By age 24, Kun Gao had already sold one company and wanted to build something new. He rounded up five friends from his time at the University of California, Berkeley, to hack together a video-sharing website that allowed users to upload their own content. Visitors especially loved watching the site's uploaded Japanese animation, and viewership grew so fast that the company, Crunchyroll, struggled to keep pace. Here, we join Gao as he pursues a profitable business model, which got him way, way outside his comfort zone. (It worked: Today, Crunchyroll has more than 700,000 subscribers, who pay $7 to $12 a month for access to Japanese content.)

-- As told to Christine Lagorio-Chafkin

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