Ask HN: How was life for a regular dev during the dot com burst?

Got stuck with a huge tax bill on my stock options when Yahoo went under, took 10 years of brutal back to back contracts to pay it off. The state didn't care that I had nowhere near the opportunities again they just mercilessly hammered me for taxes until I paid it off a couple years ago but took nearly 15 years to pay off the tax debt and meanwhile I could invest in nothing else.

Around 1992, my friend and I started doing desktop database apps as a side gig while we worked at a consulting firm doing IT. We decided to do this full time. With connections in the music industry, we started doing websites and online stores for some big names like Rolling Stones, Aerosmith, Phish, and others. By then there were about 5-6 of us, working out of my friend's house. We weren't real employees, and only got paid when my friend walked into the room and started handing out $50 bills. Our online stores morphed into an award-winning product for small and medium-sized merchants, that you could pick up for $19.99 at Staples, CompUSA, etc. In 1996 we incorporated, and I was hired as the first official employee/lead programmer. I think I was making about $50K by then; we had grown and moved into a real office. A couple of years later, we had the first single-shopping-cart online mall. I was making $85K. We had almost 70 employees. In 2000, a Canadian company bought us for $45M and I was given another raise to almost $110K, but then things fell apart quickly. The last 6-8 months I was basically paid to drink coffee and sit around. By 2001 we were kaput. My 60,000 stock options, when I could finally do anything with them were worth about $1200, down from an initial value of ~1.8M CAD. I had bought a truck, and had put a downpayment on my house, but that was about it. I flailed around for a few years looking for programming work, and then got the job I have now, doing IT at a local University. I'm making about $50K again :/ It was a lot of work, with (mostly) great people, and for a while we were on top of the world. In some ways you could say we were Amazon before Amazon. If we hadn't gone under, Amazon probably would have bought us. Perchance to dream..

That is awful. If you had more money could you have fought it? Was prison threatened?

Backdrop: I was inspired by games and went to CS undergrad with the hopes of becoming a videogame developer and ultimately a designer/director. I started college just as BBS distribution gave way to the World Wide Web; I had to learn HTML in order to distribute my shareware games.

Moonshots: I dropped out of school with only a year left to graduate because the Web development startup I launched with two of my friends was getting out of control. We were charging over $100/hr in the 90s and still having to turn down clients. We worked on amazing projects I can barely remember and made a pile of cash. But we were kids and couldn't get along so we split. I joined another startup that got bought out and put more cash in my pocket which led to me following leadership to yet another startup... that died pretty hard in the Fall of 2001.

Aftermath: Money, parties, travel, and then boom... it was over. Although I had been an irresponsible child with my earnings, I had the good fortune of having some saved some before I was laid off - and I could collect unemployment benefits.

Like everyone else, I couldn't find work anywhere. There was a flash cartoon back then called "Laid off: a day in the life". Good times, good times. I went back to school to finish earning my BS in CS. While in school I tried desperately to get a job in the service industry. I couldn't even land a job waiting tables. Managers told me that they had plenty of people that could work at any time and they didn't want to fuss with people who had school schedules. One manager told me he had over 1,500 applicants at his new restaurant. After having held a Director title in 2001, I ended up starting over again with a fresh degree and a job as a Jr Videogame Programmer in 2003. At least I was working on videogames instead of web! (spoiler, I'm back in web, but that's another story)

I still don't think I've fully come to terms with the unrealistic expectations I developed early in my career. I rose to success quickly because I had a head start in web tech just as the industry around it was taking off. After the crash I had to work hard for things like everyone else which means coming to terms with the realization that I am not as special as I thought I was.