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TIL Masayoshi Son has the distinction of losing the most money in history (approximately $70bn during the dot com crash of 2000).

I remember reading some commentary about how losing billions is perversely a good thing to have on your resume, as it implies:

- someone trusted you with billions

- you weren't too paralyzed by fear of risk to do anything useful

- you might even have learned from the experience

Also see The "Parable of the Talents", in Matthew 25:14–30.