BOB PITTMAN, 62
Last Year's Rank: 8
The uncertain nature of the radio business doesn't faze Pittman, the chairman/CEO of a company that reaches 110 million listeners each week. "Plans can lull you into a false sense of security. It's better to understand the future is unknowable," says the world traveler and licensed pilot who has logged 6,500 flying hours. That attitude could serve him well in 2016. Revenue dipped only 1.7 percent, to $4.5 billion, through September, but deep debt could reportedly lead to a financial restructuring.