A Few Bookish Questions With Max Chafkin

I so enjoyed this interview with Max that I wanted to send it as a separate email rather than just adding it onto the end of the Friday newsletter, something I’ll be doing more often here in 2022.

I’ve also made these author interviews a separate category on Substack. If you’re not interested in receiving emails about interviews, you can adjust the settings in your Substack account. Go to readmorebooks.substack.com, navigate to “My Account” at the top right, and check/uncheck “Email Notifications” as desired. (Here’s a screenshot of that page.)

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On Friday, I reviewed Max Chafkin’s The Contrarian, the gripping, sometimes shocking story of Peter Thiel’s impact on Silicon Valley and the world at large. I highly recommend it for anyone interested in tech and modern politics/power. Make sure to follow Max on Twitter too.

1. Your book adds to the growing list of Silicon Valley founder/founding stories. It's a niche I'm somewhat obsessed with. In your opinion, what are a few of the essential Silicon Valley reads? The books that best encapsulate why those few square miles hold so much of the world's power?

This is maybe a self-serving observation, but I think that the story of how Silicon Valley went from being an economic sideshow to become the economic and cultural center of the world is arguably the most important one of our lifetime. So much about the way our lives are changing is explained by that story, and the world of tech has supplied journalists (readers too) with just an endless supply of narratives and big personalities.

A good starting point is Margaret O'Mara's The Code, a comprehensive history that will give outsiders a great overview of how we got here, but that is sophisticated enough to complicate an insider's understanding of what makes the Valley special. (O'Mara's provocative thesis is that libertarian, apolitical Silicon Valley is in many ways a creation of the U.S. government.)

Everyone should read Ashlee Vance's Elon Musk biography and Brad Stone's two books about Amazon. A lot of people probably have read Walter Isaacson's Steve Jobs, which is rightly beloved, but I'd argue that the best portrait of Silicon Valley's most famous founder is actually Lisa Brennan-Jobs's Small Fry, a memoir by Jobs's estranged daughter that doubles as a love letter to him—as well as a searing indictment.

Though the book is two decades old, I find myself coming back repeatedly to Michael Lewis's The New New Thing: A Silicon Valley Story. On some selfish and competitive level, I find it annoying that this slight book from 1999, which covers the efforts of a long forgotten Silicon Valley executive Jim Cark to create an awesome computerized yacht, is such an enduring portrait of both tech optimism and tech culture. But it is.

2. The Contrarian is your first book — congrats! Are there books/writers that have particularly influenced your own approach to journalism, writing, and storytelling?

It's a cliche to mention Michael Lewis, I guess, but it's pretty hard to be a business journalist and not be influenced by him. Moneyball and Liar's Poker were two of the first business books I read. What's great about Lewis, what he understood, is that the point of writing about business isn't to better understand business—it's to understand the world.

So you think you know something about baseball, and then you read Moneyball and realize that in fact, you were missing half the story—maybe more than half. And a lot of domains of life are like that. Money is mysterious, and a lot of Very Serious Writers find business beneath them; but money makes the world work and it's a domain for many of the great human dramas. That of course created an opportunity for Lewis and anybody else who writes seriously about the topic with empathy and curiosity.

I've been a magazine writer all my career and that style of writing has shaped me, probably more than anything. One thing about working in magazines is that they make you ruthlessly unsentimental about your words. I find myself gravitating especially to the work of writers who seem to self-consciously embrace this—writing unmannered prose that, in getting out of its own way, soars to emotional heights that even the showiest writers struggle with. Right now I'm particularly enamored of Patrick Radden Keefe, who I think is the master of this style (see especially this remarkable New Yorker piece about a mass shooting) and who has written two of my favorite non-fiction books of the past few years, Say Nothing and Empire of Pain. 

3. How did you decide to tackle the complicated story of Peter Thiel? It takes a lot of courage, frankly. This is a guy who obviously revels in revenge. There are a lot of other founders you could've written about — who haven't bankrupt journalists. 

Are there though? I mean, sure, I guess there are other people to write in tech about but the lack of a serious Thiel book seemed like a gaping hole in our understanding of tech and power--and of course an opportunity. I'd written about him a few times over the years, and sort of got serious about the idea of taking a close look at Thiel after covering his endorsement of Trump at the 2016 RNC. The book grew out of that story and a series of conversations with my agent, Ethan Bassoff.

The thing that originally drew me to Thiel were the personal contradictions: Here's a gay, futurist immigrant, backing a reactionary anti-immigrant presidential candidate; here's a guy who helped create Silicon Valley as it exists today, who, for some reason, had turned critic and was beginning to take on the same industry. I also found myself interested in the dueling narratives about Thiel. His fans consider him this Ayn Rand-style superhero; the left sees him as a right wing techno supervillain. There's truth in both of those narratives, but neither is true--and it occurred to me that would create an opportunity for me to complicate everyone's understanding of this man.

