I'm a child of the internet post crash. In 2000 I was 22, sitting in the Greenwich offices of Paul Tudor Jones, working for a Tiger cub focused on cyclical industrials. We didn't own a single tech stock. We felt pretty smug watching the NASDAQ crash.
I graduated from business school in 2002 and started a post-graduate degree about marketing in recession. The twin towers had just come down, I hated all my job offers and kind of fell into helping start my first company, myblog.de. We were fans of LiveJournal and Metafilter and Neopets and, of course, Ev Williams who went on to do Odeo which became Twitter. The guy who started LiveJournal, Brad Fitzpatrick, eventually brought you OAuth. Which became "Sign up with Facebook", which started to make the internet suck. But that is Brad's fault as much as it is Ev's fault that Trump is President.
We sold Last.fm, my first angel investment, to CBS in 2007. I had joined Atlas Venture as an analyst just a few months prior. That was my first venture gig. Back then, if you wanted to figure out something about internet culture, you read Encyclopedia Dramatica. Unless you hung out on 4chan all day, it was hard to get all the references.
In 2008, KnowYourMeme got started, and for the last decade it has been the place to go to understand internet culture. The Verge has a nice feature of Brad Kim, who has worked on KnowYourMeme from the start. Go and check it out if you care about how we got to and where we go from here.