He's built his software business. Radio show started as a hobby, I suppose. The thing is, he's very talented at constructing arguments. The presentation may seem a bit eccentric, but get through this. If he can't convince, I don't know who can.
Well, his software business wasn't an outgrowth of his libertarian views on affairs unrelated to the state, I imagine. I'm not saying he's an indolent sloth; I'm just saying he hasn't put much action down next to his words, as recorded by Wikipedia.
I'm just sort of unsettled that a single radio-talk host is your entire hope for libertarianism as a philosophy larger than "government bad individual good".