He was a founder. His investment was not just financial. When he invested, he was not ultra rich. So a loss would have been significant.

Remember, we can't see the future.

By your logic: You are free to invest like him in early stage startups. You will be out zilch, so why not do what he did?

> By your logic: You are free to invest like him in early stage startups. You will be out zilch, so why not do what he did?

1. Accredited investor rules 2. Please find me a startup which will allow me to buy shares at $0.001/share while simultaneous selling to other investors at a price of 500k[0]. 3. If you say to start my own and invest in my own company that I am working for in my Roth, I'll remind you that it's explicit not allowed, and the fact that it's not allowed is the thing that most people are taking issue with.

[0] Yes, that's not the full valuation issue, but it's enough to see that the value at the time wasn't really legitimate.

"With financial support from friends and family, he raised $1 million" - from his wiki.

Yeah, I don't think this person was hurting for the paltry sum they invested. It also sounds like they would've been just fine if it had failed (aka just move on to the next venture until you hit jackpot).

The rich get richer I guess, and random folks on the internet applaud the pilfering of the commons (dodging taxes).