Who: Once a high-flying media mogul—he was one of the founders of MTV and later served as the No. 3 at AOL Time Warner—these days Pittman spends his time investing in Internet start-ups as the founder of the Pilot Group.

Backstory: The son of a Mississippi Methodist minister, Pittman didn't get off to a very auspicious start: More interested in rock 'n' roll than studying, he attended four colleges but didn't graduate from a single one. Not that it mattered. Having arrived in New York in 1977 to work at the radio station WNBC, in the early '80s he landed at Warner-Amex, where he found himself in charge of a new concept the company was toying with, a cable network that would play nothing but music videos. The idea, of course, was MTV, which launched in August 1981. Pittman went on to help revamp Nickelodeon and was part of the team that created VH1 and Nick at Nite. When the company was purchased by Viacom for more than $500 million in 1985, Pittman was named MTV's CEO. Two years later, Pittman left MTV after an unsuccessful attempt to buy out the network, and he spent a decade in a variety of other top corporate jobs. (He launched Quantum Media, ran Time Warner's Six Flags amusement parks, and served as CEO of the real estate company Century 21.)

In 1996, Pittman joined Steve Case at AOL after Case hired him as the company's president. One of the chief proponents of the 2001 merger between AOL and Time Warner, Pittman was the man responsible for selling the deal to Wall Street and following the merger, he became the No. 3 executive at the combined company. When it became abundantly clear that the deal had been a major strategic misstep and Time Warner shareholders mounted a revolt following the collapse of the dot-com boom, Pittman (along with bosses Steve Case and Jerry Levin) were shown to the door. He founded the Pilot Group shortly thereafter.

Of note: The AOL-Time Warner fallout proved to be a rare career misstep for Pittman. But he didn't skulk off and fade away, nor did he exactly walk off empty-handed. (He sold $94 million in stock in the aftermath of the merger.) He started investing in the web at the bottom. In 2003, he picked up the website Daily Candy from founder Dany Levy for $3.5 million. (In 2008, it was sold to Comcast for $125 million.) Other investments include games maker Zynga, Peoplejam, the Eurotrash social network aSmallWorld, GarageBand.com, MocoSpace, and PlumTV. He's also invested alongside his former AOL right-hand Ken Lerer: Pittman's reportedly an investor in the Huffington Post (which was founded by Lerer and Arianna Huffington), and the newsletter Thrillist, which was founded by Lerer's son, Ben Lerer.

For the record: There's a reason his company is called the Pilot Group. Pittman's a flying enthusiast and certified pilot, and he owns a 12-seat Dassault Falcon 900.

Medical file: Pittman lost his right eye when horse kicked him in the face at a Thanksgiving family reunion at the age of six. He now wears a glass eye. In case you're wondering, he holds a waiver from the FAA which allows him to fly planes despite the disability.

Personal: Pittman's first wife was 1980s social fixture Sandy Pittman, whom he married in 1979. (They met on an airplane, naturally.) Part of the city's swirling social scene and "a prime example of New York's astonishing display of late-80's wealth," Sandy is probably best remembered for climbing Mount Everest in 1996 with her espresso maker in tow, a trip that left eight people dead. (The story is famous recounted in Jon Krakauer's book, Into Thin Air.) Bob and Sandy's divorce was finalized in 1997; later that year he married divorcee Veronique Choa (right), a web designer and graphics artist. The couple has two kids, Andrew and Lucy, and Pittman also has a son with Sandy named Bo. Pittman lives in Westchester county and also owns a pied a terre in the city and a vacation home in Jamaica.

Vital Stats


Full Name: Robert W. Pittman
Date of Birth: 12/28/1953
Place of Birth: Jackson, MS
Residence(s): Katonah, NY; New York, NY; Montego Bay, Jamaica
Filed Under: Media, Business, Technology


[Photo via Getty Images]