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.
With $30,000 in savings, he enrolled in sketching classes and, in 2004, produced a run of 300 lumberjack-chic shirts. The line was sold at L.A. boutique Ron Herman and caught the eye of fashion's ruling classes. "They're this great riff on Americana," says Ken Downing, fashion director at Neiman Marcus. "They appeal to gentlemen who still like their wardrobe to be based on classic American dressing." In 2007, Sternberg sold his first women's collection at Barneys New York. He says sales were $300,000 in 2005, $1 million in 2006, and $8 million last year. He now has 12 employees based in Los Angeles and designs five Band of Outsiders micro-lines.
In 2009, Sternberg won the Council of Fashion Designers of America Menswear Award—fashion's equivalent of an Oscar. Even so, he still finds himself having to debate with retailers over whether his clothes belong in the designer or contemporary categories because of different price points within his label. That brings him back to his agency days: "The movie industry is based on risk-averse behavior," he says, "which totally translates to fashion."