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.

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".

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".

They weren’t going to make everyone happy. They want vastly more money, and every way of squeezing money out of a thing makes the thing suck more. They certainly could have fucked the PR aspect less severely, but no business in history has ever had anyone enjoy the part where VC investors try to get their returns.

They don’t want the developers to pay anything. They want the developers gone so that all the users are monetizeable through ads.

Stickers and Reddit gold are, by the wildest and most nonsensically optimistic estimates imaginable, not going to be even in the same state as the amount of revenue they’re looking for.

Venture Capital isn’t compatible with asking people to pay what something is worth. You might find a fair price that keeps enough users to make the business sustainable, but that’s what they derisively refer to as a "lifestyle business". VCs are looking for 100x profits in a couple of years, and that necessitates slimy revenue models. Nothing else works.

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."

I don't think it's a problem of not learning the lesson. The problem is that you can't succeed in making a social network if you ask anyone to pay in any way. You need it to be useful, which means you need everyone on it, and everyone won't be on it if it costs anything or is otherwise gated behind even the smallest of hurdles. So rich VCs come in and say, "here's $100,000,000 to go make this thing invaluable, and then I want my money back with a handsome profit". Everyone in the game always knows that the product is going to get shitty when it comes time to pay the piper. Being shitty is a side-effect of making money. The gamble is that it'll be so ingrained in people's life than they'll begrudging eat the shit to keep using it. They're looking for the elbow in the curve -- how shitty can it be before everyone abandons it. That spot of maximum shittiness isn't a mistake -- it's the target.