Applying the intricacies of basketball to business and life

Acing the Three-Pointer

by Will Lindner

cheesemanDouglas Cheeseman, president of the Cheeseman Insurance Group in Burlington, Milton, and Vergennes, puts a premium on hands-on local connections.

To some people basketball is a simplistic game in which two teams scurry back and forth, dribbling the ball while their opponents rudely try to slap it away from them. Eventually, somebody shoots, and the ball either caroms away or glides through the net. Someone then grabs it and the frenzy begins anew, amid the rhythmic smacking of ball against floor.

To Douglas Cheeseman, president of the Cheeseman Insurance Group in Burlington, Milton, and Vergennes, basketball is so much more. He understands, intimately, its intricacies and opportunities for invention. Basketball was his ticket out of what he believed would be an uninspiring and pedestrian life. As a star player at Burlington High School and Champlain College, it was a means for attracting attention, admiration, and the chance for greater things. It afforded life lessons that he translated to other career endeavors.

And it has been his primary means for giving back to his community, helping tomorrow’s women and men find the best in themselves, as he did when the odds were against him.

Cheeseman was born in Burlington’s Old North End in 1960, the youngest of seven children in a nose-to-the-grindstone, blue-collar family.

“My father was a truck driver, and my mother was a chambermaid at Howard Johnson’s,” he recalls, sitting in his sixth-floor office, framed by a view of Lake Champlain. “They were the hardest-working people in the world, day in and day out.”

The same, he says, was expected of their children, most of whom fulfilled that destiny by finding jobs “the minute they got out of high school.”

Dougy Cheeseman, younger by nine years than the next-youngest child, was different. He recalls, as a teenager, a heart-rending conversation with his mother, who urged him to take up a trade to make his way in the world.

“‘Mom, I’m not going to have a trade,’” he told her. “‘I’m going to go to college’” — something no one in his family had done — “‘and play basketball, and then I’ll decide what I’m going to do.’

“That shook my mother’s world,” he says. “I remember her crying at the table. ‘Doug, I’m worried about you. I don’t know what you’re going to do in life.’”

Yet there were others who weren’t worried about him. One was Dick Falkenbush, Burlington High’s longtime boys’ basketball coach.

“I remember him calling me into his office,” Cheeseman reminisces, “and telling me, ‘Look, you’re a leader of this team. I want you to take charge.’ That made a big difference, believe it or not, in my life.

“As you get older,” he observes, “you begin to figure yourself out. I’m extremely competitive. I’m extremely loyal. I’ve been married to the same woman, Priscilla, for 36 years. Up until four years ago I lived in the same house for 30 years. I’ve been in the same occupation for 35 years. When I commit, I commit. Dick Falkenbush saw something in me, and to me everything I did after that was because of that conversation. It dialed me in.”

Cheeseman led the league in scoring in his senior year, earning him a partial scholarship to Champlain College. Other attractions were that he could live inexpensively at home and help his mother care for his by-now infirm father. Plus, Priscilla, a year older, was already a student there. They married in 1981.

Meanwhile, Cheeseman was closing in on a career. While at Champlain, he did an internship with the Department of Corrections’ Probation & Parole office, which led to a brief experience as a corrections officer at the DOC prison in South Burlington. Next came a job with a Boston-based plumbing-and-heating supply company, managing its operations and $5 million inventory in Williston. He and Priscilla had their first child, daughter Melissa.

Interestingly, this ascension to the middle class put Cheeseman on the radar for a former associate at Probation & Parole, who was now selling life insurance.

“He prospected me!” Cheeseman recalls, laughing because “prospecting” — courting a potential customer — is now a major enterprise at the Cheeseman Insurance Group. While he was conferring with the insurance salesman, he was prospected again — this time by the salesman’s supervisor at Metropolitan Life, Joe Handy. Handy, however, was prospecting him as a potential addition to Metropolitan’s staff.

Recognition helped. “He said, ‘You’re Doug Cheeseman! You played basketball at Burlington High School.’”

