Bob Pittman is back in business.
After keeping a low profile for more than a year since he left America Online amid a heap of difficulties, the 49-year-old Pittman has launched a media investment firm called the Pilot Group. The firm is seeking to buy or invest in media properties, especially radio and television stations.
Before starting the firm in Manhattan alongside a few longtime colleagues, Pittman was advised by his counsel that no evidence has tied him to the ongoing federal probe of America Online's bookkeeping and dealmaking practices, according to people who have discussed the issue with him. Still, he chose to put some time and distance between his last stint and his new venture, the first time Robert W. Pittman has taken a big chunk of time off since he began hustling as a teenage radio disc jockey.
Robert W. Pittman recently launched the Pilot Group, a media investment firm.
(2001 Photo Richard Drew -- AP)
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Pittman had perhaps the highest profile of any executive after the $112 billion merger of America Online Inc. and Time Warner Inc. in January 2001. But these days, he is taking a more private approach, declining to be interviewed for this article and spreading the word about the Pilot Group through one-on-one, behind-the-scenes discussions.
Given Pittman's track record of success before AOL, some say the past year has been a difficult one. Having lost out to colleague Richard D. Parsons in the derby to succeed Gerald M. Levin as chief executive of AOL Time Warner, Pittman's touch seemed to fail him, as he struggled unsuccessfully to bring together America Online and Time Warner, before abruptly departing in the summer of 2002.
"It has been a hard year for him because he had this golden-boy reputation that everything he touched turned to lemonade, and he became the fall guy for a lot of errors," said James "Jimmy" de Castro, who worked with Pittman at AOL. "He went through rejection, and there was some anger and disappointment. That takes the human spirit a little time to get through. He has gotten through that; he is reinvigorated, reenergized, and he has lost some weight."
The entrepreneur from Mississippi -- who headed MTV, Century 21 Realty and Six Flags before rising to the top of Dulles-based America Online -- spent much of the past year piloting his own airplane and traveling to Asia, Europe, Mexico and elsewhere with his wife and, often, their two children.
"In the last year, he has been happier than I have seen him since first grade," said Pittman's older brother, Tom Pittman, who is publisher of the DeSoto Times newspaper in Mississippi. "He finally got some time to be with his family and travel around and relax and enjoy life. This is the first time Bob has had a break in his life, and it has done him good."
While Pittman enjoyed the time with family, he eventually grew restless and eager to get back to work, friends said. Known as a driven, image-savvy executive with a smooth personality, Pittman may be using the Pilot Group to identify his next opportunity to run a major company.
"He is not a financial guy, and he is not going to spend a lot of time reading through prospectuses and doing due diligence," de Castro said. "He is an awesome leader -- I saw him at a very stressful, difficult time at the end of AOL and was unbelievably impressed with his thinking and ability to take a large group of people and dig through really hard questions. It is a waste to have a guy like that not be involved in some form of leadership role."
While Pittman is moving forward with the next phase of his career, the federal criminal and civil probes hanging over America Online have made it difficult for some other former executives to move on. The Securities and Exchange Commission's investigation alone is likely to extend until sometime next year.
David M. Colburn, ousted in the summer of 2002 after heading AOL's business affairs unit, has been working privately as a consultant while waiting for authorities to complete their investigation of the company. People who know him say he has spent time doing charitable work as well. Eric Keller, who also worked in business affairs and left AOL earlier amid an internal probe into the company's dealings with a now-defunct Las Vegas-based Internet firm, has done work as a consultant, too. He has been helping out with carpools and spending additional time with family while waiting for the legal process to run its course, people who know him said. Colburn and Keller declined to comment.
In contrast, Pittman, who arrived at AOL as a rich executive, departed wealthy enough from stock-based compensation to finance the Pilot Group with his own money, rather than raising funds from investors. Under a severance agreement with AOL Time Warner, Pittman remains a consultant to the company until the fall of 2004; in exchange, the company agreed to extend the time he has to cash in some stock options.
In the past year, Pittman has devoted additional time and money to philanthropy. He previously had teamed up with the state of Mississippi and others to ensure that every classroom in the state has a personal computer with Internet access. More recently, he donated millions of dollars to build a family-life center at First United Methodist Church in Picayune, Miss. He has purchased hymnals for the church and established a fund for his father to distribute to worthy church-related causes. He also paid for missionaries to work in Mexico.
He attended his 30th high school reunion in Brookhaven, Miss., and served on the board of trustees of Millsapps College in Jackson. His older brother said that the onetime deejay, who went to work to pay for flying lessons, remains in contact with many people he grew up with or has worked with.
"It doesn't seem to me that he has left people behind," Tom Pittman said. "As he has gone up the ladder, he has taken people with him, instead of standing on top of them. I have been astonished that people Bob worked with 25 years ago as a deejay still call and write, and he gets together and has dinner with them periodically."
Pittman had dealt with adversity before. A horse kicked him in the face at a Thanksgiving family reunion when he was in second grade, causing him to lose vision in one eye. Despite that loss of sight, and lack of normal depth perception, he pursued his boyhood dream of becoming a pilot, his brother said.
"My daddy said he could take pilot lessons but had to pay for them," Tom Pittman recalled. "He started working hard full time when he was 15."
With legal turmoil and negative publicity swirling around AOL, Pittman's low-profile approach succeeded in removing his name from the headlines. With no apparent legal issues to contend with, Pittman is moving on after the hiatus.
Said a longtime colleague, "Whether he will look back in three years and say, 'This was a good year, or took a bite out of my life,' only time will tell."
