Barry Diller & Diane von Furstenberg

Barry Diller is the epitome of a self-made man. He dropped out of UCLA after just three weeks of attending and landed a job in the mailroom of William Morris Agency through a family friend. This led him to jobs at Paramount, Fox USA Broadcasting, and a healthy $4.7 billion-plus he was inducted into the TV Hall of Fame in 1994.

Despite rumors that he was gay, Diller married fashion designer Diane von Furstenberg, famous for creating wrap dresses, being the chairwoman of the Council of Fashion Designers of America, and was recently inducted into the National Women’s Hall of Fame.