This is only true if you assume that everything involved (his time, knowledge, planning, etc.) had no value. Even if it would be unreasonable to predict how valuable it’d become, $0 is hard to defend.
A simple fix for this would be to prevent private holdings from being placed into a Roth since independent valuations are hard to establish without market data but it’d be even better to simply cap the tax-free gains as suggested - if you accumulate millions in returns, paying taxes on the portion over n million is fine because you’ve still been phenomenally lucky and will retire wealthy.
This isn't a "I feel like these are worth a lot" scenario. This is a "we'll give you half a million dollars in a couple weeks" scenario and then Peter undercut that valuation.
Tim Cook might think that AAPL is worth $1000 a share, but it's not against the law for him to fill his IRA with Apple shares.
The same is true for Thiel: a private company doesn’t have such an easy way to document market value but he had insider knowledge suggesting that $0.0001/share was low, as their own SEC filings acknowledged. I would prefer that the fix be to set a tax-free cap (e.g. pay capital gains on returns over $10M) but I suspect that kind of example will get the most attention because it’s pretty clear that he low-balled it and even if that’s perfectly legal it won’t seem fair to the vast majority of the population who never have access to pre-IPO shares, much less the ability to claim their own valuation.
Claiming depreciation on your tax return is something I do with all my home office equipment every year.
If we aren't supposed to write negatively about anything someone does as long as it is legal, how would we ever come around to deciding to making something illegal?
Thats the part of your comment I am confused by...
1) the discussion of political detox week from 2016:
https://news.ycombinator.com/item?id=13108404
2) The 2019 new yorker profile on HN/dang/mod team
https://www.newyorker.com/news/letter-from-silicon-valley/th...
Key quote: In an Emacs file, Gackle collects a list of contradictory statements that people have used to describe Hacker News. (“SJW cesspool”; “a haven for alt-right and libertarian people”; “If you don’t support neoliberal fantasies, your comments probably aren’t welcome here”; “The only thing is left is to change Hacker News icon to Che Guevara emblem.”)