A business built on hard work and kindness
Ray Ciccolo reflects on his life and philanthropy
Growing up in Cambridge, Mass., in the late 1940s, Ray Ciccolo learned at an early age the importance of hard work and earning a college degree.
As a budding entrepreneur at age 11, Ciccolo balanced several gigs—selling newspapers, running a Kool-Aid stand, and collecting items for resale at a junk yard. He worked his way through high school and college, paying every penny of the cost of his higher education.
Today, Ciccolo is the celebrated founder of Village Automotive Group, one of the most successful car dealerships in the Boston area.
Right there in big type on his company’s website is his business philosophy:
About Us: At Village, we care about people, not just cars.
Ciccolo is also well known for his generous support of local nonprofit organizations. In 2025, the Ciccolo Family Scholarship at Northeastern University celebrated its 10th anniversary and since its creation, nine students have received scholarships.
Scholarship students have advanced to successful careers in marketing, investment, and digital payments. One scholar’s company educates women throughout the world about the stock market, while another scholar’s company sells beauty products with zero environmental waste.
For Ciccolo, his own life experiences re-enforce the importance of higher education. “With a college degree, your life is pretty much laid out in front of you,” he said. “Otherwise, it’s a struggle.”
A budding entrepreneur
In the late 1940s and 1950s, Cambridge was a poor community, Ciccolo explained, adding, his father and many in the neighborhood worked blue-collar jobs. “My father was a union worker, and we made ends meet. But by the time payday came around, there wasn’t very much left in the refrigerator,” he said.
Ciccolo’s first business role model was his Uncle Freddie D’Abbraccio, the owner of a small Cambridge shop with an ambitious sign: “We sell everything from a needle to an anchor.”
His uncle bought “odd lots” from stores, including Woolworth’s, the now-closed five-and-dime retailer. “I don’t think my uncle had any education whatsoever, but he was one of the smartest men I knew. Other people were trying to multiply. He could do all of that in his head,” Ciccolo said.
In high school, Ciccolo worked full time in the evenings at the Ritz-Carlton, Boston, as a bottle breaker smashing empty alcohol containers to compact the hotel’s trash. He’d return from his shifts around 11 p.m. with broken glass in his hair and smelling like a barroom.
It was then he realized that he did not want to work breaking bottles his entire life and decided that a college degree would set him on a path to a more fulfilling career. Ciccolo became the first in his family to attend college and paid every penny of the cost of his undergraduate degree, mostly through late-night shifts at Ward Baking Company in Cambridge.
When you start with nothing and you’re able to build it into something that will last for generations and generations, then the only thing left is: How can I give back?
Ray Ciccolo
A college degree, laundromat, car dealership
After completing his undergraduate degree and service in the Marines Corps Reserve, Ciccolo went in to buy his first car—and bought the dealership, too.
It was 1963 and Ciccolo’s friend, the general manager of a Newton Center dealership, suggested he buy the failing dealership. Ciccolo seized the opportunity. He sold the two coin laundromats he owned and used mostly bank credit. He was in his early 20s.
He drew courage to take the risk from his father, who after being laid off from Ward Baking Company, opened and operated a coin laundromat.
Over the years, Ciccolo’s automotive business grew. He cited a manager’s recommendation to stop selling American-made Nash cars and stick with foreign-made Volvo vehicles as a key business decision—and controversial one in its day.
Today, Ciccolo’s Village Automotive Group is a respected leader in the Greater Boston automotive community with nine locations and 10 brands. Across the country, he owns 12 dealerships and recently opened dealerships selling luxury vehicles in Denver. The flagship store, Boston Volvo Cars, is regarded as one of the nation’s preeminent Volvo dealers, with the largest sales volume in New England and largest Volvo service and parts department in the U.S.
In 2018, to recognize Ciccolo for his impact, the Massachusetts Auto Dealers Hall of Fame inducted him as an inaugural member.
Ciccolo says it’s important to him to follow his father’s lessons of kindness by valuing employee satisfaction and giving employees second chances. Some employees have worked for his company for more than 45 years.
“I grew up on a side street in Cambridge, with family and friends and neighbors coming and going at all hours of the day. For me, being with people in a festive, friendly showroom is like being home,” he said.
Northeastern: Becoming a family tradition
Throughout his life, Ciccolo has continued learning. Mid-career, he earned an executive MBA at Northeastern University-Boston, an experience that introduced him to new business case studies, included travel to Washington, D.C., and paved the way for additional local contacts.
His connection to Northeastern is stronger than ever with his grandson, Sam Caron, and twin nephews, Noah Ciccolo and Luca Ciccolo, enrolled as NU undergraduates. He drops by campus to lunch with them and says he promotes Northeastern’s strength as an academic institution whenever he can.
Not too long ago, he was honored to throw out the first pitch at a spring training Red Sox-Northeastern game.
Ciccolo notes that one of his greatest accomplishments is his marriage to his wife, Grace, and their family. They met while training to be dance instructors and, today, have been married for 61 years. The family takes pride in how their philanthropy is making a difference.
“I feel tremendously blessed. When you start with nothing and you’re able to build it into something that will last for generations and generations, then the only thing left is: How can I give back?” Ciccolo said, adding, “Through the Ciccolo Family Scholarships, I’ve been able to help students afford college, follow their dreams, and build a better life for themselves.”
This article was written by Jennifer Nejman Bohonak.
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