The tech mogul presents the same biographical problem as the professional gambler. Once you get past all the wealth, the erratic habits, and the self-mythologizing, how does a responsible author account for the subject’s success? Earlier in my career, I wrote quite a bit about the poker world, and after a while I came to the realization that, for the vast majority of so-called geniuses, there wasn’t some magical system that allowed them to print money at casinos or sports books. Most of them, it turned out, were far more broke than they let on. But what really separated all the losers from those who had been able to amass a large fortune was a whole lot of lucky breaks in a row.
The same, of course, could be said about all business biographies: nearly every story of fortune comes down to luck and timing. But at least Lee Iacocca, for instance, had a Ford Mustang to show for his efforts, and a spate of competitors who did, in fact, need to be vanquished. The speed with which tech giants make their fortunes, the seemingly arbitrary distinctions between competing startups, and the mostly ephemeral and debatably useless nature of many of their products make the typical tech success story a lot harder to tell—at least in any honest way. The logic of the standard biography—a formative event leads to an epiphany that creates the great man—doesn’t quite work when the greatness doesn’t have much to do with the man at all.
“Wonder Boy,” a new biography about Tony Hsieh, the entrepreneur behind Zappos, makes clear that its subject was a relatively unremarkable high achiever. Hsieh, who died in a fire in a Connecticut suburb in 2020, after years of rampant drug abuse and erratic behavior, grew up in a middle-class part of Marin County, in a neighborhood without too many Asian American families. He went from there into the exclusive Branson School, where he was around wealthier kids. The authors, Angel Au-Yeung and David Jeans, gesture, sometimes forcefully, at Hsieh’s Chinese American heritage, and point out, in the prologue, that Au-Yeung (who was “born to Chinese parents who fled the turmoil of communism and gave up everything for her and her two sisters to move to the United States”) felt a “deep understanding of the stereotypes that are often placed on Asian Americans, and what it takes—and costs—to break those assumptions.” But, though it’s clear that Hsieh’s parents might have had some tiger streaks in them, there wasn’t anything exceptional about the way they raised him. Nor does Hsieh’s time at Harvard prove to be particularly illuminating: he, like many annoying undergraduates there, tested out his entrepreneurial chops in his dorm room, in his case by starting a failed pizza operation with money borrowed from his friend’s wealthy mom. Later, when it came time to find seed money for one of his first tech ventures, he got two hundred thousand dollars from the same source.
Rather than fixate on these types of details, “Wonder Boy” opts to tell a psychological and personal tale of a young Asian American man who had all the talent and vision in the world, but found himself unsatisfied and increasingly dependent on booze and drugs. After making thirty-two million dollars from the sale of his first company, an online ad-sales platform called LinkExchange, Hsieh made good on a bet that he had made with his friends at college: if he became a millionaire within ten years of graduation, he owed them all a trip to the Caribbean. “While surrounded by friends in the Bahamas as a newly minted millionaire, Tony felt a sense of melancholy,” Au-Yeung and Jeans write. “What’s next? What is happiness? What am I working toward? he wondered.”
The question of whether money can buy happiness recurs throughout “Wonder Boy”—a fair thing to ask, given the nature of Hsieh’s death. (A few months after he died, the New York Times reported that Hsieh purposely locked himself in a storage shed “moments before it was consumed by the fire that would kill him.”) But it’s also a narrative choice that sets us up to expect a bit more: surely the tortured visionary was crushed by an uncaring world, or a love interest, or another clichéd antagonist. Hsieh, in his early years, came up short of that type of drama. Instead, he did what a lot of young people were doing in the late nineties, regardless of whether they had ridden the dot-com boom to millions of dollars or not: he went to raves, speculated on some domain names, did some day trading, played poker, and hung around with his friends.
Zappos, the company that ultimately made Hsieh famous, wasn’t his idea. A man named Nick Swinwurm had come to Hsieh asking him to invest in a startup that Swinmurn called shoesite.com. This is pretty standard fare in Silicon Valley—Steve Jobs didn’t invent the iPod, Elon Musk didn’t design the first Tesla—but there’s usually a moment when the “founder” comes up with some innovation or solution that transforms an idea into a gigantic, distinct, and scalable business. For Hsieh, this moment came when he and one of Zappos’s early workers decided to focus entirely on the customer experience. This decision prompted the company’s move to suburban Las Vegas, where they could find workers who had years of experience in hospitality and customer service.
Hsieh’s Vegas years, according to Au-Yeung and Jeans, were filled with booze and a type of academically approved self-help that centered around studies of happiness. Hsieh became obsessed with the question of company culture and wrote a book, “Delivering Happiness,” which resulted in a lengthy press tour and a borderline-fraudulent stay at the top of the best-seller list (Hsieh contracted out a company to buy large quantities of the book to boost sales), and which touted his four principles. To be truly happy, Hsieh believed that a person must possess “perceived control of one’s destiny, perceived perception of progress, connectedness with others, and being a part of something bigger than yourself.” To put these principles in action, Hsieh did things like splitting a single promotion into three micro promotions, so that a Zappos employee would feel more of a sense of progress, even if the net result was the same as just getting promoted once.
It doesn’t take a raving anti-corporatist to point out how silly, trite, and manipulative all this sounds. Over time, Hsieh’s interest in junk psychology extended beyond happiness and into even stupider realms. He became obsessed with Neil Strauss’s “The Game,” the infamous guide for so-called pickup artists which taught men how to manipulate women via techniques like “negging” and “peacocking.” When Hsieh ultimately embarked on an ambitious project to revitalize downtown Las Vegas and turn it into a new tech hub, he boasted to a reporter about how he had used methods from “The Game” in selling his vision for the city to potential investors.
Au-Yeung and Jeans present all this information without much commentary. Although their book has considerable strengths—exceptional reporting, for one—what it lacks is a compelling central theory about its subject. The authors portray Hsieh as a narcissist and an addict who tossed around half-baked ideas and rarely saw them through, leaving everyone else to pick up the pieces. That certainly seems true. But the structure of the book, which lays out a series of side characters, mostly former employees, who got drawn into Hsieh’s gravitational pull, feels as if Hsieh is being overheard rather than interrogated. In a recent interview, Au-Yeung and Jeans were asked what they wanted the takeaway from their book to be. “I feel like my answer for that question changes every time someone asks,” Au-Yeung responded. She then urged the public to be a “little kinder with our words” while judging these tragic founder figures, and to remember that “these people are also humans.”
The journalist’s need to humanize everything in sight can be useful, even revelatory, but it can also obscure. Hsieh, in the end, was a rich guy who, early in his career, used his Harvard connections and some seed money to buy a series of lotto tickets in the tech boom, and then used his expanding wealth and influence to spread a bunch of marketing, in the form of pseudo-psychology, into the world. He slept with his employees and terrorized his closest friends. His descent into addiction and his untimely death were certainly tragic, but I couldn’t find much to admire about Hsieh in “Wonder Boy,” nor did I understand why I was reading dozens of meticulously reported, almost snuff-film-like pages about his journey into ketamine addiction and mania. None of this means that “Wonder Boy” is a bad or dull book—on the contrary, it should be mandatory reading for anyone who is interested in big tech. But it did not give much of an answer to the question of how and why so much of the press and the public got suckered in by Hsieh’s generation of tech evangelists. 
Tony Hsieh and the Emptiness of the Tech-Mogul Myth
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