Jim called in to talk about how the Department of Homeland Security is monitoring not only the free press, but also bloggers, podcasters, and vloggers. Jim wonders if he should use a VPN as a hedge against that. Leo says that while anonymizing his content is a natural reaction, and while a VPN could be a useful tool, but it's not a privacy tool. In fact, encrypting his traffic shines a light on him more than just being a part of the "background noise." Also, a VPN only encrypts the traffic along the way.
Leo says that TOR (the Onion router) further anonymizes traffic so that it masks everything and routes through multiple servers. But it would slow him down. Dan Patterson has some great materials on how to anonymize traffic. He's trained dissidents all around the world.