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A Rebel Spirit's Confederate Motorcycles

A New Orleans litigator left his practice to found an upscale motorcycle company
Matt Chambers, the founder of Confederate Motorcycles, which counts Bruce Springsteen and Brad Pitt among its clients
Matt Chambers, the founder of Confederate Motorcycles, which counts Bruce Springsteen and Brad Pitt among its clientsPhotograph by Daymon Gardner for Bloomberg Businessweek

After 13 years arguing cases as a New Orleans trial lawyer, Matt Chambers, now 57, felt like the courtroom was closing in on him. “I was devolving, becoming the man in a box,” he says. “I wasn’t doing something that someone else couldn’t do.” So in 1994, using seed money from a settlement won in a police brutality case, Chambers set up Confederate Motorcycles’ first factory in Baton Rouge. “When I was a little kid, I read a cool book about motorcycle entrepreneurship,” he says. “I fell in love with those guys.” Two years later he delivered his first bike. By 2001 he had sold 500, at more than $50,000 each.

It’s been far from an easy ride. In 2001, Confederate filed for bankruptcy. In 2005, Hurricane Katrina destroyed its second factory, an 8,000-square-foot warehouse. Three years later, after Chambers had returned to Baton Rouge and signed a deal with luxury retailer Neiman Marcus to sell the Fighter, an extravagantly designed $110,000 bike he describes as “extroverted,” the economy crashed. “It wasn’t the time to be saying, ‘Look at my new Rolls-Royce,’” he says.