- He successfully raised money, but he was then fired because he was doing yoga and fashion stuff all the time instead of working.
- He returned to be CEO of Twitter and wasn't successful at it. Accounts from people working for him at the time described him as infuriatingly indecisive, naive, and easy to influence. He held tons of meetings about decisions instead of actually making them[1]. This was especially bad when Twitter was supposed to be deciding its stance on free speech during the 2020 election. He was eventually ousted after pressure by activist investors.
- He thought Elon Musk was the right person to run Twitter, which was obviously idiotic at the time[2] and has become (in hindsight) even more laughable. No "intelligent" businessperson has an excuse to be tricked into thinking Musk is smart, ethical, or good at running businesses.
- He falls for a lot of New Age, pseudo-science bullshit. Case in point: he endorsed RFK, Jr., a conspiracy nut, for president of the United States. That might be one of the dumbest thing he's publicly done. Tulsi Gabbard was another of his favorite candidates.
- He's a blockchain/Bitcoin enthusiast.
- His Twitter/X feed reads like a hippie stoner, not like a sharp observer of the world. I suspect he and Musk bonded over enjoying being high most of the time.
1. https://www.theverge.com/2018/8/17/17706256/twitter-alex-jon...
