Thiel's $27M Roth IRA

A story about how Peter Thiel used a Roth IRA to turn PayPal shares into billions of tax-free investments.

"Peter Thiel bought his founder shares at PayPal with his Roth IRA. He spent like $2,000 to buy PayPal shares that became worth $27 million when PayPal sold. Then he had $27 million to make all kinds of investments - he allegedly bought 10% of Facebook from his Roth IRA.

He's gonna turn 59 and a half in a year and he's gonna have $5 billion tax-free, which is pretty wild. What we don't know is if Peter Thiel had other shares not in his Roth IRA, which is quite possible."

The strategy was both genius and possibly illegal, as you typically can only put in $7,000 into a Roth IRA traditionally. But by buying founder shares through the Roth IRA, he was able to capture massive gains tax-free.

31:36 - 32:47
Full video: 56:44
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Ankur Nagpal

Founded and sold Teachable, an online course platform. Backs Circle, a community-centric platform valued at $200 million.

Authored a comprehensive guide on personal finance for startup founders.

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