This was my first reaction as well, but on second thought, this seems like a flagrant abuse of the Roth IRA. I'm not saying Thiel should be punished, but something is clearly wrong here. Let's say I invest in a freelancing company that only employs myself, and buy 100% of the equity for $500, which I use to buy a work laptop. I only take 1/3 of my income as salary and then leave the rest of the money in the freelancing company, which invests it in stocks. Combine this with a Double Irish arrangement, and I could basically avoid paying taxes completely.