The appearance of "smartphones" and Facebook killed the cool for me. That, and hearing tech-illiterate morons extol web 2.0 with tireless aplomb. It was sometime in 2008.
Replying on my own comment - I just want to add that if one truly avoids smartphones and social media... if one sticks to things like IRC, basic email and snail mail... if one avoids laptops and sticks with large, immobile desktop computers... very little value is lost, and so much of the old magic is still right there at your fingertips!
The cool of the culture died with smartphones and social media for me, but my love for the magic of software and hardware has not waned.
I remember feeling in the mid aughts like a bunch of marketing bros who didn't know shit about tech, were flooding into tech. They were what ruined it imo. They were incapable of having any passion for the engineering because they didn't understand it. They were just there to invent buzzwords and optimize monetization and all that junk and we got Web 2.0 and algorithmic feeds and it's all been downhill since.