Will Andrew started silk-screening T-shirts for his high-school friends, a hobby that he said turned into a business almost before he knew it. Learning on the fly, he eventually built a factory, only to watch it all collapse after about a decade of hard work. Still, the humility and business savvy he gleaned from that failed business may have helped his next company, Elevate Sport, win the active-wear license for the 2010 Winter Olympics in Vancouver, British Columbia.

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