It was genuinely such an exciting time back then. People were still optimistic about the web and new platform like mobile. There was so much to build, yet relativity few people working in tech. And those of us who were weird enough to work in tech loved it. It felt like almost every week there was some new startup asking around for tech talent and they'd take almost anyone they could get. And when you joined you built cool things that had never been built before.
Today tech feel so stale. People who work in tech are not techies, but just see it as a career. There's so few novel things to build that SWE has basically become a profession of plumbing already built libraries and SaaS tools together. Even startups feel so much more mature from the get go. Back then startups were often bootstrapped projects by a dude in his bedroom. Today before a single line of code is written startups already have CEOs, CTOs, CFOs and several million dollars of investment.
Perhaps this guy should have kept up with trends, but 20 years ago the dude would have had a job at a company where he was respected greatly for being the dude who could throw together an e-commerce store in a few days or something. He probably would have been building genuinely new stuff with a team of other people who loved tech.