I didn't find this interview convincing. Although Paul is definitely a charismatic humorous person (especially for an old man), he seemed to avoid the question "Do you have an example of a free society that has been successful ?" by using the usual stereotyped formal politician language. The question was straightforward so the answer should have been on the same level. I agree that it's not something easy to do, Friedman in The Machinery of Freedom used the medieval Icelandic society as an example of a private justice but it may be boring to mention this on this kind of show. Maybe a good answer would have been the Internet. It's something massively used by billion of people all around the world and the government hardly has control of it. Besides, it's something popular to the young generation (the target of The Daily Show)