Class of 2021

Michael Regan

Owner and President, Clayton Insurance Agency; Age 38

Integrity means a great deal to Michael Regan.

As an insurance professional who had been steadily growing in his career, Regan was ready to pursue his next business goal: to run his own agency. He had heard that Martin Clayton, longtime owner of the Clayton Insurance Agency in Holyoke, was looking for a young person to carry on the legacy of his business.

While he appreciated Regan’s 10-plus years of experience with Goss and McLain Insurance Agency, Clayton was particularly impressed that the Greater Holyoke Chamber of Commerce had honored Regan with the Henry A. Fifeld Award for Voluntary Service to the Chamber.

“It turns out Clayton knew Fifeld and told me, ‘if you won Hank’s award, you must be a pretty good citizen,’” Regan recalled, adding that the conversation was a key step toward eventually acquiring the agency.

Once he settled in as the new owner at Clayton, he admits he felt some pressure to uphold the integrity of the firm and to make sure customers receive the same quality service they always have.

“I gave Martin my word that I would continue the legacy of the agency,” Regan said. “I work very hard to always keep my word.”

He had the option to change the name of the agency or add his name to it, and Clayton even encouraged it. But Regan decided he didn’t need his name on the sign. “The Clayton Insurance Agency has such a good reputation, I didn’t feel the need to mix that up and add my name. It’s not about me, it’s about continuing the agency and taking care of employees and customers.”

Since Regan took the helm in 2019, the agency has grown by just over 30%, a trajectory he hopes to continue for years to come.

“We’re looking to bring on more staff in the next couple of years and to keep the agency moving forward,” he said.

Regan is extremely community-minded, from funding scholarships to running food drives; from collecting donations for youth sports in Granby to volunteering with the First Tee program to teach inner-city kids about golf, a sport he’s also introduced to his four daughters.

Meanwhile, he hopes to continue the legacy of his agency until he’s ready to pass it along. “Fast-forward 50 years, I want to look back the same way Marty did and find a successor who can continue the Clayton Insurance Agency even further.”


—Mark Morris