Instead of giving descriptions for these, I’m just going to list titles. You need to read ALL of them. Especially the ones marked with an *, as they are the ones the illustrate the darker side of the web.
Here Comes Everybody: The Power of Organizing Without Organizations by Clay Shirky
Brave New War: The Next Stage of Terrorism and the End of Globalization* by John Robb
The Pirate’s Dilemma by Matt Mason
You Are Not a Gadget: A Manifesto* by Jaron Lanier
The New New Thing by Michael Lewis
Founders at Work by Jessica Livingston (interviews with technology founders from one of the best investors of all time)
The Net Delusion: The Dark Side of Internet Freedom* by Evgeny Morozov
Hackers and Painters: Big Ideas from the Computer Age by Paul Graham (or you can read his essays here)
Wikinomics: How Mass Collaboration Changes Everything by Don Tapscott
The Cathedral and the Bazaar: Musings on Linux and Open Source by Eric S Raymond