Well, OK, so he's not perfect. But read his latest, Rules Are no Obstacles for Committed People, and then go read my latest again. He gets it.
He's not my kind of guy, philosophically. But he reinforces something I've long known, that people are what they are despite their expressed philosophy. Here's a guy with a strong liberal world view, yet he shows symptoms of being as virulent a capitalist as there is on this planet.
Philosophy just isn't a guiding force in most people's life. Hell, it's not a guiding force in almost anybody's life. Sure, some people live for their philosophy, but even those people were those kind of people before they landed on that philosophy, not because of it.
People just want to get on with their own lives. Someone who wants a life of ease will mold whatever philosophy they believe in to one that allows them to be a parasite, or will seek out one that's already so molded. People who want to be busybodies can find plenty of opportunity within conservativism or liberalism, and there's even some that have found a way to reconcile it - in their own minds, at least - with libertarianism. People who are naturally rebellious can find their way to John Birch or the Greens as easily as they can to the libertarianism or objectivism.
Philosophy is not irrelevant. A bad philosophy will make it harder for a Steve Pavlina to get on with his life, but a guy like him will get on with it no matter the obstacles, self imposed or external. A bad philosophy will lead a busybody or a parasite to do great damage to himself and his society, but such a person would have done some damage anyway. Philosophy is not an obstacle to committed people.