The gig: As president of Warner Bros.' Telepictures Productions, Hilary Estey McLoughlin, 47, oversees one of the biggest syndication companies in television. Telepictures has more than 1,200 employees and nine shows on the air, including "The Ellen DeGeneres Show," George Lopez's late-night talk show "Lopez Tonight" and "Extra." It also owns Harvey Levin's tabloid empire, TMZ.
A seed is planted: Estey McLoughlin grew up in Queens, New York, obsessed with television. "The thing about Queens is, everyone's TV is on all the time. The whole town is lit up by TVs," she said. During the school year she'd race home at lunch to watch game shows, and after school she'd spend afternoons with Mike Douglas, to the chagrin of her teacher mother. "She was always trying to lure me away from the television, she didn't like it."
Early rejection: Estey McLoughlin had the same dream of every Queens kid: to be a ball girl at the U.S. Open tennis tournament in the Forest Hills neighborhood (since moved to Flushing Meadows). "It seemed like the most amazing thing you could do was be on a court with Bjorn Borg." Alas, she was too slow. "The people who were trying out were like superhuman. I didn't have a chance."
First job: After graduating from Boston University's School of Public Communications ("I realized you could make a career out of television," she laughs), in 1984 Estey McLoughlin went back to New York as a researcher at Seltel, a consulting firm that advised television stations on what programming to buy.
Big move: In 1986, Estey McLoughlin quit Seltel and packed up for Los Angeles without a job, an apartment or any connections. She crashed at a friend's place and sent research presentations to all the major studios and syndication companies deconstructing their television shows, hoping to land an interview. "I ended up at [Warner Bros. research chief] Bruce K. Rosenblum's doorstep. . . . He hired me as a temp."
A shot at the big time: A facile number-cruncher, Estey McLoughlin by 1989 wanted to see how the sausage got made. She begged Jim Paratore, then president of Telepictures, for a job in development. Paratore thought she was too much of a research geek to make the transition to dealing with temperamental producers and agents and creating programming.
"He told me I was too introverted to be in development. He assumed there would be a lot of producers that would be aggressive and roll over me. I told him I had been riding a subway by myself in New York since I was 7."
Putting her mouth where the money is: In 1996, turmoil behind the scenes of Rosie O'Donnell's talk show gave Estey McLoughlin the opening to leave her cushy desk gig and become executive producer of the show, even though she had no experience. "I just kind of dove in. . . . I had to learn the nuts and bolts."
Estey McLoughlin guided O'Donnell's ratings rise, and running the show "gave me a lot of credibility. . . . Sometimes it's hard to manage creative people if you haven't done it, so that became a badge of honor."
Finding balance. The O'Donnell show took a toll on Estey McLoughlin's family, particularly her young daughter. "I got [to work] a little before 7 a.m. and got home between 7 p.m. and 8 p.m. My daughter used to hit me when I got home. It was a very hard job for a mom," she said.
After about a year and a half running the show, Estey McLoughlin returned to executive life, and in 2006 she became president of Telepictures, succeeding Paratore, who moved on to full-time producing.
Fun with TMZ: Estey McLoughlin has oversight of both the TMZ TV show and website. That can make for awkward moments, such as when Charlie Sheen -- whose CBS hit "Two and a Half Men" is made by Warner Bros. TV -- gets in hot water and finds himself in TMZ's camera sights.
"We don't tell them what to say. We made that as kind of our basic promise," she said of TMZ's editorial freedom. "We make an exception for one and it [becomes] a slippery slope."
A lot of celebrities like the attention, she said. "You don't go to the Ivy unless you want someone to take your picture."
Challenges ahead: It was a mixed year for Telepictures. Tyra Banks is ending her show, and efforts to launch a morning chat program called "Mom Logic" fell short as local television stations reined in programming expenditures. "There was no cash in the market and this was an expensive show," Estey McLoughlin said.
On the plus side, with Oprah Winfrey's approaching departure from daytime TV in fall 2011, DeGeneres has emerged as the heir apparent for her audience and advertisers. Telepictures also successfully launched the Lopez cable show.
Personal: Estey McLoughlin lives in Brentwood with her husband and daughter. She's still working on her tennis game.