Bennett had an inkling Rich’s was not going to last. In 1994, he got his real estate and broker’s license “because I could see the handwriting was on the wall. I had a Plan B.” He worked for Vernon Martin Real Estate and started his own business in 1999.
When Rich’s recruited Bennett, he moved to Maple Street in Danvers in 1984. In 1999, he moved to Page Street. His real estate office is on a separate building on the property.
In 1993, Bennett got his first taste of town politics when he ran for Town Meeting. While he had always liked the idea of politics, his need to travel for work at Rich’s kept him from being active.
In 1997, he ran for the School Committee amid a push to renovate the high and middle schools.
In 2000 the town tried to move ahead with a debt exclusion override for a single school complex on Cabot Road. Bennett was school board chairman.
“As we all know, that is not welcome by the taxpayers,” Bennett said of the override. He recalled how he had told then-selectmen Chairman Emery Todd that residents wanted to reuse the Holten Richmond school building, but Todd did not listen. The override failed.
“I got, if you will, thrown under the bus because of the debt exclusion,” said Bennett, who was voted out. “And that gives you more personal growth. Failure is a great teaching tool if you live through it.”
In 2002, selectmen recommended Bennett serve as a trustee for Essex Aggie, giving him the opportunity to work on the merger of the agricultural school with North Shore Technical High and Peabody’s high school vocational programs. The $133 million project to build the school is now ongoing. Bennett said some at the Aggie viewed the merger as a hostile takeover, but he was a strong advocate, and that helped overcome some of the animosity.