I came out of college in 1999 and went to work at Cisco. Cisco was pretty terrible and I went to work at a startup in 2001 that was working on a GPRS switch system.. (predecessor to 3G for mobiles.) . I was working on management software.

We basically ran out of money as the bust happened. Alcatel had their eye on buying us.. what they did is wait till the company was running out of money and had laid everyone off in waves. Once the company was a skeleton they bought it for a song. They had to hire a few of the principal engineers back as consultants but not 24 year olds like me! There was some bad behavior along the way from management, they were hiding the true financial situation from the employees.

The other aspect of the bust I remember is a Morgan Stanley "financial adviser" trying to take me for everything I was worth when I was leaving Cisco. The Cisco stock was like $150/share or something when I was leaving. I didn't have enough money to buy the shares. Morgan Stanley had some kind of deal with Cisco where they assigned us financial advisers. The adviser was trying to get me to take out a near six-figures loan to buy options on margin. "You can just keep it for a year and then sell it and make a pretty penny after paying off the loan!" I declined and within a month or two of my leaving the bust hit and my shares would have been underwater by > $100 a share. It would have seriously messed up my financial future in a major way. That guy was such a crook.

The actual layoff in the bust wasn't that bad but it still set me back a bit. I was out of work for about 2 months, I lived with my parents for a bit but found a contract that I kept for 2 years. Taking the contracting work was pretty lucrative but not that smart in the long term. After that 2 year stint things were still pretty bad as that was the era of "outsourcing overseas is the future!" and I had another 2 years of sideways work that wasn't great for my career. Things started looking up in 2006 and were vastly better by 2010. The "great recession" had 0 effect on me.

I was totally delusional in my early to mid 20s about how easy it was going to be to work at a startup and be successful. It was also a super different era in terms of office and overall culture. You were a near social pariah as soon as anyone found out you were a software engineer, it was 100% not cool to be a tech worker. Women would immediately lose interest in you and practically run away as soon as they heard the word engineer. We were all still 100% considered nerds, not cool in any way. Also there were NO young people in the office. In my 20s there was almost no job I ever had were there was anyone else in the office under 20.

Other aspects I remember.. almost no perks in the office, way more crunch time, much longer hours at the startups. In the last 10 years I worked at 3 startups, one had the long hours like a 1990s-early 2000s startup, but the others are/were so incredibly cushy that it felt like no work was getting done. People yelled a lot more in the office. Stuff that was regularly done then would be considered abusive today and would generate lots of reports to HR.

AFAICT around 2010 when everyone started saying "Millenials" a lot things really, really changed in our industry. Mostly for the better.

In 2002 when I got layed off (Boston area) it was pretty grim. The war in Iraq had not started. So there was an absolute army of highly qualified highly experienced engineers that had been laid off by the defense contractors. Career fairs were scary scenes. Obviously they all went back to defense as soon as the Iraq war started... so the rest of us who weren't interested in the defense path didn't have to compete with them. But it was real scary going to career fairs.

A lot of job postings at that time in the bust had ridiculous/fake requirements. You'd see things like "10 years of experience in J2EE". J2EE was new and hot. But it was like 2-3 years old at that point! The postings were mostly about companies trying to fake that they were doing well... put up the fake job postings to make it look like you were growing when in actuality they were barely hanging on.