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Re:Peter Thiel turned a Roth IRA into a $5B tax-free piggy bank by tylermenezes on Thursday June 24, 2021 @05:19PM (#27623918)
When the company is formed the valuation is genuinely very small because it has no assets, customers, etc. Buying some of your shares in a Roth IRA at this point is relatively common, enough so that I've heard multiple people suggest that founders do it.
Re:Peter Thiel turned a Roth IRA into a $5B tax-free piggy bank by Scoundreller on Thursday June 24, 2021 @05:46PM (#27624227)
Yeah, I doubt Thiel came up with this himself. Was probably recommended by accountants whom should all be familiar with Roth IRAs.

But the possibilities of windfall tax-free profits made sure everyone kept quiet about it.