May 19, 2024

Why Is This Man Smiling?

TONY HSIEH, chief executive of, the online shoe and clothing retailer, was sitting in an office he rarely uses at the company’s headquarters here, recollecting the high and low points of his childhood. He had just finished putting a roomful of corporate managers through the same exercise, and now it was Mr. Hsieh’s turn.

After pondering for a long moment, Mr. Hsieh, who sold Zappos to for more than $1 billion in 2009 and whose book, “Delivering Happiness: A Path to Profits, Passion and Purpose,” spent 27 weeks on the New York Times best-seller list last year, identified the high as a Halloween night in middle school, when a group of trick-or-treating friends ended up at his family’s home.

The low point: missing the last dance of eighth grade because he was taking an SAT test the next morning. “I remember being pretty disappointed,” he recalled.

Mr. Hsieh, 37, seems in some ways to have spent his career trying to recreate that Halloween night while salving the wounds left by that missed dance.

So there he was on a balmy midwinter night, hosting a party at his suburban Las Vegas home for a group of managers and would-be entrepreneurs who had paid $4,000 each to be marinated in Zappos’s wacky, free-to-be-me ethos for the company’s two-day Culture Boot Camp. Mr. Hsieh circulated discreetly in a Zappos hoodie sweatshirt, jeans and black Donald J. Pliner slip-ons, wandering among the living room, with its enormous flat-panel television and custom-built scooter rack, a room done up like a hookah bar, and the back patio, where a shimmering pool was surrounded by Miami Beach-style beds.

The festivities were in keeping with Mr. Hsieh’s ongoing campaign to build his community, or, as he frequently writes in his book, his “tribe.” In the Zappos offices, costume parades are commonplace, as employees wind among cubicles plastered with posters and mementos that give the headquarters a teenage aesthetic. Zappos recruits talk breathlessly of the Fourth of July barbecues and New Year’s Eve parties that Mr. Hsieh hosts every year at his home. And although he lives alone, an assortment of friends, business associates and people he’s met on book tours keep his five guestrooms in heavy use.

Unlike fellow Harvardian Mark Zuckerberg, Mr. Hsieh (pronounced shay) is not yet a household name, even among the legions of customers who delight in Zappos’s large selection, free shipping and free returns. There is not yet a movie cribbing his rise to dot-com success. But he has become a celebrity in entrepreneurial circles, having sold his first company, LinkExchange, to Microsoft for $265 million when he was just 24, and for turning Zappos into the largest seller of shoes online.

His profile is also growing: He appeared as a judge on “Celebrity Apprentice” two years ago, he has 1.8 million followers on Twitter (One recent post: “Swam in Silverton mermaid aquarium on my birthday! Wore costume b/c they don’t allow birthday suits.”/) and his book appeals to a broad swath of teachers, students, parents and even dating gurus who see in it a broader message of self-improvement. The Culture Boot Camp drew a mix of entrepreneurs and managers eager to meet Mr. Hsieh, including the head of retail operations for the Marine Corps and a church youth-group consultant.

NOW, Mr. Hsieh is hoping to spread his vision to downtown Las Vegas, where Zappos recently announced it would be moving its headquarters to the former City Hall. In an unglitzy area of the city rarely seen by casino-bound tourists, Mr. Hsieh envisions, among other things, a zipline connecting bars, clubs and the Zappos offices.

Reading “Delivering Happiness,” one could get the impression of Mr. Hsieh as a gung-ho Michael Scott type (if he had actually motivated his employees on “The Office”). He misquotes from his favorite movie, “Pretty Woman” (“I was living the fairy tale,” his version of “I want the fairy tale”), describes elaborate office pranks, and urges companies to “make WOW a verb.”

Yet in person, Mr. Hsieh, who has close-cropped black hair, speaks quietly and with little inflection. In a group, he calls little attention to himself, and often lingers on the sidelines. “He draws energy from people,” said Alfred Lin, a Harvard classmate of Mr. Hsieh’s who was Zappos’s chief financial officer until last year. “But he’s not an overtly ‘Hey, I’m the center of the party’ kind of guy.’ ”

At times, Mr. Hsieh comes across as an alien who has studied human beings in order to live among them. That can intimidate those who are not accustomed to his watchful style. “I have been in job interviews with him where you are expecting more, and it can be awkward silences,” said Ned Farra, who manages relationships with other Web sites for Zappos. “He is not afraid of it. It is almost like he is testing you.”

Mr. Hsieh said that he surrounds himself with people who are more outgoing than he is, in part to draw himself out. “My view is that I am more of a mirror of who I am around,” he said. “So if I am around an introverted person that is really awkward. But if I am around an extroverted person I will be whoever they are times point-5.”

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