After graduating from Columbia University and NYU School of Law, he started working for a successful law firm on track to make partner, but decided to quit and start his own practice. His practice folds in the show's second season after his main client Harlin Polk (Gary Grubbs) fires him, and he begins working for the law firm Doucette & Stein (Doucette played by Gregory Hines and Stein played by Gene Wilder), where he remains until the end of the seventh season, when he quits to do something more meaningful with his life.