I.e., don't you think it's possible that his individualist, pro-free thinker views inform both his libertarian political views and also his views that our rigid college-based gatekeeping system is unnecessary?
Probably not since one doesn't naturally flow from the other. Especially since he creates and participates in a several other gatekeeping systems.
Peter Thiel as a libertarian is depressed simply because, despte being white and rich, he can't find a way to deprive other groups of some basic civil rights. What freedom do you have if you can't deprive others of theirs? Indeed Mr. Thiel.
If you are making statements like this, you clearly know nothing about either libertarianism or Peter Thiel.