> How was this not "equitable"?

We could back up and debate why/whether we tax, and who should pay and how much, and based on what, but that's too much for an HN comment thread. Currently, there's a broad consensus that it's equitable to tax a percentage of income. Now, Roth IRAs are an exception to that rule, for the stated purpose of encouraging people to save for their retirement -- and thus reduce the societal problem of a large number of destitute seniors. Here we have a cases where Roth IRAs are protecting very large amounts of income from taxation, yet not for the intended beneficial purpose. So we may want to update the rules for Roth IRAs so they can continue to serve their intended purpose without shielding more income than is necessary from taxation.

> Was Thiel playing by a different set of rules?

Not that I know of.

> Or are you simply upset that he didn't pay taxes on income that you thought should have been taxed?

No, I'm not upset. Tax policy is pretty dry, so I don't feel a lot of emotion one way or the other. And as far as I know this is legal, so, no, obviously he should not pay taxes he's not required to pay. It seems almost silly to have to state that. But if the question is do I think the tax code should be updated to require that taxes be paid on income at that level through a Roth IRA then the answer is yes. (IMO A rule change like that should not apply retroactively to income already accrued though.) Not sure the best way to do it -- the starting point would be to simply cap the amount of income that is tax free, say $5M, after which it's taxed as normal income. There's probably some reason that's too simple, but at least it gives you an idea of the kind of change that could be enacted.