I mean, these people aren't well my guy. It's not a huge stretch to imagine a bunch of repressed self-loathing around one's identity being at or near the core of it.

Thiel grew up in the 90s. Whatever one deems the tolerance situation today, it was worse then.

More like the 80s but true. Also maybe worth remembering that Thiel was outed by Gawker. He didn't come out as gay of his own volition and perhaps never would have.

I’m still waiting on him to pull a Milo Yiannopoulos and no longer be gay. His flirting with “libertarianism” already gives him a solid track record.

It makes perfect sense if you think about it from Thiel's perspective. Other than legal technicalities like marriage, the consequences of being gay are mainly determined by societal attitudes and not electoral politics. No legal changes that the Republicans would make do anything to stop a powerful billionaire from being openly gay. So it makes perfect sense that he would favor his business interests when he takes sides in politics.