They weren't the same people though. Even the academic types were the type of sandel wearing, long bearded hippies (not an insult BTW) that nixon raged against. Followed by the tinkering kids and phreakers etc.

There was never a single overarching software culture.

It seems like a fallacy to go backward from "Things are this way in 2021, therefore it could never have been any other way in the 1980s-early 2000s".

Go to Barnes and Noble (or online) and pick up the magazine 2600, which still gives off a very amateur, hacking-positive pre-social-media vibe of the internet, telecom, and computing.

Also, the book "Steal This Computer Book" while outdated was a fun glance-through when I was younger, though it didn't talk philosophy.

You had things like the Declaration of Independence of Cyberspace[1] and other essays and myriad discussions about the potential of the World Wide Web.

The Web was smaller, less corporate, and the nerds ran the show. It shouldn't be blamed on them/us that the net is "corporate".

If you're ever interested in embarking upon an interesting cultural study of the 1990s, look at some of RATM's label mates on Epic Records. It was a strange decade...