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MIAMI BEACH, Fla. — It’s Friday night in South Beach and the party is just getting started at Plunge, the trendy poolside lounge atop the Gansevoort Hotel. As the sun sets and weekend revelers roll in, Tony Hsieh hands out vodka drinks on the makeshift set where he’s about to go live for a “virtual” happy hour.
The early May gathering is part of a weekly series leading up to next week’s debut of the Zappos.com CEO’s first book, “Delivering Happiness: A Path to Profits, Passion and Purpose.”
Hsieh sits down beside Jenn Lim — his “backup brain” and best friend — in front of a bank of laptops they are using to stream the event to thousands of fans logging in at home. Throughout the hour, the pair is joined by several friends who talk about their own pursuits of happiness, as well as surprise visitors, including one from the local zoo.
“Last guest at Happy Hour was ... a kangaroo! Yes, we said a kangaroo,” tweets a member of Hsieh’s onsite book team.
The virtual event seems like the perfect marketing strategy for an entrepreneur who has built an online powerhouse and racked up nearly 1.7 million followers on Twitter.
“The happy hours are a way to reach out for the book,” Hsieh said, “but also, we’re just having fun.”
Having fun has always been at the top of the CEO’s agenda, especially at Zappos, where the primary mission is to foster culture and keep employees fulfilled.
“Part of the goal [of the project] is getting the [culture] message out in a more scalable way, beyond Zappos,” Hsieh said in an interview the next day at the Delano Hotel pool, where he was camped out with friends.
Writing a book also had been a lifelong aspiration, much like running a marathon. (He checked that feat off his list a few years ago at the Zappos-sponsored race in Las Vegas.)
But for the the past year, Hsieh has been sprinting.
Last summer, he revealed plans to sell Zappos to Amazon and is now juggling his CEO duties with the new role of author, as well as maintaining an exhausting speaking schedule.
“I’m glad there’s an end in sight,” Hsieh said. “This is definitely not sustainable.”
Hsieh began writing the 272-page book just before Labor Day last year, when he and Lim retreated to Lake Tahoe for a week. By both their accounts, the process turned out to be much different than expected.
“We went to Staples the first day we got there and bought a bunch of paper, a printer, colored index cards and a bunch of stickies — everything you can imagine,” recalled Lim. “But we didn’t end up using any of it.”
Hsieh said he would churn out 2,000 to 3,000 words at a time and send them off to his editor in New York.
“We didn’t really stick to an outline. It was more stream of consciousness,” he said, adding that, after Tahoe, he spent two additional weekends at home writing and editing.
The book, which is divided into three main sections, opens with Hsieh’s account of his first venture — worm farming — at age nine. (It didn’t go quite as planned.) The first pages also give a glimpse into his experience growing up with “typical” Asian-American parents, who pushed him to excel both academically and musically.
Hsieh spent most of his teenage and college years dreaming up new business ideas, including the now-famous pizza venture during which he met Zappos COO/CFO Alfred Lin. Post-Harvard, he landed at Oracle, and shortly after co-founded LinkExchange. After selling that company to Microsoft for $265 million — and becoming a multimillionaire at age 24 — Hsieh realized he was no longer driven by money and left the company. But he wasn’t sure what to do next.