This guy is really cool. And not in that traditional, 'the Fonz' kinda way, but in the independent, orginal, and creative thinker way.
Cory Doctorow has an abiding sense of anomie and what it means to be an outsider in this wildly interconnected world. He's written a few novels, a number of stories and even some non-fiction. He gives access to most of his work gratis on his website. I think my favorite concept from his work is "whuffie," which are the reputation points that replace money once society reaches the ubiquitous computing stage. The great thing is that this system allows you to 'earn' a living just by doing really cool and creative things.
I suggest starting with A Place So Foreign, some recent short stories, or with Down and Out in the Magic Kingdom, his first novel. Diehard fantasy geeks may prefer Someone Comes To Town, Someone Leaves Town, but I've still got mixed feelings about its value in the Doctorow bibliography.
He's also one of the five or so people who update BoingBoing. Then there's his work/advocacy for the Electronic Freedom Foundation (who help bloggers, Myspace.com users, and those who've purchased Sony cd's). If you're a Second Life player/member you can usually catch him doing in-world interviews whenever he's releasing something new. And I totally forgot to mention his podcasts of short stories he's written/writing.
Also, if you find yourself really diggin' on Down & Out or EST, then you should check out Accelerando by Charles Stross.
