1. There’s a massive arbitrage opportunity in going against social desirability bias. Supporting Clinton is like starting a restaurant. There’s no margin. Trump OTOH is starved for elite support. This is a pure Zero to One play. Why wouldn’t Thiel seize a once in a lifetime chance to have direct influence over the POTUS at the cost of mild embarrassment?

2. Trump delegates. This is not merely a chance for Thiel to have the ear of the most powerful person earth. Given Trumps management style, he may just give Thiel full control over whatever portfolio he wants.

3. Palantir. Bloomberg’s profile of Thiel gets this exactly right. Two of Founder Funds biggest investments, SpaceX and Palantir, depend on government contracts. Palantir, in particular, has been struggling lately (valued at a 40% discount by internal documents). This motivation is directly alluded to in Thiel’s speech, where he references both the Apollo program and outdated government IT systems.

4. Neoreaction. Thiel is labeled a libertarian but more properly thought of as a corporate feudalist. Think seasteading. Think his hatred of the Cathedral. It has nothing to do with inalienable rights. Rather, it’s competition between Kings for their subjects. Democracy is incompatible with freedom. Civilization is in terminal decay. Thus he, like Mencius Moldbug, would love to see Larry Page become CEO of America to RAGE (retire all government employees) and get our institutions back on track. Or better yet, Thiel could be the official CTO and shadow CEO of America. Trump would be a real King after all.

5. Rebalancing. Related to 4. the people I know at the Seasteading Institute and within proprietary city movement are supporting Trump. Why? Because they’re vehemently anti-NATO (so was Thiel-supported Ron Paul) and pro-Chinese and Russian authoritarian qua feudalist style government. Trump would gut NATO and rebalance power to the East. In particular, China is much more open to a kind of neocolonial development policy that includes extensive use of Special Economic Zones. A blow to liberal cosmopolitan democracy is a bump to his vision of Freedom via Tiebout sorting.

PS: I’m open to writing more on this topic with the right publication.