Cheeseman went to work for Metropolitan Life, and to this day credits Handy for teaching him skills critical to his company’s success: how to work productively in a field that’s based on speculation (identifying, securing, and then serving potential customers), and how to evaluate, orient, inspire, and manage new employees, like he was then.

“I like to hire ex-athletes,” Cheeseman acknowledges, “because you have to be able to accept losing. Because if our producers are talking to 10 potential new insureds, if we get three of them we’re happy. If we get five, we’re really, really happy.”

In 1984, Cheeseman audaciously went out on his own. Metropolitan’s focus was life insurance; Cheeseman’s preference was property and casualty.

He was also following a muse embedded since he saw his parents struggle with their employers: the urge to be independent — an entrepreneur.

Growth wasn’t easy. Cheeseman worked both ends of the spectrum, finding people who needed commercial and/or personal insurance, and, correspondingly, identifying insurance providers with what he calls the “appetite” for the property in question.

“If you’re married and living in a four-bedroom colonial, there’s a chance you’ll have younger kids driving your cars,” Cheeseman explains. “Some companies don’t have an appetite for that. If they’re pricing really high for a policy, it’s not a market they want to be in.”

The challenge for Cheeseman and his 16 staff members at the three offices his insurance group now occupies in Burlington, Milton, and Vergennes, is to navigate these interests. They serve clients by finding coverage they can depend on and afford; they serve the providers, whose headquarters are likely to be far away, by knowing the risks and rewards they might experience.

“Vermont is a pretty favorable state to write insurance in,” Cheeseman explains. “You don’t have the weather disasters; it’s relatively low-crime; properties are typically well-managed; we have good neighborhoods and a high percentage of [home and local] ownership.”

The Cheeseman Insurance Group appears to have served both constituencies well. His first local insured is still in the fold, he says, “and some of the companies, we’ve represented for 20 years.”

One new account, however, is Bugbee Insulation in Williston. Office Manager Sindy Hayden has known the Cheeseman family for years. (“Doug’s sister, Mary, is a very dear friend of mine”), but when a problem developed with Bugbee’s insurance provider earlier this year, familiarity was not the selling point. Professionalism, prompt service (Cheeseman’s son, Mike, prospected this account), and a surprisingly favorable rate for a new policy sealed the deal.

“As soon as they came back with a quote we knew we were going to go with them,” says Hayden. “I cancelled the other appointments I had scheduled because I was so impressed with their service. Also, they gave us a lot of advice that was helpful for a policy that would really fit out needs.”

Hands-on, local connections are central to Cheeseman’s philosophy. “I think a local agency, privately held, owned and staffed by members of the community who are involved with the community, is where it’s at.”

Going back to his 20s, he has lived up to this standard, primarily by coaching basketball. Falkenbush recruited him to coach in the boys’ basketball program at Burlington High School.

When Cheeseman’s daughters reached high school age, he became head coach of the girls’ varsity team, which he did for 20 years — riding school buses to evening games in Bennington, then arriving at his office by 7 a.m. for a meeting with his sales team. With Falkenbush and Bill Callahan, he now directs the Vermont Cats, an AAU basketball program for school-age children.

“Doug does what he can to help kids develop as players and as people,” Falkenbush emphasizes. “Doug is a success story … where he came from, what he’s developed into, and the family man he is. With him, it’s not just about monetary things. He works very hard to improve the lives of young people.”

The youngsters who delight him most, though, are his and Priscilla’s eight grandchildren. Parents of four adult children — Melissa, Michelle, Megan, and Mike — their grandchildren are bunched between toddlerhood and age 6.

While they escape to their Florida condominium twice a year, and Cheeseman enjoys golfing regularly, his greatest joy comes with exercising the listening skills he has developed as a sales “producer.” When in the grandkids’ company, he’s all ears.

“I just love to listen to them, at the stage of life they’re in, the way they see things,” he says. “To go for a bike ride with the two older kids and listen to them talk, and be silent … Just to be a part of that, that’s pretty special.”