One of the big author names to drop in the 1990s, besides the cyberpunks, was Hakim Bey, a philosopher who wrote Pirate Utopias and The Temporary Autonomous Zone. Temporary autonomous zones empowered the kinder, gentler post-modern anarchist to create safe havens of sane behavior outside the restrictions of hegemonic societal control. The archetypal TAZ was a rave, a momentary bubble of peaceful anarchy, but other implementations existed (most obviously Burning Man and Usenet).
Another big author name to drop in the 1990s: the brilliant Benoit Mandelbrot, who remains more worth reading than almost anyone since Shakespeare. You can also find Upski's name on that list too, but only in an alternate universe ruled by truth and light.
If it seems maudlin for me to dredge up forgotten underground literary heroes, I have a reason. Anil Dash wrote a wonderful post dredging up a forgotten underground World Wide Web, one whose businesses and communities respected crucial principles of online culture like data interoperability, user privacy, pseudonymity, microformats, and remixing.
It's not a coincidence that this WWW is the one which flourished after the collapse of the first dot-com boom, nor is it a coincidence that this is the WWW which birthed Rails. Nothing made the Web a better, more idealistic, or well-built place than the venture capital exodus of the early 2000s; nothing sent more programmers off to live in their moms' basements, either.
Dash seems defensive to me:
This isn't some standard polemic about "those stupid walled-garden networks are bad!" I know that Facebook and Twitter and Pinterest and LinkedIn and the rest are great sites, and they give their users a lot of value. They're amazing achievements, from a pure software perspective. But they're based on a few assumptions that aren't necessarily correct. The primary fallacy that underpins many of their mistakes is that user flexibility and control necessarily lead to a user experience complexity that hurts growth. And the second, more grave fallacy, is the thinking that exerting extreme control over users is the best way to maximize the profitability and sustainability of their networks.
The first step to disabusing them of this notion is for the people creating the next generation of social applications to learn a little bit of history, to know your shit, whether that's about Twitter's business model or Google's social features or anything else. We have to know what's been tried and failed, what good ideas were simply ahead of their time, and what opportunities have been lost in the current generation of dominant social networks.
I'm sorry to say that my take on this is more fatalistic; in my opinion, many of the functions of the venture capital system actively thwart the production of good software, but perform marvelously if you view them as a bridge for transferring the population of an aristocracy from positions which control the social and economic systems of the past to positions which control the social and economic systems of the future.
In my opinion, another dot-com crash would purge VC influence from the Web, restoring some measure of sanity to it, and allowing it to regain many of the virtues Dash eulogizes; however, that crash would have a pretty severe downside for many people. Anarchists throw incredible parties, but they're less effective at organizing stable social systems.