Wonder Boy: Tony Hsieh, Zappos, and the Myth of Happiness in Silicon Valley by Angel Au-Yeung and David Jeans

When Tony Hsieh, the founder of the online shoe empire Zappos, was a child, he wrote a poem. He placed his words within a drawing of a lurking, menacing octopus with “large, soulless eyes.”

“I am running down my street … a slimy smiling octopus is chasing me,” he wrote. “I try to climb a brown wooden wall. I keep slipping. No one is around to help me.”

His childhood poem would later seem chillingly prescient, as Angel Au-Yeung and David Jeans write in their new book, Wonder Boy: Tony Hsieh, Zappos, and the Myth of Happiness in Silicon Valley. Hsieh died in November 2020 from smoke asphyxiation, alone in the pandemic fall in a freezing shed, surrounded by empty canisters of laughing gas, a locked door, whether locked accidentally or on purpose no one will ever know, preventing anyone from saving him from the fire that killed him. He was 46.

The contrast between the image Hsieh presented and the tragic final years of his life is stark. Hsieh, an entrepreneur best known for starting the online shoe retailer Zappos, was a brilliant maverick, an odd mix of socially awkward and obsessed with human connectivity, of conventional achievement and total nonconformity. He was so talented that he could have done anything.

Hsieh in 2008, the year before he sold Zappos to Amazon for roughly $1.2 billion.

In the first dot-com boom, he founded a company called LinkExchange, which was a pioneer in the business of online advertising. By age 25, Hsieh’s stake in the company was worth $32 million, after Microsoft purchased his company. He parlayed it all into Zappos, selling everything he owned in order to fund the company through the collapse of the dot-com bubble in the early 2000s.

In 2009, he sold Zappos to Amazon for roughly $1.2 billion, and put $350 million of his fortune into rebuilding the decrepit part of Las Vegas known as Fremont East, which Hsieh had gotten to know after he’d moved Zappos from expensive San Francisco to Henderson, Nevada. Followers and dreamers and would-be acolytes flocked to join what was called the Downtown Project. When he died, everyone from Bill Clinton to Jeff Bezos offered tributes.

The style of management Hsieh pioneered at Zappos was all about one word: “happy.” In his autobiography, Delivering Happiness: A Path to Profits, Passion, and Purpose, Hsieh laid out a “revolutionary way to run corporations—by focusing on your employees and ensuring they are happy, you’ll have happy customers, and then your profits will soar.”

This was a direct result of his own personal obsession with the science of happiness. He seemed to believe, as the authors write, that “this ephemeral state of mind was an end output that could be achieved only with a source code”—and that he could find that source code if he thought hard enough and experimented broadly enough. But the authors also note, “When Tony’s obsession with happiness began, few had the foresight to ask: what was he looking for?”

Under the shiny surface, it was always all falling apart. Even on the Delivering Happiness bus tour, the superficial “embodiment of joy” masked misery, discontent, and squabbling. The Downtown Project was marred by suicides and business failures. Hsieh’s alcohol problems became drug problems, and begat a state of delusion. His final year was spent in mansions that looked lavish on the outside but had been trashed, with “feces on the ground, plants in his toilets, rotten food under the bed.”

The dichotomy between outside and inside was a metaphor for his life. As the end neared, “it was hard to ignore that his outlandish ideas, once seen as the musings of a contrarian thinker, could now be interpreted as symptoms of psychosis,” the authors write.

Wonder Boy is a compelling and tragic story, but it’s also more than that. The authors pose questions that reverberate beyond Hsieh’s life. Are entrepreneurs more subject to mental-health problems than the average population? They note a study saying that 49 percent of entrepreneurs reported having one or more mental-health conditions in their lifetime, compared to 32 percent of non-entrepreneurs, with twice as much depression as the regular population.

Hsieh at his desk at the Zappos headquarters, in Henderson, Nevada, in 2011.

Another question: Why didn’t anyone save Hsieh? The easy answer, and maybe the right one, is that he increasingly surrounded himself with people who were taking his money and said only yes to him, whether it was yes to wild ideas or yes to alcohol and drugs. “Rather than pushing people to chase their dreams, Tony had used his wealth to goad compliance,” they write.

But Au Yeung and Jeans push further into the vagaries of human nature. They note that “there were no heroes or villains” in Hsieh’s story. Maybe those who surrounded him in his final year, including his brother Andy, were just cynically scavenging what they could. But some may have believed they could do more good by staying than by being exiled—the fate of those who challenged Hsieh. Some may have still believed the myth. “After all, he was the Tony Hsieh,” the authors write. “Surely he could handle himself.”

An exception to the “no hero” rule might be the singer Jewel, who warned Hsieh that “the people you are surrounding yourself with are either ignorant or willing to be complicit in you killing yourself.” And a clear villain is a longtime assistant named Mimi Pham, who after living off of Hsieh and milking him for tens of millions of dollars still had the amorality necessary to file a lawsuit against his estate and his family after his death, claiming she was owed at least $130 million.

And then there’s the central question that Hsieh’s life raises about happiness. We probably knew that great wealth doesn’t buy happiness, and that alcohol and drugs as a path to enlightenment doesn’t work, either. But nor does applying your own great brain to the study of happiness get you to that maybe-mythical state.

Or maybe, by convincing Hsieh that happiness could be permanent and omnipresent, it did the opposite. “With happiness as the goal,” the authors write, “Tony eventually found himself running on a hedonic treadmill, perpetually in search of something that couldn’t be sustained.”

Bethany McLean is a journalist and the author of several books, including The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron (co-authored with Peter Elkind) and, most recently, Saudi America: The Truth About Fracking and How It’s Changing the World