But the PayPal cofounder says that none of his success would have happened if he had continued on his career path as a lawyer, which was, as he describes, a "familiar track." Instead of continuing down his path in law, he moved out to California, co-founded a technology startup, and made a fortune.
During a commencement speech at Hamilton College on Sunday, Thiel spoke out against conventional wisdom and the familiar track, pointing out two big clichés that end up being wrong more often than they're right.
The first cliche that Thiel takes a shot at is "to thine own self be true." Thiel said:
Now Shakespeare wrote that, but he didn't say it. He put it in the mouth of a character named Polonius, who Hamlet accurately describes as a tedious old fool, even though Polonius was senior counselor to the King of Denmark.
And so, in reality, Shakespeare is telling us two things. First, do not be true to yourself. How do you know you even have such a thing as a self? Your self might be motivated by competition with others, like I was. You need to discipline your self, to cultivate it and care for it. Not to follow it blindly. Second, Shakespeare's saying that you should be skeptical of advice, even from your elders. Polonius is a father speaking to his daughter, but his advice is terrible. Here Shakespeare's a faithful example of our western tradition, which does not honor what is merely inherited.
The other piece of advice that Thiel believes is not justified is "live each day as if it were your last." He explained:
The best way to take this as advice is to do exactly the opposite. Live each day as if you will live forever. That means, first and foremost, that you should treat the people around you as if they too will be around for a very long time to come. The choices that you make today matter, because their consequences will grow greater and greater.
The key to Thiel's speech is to avoid trusting the wisdom of crowds. Although Thiel says that teaching and tradition can still have value, he urged the recent graduates to do new things, and not blindly follow in the footsteps of their teachers and parents.
Thiel certainly has started backed some unconventional ideas about college. In 2010, he started the Thiel Fellowship, which has pays teenagers $100,000 to drop out of college and start their own companies.
Watch the full commencement speech below: