Chicago Reader
Randy Barnett is a law professor at Georgetown University who, according to a profile in The New York Times, "has helped drive the question of the health care law’s constitutionality from the fringes of academia into the mainstream of American legal debate and right onto the agenda of the United States Supreme Court."

But before he was underemployed hipsters' worst nightmare, Barnett was an ad rep for the Chicago Reader, writes Michael Miner. Former Reader co-owner Tom Yoder says Barnett was "the first successful Reader ad salesperson" after the paper launched in the early '70s. "He always said we made it possible for him to go to Harvard," Yoder tells Miner.