AGE: 39
OCCUPATION: entrepreneur
HOMETOWN: Orland Park
LIVES IN: Hinsdale

Seven years ago, Bill Rancic won the first season of The Apprentice, Donald Trump’s still hugely popular reality show, and the experience changed his life. Trump gave Rancic an insider’s tour of New York City and inculcated him with business savvy, tycoon-style. “It was a whole different world,” Rancic says. “I’m a kid from the South Side. My parents were schoolteachers.” Today, he seems amazed that the ride hasn’t ended—pausing mid-interview to literally knock on wood every time he talks about his good fortune. Current projects include gearing up for season 4 of Giuliana & Bill, the reality show starring Rancic and his wife, who is a broadcast reporter for E!; the debut of the Discovery Channel’s Airplane Repo, a show he produced about an airplane repossessor named Nick Popovich; and promoting the new book he wrote with Giuliana about modern marriage, titled I Do, Now What? Asked if people ever told him he was handsome growing up, Rancic just laughs and says, “I grew up with three older sisters, so my feet never got off the ground.”



Photograph: Maria Ponce