Well, firstly I don't know that we would have considered the late 90s to be the early days. I was pretty active during a time where the scene was transitioning

Well, firstly I don't know that we would have considered the late 90s to be the early days. I was pretty active during a time where the scene was transitioning from underground bulletin boards to the internet/irc, circa ~1991 and even then it was common to find textfiles describing esoteric systems that were hard to find anymore. I'm not active at all anymore in infosec (white or blackhat), so it's impossible for me to draw a comparison. But I can tell you that back then it was very much more about trading information and socializing. Google around for anything published from a guy named Fravia. When I remember those days, he more than anybody captured the philosophy I wanted to subscribe to. These days it sounds pretty scary. Back then you could get in trouble for phreaking some phone calls and end up with a stern talking to from the telco. Now you aim a webcrawler at the wrong service and they lock you up. It also seems like blackhats now have a much more mature ecosystem and financial motives. Right around Defcon6 I think it was, hacker groups started building commercial product and people landed on episodes of MTV True Life. I think that was a pretty important shift. tl;dr more fun, way less scary? Edit: If you're talking about programming in general and the dot-com bubble, that's a different story. I may have missed the point.