Max Chafkin, “The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power” (2021) (read aloud by Will Damron) – I’m a little behind on reviews. This was a pretty good audiobook about a juicy subject, but god help me if I’m not stuck on one weird thing. Journalist Max Chafkin, in relating the story of billionaire tech investor and political wirepuller Peter Thiel’s childhood, to portray the boy Thiel as bullied. California in the seventies, Peter Thiel a weird, hostile, skinny nerd, not hard to believe. That said, the one example anecdote Chafkin could pull out was some of Thiel’s high school classmates going around their town, stealing “for sale” signs, and setting them up on Thiel’s house’s front yard in the night. They then asked Thiel when he got to school “hey, you’re moving?!”

I mean… that doesn’t sound that bad? That actually doesn’t sound bad at all? Sounds kind of goofy? Maybe if there was an implied threat, like, “you better leave town,” but Chafkin didn’t imply there was, and probably wouldn’t leave it unsaid if there was. 

Beyond it just sticking in my head, why do I lead with this? Ultimately, I tell this story because it illustrates the ways in which Thiel was shaped — and then went on to shape himself — the myths and lacunae of late capitalist culture in the US. More than a bullied kid, Thiel seems like one of those kids who just doesn’t like anything, someone who never outgrew a sort of infantile colic (I’ve known kids like that- and other kids do wind up bullying them, in part because damn near any interaction with kids afflicted that way turn out to be experienced as bullying). It’s not quite depression, at least not as I know it, just a general disdain for and dissatisfaction towards the world. His parents, German immigrants, sound unpleasant, but not abusive. Who knows how people get that way? But “bullied nerd makes good, takes revenge” is part of the Silicon Valley myth. Thiel probably believes it- Chafkin, normally pretty perceptive, might have gotten taken for that ride, too. 

I’ve been thinking a lot about Generation X lately, for my birthday lecture. They all thought they got dealt a pretty shitty hand, and it didn’t help that many of them came of age during the recession in the late eighties/early nineties, but really, it was about as good a time as any for a superficially smart white American with ideas and grudges. Thiel didn’t start out as a tech guy. He started out as a politics guy. In eighties Stanford, he edited a review, like the ones Anne Coulter had at Cornell and Dinesh D’Souza had at Dartmouth, dedicated to ponderous conservative essay-writing next to brazen bigoted provocation. More than promoting any policy agenda, Thiel just hated the culture around him, though even that is more myth than reality. Thiel said his issue was the permissiveness, hedonism, and lack of standards supposedly inherited from the sixties counterculture. But like… at Stanford? The most preppy school in Northern California? It wasn’t that countercultural, never was. Maybe hedonistic, in a lightweight collegiate way, but still. The point is, Thiel hated, and put himself in the script that allowed that hate to flourish. 

He became a corporate lawyer in New York and tried to get into higher-end political law by clerking for federal judges. At some point he got sick of it, went back out west, and started a hedge fund. This was the mid-nineties, and one of his investment fields was online payment systems. You could say Thiel has a decent nose for opportunities. You’d probably be right, but again, it’s possible to overstate, and he’s banked on some weird shit over time too. Part of his motivation to look into moving money online was his anti-statism. He was a big fan of Neal Stephenson’s “Cryptonomicon,” all about daring tech entrepreneurs chasing gold to make a non-state crypto-currency (I read that book myself several times as a teenager- these days, I’d say it’s mid-rank Stephenson). Eventually, all of this led to PayPal.

One interesting point Chafkin makes is the inflection point Thiel’s rise represents in internal Silicon Valley culture. There was always a ruthlessness there- it’s capitalism, and the military-industrial complex always had a major hand in the tech industry. But it was, if not tempered, then modulated by countercultural values and promises. Hippie bullshit didn’t stop Steve Jobs from being a dick to all and sundry (until some genius convinced him he could stop cancer with juice); it did stop him from crowing about it, and perhaps inflected the culture around his businesses, making for a mellower corporate culture. Chafkin depicts Thiel, whose original bugbear was hippies, as leading the turn away from this ethos, to the “move fast and break stuff” era. The counterculture-cyberculture lineage had a vision of a sort of techno-pastoral idyll as the end point – the anarcho-capitalist Thielian vision is more like rolling around a blasted Earth in a robot body, absorbing hippies and other lesser breeds for the energy in their blood. Ironically, both are meant to be visions of liberation. 

