Peter Thiel carries an air of mystery. His story intertwines erudition, success, political controversy, out-there contrarianism, and ideological views that sometimes seem self-contradictory. His position in popular culture reminds of a conservative George Soros: an academic philosopher turned financier, heavily politically active, and vilified by the opposition press. They are exceptionally successful investors, each cementing their status with one legendary deal.1 Their empires sprawl so far that they always show up somewhere if you dig far enough – turning them into Keyser Soze-style boogeymen to their detractors.

This popular fascination with Thiel brings us to Max Chafkin’s recent biography, The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power. In short: the book is not great. It comes close to being a smear. Its strong side is some original journalism about Thiel’s early years, bringing to light some colorful anecdotes. The rest of the book is weaker: basically everything after 1999 is a retelling of well-worn stories with little new content. Chafkin goes over Thiel and PayPal, Seasteading, Thiel Fellowships, Palantir, Gawker, Trump, etc., all of which is common lore to a Silicon Valley reader. Chafkin doesn’t offer much of his own analysis, but tries to tie these stories together via the Peter Thiel as White Nationalist narrative that others have explored before.

I take this sort of exposé with a grain of salt. When you’re looking at a prolific person with vast dealings in all kinds of esoteric stuff, it’s always easy to construct a hostile narrative. And while I don’t know Thiel personally, I’m close enough in the general ecosystem to know that some of these theories surrounding Thiel are more fever-dream that not.

What I found most disappointing about Chafkin’s work was that it doesn’t get any closer to the person: Thiel is viewed as an outrageously sharp man who has espoused lots of unconventional things, and taken big successes and failures2 along the way. Who is this guy? What does he think today? How does one explain or reconcile his technological and political positions, which at first glance often seem directly opposed to each other? What’s the role of Christianity in his belief system? Hell, what food does he like? Does he tip? Chafkin’s chronicling of the last 22 years of Thiel’s life is very political, but it is not personal at all. That’s a dire loss when writing about a man who is precisely so personally mysterious.

However, Chafkin did a fine job in documenting less-known stories about Thiel’s early years. And perhaps Chafkin’s generally negative framing colors my perception, but I was surprised to find that Thiel was a loser in his 20s.

That’s not a point that Chafkin makes. But I get that impression. I’ve been in similar institutions and environments as Thiel in my 20s, and some of Chafkin’s anecdotes resonate clearly with my reference points from that time.

When Thiel was at Stanford, apparently he would drive home to his parents every Friday to spend the weekend. At Princeton, those guys were always dweeby and weirdly sheltered.3 He had a love-hate relationship with Stanford, but he stayed another three years for law school. Again, the kids at Princeton who were strong enough to get into the competitive graduate programs usually went elsewhere, if for nothing but a change of scenery. The people who stayed for more than four years always seemed a little off to me.

After law school, Thiel goes to clerk in Atlanta for a year.4 Then, aged 26, he continues on the cookie-cutter track, goes to a prestigious law firm, and lasts seven months. This happens often in law – years of preparation only to find that you hate the job – and it usually happens to people who didn’t introspect enough at the start of the track.

Thiel then trades derivatives at Credit Suisse5 for a year, and then goes home. That’s right: Peter Thiel, 28 years old, living at home with his parents. During that time, he published The Diversity Myth, railing against political correctness on college campuses before today’s wokesters were even born. He tried to turn that into a Charlie Kirk-style6 conservative media career, which didn’t pan out. Instead, he scraped together some money7 to start a hedge fund, but made losses trading currencies while the stock market was booming.

In summer 1998 – Peter is now almost 31 – he’s hanging around Stanford, meets Max Levchin (aged 23), they started PayPal, and the rest is history.

Up until PayPal’s runaway success, the archetypes all pile up: the academic who struggles to fit into industry and goes home. The unpleasant, alienating politics and attempt to grift off them. The “hedge fund” guy making losses with friends & family money. The non-technical 30-year old alumnus who comes back to school to recruit undergraduate coders for his app. I know people like this, and it’s a real cringefest.

I found this chapter of Thiel’s life surprising. There are six undistinguished years filled with a palette of somewhat gross, directionless activities, and unglamorous failures.8 9

But if the account of those years is fair, then it may answer some of the questions I posed earlier: maybe there is no unifying theory to Peter Thiel’s thought. In a way, these years humanize Thiel – like many others, he was a bit of a misfit who tried lots of things and struck gold one day. He stands out in that he struck extraordinary gold very early, and has been good to let that advantage compound into the present day.

When journalists like Chafkin try to make sense of Thiel, they usually try to mold him into a simple (and spooky) narrative. But as I see him – smart misfit who struck gold – his actions and positions don’t have to fit an internally coherent framework. Like most people, he holds a smorgasbord of views, not all of which are consistent with one another. If an opportunity for sufficiently good personal enrichment comes along, then that dominates whatever views, anyway. People look at Thiel today and ask what is his grand narrative, expecting some erudite glass clockwork. I look at the Thiel from thirty years ago, and answer that it’s not clear that there is one.



  1. That deal will be famous or infamous, depending on who you ask. 

  2. For example: for a very long time, Thiel styled himself as a hedge fund man. His flagship fund, Clarium Capital, shuttered after staying short in 2009 and missing the post-recession recovery. 

  3. Not to read too much into the highly competitive chess playing, but… 

  4. What happened during that year? What cases did he work on? Obviously the first job out of school – the first time in his entire life that he’s more than 50 miles away from home for a prolonged period – is a pivotal experience, but Chafkin totally missed the boat here. 

  5. Unimaginably today, Credit Suisse was a prestigious institution then. 

  6. You might read this comparison as ridiculous because Charlie Kirk is such a joke and an obvious grifter, but I think the comparison really applies. Thiel was basically aping Dinesh D’Souza at the time, who was the leading “young conservative activist against political correctness on college campuses”. This describes Kirk to a tee – in 2021, the aesthetics are just a little different. 

  7. Apparently about (a little under?) a million dollars of friends-and-family money. 

  8. I differentiate this from glamorous failures, e.g. early-stage startups that try to build something great, can’t get there, and then do something better after. 

  9. Perhaps that’s a worthwhile reminder that not every great success is made overnight. Years of unglamorous, difficult toil often precede a reward that may not even be strictly related.