From Student to Shoe Salesman: The Early Years of Zappos’ Tony Hsieh

When Tony Hsieh's parents emigrated from Taiwan, they were in search of a better life, what many call the American Dream. They might not have found it themselves, but their son most definitely did. A millionaire by the time he was 26 years old, Hsieh sold his first company to Microsoft and would go on to build an even greater one in the hugely successful Zappos.com. Hsieh was born on December 12, 1973. He grew up in Marin County, California and showed early signs of an eager entrepreneurial spirit. The oldest of three brothers, Hsieh would graduate from Harvard University with a BA in Computer Science.

Straight out of university, Hsieh landed a promising job as a software engineer with Oracle, but could never really adjust to the idea of working for someone else. He quit that job and in 1996, co-founded LinkExchange with roommate Sanjay Mandan. It was a popular internet advertising network that, at its peak, reached over half of all Internet users each month. It became so successful that in 1999, Microsoft approached Hsieh with a bid to buy it.

Hsieh considered the bid carefully. "I just didn't look forward to going to the office. The passion and excitement were no longer there," recalls Hsieh. "That's kind of a weird feeling for me because this was a company I co-founded, and if I was feeling that way, how must the other employees feel? That's actually why we ended up selling the company."

The deal was made final for $265 million, and Hsieh became a millionaire. But it was far from the end for Hsieh.

"Financially, it meant I didn't have to work again if I didn't want to," he says. "So that was the lens through which I was looking at things. It's basically asking the question, what would you want to do if you won the lottery? For me, I didn't want to be part of a company where I dreaded going into the office."

At the same time, Hsieh had co-founded a small investment firm called Venture Frogs. "We invested in 20 or so different Internet companies," he says, including Ask Jeeves, MongoMusic, MyAble, and Tellme Networks.

It was there that Hsieh first learned about a young online shoe retailer called Zappos, founded by Nick Swinmurn. He invested in it like all the rest, but slowly his involvement began to change.

"Nick left a message saying he wanted to start a company that sold shoes online," recalls Hsieh. "I didn't think consumers would buy shoes sight unseen, and Nick didn't have a footwear background. It sounded like the poster child of bad Internet ideas.

"But right before I hit Delete, Nick mentioned the size of the retail shoe market - $40 billion. And the more interesting thing was that 5 percent was already being done through mail order catalogs. That intrigued me. Initially, I was just an adviser. But I got sucked in."

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