Tom Freston, Runaway Mogul
Credit: Photograph by Mark Seliger
After more than 30 years in the entertainment business, Tom Freston knows how to make the talent feel at ease. Described by friends as a mash-up of Jack Kerouac and Jack Welch, who weds a Zelig-like talent for friendship to a pirate's eye for opportunity, Freston saw his job at MTV Networks as making people like Jon Stewart or Bono or Beyoncé feel as if they were stars in a corporate firmament he was running on their behalf. In Freston's world, where everything and everyone are potential content to be provided to somebody somewhere, Ralph Reed and Butt Naked might very well be the next 'Beavis and Butt-Head.'

"He would never say, 'Gee, that guy is a rich, right-wing Republican, therefore he's my enemy,'" says Bill Flanagan, a longtime friend from MTV. "In the same way, he'll go hang out with a cannibal."

Indeed, even Butt Naked becomes an F.O.T. (Friend of Tom), asking Freston on the phone the next day to help him procure a visa to the U.S. so he can hang out with Reed and other American evangelicals. (Freston says he'll try, though the murderous coup might be an issue.)

A child of the 1960s, Freston spent his late twenties and early thirties as a clothing exporter living in Afghanistan and India – until he lost his fortune and stumbled, serendipitously, into a job at a nascent cable channel in 1980. The rest is the history of MTV. Freston would run the network for 18 years, turning it into a global powerhouse by introducing reality TV and hip-hop to mainstream audiences, expanding MTV into Asia and Europe, and eventually overseeing the parent company, Viacom, one of the largest film and TV conglomerates on Earth (including 'The Daily Show,' Nick at Nite, Spike TV, and Paramount Pictures).

Seven years ago, however, Freston got fired from Viacom, extinguishing his media-mogul mojo and throwing him into a post-power-player identity crisis. As he told a crowd of college students in 2007: "Here I am giving a commencement speech when I'm back right where I started, wondering, like you, 'Dear God – what the hell am I going to do now?'"

If Freston were a typical corporate chieftain, he might have sought a new corporate perch and tried recovering all the trappings of power: the easy access to celebrity and fame, the private jet, the company cars, the armies of assistants to micromanage his every waking minute – minutes he would spend determining who gets paid the millions and appears on TV and movie screens around the globe. But he didn't do that. Instead, he has tried reinventing himself as something more idiosyncratic: an independently wealthy media broker with an assortment of off-grid interests that, together, seem to circle back to a previous incarnation of Tom Freston – the one who freewheeled his way to fun and profit in the 1970s and then lucked into the best job in American media.

In the past several years, he has become an adviser and investor in the insouciant male-centric media company Vice, which he likens to an early MTV, and a consultant and board member to Moby Group, a fast-growing TV company in Afghanistan that Freston also likens to an early MTV. Simultaneously, he's helped re-engineer the antipoverty campaigns founded by Bono, a friend Freston helped make famous in the early days of MTV. His new schedule has made him a nonstop traveler to the Middle East and Africa, places he roamed in his twenties, and later as a CEO expanding the global reach of MTV.

At 67, Freston has the wealth and access to seed youthful new media ventures and concoct global adventures worthy of his own legend. What's not yet clear is whether he can reinvent his own wheel.