Zappos CEO Tony Hsieh on Selling to Amazon Vs. Microsoft, Fixing His Biggest Mistakes, and Why Harvard Entrepreneurs Go West

9/28/10Follow @gthuang

What do Bill Gates, Mark Zuckerberg, and Tony Hsieh have in common? That’s right, they all went to Harvard. And they have all run billion-dollar companies. Unlike Bill G. and Zuck, though, Hsieh actually graduated, in 1995. The CEO of Zappos, the Las Vegas-based online shoe retailer now owned by Amazon.com, was in Boston yesterday as part of a two-month nationwide tour. He’s out promoting his book, Delivering Happiness: A Path to Profits, Passion, and Purpose.

The book is part autobiography, part business case study, and part personal philosophy. In it, Hsieh (pronounced “shay”) discusses the ups and downs of Zappos, the ins and outs of the firm’s vaunted culture, and some important life lessons. He also writes about selling LinkExchange to Microsoft for $265 million in 1998, and his decision to let Zappos be acquired by Amazon.com for more than $1 billion last year. (Hsieh recently spilled the beans about that process in a magazine article, complete with classic entrepreneur-vs.-board-VC conflicts over whether to focus on employee happiness and culture vs. profits and an exit.)

Yesterday, I met with Hsieh aboard his “delivering happiness” tour bus—it’s a rock-star style, 50-foot, baby-blue rolling billboard that sleeps 10. The bus was parked in Boston’s Seaport District, where Hsieh and his entourage (including Jenn Lim, chief happiness officer) were attending a private party at Kel & Partners. Their 20-city tour started in New York and Rhode Island, and is going down south before heading west and eventually ending in Seattle just before Thanksgiving.

I learned two personal things about Hsieh. First, he does have nice shoes, though I don’t know what brand they were. Second, he was born in Champaign-Urbana, IL, my hometown, before he grew up in the San Francisco Bay Area. (“The only thing I remember [in Urbana] is catching fireflies,” he said.)

Hsieh professed not to know a lot about Boston-area startups. But at least one local company—Kiva Systems, the Woburn, MA, maker of warehouse robots (and a Zappos partner)—was pretty psyched last summer when Zappos said it was becoming part of Amazon.

In our Q&A yesterday, we covered a range of topics, and here are some highlights: Bad hires have cost Zappos $100 million-plus over its lifetime. Hsieh sees Amazon CEO Jeff Bezos only once a quarter. Entrepreneurs don’t necessarily need money. And there’s a reason why Harvard undergrads head west to make their fortunes. Read on for more:

Xconomy: What’s up with Harvard not being able to keep its best entrepreneurs in town?

Tony Hsieh: I would say, I had a hard time just getting Harvard to forward my e-mails to me. They might do it now, but at the time, I specifically asked the head of computer science who then … Next Page »

Gregory T. Huang is Xconomy's Deputy Editor, National IT Editor, and the Editor of Xconomy Boston. You can e-mail him at gthuang@xconomy.com. Follow @gthuang

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  • http://www.zapposinsights.com Robert Richman

    Great interview!

  • http://www.careerencore.com Courtney Homer

    Phenomenal interview. Really well done. As a recruiting professional myself, it’s validating to read that with all of Tony’s notable experience, employees are the key to his success/failure. Very motivating! Thanks for sharing.

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  • http://www.linkedin.com/in/matthewtagg Matt Tagg

    Tony Hsieh is a beast.