No snarky replies please. I am genuinely curious.
On the other hand he does seem very interested in wielding his influence to create the world he wants to live in. See Trump, see Gawker for example. My hunch is that he's taking a wider view on liberty -- he sees it as under threat (by China, but also others -- including internal actors within the US), and doesn't trust that liberty will "sell itself" any more than he believes software will sell itself (see zero to one chapter 11). I don't know if he's wrong either -- if China can get the upper hand and solidify some amount of control over the United States, however soft, that could be a very bad thing indeed for liberty -- why not be a pragmatist and sacrifice a little now for a lot more later? The danger of course is if it's not temporary and becomes the seed of the United States own version of totalitarianism.
Thiel is someone who has shown time and time again that he refuses to simply buy any particular narrative hook, line, and sinker. He's very woke to the danger in that kind of "feeling-thinking" combo -- and that goes for the libertarian narrative as well. He's shown himself to be willing to be pragmatic, even opportunistic in his attempts to stay ahead of things and sacrifice money in exchange for being in a position to shape the world. We, of course, see the times he's been right, but I'm far more curious about his failures -- based on how often he's been right I can only guess there are lots of them.
The problem with that of course is the "strategically". He's made what seem to be deals with the devil on many occasions -- Trump being the obvious example, and having a hand in pardoning Levandowski being the most recent one. I'm not so sure that he's crossed the line into "evil villain" territory as many think, but is he headed that way? Maybe.
I have watched quite a few videos with Thiel. He has degrees in law and philosophy and is quite financially successful. Thomas Jefferson he is not, but I don’t think he is “just not that smart.”
If it’s a prisoner’s dilemma, you might believe cooperation is the best way, and yet defect if you’re playing the game.
Thiel’s choice would be between: Living out his libertarian beliefs in practice v. Taking opportunities in a big state world and making money.
On the other end of some spectrum might be a radical minded idealist who wants the system to collapse but in practice still chooses to buy a laptop and goes to college.
I’d venture many people have dreamy beliefs about politics that they nevertheless don’t pursue unilaterally.
[0]: Strauss was a political philosopher who advocated reading the "esoteric" meaning in works of literature. I.e. he thought that thinkers did not write what the actually thought but wrote in a veiled way so that their true meaning was apparent by those in the know, but not to casual readers.
Perhaps his libertarianism extends only so far as the deep state can't blackmail him into doing their bidding. Or...maybe all he cares about is power and ambition, and he'll do whatever it takes to climb that ladder, integrity be damned. Which does seem "borderline autistic", perhaps unsurprisingly, because Thiel claims he's "on the spectrum." He's seeming more like a queer (in the old sense) J Edgar Hoover-type figure. I feel sorry for him.