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How the tech entrepreneur made a tax-free fortune

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A Roth IRA is, under the right circumstances, the best retirement vehicle you can have. Just ask Peter Thiel.

According to ProPublica reports, sourced from IRS data, Thiel grew his Roth IRA from $2,000 to more than $5 billion between 1999 and 2021. This is significantly more than the average household’s IRA balance, which is about $129,000, according to Fidelity.

The question is: how did Thiel do it?

Thiel is a recognized investor who, as a founder and investor in the early years of technology, had access to some of the most lucrative pre-IPO stock opportunities in history. This allowed Thiel to use his Roth portfolio to hold private stocks with extraordinary returns, such as PayPal and Facebook. These assets have generated outsized returns that have created a huge amount of completely tax-free wealth for Thiel’s portfolio. Here’s how it works.

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Peter Thiel has long been one of the richest individuals in the world. He made his money as an early investor in technology companies, founding companies like PayPal and Facebook and investing in the early days of the Internet.

Stocks like these are not legally or practically available to most investors. Legally, ordinary investors cannot freely trade private stocks. You must be an accredited investor to buy and sell these assets, a law intended to protect investors from predatory, confusing or opaque investments. Investors can be accredited if they meet certain criteria, such as a net worth of $1 million, meet the recurring annual salary threshold of $200,000, or have certain financial certifications.

In practice, ordinary investors usually do not have access to these options. The average person doesn’t have access to brand new startups and tech founders looking for investments. However, Thiel did. Thiel has long been one of the biggest investors and founders in the tech world. His largest companies include PayPal, Palantir Technologies, Facebook (in which Thiel was one of the original investors), and the Founders Fund (which made Thiel an early investor in many successful technology companies).

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This is how Thiel’s Roth IRA became so valuable.

Thiel has a self-directed account, meaning he manages the investments in the portfolio. Over the years, he has used his Roth IRA to invest in many early-stage startups, most notably when he used it to hold early shares in PayPal. This allowed Thiel’s portfolio to generate the kind of explosive growth associated with successful tech startups, and Thiel then used those profits to fund future investments. His Roth IRA has at various times owned assets such as Facebook, Airbnb, Palantir and SpaceX, usually all purchased in the early days of a particular company when the stock sold for very little. The tax-free nature of Roth IRA growth allows assets within the account to be sold and purchased without taxes eroding their value.

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