I have a hard time taking his libertarianism as anything other than a cynical maneuver to clear the way for corporate autocracy. He writes manifestos arguing against democracy, sits on the board of not one, but two private surveillance firms, and wrote a book about how the best business to be in is monopolies. It's like some negative image of Leninism, where the vanguard party is venture capitalists so the revolution is sabotaged before it begins