Bob
Pittman

Alongside such business tycoons as Barry Diller and Les Moonves, you might find Bob Pittman’s name. Currently in his seventh year of running radio and outdoor media giant iHeartMedia, Pittman served in game-changing positions at MTV, which he cofounded, AOL Networks, where he was COO through its merger with Time Warner, and held senior titles at Six Flags Theme Parks and Century 21 Real Estate.

But it’s his rebranding of iHeart, the formerly (tarnished) Clear Channel Communications, that has truly defined his place in music industry history. Reaching more than 800 stations across the country, and millions more through its streaming app and special events (like the iHeartRadio Music Festival and annual Jingle Ball tour), Pittman has streamlined popular music, bringing to it a face (Ryan Seacrest, whose daily radio show is syndicated throughout the iHeart network), a voice (Elvis Duran), blurring genre lines when a song is reacting, and finding a niche audience if an alternate strategy is a wiser move.
It’s one reason why record companies covet and actively maintain their relationships with the radio company, even while some point to a declining audience for FM overall in the digital age.

Pittman’s view has always been that the advertising, the engine on which all radio runs, is there for the taking, and he’s expanded that notion to include branding partnerships and sponsorships for the hundreds of companies looking to reach a dedicated, quantifiable audience – for a price.

At the same time, iHeart has been saddled with debt – to the tune of $20 billion — going back to Clear Channel’s initial transition to a private company in 2007, and has fended off bankruptcy for the last two years. Many in the business community see chapter 11 as an inevitability, but Pittman, who makes an annual pilgrimage to Burning Man alongside revelers who go to clear their heads, may still have an exit strategy up his sleeve.