From Hollywood Insider to Band of Outsiders

During his first week as an assistant at Creative Artists Agency in 1997, Scott Sternberg, 36, realized he didn't want to be a talent agent. "I wasn't going to stake my claim in life on having a good 'drink session,'" he says. However, his Hollywood pedigree eventually helped him launch his fashion label, Band of Outsiders.

After a year at CAA, Sternberg left to assist screenwriter Ed Solomon by reading scripts and, as he puts it, "making friends with people." But when CAA began a new media group the next year, it lured back the Washington University graduate. Still, Sternberg quickly grew restless. The entrepreneurs he met on the job fueled his desire to start his own business. When Emily Woods, the J. Crew (JCG) co-founder, asked him to be the third partner in a media venture she was launching with her husband, Nantucket Nectars co-founder Tom Scott, Sternberg jumped. For nearly a year he worked on consulting projects, including junior clothing concepts. However, when his partners went to Nantucket in 2003 to start Plum TV, Sternberg opted out to start his own clothing line.