It's kind of odd to admit, but I didn't really think too much about about courage it would require to do a book on Thiel until after I started writing. But of course, at that point, I thought about it a lot. Thiel's takedown of Gawker, I think, was deliberately designed to create a chilling effect on both journalists and sources—and any reporter who tries to write about him will inevitably face additional scrutiny from editors (and newsroom lawyers) who on some level would rather not deal with the hassle of covering about a potentially litigious person.

So I worried: I have three young children, and didn't want to put my the financial security of my wife and kids at risk because I wanted to write a book about tech power. But ultimately I decided that, if the whole point of the Gawker takedown was to create a chilling effect, I could combat that by simply deciding not to be afraid, and second, by just approaching the subject with the same rigor and fairness I'd bring to any story. That may have been more of a coping mechanism, than a strategy, but I think it worked.

4. Beyond Thiel himself, your book is very much about modern America as a whole — how politics and technology and nationalism have become so intertwined. Are there books you'd recommend about how America got to where we are today? (I noticed a George Packer shoutout in your acknowledgments; his writing is just... *chef's kiss*.) 

I love Packer's work and I wanted to acknowledge him because he had written what I think had been the definitive portrait of Thiel (a New Yorker profile, that was adapted to be part of his book, The Unwinding). I don't agree with the entirety of Packer's analysis. Like many people who obviously admire Thiel, he seemed unwilling to really take a hard look at the extreme parts of Thiel's ideology—but the profile was exceedingly well done and it informed my understanding of Thiel. I'm also a huge fan of Rick Perlstein's books about the rise of the New Right; I especially loved Nixonland.

5. I assume most of your reading is in the non-fiction realm: interviews, background material, quarterly reports, etc. What do you read in your "off" hours (if those hours exist)? Any authors or subjects you can't resist?

Like many people, I suppose, I've been obsessed with the pandemic, and devour pretty much everything that is produced on Covid, vaccines, and viruses generally. I listen, semi-obsessively to a talky (and super nerdy) podcast, This Week In Virology, in which a group of academic virologists talk about the latest research. Most everyone to whom I've recommended it finds it deadly boring. I love it.

The book I've recommended the most to people in light of all this actually isn't about Covid; it's David France's How to Survive a Plague. France covers both the activism that ultimately led to the discovery of treatments for HIV—and tells a beautiful, heartbreaking story about the young men who confronted the AIDS epidemic, and who somehow, miraculously survived it. It's not science journalism, really, and yet it’s one of the best things I've ever read about medicine and drug development. I found it mind-expanding in so many ways, and also, just unbelievably hopeful, especially over the past two years.

6. What are you reading and enjoying right now? What’s next on your list?

One amazing thing about having children is having a reasonable excuse to read children's literature that you somehow missed. We just read Charlotte's Web, and then immediately started reading it again. It is such a perfect little book.

I just read American Prometheus, the biography of Robert Oppenheimer, which is wonderful and also kind of a cool sideways look at the history of technology.

Right now I'm reading The Firm, which is Duff McDonald's history of McKinsey, the management consultancy. That maybe sounds dull, but I've found it to be a totally engrossing and hilarious look at one of the strangest institutions that has shaped American power. McDonald presents the firm as this modern day priesthood—complete with sacred texts and special clothing (no argyle socks!)—which I think gets at why McKinsey has been so successful and influential, but also hints at its essentially shallow quality. They are, on some level, gigantic phonies.

7. Are there books you find yourself referencing, thinking about, and/or recommending over and over again? Basically, do you have any all-time favorites that have shaped your life and your thinking?

I read a lot of Russian literature in college, and I still go back to War and Peace. Tolstoy is such a master of human emotion, and the book probably tells you everything you need to know about love, loss, ambition, and history.

I think about The Great Gatsby a lot too—partly because I go running a few times a week in the wonderful park that was the dump that Fitzgerald called the "Valley of Ashes," and partly because I see parallels between Thiel and Gatsby.  Thiel is, like Gatsby, this quintessentially American hero: He is self-created in every sense, mysterious, and, of course, fabulously rich--and yet there's always a question of what is below that irresistible exterior. Is there anything?

I'm going to continue to be utterly predictable and mention Robert Caro's The Power Broker. If you grew up in or around New York City, like I did, the book has a special resonance, but it's also just a remarkable character study that doubles as the definitive study of power itself. While I drive over the Triborough Bridge, I feel Robert Moses's presence—that is such an achievement, both on Moses's part and Caro's.

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Thanks so much for reading!

-Jeremy