That politics makes strange bedfellows. Stick to certain issues and libertarians agree with democratic socialists in general. My favourite interview that I've ever heard with Cory is the one he did back in 2008 with Free Talk Live. The host had read Little Brother and says "The author of this book's a libertarian, there's no doubt in my mind." Which if you're going just by Little Brother, might make sense. I'm going to guess they didn't enjoy For The Win (dealing with unionizing gold farmers) quite as much.