Dean of the Dream Job: From Radio Executive to Education Entrepreneur

by Alfred Gingold

Tom Hooper had dreamed of becoming a teacher. At 42, the two-time entrepreneur dusted off his dream and reinvented himself as director of development at a new private school.


As a college undergrad, Tom Hooper had two dream jobs: to get into politics and to teach first grade. The political dream died of disillusionment after a summer interning for a congressman. The teaching dream was dropped because “I wanted to do something important and still make money.”

Armed with a Harvard MBA, Hooper decided he wanted to buy a radio station. By 1981, he and his wife owned a 50,000-watt, daytime station in Greenville, S.C. They ran it successfully for six years. But Greenville began to pall, so he sold the station in 1987, weeks before the stock market crashed. For the next seven years, Hooper worked as a self-employed “turnaround specialist,” consulting with radio stations in trouble. He settled in Montclair, N.J., and took a job with a nearby radio station. He also joined a career transition group at Burton Strategies in New York.

He recalls the group leader remarking that she could see him working at a school. It was an insightful remark. Hooper had worked at a Montessori school in college. He loved it and so did the kids. “They crawled all over me.” But in the group, talking about a career change, his reply was automatic: “You can’t make money at a school.” By 1994, Hooper was floundering. The radio industry was consolidating and jobs were drying up. He went to work on the sales floor of a nearby Macy’s and wondered what to do with his life.

An Old Classmate Mentions a New School

Then he attended a reunion at his prep school in Middletown, Del., where he’d been one of seven or eight black students in the whole school. A classmate mentioned a new school in Newark called St. Phillips and suggested he check it out. At the age of 42, he found a fresh start. “I walked into that school, met the people, saw the fire in their eyes and knew I wanted to be there.” His wife’s reaction was equally clear: “That’s the place you need to be,” she says. In 1996, he signed on as director of development; his starting salary was $45,000 a year.

“It was a step up from Macy’s, but it wasn’t what I'd been earning before,” Hooper recalls.

St. Phillips is a K-8 state school where every student receives some measure of financial aid. For some, the school provides everything from books to lunch to uniforms. “Our goal is to get these kids into good high schools and then into college,” Hooper says. When Hooper arrived, the school had raised about $400,000 a year to cover expenses. In 2005 it raised $2 million, and it had successfully collected $16 million toward a $21 million fund. Tom now earns a good deal more than he did when he started at St. Phillips, but that’s not what keeps him there. What does is the opportunity to serve as a role model for St. Phillips students. Tom keenly recalls the lack of mentors during his own high school days. After years as a hired gun, he has learned that he loves being part of a team and, more importantly, that “I have to be with people who share my values.” Those values are simple: “equity and justice.” Hooper plans to work into his 80s. It’s a safe bet many will benefit from his efforts.    

by Alfred Gingold | Friday, May 1, 2009 | Career Change, Education Careers

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