The first is a young man I met at the Hollywood Hills home of the billionaire Peter Thiel while writing a book about Thiel’s ten year conspiracy to destroy a website called Gawker Media. Now, I’d heard that Thiel did not pull off this incredible feat alone, but I had yet to meet the man credited by several people close to Thiel with helping him do it. They described to me a young man they called “Mr. A” who first pitched Thiel on going after Gawker and, eventually, found himself in charge of the multi-year, multi-million dollar operation. Each one of them borrowed Caro’s description to explain how Mr. A managed to convince a billionaire to entrust him with such a project: Mr. A is the professional son. In fact, Mr. A would identify with that label openly himself and Peter probably wouldn’t be offended to hear it either.
But why him? Why Mr. A? Peter Thiel has long had his pick of ambitious upstarts. He can draw from what Alexandra Wolfe called the “eternal freshman herds” of Silicon Valley to fuel his startups, to supply him with ideas and insights, and to sit tableside at long dinners over which he enjoys discussing provocative and politically incorrect ideas. The so-called “PayPal Mafia” is largely made up of these people. There are names you may have heard of: Elon Musk, Max Levchin, Reid Hoffman, and Jeremy Stoppelman. And some you haven’t heard of: Andrew McCormack, Premal Shah, Keith Rabois, and Ken Howery. Each one has been part of Thiel’s network and each has become extraordinarily wealthy as a result of that association.
Yet few of them have had as intense a relationship with Thiel as Mr. A. What was different about him, or his approach? As I wrote in Conspiracy, their relationship began over a dinner in Berlin in April 2011. Peter had struggled publicly and privately with his frustrations over the articles that Gawker published about him and other people. At this dinner, Mr. A both commiserated and challenged Thiel to do something about it. It was almost an absurd scene, a college student questioning a billionaire over why he was taking this treatment lying down. But it was exactly what Thiel needed and wanted to hear. Openly challenging the conventional wisdom has been a hallmark of Peter Thiel’s approach to ideas since his days at Stanford. The balls it took for Mr. A to do it, in their first encounter no less, is one of the first things a professional father like Thiel wants to see in a professional son: something that reminds them of themselves.
Contained in Mr. A’s pitch was the second thing, a subtler but essential element, something Lyndon Johnson also expertly exploited. A professional son needs to be able to do something the professional father wishes they could do but can’t. Lyndon Johnson, as a connected, charismatic, ambitious Southern Democrat presented an opportunity to Sam Rayburn and Richard Russell for which they had yearned for a very long time: A national candidate cut from their same cloth. Neither of them were likely to ever become president. Johnson, on the other hand, had a shot. So the relationship was symbiotic. As he was looking to them for favors, they were in turn grooming him, hoping to get access to the White House through him.
Thiel, for his part, hated Gawker but was far too busy and far too conspicuous to be able to go after them himself. Mr. A’s assets were his age, his energy, and his low profile. He got access to Thiel, but Thiel in turn could deploy Mr. A to do the thing he’d wanted to do but couldn’t. More, Mr. A had convinced him how urgent and important it was that he do this, that it was actually a “positive good” for Thiel to use his wealth and power to pursue this end he’d originally declined to go after.
There has long been a similar dynamic between Barack Obama, a man with two daughters, and Ben Rhodes, the writer and aide who he developed a “mind meld” with over eight years in office. In a considerably more toxic form, there was also a connection like this between lawyer Roy Cohn and Donald Trump, as shown by Frank Rich a recent New York Magazine piece. Cohn was a lonely, bitter man whose star had fallen since his time as an attack dog for Joseph McCarthy and for being a U.S. Department of Justice prosecutor at the trial of Julius and Ethel Rosenberg. In Trump, he saw a very rich, very ambitious — but very clueless — young man. He saw that Trump was willing and able to be taught how power worked in New York and DC, and was willing to play the kind of dirty games Cohn had elevated to an art form. Trump made Cohn feel special, like he was loved — and most important, he offered himself to Cohn as a weapon for Cohn to inflict on the world. Trump had Cohn wrapped around his finger until Trump no longer needed him, and then cut him loose as the man died of liver cancer. “Donald pisses ice water,” is how Cohn described this betrayal, which, as hurtful as it was, must have also made him kind of proud.
The professional son understands what every father wants — a progeny worth his time, someone to invest in, someone who can further his legacy. The professional father wants to see his greatness given a second body — a younger one, with more energy, with the benefit of his hard-won experiences.
This is something most people who want mentorships miss. They either think that mentorships are some sort of pro bono obligation that successful people must endure, or they despair of getting one because “What do I have to offer anyone?” As Sheryl Sandberg has written, it’s not “Get a mentor and you will excel,” it’s “Excel and you will get a mentor.” Being young, being plugged into what’s going on in your generation, having energy or passion — these can be attractive forms of excellence, too. So is being able to play to a successful person’s ego (as George Packer wrote in The New Yorker about Ben Rhodes, though he was a talented writer and policy expert, Rhodes’s “essential role was to be the President’s mirror and echo”). Making a person feel that you can further their greatness, that you understand them and will be a vessel for that greatness, is what gets you adopted as a professional son or daughter.
In my interviews with Mr. A, he would slowly reveal some of his artistry. You always want to deliver good news, he said. You have to show them you’re making progress and their investment in you has been worth it. It requires a kind of osmotic compartmentalization too — their problems become your problems, but your problems can never be made their problems. He also specialized in thoughtful gifts — going almost to an obsessive degree, I would hear — to show his affection and his adoration of the powerful person he was forging a connection with. He seemed to know Peter as well or better than Peter knew himself, and thus was able to make Peter feel good, feel more fully himself each time they interacted. In turn, Peter — as all professional fathers do — became deeply attached to Mr. A, and came to take a personal interest in his success.
Other professional sons I would speak to were reluctant to go on the record, which is another lesson. It can’t ever look transactional, you can’t ever look like you have or had an agenda. But they did give me some other insights. They spoke about a need to be unfailingly optimistic and energetic; this is what makes all their interactions positive. One told me about the art of asking intelligent questions, the kind that are gratifying and fun to answer. The, “Ah-let-me-tell-you’s” and the “I’ve never thought about it that way, but…”s and the “Good question. Here’s the thing”s. The process is self-reinforcing, as Ben Franklin (a master professional son himself) figured out, because the more emotionally invested someone is in you, the more they will continue to invest. Another told me about the importance of sprezzatura — making it all look effortless. The stink of desperation must be avoided at all costs.