Hey there! Welcome to the Carry Letter 👋 We’ll be exploring the latest financial news and discussing how it affects entrepreneurs like you. Plus, we'll share some awesome wealth creation insights from successful entrepreneurs.

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In 2027, Peter Thiel is reportedly set to unlock a Roth IRA worth nearly $5 billion and he might not owe a cent in taxes on it.

Here’s how the story goes and what you can take away from it:

The Roth IRA basics (real quick)

Roth IRAs are funded with after-tax dollars → they grow tax-free → and you can withdraw your gains tax-free after age 59.5.

No matter how much your account grows, you don’t owe taxes on the back end.
The catch? Annual contribution limits are low (just $7,000 in 2025).

So how did Thiel grow his into billions?

He used it to buy founder shares in PayPal (1.7M shares for just $1,700)

That’s ~$0.001 per share.
When PayPal was acquired by eBay, that turned into $28.5 million of tax free earnings, because it was all inside a Roth.

He reportedly did it again with Facebook

Using funds from the Roth, Thiel invested $500K for 10% of Facebook.
High risk, high reward. His Roth snowballed into a $5B powerhouse, growing tax-free the whole way.

Could you do something similar?

It’s important to be aware that many startup investments end up worthless. Plus, founders need to be extremely careful as IRAs can’t invest in companies you control (known as “self-dealing”). Thiel likely structured PayPal carefully to avoid that and discussed his options with professional advisors.

But if you’re an employee, advisor, or early investor this could be a real strategy.

Here's how to explore it:

1️⃣ Open or fund a Roth IRA
Even high earners may qualify via the Backdoor Roth (yes, it’s legal).

2️⃣ Use a Roth IRA with access to alternative investing
Some platforms let you invest a Roth in alternatives like startups, real estate, crypto, and more. You’re not limited to public stocks.

3️⃣ Let it grow
If you land a big win inside the Roth? You can reinvest it no taxes slowing you down.

The takeaway:

Roth IRAs may not be flashy, but with the right setup, they can be one of the most powerful tools in your financial playbook.

While nearing $5 billion’s probably unlikely, seeing a few smart, tax-free wins?
That’s a game-changer.

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If you want more resources on building wealth as a solopreneur/entrepreneur, check these out:

• The Solo 401k handbook

• The Roth IRA handbook

• The Self-Directed IRA handbook

• The Guide to Paying Less in Taxes

• What is a Solo 401k?

• How to Open a Solo 401k