Chafkin entertainingly relates the twists and turns in Thiel’s career. He fucked over Elon Musk — Musk spoke on the record about Thiel to Chafkin, seemingy in tones of wistful regret “but make it stupid” — and Meg Whitman at Ebay and whoever else he felt he could get a dollar out of. It’s a mistake to make too strong of a distinction between the hacker as hippie and the hacker as hateful nerd: both take glee in breaking rules, and Thiel certainly did plenty at PayPal. Say what you want about Apple, but it did and does make a product that people want, that’s different from what came before. Thiel was a pioneer of that other way to make a bundle: backdoor deregulating an industry, destroying competitors through the competitive advantages unpunished rule-breaking gives you, and establishing a monopoly. That’s what PayPal did, up to and including facilitating fraud and burning through millions of dollars of venture capital to lose money to hook people on their product. This is what a number of later Silicon Valley unicorns, most of which Thiel invested in, did and do as well- Uber, Airbnb, on and on. 

It’s another myth, the myth of disruption. Disruption “works” in the sense of “succeeds” — within the structures we live in, you can make a lot of money doing it. Maybe that’s the typical Gen X thing- acting like exploiting what we already have is the supreme genius, and that trying to create something fundamentally different is the ultimate stupidity. In any event, Thiel also sought to “disrupt” politics. He took the same view of establishment politics as he did of the likes of Meg Whitman- Thiel may be pro-capitalism, but he hates most successful capitalists for being office creatures, not Randian entrepreneurial supermen like himself. There’s a conspiracy, you see, of intellectuals and administrators — the bad kind of nerds — to lord it over both normal people and, crucially, entrepreneurs and visionaries (good nerds, for those keeping score) through rules, regulations, and encouraging cultural values inimical to the people who (supposedly) create value. Thiel, and other Silicon Valley right-wingers like Balaji Srinivasan and Thiel’s court philosopher, Curtis “Mencius Moldbug” Yarvin, think they can disrupt this government/academia/corporate complex the same way Uber disrupted taxis. 

As it turns out, Thiel could do a lot in that vein, but not enough to satisfy. He could destroy Gawker for its cheek in covering him negatively (also, for violating his privacy in the matter of his sexuality — he was partially in the closet when Gawker publicly wrote about him being gay — but it seems clear he would have gone after them anyway). And he invested in Donald Trump’s political career back when everyone thought the alliance between the Silicon Valley giants and the Democratic Party would last forever. That’s one of his bigger “everyone thought he was crazy but he was right” moments. He celebrated the victory alongside his friend, openly racist blogger Moldbug Yarvin. 

It wasn’t really to be, though. Disrupt something big enough, and you can’t control it. Something the old hippie capitalists could have told Thiel- at times, you need to surrender control, blah blah surfing, etc etc taoism. Needless to say, Trump’s personal style and that of Thiel did not mesh. Thiel didn’t succeed in his big goal of appointing his people on to various regulatory boards, in order to “destroy the administrative state” or whatever, really stick it to those bad nerds. You have to wonder… does he really not notice how sickly the regulatory state was already? Maybe half a regulatory state makes people even madder than a real one… but in any event, Trump couldn’t do whatever it is Thiel wanted him to do. 

The world still irks Thiel. It makes sense, because the world still has the source of all of Peter Thiel’s troubles in it, in the form of Peter Thiel. He can’t understand that, though, so he has to pour everything into narcissistic fantasies: New Zealand bugout bunkers, seasteading, life extension. Thiel’s on record as saying that he sees death as the ultimate evil. Revealing my own personal biases, there are few postures I respect less than an exaggerated fear of natural death. Especially from someone, like Thiel, who quite clearly does not actually enjoy life! So yeah, uhh, this dude sucks. The way he sucks is interesting, somewhat. One funny thing about contemporary life: we’ve put so much power at in the hands of so few people, and have ensconced hierarchy and elitism so thoroughly in the structures of life, that there’s a certain extent to which a few key people really are crucial to the functioning of many key bodies, organizations, and movements. Get rid of Trump, Musk, Thiel, and it’s pretty clear there’s no replacement, not really- someone can take their offices, but not their mana. It’s not because they’re actually that smart, talented, or even charismatic. It’s just a function of how power works, now. You’d figure people would draw some obvious strategic conclusions from that… but that’s not Chafkin’s job, here. ****’