 60!

Powerful stuff.

And if you are able to somehow combine this with any investments with asymmetric upside in a self-directed IRA, you could potentially even shoot for a true hundred million dollar Roth IRA.

I try and keep this newsletter as light on promotion as possible, but if you are looking for a technology platform that lets you run a self-directed Roth IRA, check out Carry.

Until next week!

P.S. I’m hosting a free workshop next Wednesday breaking down my 3 favorite tax saving strategies for high earners, you can sign up here. I’ll also send a replay to everyone who joins!