At Point of Inquiry, Michael Shermer talks about the implications of skepticism and how it could lead one to a libertarian viewpoint. It’s a good discussion which you can see here.
On my perspective, I think a healthy dose of skepticism is necessary in order to inquire about the world, but I don’t think it necessarily leads one to libertarianism. Some of the listener’s comments are actually more insightful, I believe, and they really bring up valid points against Shermer. There are some moments where Shermer says things which I just wanted to reply, “Why do you believe that?” He’s the founder of the skeptic society and I would’ve figured that he would’ve at least questioned some of his beliefs, but he seems to hold on to them dogmatically. Being a skeptic means you withhold the belief until sufficient evidence comes about, but Shermer seems to hold onto certain beliefs without question. Such a shame!