Ray Ciccolo’s entrepreneurial streak emerged early, leading him from the corner Kool-Aid stands he ran in Cambridge as a youngster to the fleet of a dozen automotive dealerships he oversees from the North Shore to the South Shore today.
But his make-or-break moment was literally that: a high-school job breaking bottles in the kitchen of Boston’s Ritz-Carlton Hotel. It’s the kind of gig that disappeared with the advent of recycling, but it made a lasting impression on Ciccolo, BS ’59, who realized he wanted bigger and better things. It also set him on the path to Suffolk— he was the first member of his family to attend college.
“College was a lot more flexible. You could arrange your classes so you could have a couple of days off. So, I would work those days and pay for it,” he says.
Ciccolo attended college in an era before federal financial aid programs, and fewer than 10% of adults who completed high school went on to graduate from a four-year college, according to the US Census Bureau. Many students were paying their way, and after the bottle-breaking job, Ciccolo opened a coin-operated launderette. By the time he graduated, he had expanded to two launderettes in Cambridge and one in Chelsea.
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Photography by Adam DeTour
FEATURES
| Fall 2022
By Katy Ibsen
He would eventually go on to sell all three to purchase a new-car dealership in Newton selling Nash and Volvo—the one that started Village Automotive Group. As Ciccolo recalls, the bank wasn’t happy with the owner at the time; seeing an opportunity, he made an offer.
“I went in to buy a car, and I came out with the dealership,” he jokes.
Over the next five-plus decades, the coursework Ciccolo completed at Suffolk would prove invaluable in growing Village Automotive to a recognized dealership brand stretching across the Boston area. As an 18-year-old, he took away business knowledge in accounting, bookkeeping—and human relations.
“I remember doing some case studies at Suffolk, and one in particular where they found that if the environment was more pleasant—let’s say in a factory, and you had music on—the productivity went up,” he recalls. “Well, it didn’t take much to figure out that in the business world, if you’ve got happier employees, they produce more.”
Building on that philosophy, Ciccolo created an environment and culture where team members were treated like family, and that was passed on to their customers.
Ciccolo knows the value of hard work when an opportunity presents itself. Through his philanthropic endeavors, Ciccolo has paid that success forward. He and his family fund a wide variety of cultural, health, education, and environmental organizations through the Ciccolo Family Foundation, and recently made a $250,000 commitment to continue their support of their scholarship fund at Suffolk, which rewards graduates of the Cambridge Rindge and Latin High School with a similar hard-working mindset.
"When I established a scholarship at Suffolk, I said I don’t want this to go to the smartest kid in the class or even the neediest,” he says. “I wanted it to go to somebody with a background similar to mine, a first-generation person who could just use a little helping hand.”