As someone born in the 90s, looking back at the "rage against the machine" culture in software seems very fake for an industry that went from academia to an extension of the financial services sector...
There was never a single overarching software culture.
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Also, the book "Steal This Computer Book" while outdated was a fun glance-through when I was younger, though it didn't talk philosophy.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".