At work, Harpo Productions Executive V.P. Jon Sinclair hangs out with some of the biggest celebs in America.
But at home in Wilmette, with his wife, Meredith, and sons, Max and Truman, it’s a laid-back, authentic lifestyle he appreciates most.
When asked about living in the Chicago ‘burbs versus entertainment capitals like New York or L.A., Sinclair, 43, just shrugs. “I work all day, I like to come home and live,” he says. “I like to have people around who do different jobs. In reality TV, you have to think like the viewers, and if you’re not tapped into real life, it doesn’t work.”
“I love Wilmette,” he says. “I love how you don’t have to get in your car on weekends; you can walk to Chuck Wagon, go see Joe at the Bottle Shop for a bottle of wine. I like the trees on the street and the Saturday morning soccer thing when everybody’s sleepy on the sidelines and all coffee-ed up. I like running into my neighbors at Starbucks and living near people who get it.”
He may talk like a regular joe, but Sinclair’s office job is far more star-studded than the average North Shore dad. He started with “The Oprah Winfrey Show” in 1996 in creative services, writing and producing the promo spots for upcoming episodes. If you remember any of the thousands of times Oprah said, “On the next Oprah,” you’ve probably seen his work.
In time, Sinclair became head of Creative Services, then went on to work in Harpo’s development group, producing one-time programs like “Oprah’s Oscar Special” and launching the Dr. Oz and Nate Berkus talk shows. Now he, along with his partner, Jill Van Lokeren, develops new shows for Oprah’s cable channel, OWN. One of the projects he’s most excited about now is “Oprah Presents Master Class.”
“Master Class,” which will premiere in February, is inspired by Oprah’s belief that “everybody has a story and there’s something to be learned from every experience.” The show features famous people such as Simon Cowell, Condoleeza Rice, Lorne Michaels of “Saturday Night Live,” and Diane Sawyer, talking about the experiences and life lessons that shaped their careers, values and philosophies. The format is spare—just the celebrity talking directly to the camera—and Sinclair had a lot to do with that.
“I like simple things,” he says. “I like people looking into the camera and telling you their stories. I like the negative spaces—like when Morgan Freeman pauses, thinking, we let it lay there as if it’s a real conversation.”
He says the stars have been incredibly generous and down to earth—no egos or entourages or hysterics. “These people are so accomplished, they don’t have the need for all that folderol,” he says. “It’s really refreshing to see.”
As you might expect of a man who has been witness to the life stories of an impressive cadre of motivating guests (not to mention 15 years of working with Oprah Winfrey), Sinclair is an evolved guy. He’s often so inspired by one of his “Master Class” guests that he’ll call up his sons to discuss what he learned. “I’m a dad first,” he says.
For Sinclair, keeping life in balance is a chief priority. So, despite his high-powered job, he makes sure he has plenty of quality time and involvement with his boys and his wife, who (he wants everyone to know) asked him out on their first date, way back in high school.