[pkaye]

He lost a lot in the dotcom collapse around 2000. https://dealbook.nytimes.com/2010/12/13/a-key-figure-in-the-...

[kamyarg]

To be precise:

> ... having the distinction of losing the most money in history (approximately $70bn during the dot com crash of 2000).

* https://en.wikipedia.org/wiki/Masayoshi_Son