Icebreakers with...author Michael Lewis

Before Michael Lewis became a bestselling author of books like The Big Short and Moneyball, he was a young bond salesman making boatloads of money on Wall Street in its most culturally ogled era—the 1980s. He eventually left his job to write about the fratty, excessive finance-world behavior he bore witness to in the book that launched his career, Liar’s Poker.

“Never before have so many unskilled 24-year-olds made so much money in so little time,” Lewis wrote in the book’s preface. More than 30 years after its publication, Liar’s Poker has a new unabridged audiobook and a five-episode companion podcast called “Other People’s Money.” Morning Brew spoke over the phone with Lewis about Wall Street, sports, and his writing philosophy.

A lot of your work focuses on smart, capable people operating in bad, compromised systems. How do you invest yourself in those stories and struggles without pulling all your hair out or becoming disillusioned?

[Laughs] Well, you know, I don’t exactly think of my work that way. But that doesn’t mean it isn't that way. It’s true that some of the books are just that: a person in the system trying to understand or fix or change the system. To me, I think in every case—I mean even the pandemic, which was like, talk about pull your hair out—I think I find the characters so exhilarating that my focus tends to be on them. My emotional energy is in them. So I’m not sitting there thinking, oh how depressing the world is. I’m thinking: Jesus, how much fun it is to write about this person. And so yes, this person is in a mess, and this person might be tearing their hair out, but I’m not because I’ve been handed this pot of gold in the form of a character in a situation that I know I can really make something of on the page. So I guess I’m distracted by the joy of the things I’m writing about. And I’d say that that must be kind of important, because I can’t imagine writing anything book-length about people who don’t make me feel that way. Like, people who I thought were awful or evil or whatever, I think that I wouldn’t be able to do it. Because I think what sustains me is the pleasure of the characters.

When Liar’s Poker was originally published, you thought you were capturing excess we’d never see again. What’s it like to see what’s happening now?

Well, it really was true that when I sat down to write the book, I thought: I better get this down, because nothing like this will ever happen again. And it was very personal—it was insane that people were giving me huge sums of money to give financial advice. I knew what it was worth. So I just knew how out of whack the capitalist system had gotten—it was not paying people what they were worth, and I was the prime example.

And so I look around now, and I think we’re getting to a point where it feels like parody. It feels like with cryptocurrency, with NFTs, with memestocks, you have the little people almost performing a satire of what the big people have been doing. It's this arbitrary bestowing of wealth on people for no particular reason. Because, you know, I happened to be given a bitcoin wallet six years ago, or you got into GameStop, or whatever it is. So I do feel like I’ve been watching—not the system ever reform itself—but instead just becoming more and more itself, more and more extreme. And I keep waiting for the moment where people say, “Oh, this whole financialization of our lives and our economy—it's gotten a little out of hand.” It really hasn’t happened. The financial sector has just gotten more and more important, and not just as a percentage of activity in the economy, but also in the imagination of people.

What has it been like to revisit your first big piece of writing (Liar’s Poker)? Do you critique your past self?

It felt a bit like watching home videos from your awkward teenage years. Sure, it’s me—and I’m not a self-loathing person—but God, can we just keep this away from the eyes of people? It’s kind of like, oh, I forgot how many pimples I had and how awkward I was and how much funnier I thought I was than I was. It felt adolescent. I can remember a very big-time New York agent who I somehow got the manuscript to, writing me a curt note saying he wasn’t going to represent it because it was so callow. And I thought, well callow’s all I got.

So at the same time it was cringeworthy, there was also a charm to seeing this innocence. Until I read this thing two months ago for the audiobook, I had not reread the book—I just don’t reread my things. It was striking how much I had to learn. It was also striking how great the material I had was. I mean, I got it illicitly, but what material. It’s hard to imagine even someone who violates their nondisclosure agreement now, and writes an inside story. Because the places have gotten so careful about who knows what, and so balkanized. And I kind of marched around the firm and had a full worm’s eye view of the whole place. So that was striking.

Having written extensively about athletes and coaches, who’s someone you’re in awe of right now in sports?

What Steve Kerr has done with the Golden State Warriors, I don’t understand it, but they weren’t supposed to be anything like what they are. He gets people to buy in, when they don’t actually have to buy in, and the whole world is screaming at them, “Watch out for yourself.” I think it’s a model for how a modern manager has to behave in a world where he really has no control over his employees. [Kerr]’s modeling something there that would be very useful for lots of people in positions of authority to pay attention to.

Speaking of sports, do you have any writing superstitions?

When I played sports I would try to notice [superstitions] early and prevent them from taking root. It’s like weeding your psychological garden. And I’m naturally kind of superstitious. So I do notice it trying to creep into my writing life. Like, for example, getting wedded to a particular laptop. Or getting wedded to the idea I have to write in a certain place. And so I try to break it up, so that I don't allow myself to ever fall into such a routine that the routine becomes a crutch. There are still things I do that make it easier for me to write. Like I stick on headphones and listen to music while I'm writing.

What’s your go-to writing music?

My oldest child, my daughter, sends me playlists and I pluck stuff off if it seems like it’s not gonna cause me to think in any way. And it tends to be kind of poppy music, it’s not art. Well, some of it is, that’s not fair—it’s accidental if it’s art. But it’s a playlist that I change up between books. But basically, it’s the same song over and over.

What’s the last great book you read?

Ada Ferrer’s new book, Cuba: An American History.

This interview has been edited and condensed for clarity.