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Toms Founder Blake Mycoskie's Fashion-Forward Childhood

In adolescent angst lies true meaning. "Whether Hello Kitty diaries, homecoming photos, or some crappy high-school poetry, they reveal profound things about the people we've become," says Dave Nadelberg, cocreator of Sundance Channel's The Mortified Sessions (premiering December 6). The star-studded series, a take on Nadelberg and Neil Katcher's popular stage show, examines the awkward mementos of successful people's pasts. Sounds fun. Let's try one.

Blake Mycoskie Founder, Toms Shoes

This risk-taking child (fashionably speaking) is now a bold entrepreneur. A commercial and social success, Toms has delivered more than 2 million pairs of shoes to children in need.

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Photo by Sam Kaplan

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