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There is a scene in the movie The Assassination of Jesse James by the Coward Robert Ford. At the beginning, in the woods, Robert Ford, played by Casey Affleck, illustrates this phenomenon. He thinks the outlaw Jesse James is a great man. He thinks that he, himself, is a great man, too. He wants someone to recognize that in him. He wants someone to give him an opportunity—a project through which he can prove his worth. It just happens that Frank James would size the delusional, awkward boy up in the woods outside Blue Cut, Missouri: “You don’t have the ingredients, son.” In contrast, Mr. A is ambitious, but it’s paired with self-confidence, social adeptness, and a clear sense of what Thiel wanted. Even so, the prospect of meeting with Thiel is intimidating: his stomach churning, every nerve and synapse alive and flowing. He’s twenty-six years old. He’s sitting down for a one-on-one evening with a man worth, by 2011, some $ 1.5 billion and who owns a significant chunk of the biggest social network in the world, on whose board of directors he also sits. 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 and he couldn’t pretend to be familiar with them if he wanted to.
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Ryan Holiday (Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue)