Family business: Third generation joins insurance brokerage

Jul 24, 2021

In 1985, Margaret J. Grassi quit her corporate job in Boston to open her own insurance brokerage firm in Wareham.

In 1989, her daughter, Deb, joined. 

And now, Deb’s son Matt is part of the team — the third generation to be a part of the company.

Margaret said that she never imagined her company would become a family business when she struck out on her own. She faced some resistance from the corporate job she was quitting.

“The big boss came down from New York and said I couldn’t afford to quit,” Margaret recalled. “I was determined I was going to make it.”

She was one of two women who owned their own brokerages in the area at the time, Deb said. Insurance brokers work to help clients find the right insurance plan, and work with a variety of insurance carriers. Brokers also advocate for clients when they need to use their insurance and help them work through the required paperwork and other processes. 

“I enjoyed it because insurance is complicated and you learn a lot,” Margaret said. “Every year it changes.”

Deb Grassi joined her mother’s firm after moving back to the area from California, and didn’t initially plan on staying long. 

“Insurance is one of the industries no one ever plans to be in,” Deb joked.

But she grew to enjoy the work, and made it her career.

“She loved what she was doing, and it shows,” Margaret said.

Grassi Insurance is one of a dwindling number of small insurance brokerages. In the early 2000s, Deb explained, regulations changed to allow banks to provide insurance. Since then, many small firms have been absorbed into larger corporations. And more consumers are purchasing insurance directly from a large company.

“The big ones are eating the little ones,” Margaret said. “No more mom and pop stores.”

The fact that Grassi Insurance has stayed small is what sets the company apart, Deb said: “We give that small business attention to customers.”

The small business feel is what drew Matt to join the firm. After graduating college, he worked at several large corporations before reevaluating where he wanted to take his career.

“It was a decision about coming to the small business side or climbing the corporate ladder,” Matt said.

Small business won out because there’s “less fluff,” Matt said.

“We literally had meetings to discuss the scheduling of another meeting,” he said. At Grassi Insurance, he said, he spends his time doing the real work. 

“Working with grandchildren is satisfying,” Margaret said. “I learn from him.”

Matt has a young daughter, but he said he has no idea whether she will want to join the family business.

“This just so happened because it seemed like everyone had an interest,” Margaret said.

The best part of the family business, the three agreed, is spending time together.

Grassi Insurance can be reached by email at or by phone at (508) 295-2007.