There are lots of ways to "go against the grain" in the way you point out. You could be an unthinking dogmatist. Nothing would change the way you feel, not even the censure of your peers. (Is Thiel being censured? Sure, by Pinboard on twitter. By his peers? Not that I can see. His richy-rich pals all still love him, AFAICT.) Is there something admirable about having your head in the ground? Not really---and I don't think that, on the broader social level, we tend to applaud people who still think gay sex is shameful and should be illegal, even though, you know, they really go against the grain.
You could be, say, a modern Cato. But Cato is admirable not just because he fell on his sword but because he fell on his sword out of devotion to an admirable ideal.
I see no reason, incidentally, to believe your claim that "Thiel stands alone in his strength to go against the grain". If other people aren't going against the grain, it might be that they think the grain is largely going in the right direction already, and not that they lack the strength to go against it. And, on the other hand, you have to pay a little attention to threads about diversity of race or gender to find a lot of people with the strength to go against the grain. Guess what: the grain they go against, Thiel goes with.