How a tech star lost her way

WONDER BOY: Tony Hsieh, Zappos and the myth of happiness in Silicon Valley, Through Angel Au-Yeung and David Jeans

A few chapters into “Wonder Boy”, Tony Hsieh sells his first company to Microsoft for $265 million. At 24 years old, he is fabulously wealthy and one of the rising stars in the tech firmament. But he is inexplicably sad – suddenly realizing that what he has is not enough.

So he sits down to write a list of the happiest periods in his life. “Connecting with a friend and talking all night until the sun came up made me happy,” he writes. “High school trick-or-treating with a group of my best friends made me happy.”

If this moment in Hsieh’s story is filled with fear, it’s because we know how the story of this man who valued friendship so much ends.

He died in appalling conditions. At age 46, traveling with a crowd of personal assistants and hangers-on, he locked himself in a friend’s storage shed and asked an employee to bring him nitrous oxide, marijuana, a lighter, pizza, and candles. The assistant did as he was told, and Hsieh, drunk, lit a fire. Lying on the icy ground on a dirty blanket, he suffered from smoke inhalation that would kill him.

Hsieh was a public figure — lauded for his leadership of Zappos, the online shoe retailer — and much of his story appeared in the press as it unfolded. “Wonder Boy,” written by journalists Angel Au-Yeung and David Jeans, tells it from start to finish. It’s a poignant, uncomfortable read. One wants to identify the moment when Hsieh’s life took a turn. Was it when he got so rich he never had to work again? When he was introduced to ketamine? When the last of his friends were replaced by employees?

At its core, this is a story about addiction. The child of Taiwanese immigrants, Hsieh spent his early years under extraordinary pressure to succeed. It wasn’t until he got to Harvard that he fell into a close circle of friends, enjoying a warm glow of belonging that he would spend the rest of his life trying to recreate. In his twenties, partying got wrapped up in his work persona. The San Francisco rave scene introduced him to club drugs like MDMA; and Burning Man, ill-fated, to ketamine.

However, Au-Yeung and Jeans, who covered Hsieh’s death for Forbes magazine, want to tell another story about the dark side of the tech boom. There’s something about this. In the 1990s, investors liked that their founders were risk takers, a bit extreme. In those days the brilliant, off-the-wall founder used to be the brand, which held panel discussions for an audience of MBAs and plutocrats who led much more cautious lives.

Hsieh certainly fit the bill. He threw grandiose ideas like sparks and scribbled them on sticky notes as his subordinates scrambled to keep up. He threw himself into a study of the science of happiness, an idea that had taken root in Harvard’s psychology department, and looked for ways to develop it. In his 30s, he announced a $350 million project to turn a corner of Las Vegas into an engineering utopia, and persuaded friends to move with him to an urban commune of sorts, a collection of Airstream trailers on a vacant lot, where the nights ended with campfires and jam sessions.

But there was a flaw in Hsieh’s social engineering: he was trying to create community by dividing money into giant blobs. As he got older, his friends got younger and less able to say no to him. His drug use, once confined to festivals, came into focus. In 2020, Hsieh was snorting between three and five grams of ketamine daily, the authors say. He lost weight and barely slept.

During his final months, Hsieh’s behavior became increasingly paranoid and bizarre. He demanded taps be turned on so he could hear the sound of water; he wrote on the walls; he lit dozens of candles. He hired court reporters to stand around and transcribe the conversations between housemates.

Friends and family tried to intervene, but his aides found ways to avert them. After a visit in August, his friend Jewel, the singer-songwriter, wrote him a stern letter warning him that “if you look around and realize everyone around you is on your payroll, you’re in trouble .” But it was too late. He was dead by Christmas.

Why didn’t anyone force Hsieh into treatment? Au-Yeung and Jeans did a real service by trying to find out by interviewing many of his inner circle. Their writing is frustratingly clumsy, like it was written in a hurry. But the material is compelling, with the rising tension of disaster in slow motion. The final chapters, which document a series of interventions that went nowhere, are riveting.

The account of the past few months has come almost entirely from anonymous sources, presumably the same friends who were there to watch him spiral. Hsieh’s family didn’t participate in the project, and one wonders how their perspective would have changed the story. Journalists tend to lean towards their most helpful sources, and this seems to have happened here. Ultimately, the authors hold no one responsible.

“What emerged from the hundreds of hours of interviews we conducted with people who witnessed Tony’s descent was that there were no heroes or villains,” they write. “Some well-meaning actors gave in to the temptations of greed, while supposed bad actors had complicated histories that gave context to their roles.”

They routinely come to a conclusion worthy of a TED Talk: that Hsieh was doomed because happiness is an intrinsically unattainable goal. He thought “he could build his way to happiness,” they write. “He kept building and acquiring until finally he had everything in the world – and it still wasn’t enough.”

This is an unsatisfactory ending, given the evidence they’ve given in the preceding pages.

We live in a society where people in crisis are often left to deteriorate, though rarely in such a visible and florid way. The reason for unpacking these tragedies is to try to get better, to close the gaps. Our culture gives elites a free pass for substance abuse. Our laws make it difficult to treat people without their consent. When wealthy celebrities break up, they don’t need sycophants. It’s an ugly story. There’s plenty of guilt to go around.

Ellen Barry treats mental health for The Times.