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Toby Lenk

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THEN: eToys Founder and CEO (1997)
NOW: President of Gap Inc. Direct

Toby Lenk left a stable job at Disney, as vice president of strategic planning, to found eToys. Venture capitalists readily poured money into the much-hyped e-tailer, which launched a memorable $20 million advertising campaign (see clip below) which cost nearly 70% of the company’s revenue from the previous year.

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When the bubble burst, Lenk held on to his 10 million shares -- with senior management following suit -- to signal confidence to Wall Street. The costly move failed, and eToys filed for bankruptcy in 2001.

A year later, Lenk went on to co-found Gamefly, an online video game subscription site. In 2003, he became president of Gap Inc. Direct, the e-commerce portion of Gap Inc., where he remains today.

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