Immigrants from the Caribbean have long contributed to Boston’s kaleidoscope of businesses and cultures—just drive around and you’ll see for yourself.   

In Mattapan Square, there’s Le Foyer Haitian bakery. And then there’s Garden of Eden, a Jamaican restaurant in Roxbury. People like 91-year-old real estate developer Ken Guscott, the son of Jamaican immigrants, who tragically died in a house fire in early March, helped turn parts of Roxbury and Dorcester into vibrant commercial hubs.  

A noted area landmark, Merengue Restaurant on Blue Hill Avenue, is owned by Hector Pina, an immigrant from the Dominican Republic. 

“I am Dominican. I love my country, but I am also American,” he said. “My contribution to employment and taxes are also part of the economic driving of this country. This is why sometimes I hear people say that immigrants do bad to this country. We do good. We create businesses. We are part of the economic development of this country.”

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Restaurant owner Hector Pina at his newest establishment, Dona Habana, on the border of Roxbury and the South End.
Phillip Martin/WGBH News

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Inside of the Cuban-themed Caribbean restaurant, Dona Habana.
Phillip Martin/WGBH News

And it’s not just ethnic restaurants that have sprung from the entrepreneurial imagination of Caribbean immigrants.  Across the state there are also small Caribbean-owned construction and moving companies, barber and auto-repair shops and doctors and dentists with their own practices. Economist and Northeastern University professor Barry Bluestone said that is par for course. 

"Our research has shown that we have quite an entrepreneurial spirit among our immigrant labor from all over the world, but particularly from the Caribbean," he said.

Bluestone says, for example, that home health aides and carpenters often start their own businesses, as do college-educated professionals who immigrate from the islands. Among the most successful he notes is a local businesswoman named Colette Phillips.

“Colette is from Antigua and for years she has been one of the most important people in the Commonwealth, not only because of her communications company, which is very highly regarded but the work she does in the community," Bluestone said. "She’s somebody who represents what the Caribbean brings to Massachusetts.”

Phillips has been her own boss for more than 30 years, running Colette Phillips Communications

“Entrepreneurship is sort of in the DNA of Caribbean people," she said. “My parents were entrepreneurs growing up so I saw that you could go off and make your own living, and I decided that I wanted to be an entrepreneur. I wanted to start something I could control.”

Shortly after graduating from Emerson College in the 1980s with a master’s degree, Phillips started working for a cable company, but was laid off. 

“I was fortunate enough within a month of losing that job to be hired by Sonesta Hotels International and I told them that I wanted to eventually start my own business," Phillips said, "and I made them a promise of what I would do for them and that if I accomplished those goals that I wanted them to become my first client, and the rest, as they say, is history."

Colette Phillips Communications is not the biggest public relations firm in the state—not even close. It ranks in the top 25, however, among more than 100 firms listed statewide.   

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Colette Phillips, owner of Colette Phillips Communications, presides over a Get Konnected event at the firm McKinsey & Company.
Courtesy of Jim Harrison

“Could my business be a lot more successful? If you measure success by the bottom line absolutely it could be," Phillips said.  "The fact that I've been able keep my business afloat for 30 years is nothing less than remarkable and I think it's more of a tribute to my Caribbean roots of tenacity, dedication, hard work and ethical conduct than it is to anything else.”   

And the bottom line?

“My company has veered anywhere between a half a million dollars and almost two million," she said. "I would have liked to have seen it be even more.”

Phillips said years ago she made a decision to turn down all offers to promote cigarettes and alcohol, even though her father sold them back in Antigua. These are the staple products of many black-owned PR and marketing firms, but products that Phillip says have major negative impacts on black communities.    

“My focus mostly with clients are about helping them understand how to build their brand among culturally diverse consumers and women, and to advise them on their corporate social responsibility," Phillips said.

Phillips says her business model sets her apart from her competitors: market-branding based almost entirely on knocking down walls separating ethnic groups and immigrants and non-immigrants—sort of like the old Benneton model of selling clothing, but in the age of Donald Trump.

Every other month, Phillips convenes an event called Get Konnected, which has become Boston’s premier cross cultural gathering of small and large businesses executives.  Boston Mayor Marty Walsh spoke at a recent Get Konnected event.

“Colette has used her podium to bring different areas together, whether through business opportunities to business connections," Walsh said. "Look around the room tonight, you see a real cross-section of people that otherwise wouldn't be spending nights together. She has a unique way to pull people together. People respect her.”                    

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Colette Phillips with officials representatives from Mexico, Japan and Israel at a recent Get Konnected event.
Courtesy of Jim Harrison

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Colette Phillips and Mayor Marty Walsh at the regular Get Konnected event.
Courtesy of Jim Harrison

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Colette Phillips speaking with Get Konnected attendees.
Courtesy of Jim Harrison

Hector Pina, holding court at his newest restaurant Dona Habana, says Colette Phillips has become a model for other Caribbean entrepreneurs, including himself.

“Just imagine as an African American woman to break the ceiling and get big corporate contracts," he said. "Like, she was the PR for the Boston Red Sox. You have to really be more than qualified!"

But while that can-do attitude is real, says Avi Chomsky, a Caribbean specialist at Salem State University, it’s an overstatement to say there is a Caribbean entrepreneurial spirit that distinguishes it from other parts of the world. What is distinctive, says Chomsky, the author of' 'How Immigration Became Illegal' is a history of slavery that has spurred inventiveness from desperation.  

“The Caribbean consists of many islands with very different histories, so to the extent that there's a common history that we could say leads to an entrepreneurial spirit, that might contribute to it," Chomsky said. "Many parts of the Caribbean developed a tradition of markets where enslaved people could sell their produce. The Caribbean also has a history of escaped slave communities that became self-sufficient and produced for themselves.”   

The results of that tortured history can be observed today both along Blue Hill Avenue and in the market stalls of communities stretching across the Caribbean, including in Colette Phillip’s homeland, Antigua. That's where we head next.

Reporting for this story was supported by the International Center for Journalists and S&P Global. This story is Part One of a two-part series. Click the link below for Part Two.