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He also talked a struggling U.S. Grant into writing an autobiography which Twain then published. This basically saved Grant's family economically. (Grant's autobiography is a great book, btw)

He was also an anti-imperialist and protested eg the US occupation of Philippines. (These writings aren’t well known). I’d like to think if he was alive today he’d be a dissident.

The original masayoshi son. Anyway, I thought he invested a ton in this startup for movable type though.I wasn't aware that he invested in other startups as well

He was financially ruined by his investments. Are you saying it’s a lot easier today to fail upwards as an investor?