The CEO of the SoftBank did lose a ton of money back in the Dotcom bust. I guess he is a huge risk taker. From Wikipedia:
https://en.wikipedia.org/wiki/Masayoshi_Son
>According to Forbes magazine, Son's estimated net worth is US$23 billion, and he is the second richest man in Japan,[1] despite having the distinction of losing the most money in history (approximately $70bn during the dot com crash of 2000).[3]