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deong ,

If I recall correctly, he had the x.com domain and tried to rebrand PayPal to X. The board went, "are you a fucking idiot?" and replace him with Peter Thiel.

He's been trying to call stuff "X" since he was an edgy teenager. He just never had the good sense to grow out of it, and he fell ass backward into enough money that we all get to watch him go all "Star Wars kid" over and over again in public.

deong ,

The line I always liked but is unusable in reality for sexual harassment reasons is the Seinfeld reference of telling someone who sneezed, "You are soooo good-looking".

deong ,

I will say, the internet in 1998 looked nothing like the internet today. There was barely any commerce at all. 1998 is maybe the year you'd start to say that Amazon "made it", but even then the common take from established reporters was that they'd never be able to compete with brick and mortar booksellers like Barnes and Noble. To the extent that the average person was even aware that you could buy things on the internet, it was mostly because they'd heard that it was dangerous to use your credit card online.

At the time, the web was still pretty small. Google launched in 1998 -- prior to that Yahoo was the most popular "search engine", but Yahoo was mostly a human-curated list of web pages organized by topic. Windows 95 was still what most people used, and it didn't even come with a TCP/IP stack enabled.

Certainly not a brilliant prediction, but it's hindsight that takes it from "pretty mediocre take" to "comically stupid".

deong ,

I mean, there was never going to be an ending here where they came out and said, "You know, we've heard you, and more importantly, our VC investors who've given us 1.3 Billion dollars have heard you, and they've told us that your community matters more than their exit."

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