It’s rarely appropriate to open an interview by asking what the person at the other end of the line is wearing. Sure, you might conceivably pose that to Anna Wintour, not that you’re ever going to get to talk to her. Someone like Gucci’s Alessandro Michele would also be fair game. And it seems a reasonable enough question to ask Gary Shteyngart—but only because you know that he shares a fetish with Barry Cohen, the hedge-fund-manager protagonist of the Russian-American writer’s new book, Lake Success.

Watches. Very expensive watches.

“Today is a Rolex Air-King day,” Shteyngart relates, reached at home in New York City. “This is one of the very basic models, and I got it a couple of years ago, when I became obsessed with watches. This watch is very low-key, and in fact I wore it on the very long Greyhound trip that I took across the country when I was researching Lake Success, because it’s a watch that doesn’t pick up any attention. But it’s a very cute watch: very small, and suitable for my small wrists—as well as Barry’s small wrists.”

Watches, for the novelist, are “very melancholy objects”. “They hold the passing of time,” he explains, “and we’re not getting any more time with every second. So Barry’s obsession with watches is, I think, twofold. One is that he’s wasted some parts of his life, as many of us do. He’s not happy with how his childhood worked out, and he was hoping for the perfect wife, the perfect job, the perfect child, and none of that came to pass as well, so the watch is a constant reminder of that passing. But also, he desperately needs something to take his mind off things—which is why I got into watches. I got into watches when I realized Trump was going to win, and I needed something to read other than more election news. So for Barry as well as me, it’s a way to self-soothe, and to self-regulate.”

Mechanical panaceas don’t solve Cohen’s problems, however. When we meet the financier, he’s recently learned that his young child is deeply autistic, and his marriage is imploding. His fund, This Side of Capital, is about to collapse, thanks to a high-risk investment in a shady pharmaceutical business. His literary ambitions—note the F. Scott Fitzgerald reference in his company’s name—have long been in tatters. And his prized Universal Genève Tri-Compax no longer keeps accurate time, which, unbeknownst to Cohen, prefigures a deeper structural problem inside its mechanism.

Grabbing a forged passport, binning his high-end Visa card, and lighting out for the West Coast by bus seems like a reasonable choice.

With its explicit allusions to Fitzgerald, Ernest Hemingway, and Jack Kerouac, Lake Success is clearly Shteyngart’s take on the Great American Novel. Except that these days America is not so great, and Cohen, like his country, is both addled by greed and paralyzed by his loss of promise. Nonetheless, the book delivers both a fantastically picaresque ride through the underbelly of the USA and a savage critique of that country’s moral and economic decline.

Shteyngart also achieves a small miracle by making the entirely reprehensible Cohen an engaging, almost sympathetic character. “Everyone’s a human being on some level, and everyone goes through the same questions,” the author explains. “Why am I here? What’s going on? How do I relate to my own mortality and to the difficulties of raising a family?”

Those, he says, were among the issues that kept coming up when he was researching Lake Success, which required a lot of late-night drinking with bond traders and tech bros. “Over the years, some of them became very friendly with me, and I began to feel like I was their therapist, in a sense,” he explains. “The hedge-fund whisperer, if you will. I would take them out of their lives, which are often so boring and circumscribed, and many of them would drink quite a lot and open up at 2 or 3 in the morning, so there was a feeling of getting to know them. I wasn’t taking them on a Greyhound, but I was taking them on some kind of journey.”

And just as Shteyngart might have opened the eyes of some of his fellow Manhattanites, the other Americans he met on his cross-country bus trip offered revelations of their own, which might explain the streak of optimism that runs through the otherwise dark fable that is Lake Success.

“Lots of the people that I met were kind of on the up. There’s an ascendancy to a lot of people—a lot of first-generation people, people who have just moved to this country, especially from Latin America,” says the Leningrad-born Shteyngart, a first-generation American himself. “There was a kind of cynicism in hanging out with the hedge-funders, but there was sometimes a kind of buoyancy on the Greyhound. But there’s also a reality. There’s a line in the book where Barry says that on the Greyhound, people discuss where they went to jail the same way that people on the Acela [high-speed rail line] discuss where they went to law school. There was a feeling that there are better jails. So it was a kind of reality that a lot of people in my world don’t get, whether that world is writing or academia or TV. It’s very, very different.”

Gary Shteyngart opens the Cherie Smith JCC Jewish Book Festival at the Norman and Annette Rothstein Theatre on February 8. For more information, visit the festival's website.