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You don’t often see the term “Roth IRA” trending online, but in 2021, tech investor Peter Thiel made headlines for his $5 billion tax-free Roth IRA piggy bank. How did he do it? The answer is alternative investments. He used a self-directed IRA to invest in early-stage tech companies multiple times over. Is it a loophole? Possibly. But it happened, it got attention, and the IRA structure in question could come under further scrutiny.

“Thiel has taken a retirement account worth less than $2,000 in 1999 and spun it into a $5 billion windfall.” – ProPublica (2021)

Let’s look at six common risks associated with self-directed and…



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