I don't think this quip makes any sense. It's like the reverse of a gambler telling you how much they made without telling you how much they lost.
Edit: For clarity, I think if you want to ask how much he made/lost in the dotcom boom, you have to compare his worth before the boom to his worth after the crash. Not his worth at the peak of the boom to after the crash. If you think that's wrong I'm interested to hear why.
https://www.cnbc.com/2019/09/07/uber-wework-and-slack-public...
So I would assume he knows a little about business.
Knowledge about business -> Current net worth
Remove that.. and he's at 0 or even negative. Is that luck or skill?
It's like, maybe the order in which you have your life experiences is everything.
But it could be just one-in-a-billion luck.
> ... having the distinction of losing the most money in history (approximately $70bn during the dot com crash of 2000).