It was silly. Inexperienced people putting up really simplistic sites with no business model, and people throwing money at it.

But the biggest difference is that nobody really knew what we were doing. The thing YC and others have brought to the industry is a consistent path for startups to follow. If you want to start something, and want to go down that high-risk path, there are playbooks to follow and incubators to apply to, with easy access to information on how it will look.

None of that existed back then. Nobody was walking around talking about the pros and cons of VC vs. bootstrapping, or how to get funding, or how to avoid getting scammed. The basic practices of developing a product, finding product/market fit, iterating based on feedback... those weren't common knowledge.

Now lets also get rid of stack overflow, blogs, and pretty much most sources of information online -- all of that came later. You bought books and read them. You asked your friends for info, and hopefully they knew something. Usenet was a thing, and that is where you might find better info.

Lets get rid of the Agile manifesto, too -- people were either doing waterfall or winging it with their own processes. And the jobs were mostly consulting gigs, requiring lots of meeting and proposals, not self-service signups to a SaaS.

Let us not forget that we did not have git, either. We used old-school source control (if any), self-hosted, check-in-check-out style workflows.

In short, we were (mostly) all inexperienced beginners, without access to much information, flailing about trying to do something new, using really old practices. It didn't really work. But it was kinda fun.

My first job was an internship in a dot com working on anti-spam around when Gmail came out. The job itself was fun. As an intern I would help with everything from bash scripts to web pages to fishing ethernet cables through the suburban house we worked out of to cooking lunch. We'd work all day and then stick around and play video games through the night, falling asleep on the couches to our boss walking in the next morning and chuckling. It felt like a college dorm at times.

Our technology was novel and patented, but relied on the cooperation of ISPs, which we never got. (It was basically mass statistical analysis, but sourced and shared across ISPs. That model lost to huge free webmail providers instead.)

Because anti spam wasn't making money, the founder decided to sell the technology to the Chinese government instead, to use to censor dissidents. I had a long, angry chat with him and resigned that same day.

Extremely exciting, in that there was a lot of demand for tech. However the hype was much like the hype around crypto or now AI. A lot of grifters and people who had no business being in the industry. However because the barrier to entry was a bit higher, there wasn't such widespread madness that is observable with the crypto and AI hypetrains. It was definitely a period where if you had an idea, there were a lot fewer people in that space, and both tech and business were less developed in the industry. So there was a lot more space to shine, but you'd have to do a lot more legwork.

I use the heuristic that if there are loads of billboards everywhere advertising stuff that should be incomprehensible to the layman, then things have got too frothy.

I remember refreshing f*ckedcompany.com daily and seeing the long list of failed/failing companies listed. I was working for a shrink-wrap box application vendor and really wanted to get in on the Internet wave. The bubble pop made it easier to see who was going to survive, which really helped with the next job move to an early SaaS vendor. Didn't lose too much money in market because I didn't have much to lose. Interesting times.

I did technically work in the dotcom bubble, but I was paid minimum wage writing HTML and SQL while I was a young teenager. So, not a typical experience.

Fast forward 5 years though, and one of my first full time jobs was being a contractor for a small e-commerce company that (barely) survived the dotcom bubble.

They had a lease for a full floor on a high rise, but were down to a skeleton crew when I was brought in. I got to pick any office I wanted, since there were so few workers, so naturally I picked a corner office with an ocean view.

I thought life was great since I was getting paid decent money, I was in my young twenties, and the company was pretty chill about me just adding some features here and there and keeping things running.

The other folks though would speak about the 'good times' when they'd throw lavish parties, when the boss would hand out $100 bills to all the employees, etc. Sounded wild.

Incredibly good both before and after. Before, I was working at Microsoft in an incredible group (now called DevDiv). I joined Microsoft when everyone thought they would lose the Internet battle, but just knowing their history, and hearing what Marc Andreessen said about them, told me that Microsoft would be a fantastic move, and it was.

I quit before the bubble burst, but, later, that year I purchased a dotcom business at a rock-bottom price, and turned it into a great job for the next 20 years.