While Thiel was endorsing/investing who would ultimately win - YC's President did the opposite.
While Theil's endorsement/investment in Trump was based on principal - I don't know if the same can be said for YC's endorsement of Hillary. At the time, it came as a surprise ie- a prominent tech company claiming to invest in 'hackers' endorsing a candidate who had just been exposed as technically incompetent (and/or corrupt) via thousands of leaked emails.
It also came across as contrived. Because those same emails revealed Eric Schmidt's role as technical/marketing/search consultant for Hillary's campaign and so it was not a stretch to assume Eric was leveraging his prominence & connections in tech to solicit endorsements from SV 'leaders'.