I can't find a source right now, but I remember reading about that Elon Musk tried to fight for Paypal to use Microsoft software instead of Linux when he became the CEO after the X.com merge. Since Paypal wanted to continue using Linux (who wouldn't?) they instead switched CEOs.

Edit

> I never heard that he didn’t pull his weight from Peter thiel or the others

I don't know. A letter of no-confidence to the board in order to replace Musk with Thiel doesn't exactly shine a lot of good light on Musk. From https://www.cnbc.com/2019/11/02/why-elon-musk-says-taking-va...

> At the time, he was CEO of X.com, and company executives were not pleased with his leadership. While Musk was on the plane with Justine, executives delivered a letter of no-confidence to the company’s board, pushing Musk out as CEO, and replacing him with Peter Thiel.

As a big linux fan, Microsoft probably was the better choice 20 years ago.

As a Linux and Microsoft user for more than 20 years and dealing with hosting 20 years ago, I can say Microsoft was absolutely not the better choice.

2000 was the year of Windows 2000 and Windows ME. Did you ever use those in a professional capacity at the time? I think if you did, you wouldn't say you're a big Linux fan _and_ advice a company to use Windows. Or maybe we simply have different definitions of what a "fan" means.

I was more thinking in terms of what you could readily hire programmers for around that time. Definitely did not mean to imply that Windows was the actual better tech stack, just that for various business reasons going with Microsoft may well have been a better choice.

Though in regard to tech stacks, I also thought X.com might've been using .NET and (if that had been the case) then to my mind it was the better option, compared to what many people were using for scrappy Linux web backends in that era – PHP (which I say as someone who wrote his first web backend in PHP). But after looking up the timelines, I realize that this wasn't the case. Musk was replaced as CEO in 2000 and .NET was released in 2002.

This is also 20 years ago.

How does that change the fact that the statement was "he didn’t pull his weight from Peter thiel" and it seems that he meaninglessly fought existing culture and also was ousted, which seems to indicate that he did in fact not pull his weight according to the board?

I only wish I was slightly older during the dot com boom. I had to finish college and do it with flying colors, being from a poor family. If you had the means and some padding to take fairly reasonable risks, you walked away with riches. These people were at the right place and the right time, let's not lionize them as investment geniuses. They had money to put down on some horses, that is ALL.

That doesn’t line up with what I’ve read about that time period. A lot of the companies that were well funded by such bets went bankrupt. In all likelihood you would have lost money during the bust. The companies that weathered the storm were actually delivering good products and had cash flow. That takes a lot of work on the tech and business sides.

Maybe you could have timed the bubble and exited with a pile of cash, who knows. If you want to make those kinds of bets you could make them right now.

The far more common scenario in the dot-bomb era was that you lost your job (which almost certainly wasn't paying the kind of salary many developers expect today), were left with a pile of worthless stock options, and maybe spent a couple years asking people if they'd like fries with that. (That's only a slight exaggeration. I was very very lucky to almost immediately land another position--which then went through its own rough times but not to the point of being unemployed.)

Some people made out of course, but in general ~2001-2004 was not a great time to be in tech.

For this specifically, Musk was so immature and inexperienced that he was either kept away or removed from higher posts, but since the ideas themselves materialized and were successful (see Zip2. X dot com), he walked away with millions. He was the definition of failing upwards. And once you have 200 bars of walkaway money, it's really, really hard to fail.

Per Wikipedia: "Within the merged company [PayPal], Musk returned as CEO. Musk's preference for Microsoft software over Linux created a rift in the company and caused Thiel to resign. Due to resulting technological issues and lack of a cohesive business model, the board ousted Musk and replaced him with Thiel in September 2000."

Having been there as an adult, I can say right now is a far better time to walk away with riches. There were a lot of scams that made scammers money, but very few made real money if they were legitimately trying to build a business.

I agree with that. Certainly there were lottery winners who got in on the ground floor of ultimately very successful companies. And there were others who had disposable income who bought into companies like Yahoo early and got out in time.

But, in general, salaries were mostly unexceptional in tech even in Silicon Valley, a lot of companies went bust, and even most of the surviving firms--including the big systems/storage/chip/networking/etc. players--went through some very lean years with a bunch of layoffs.

True. I think there are more lottery winners today, but we know the names of the previous generation more.

It was certainly no sure thing, and it’s easy to say that in hindsight. There were definitely a lot of people who walked away from the dot-com era with worthless stock options and wounded egos. Plenty of people ended up taking the “safe” route too and getting a job at IBM.

We’re in the same place with crypto right now. People will look back and say “oh jeez if only”. The early bazillionaires are already minted but there are a lot of crypto millionaires made every day. It’s just a lot of people dumping their life savings into BTC/ETH and enjoying the ride.

Hindsight makes history look easy and obvious. It is far from the truth.

There's a strong survivorship bias in what you hear about. A few hundred folks made solid money, but many, many more had to go hunting for jobs after the bubble burst.

It was an exciting time in other ways, but not for making money.