People in this thread tend to be supportive of the idea that he is simply playing by the rules. While I have no reason to doubt the legality of this strategy,

People in this thread tend to be supportive of the idea that he is simply playing by the rules. While I have no reason to doubt the legality of this strategy, I question whether it ought to be legally appropriate for Peter Thiel to decide the valuation of his own investment (more or less) by himself. His initial deposit into his Roth IRA doesn't strike me as an arm's length independent valuation. It was simply the par-value of the stock, which AFAIU is a valuation for accounting purposes and not at all an independent appraisal of the stock's value. That said, when this topic came up last year on Hacker News, it did make me rethink my own personal tax-sheltered strategy. (I'm in Canada, so I'm thinking about TFSA instead of Roth IRA). Before I had been following the advice to shelter my high-tax items, which for Canada would be bonds. But after reading about this, I've rearranged things to instead shelter (hopefully) high growth items (e.g. VTI). The idea being that by growing room in my sheltered accounts I can eventually save more on taxes than I would by sheltering bonds I'd be interested in other people's comments on tax-sheltered-account strategies for tech workers.