Even if Thiel were just an ordinary investor, dinner with him would make anyone nervous.
One quickly finds that he is a man notoriously averse to small talk, or what a friend once deemed “casual bar talk.”
Even the most perfunctory comment to Thiel can elicit long, deep pauses of consideration in response—so long you wonder if you’ve said something monumentally stupid.
The tiny assumptions that grease the wheels of conversation find no quarter with Thiel.
There is no chatting with Peter about the weather or about politics in general.
It’s got to be, “I’ve been studying opening moves in chess, and I think king’s pawn might be the best one.”
Or, “What do you think of the bubble in higher education?”
And then you have to be prepared to talk about it at the expert level for hours on end.
You can’t talk about television or music or pop culture because the person you’re sitting across from doesn’t care about these things
from 'Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue' by Ryan Holiday https://www.amazon.com/dp/B0775122NK