In the course of my many interviews with Thiel for my book Conspiracy I would observe his extraordinarily sharp mind in action. Below are a few anecdotes worth sharing. I’d preface this by saying that a friend of his would say that Thiel is averse to “casual bar talk” and I think part of the reason for that is that he is not well versed in the topics that typically make up those conversations. In one of our meetings I made an observation about how the HBO show Girls gets much more media attention than the the CBS show The Big Bang Theory even though the latter has a much, much larger audience than the former. This observation fell flat because Thiel was not familiar with either show. However, when I mentioned an obscure chapter in Machiavelli’s Discourses on Livy, Thiel could cite it from memory and discuss at length. The same went for the Battle of Valmy, an early episode in the French Revolution. This is because Thiel is extremely well-read and again, tends to focus on talking about and thinking about deep, obscure topics rather than superficial, trivial matters. And Thiel’s friend who made the comment on the “casual bar talk”? He didn’t simply mean to put Thiel down and accuse him of being dull. On the contrary, he would compliment him about the fascinating range of knowledge the man possesses: “The ability to recall a data point – what was gold trading at on day five of the Second World War and what was the impact of that? He has it like a record-book.” Another example from my conversations with him: When he originally set out on his conspiracy against Gawker, his options, as a powerful billionaire were nearly limitless. He could have bribed employees at Gawker to leak information, or hired operatives to ruin the company from the inside. Thiel could have directed hackers to break into Gawker’s email servers. Someone could have followed Nick Denton, the founder of Gawker, and while he dined at Balthazar one morning stolen his cell phone. A team could have attempted to bug the Gawker offices. You could fund a rival website, operate it at a loss, and slowly eat away at the razor-thin margins of Gawker’s business. Or create a blog that does nothing but report on gossip about Gawker writers— returning the very pressure and scrutiny they’d put on other people. If you were think about it amorally, there was very little he couldn’t have done. There was of course a part of him that thought about this. “There are things that were very tempting, an eye for an eye, tooth for a tooth. Retributive justice,” Peter would tell me. “But I think those would’ve ultimately been self-defeating. That’s where you just become that which you hate.” The victory would be pyrrhic, too, easier but at a higher personal cost. But ultimately, he told me that the gating resource for his plan wasn’t money but having a creative idea that other people hadn’t thought of. In the end, he and his team came up with the idea of looking for legal technicalities and ruthlessly pursuing Gawker about them in court. One of those cases ended up being the privacy violation of Hulk Hogan (when Gawker published his sex tape) but dozens, perhaps hundreds of other cases were considered. Gawker was caught off guard by this, thinking that such technicalities would never make it to a jury verdict as most ligitigants settle. Thiel realized that Gawker thought this and in a sense, called their bluff. In a way, this summarizes Thiel’s approach, to to look for an edge—the edge no one else is thinking about. As he would say in an interview with Wired back in 2010, “Am I right and early, or am I just wrong? You always have to wonder. But the things that I think I’m right about, other people are in some sense not even wrong about, because they’re not thinking about them.” Or as he would say at a conference about seasteading, "There are quite a lot of people who think it's not possible. That's a good thing. We don't need to really worry about those people very much, because since they don't think it's possible they won't take us very seriously. And they will not actually try to stop us until it's too late." Throughout his life, Thiel’s intention has been to exploit humanity’s blindspot of the potential range of actions that are possible. That approach of operating and thinking about the world—actively seeking knowledge that is not yet conventional—is further elaborated in his bestselling book Zero to One. In a chapter titled “Secrets,” Thiel writes that “the best entrepreneurs know this: every great business is built around a secret that’s hidden from the outside. A great company is a conspiracy to change the world; when you share your secret, the recipient becomes a fellow conspirator.” He concludes the with a verse from Tolkien, one of Thiel’s favorite writers, urging his readers to take the hidden paths. Still round the corner there may wait A new road or a secret gate, And though we pass them by today, Tomorrow we may come this way And take the hidden paths that run Towards the Moon or to the Sun. And to close this, there is a paragraph in PayPal Wars, which is worth sharing in full. It describes an important moment in the early evolution of PayPal, which Peter co-founded, after a key merger, but you don’t need to know the details to appreciate the remarkable moment: “Peter stepped up to speak last. Looking fairly relaxed, it was evident that he had not prepared any statement prior to the meeting. Instead, he went into detail on a specific topic that he knew was of interest to Confinity employees, their stock options. "Let's see, every old share of Confinity is now exchanged into shares of Hat," he said. "That's roughly, hmm..." he paused, looking upward for a second, "about 2.0207 shares of Hat stock for every share of Confinity." Bill Harris laughed hard at the fact that his senior vice president could do division to the ten-thousandth decimal place in his head.”
