BON VOYAGE: Vincent Flanagan leaves Homeless Empowerment Project

“Arguing and advocating are something that are part of my being,” begins Vincent Flanagan, outgoing executive director of the Homeless Empowerment Project (HEP).

Flanagan, who has held the position since May 2012, announced last month that he would be leaving. The Homeless Empowerment Project is the nonprofit which publishes Spare Change News.

Flanagan, soft-spoken but assertive, says that his choice to do advocacy work has been a “calling” throughout his life. When he was only five years old, his father died, leaving his mother with two children, no insurance, and no savings. From an early age, he knew what poverty felt like, and that he wanted to help others.

“I felt that it was a disgrace that in a country as rich as ours there were people living on the street, people who were going to bed hungry, and children who were malnourished. And I thought that if you really believed it was a disgrace you should do something about it.” Flanagan says this maxim has stayed with him through his career.

“When I was in college, I wanted to be a psychiatrist. I changed my mind when I realized I couldn’t afford to go to medical school,” Flanagan remembers. He was able to go to law school at Fordham instead, and his interest in the issues of poverty and homelessness remained hugely important to him.

While living in New York, Flanagan worked for the Neighborhood Coalition for Shelter, which offers an “array of housing and comprehensive services, including counseling, substance abuse treatment, vocational and educational programs, and employment support,” according to its website.

But when he arrived in Boston, Flanagan’s new job in the federal court system was extremely demanding. Though he wished he could contribute to a nonprofit, he barely had any time at all to himself.

Luckily, in 2001 he took a less demanding position, and he got the chance once again to follow his passions. In his spare time, he eventually started working with Give Us Your Poor, an organization headquartered at UMass Boston.

But Flanagan always was looking for ways to contribute more. When he heard that legal services for the homeless in Boston were “woefully understaffed,” for example, he called every single one. “They turned away two people for every one they could help,” he explains. Concerned, he started a new program to recruit more attorneys who could help.


In early 2012, when buying the most recent edition of Spare Change News, Flanagan was alerted by vendor Charles Stallings to the open executive director position at the Homeless Empowerment Project. Flanagan applied right away, and got the job.

Though, in the early days of his time at HEP, the non-profit could sometimes seem disorganized, a man named Bob Hurlbut gave Flanagan hope that he could make a difference. Hurlbut was, at the time, the executive director of the Cambridge Community Foundation, and helped to dramatically increase the organization’s endowment from $4 million in 1994 to $32 million in 2014 (he retired early this year). He is the “ultimate person who knows how to bring people together to solve a problem,” reflects Flanagan. He says that he thought at the time, “if he could do that [at CCF], and I listen to his advice, maybe I can really make a difference at Spare Change.”

Flanagan characterizes his experience with Hurlbut as a defining moment of the early days of his tenure at Spare Change, and says that Hurlbut’s guidance made him realize the importance of networking, and connecting to as many local businesses and organizations as possible.

It was also in these early days at the HEP that Flanagan truly began to see the profound importance of Spare Change News in Boston firsthand.

First of all, Spare Change News provides a “hand-up” for vendors: “the vast majority of our vendors are people who have had difficulty finding mainstream employment,” states Flanagan. Spare Change News does not require background tests, drug tests, or interviews, unlike most companies or organizations: being a vendor might be the perfect opportunity for someone who wants to work but can’t get a regular job. “Having an organization which gives people the chance to have a job is really unique.”

Secondly, “the mainstream press doesn’t really cover a lot of issues relating to homelessness and addiction,” Flanagan states. “Someone needs to cover [these issues] and inform the public about what’s going on. Also, someone needs to inform the public about the truth about homelessness. Most people think that most homeless people are alcoholics, drug addicts, mentally ill, thieves. It’s simply incorrect.”

“When you help dispel the myths, and you help educate the people on what the truth is, people are going to be more willing to do something about it.”

HEP has faced many challenges since Flanagan took over as Executive Director. The biggest one, Flanagan says, is also the most predictable: raising enough revenue each year. Flanagan has been extremely successful: this past year, the Project raised about $16,000 more than had been expected. However, “It’s always a challenge to find sources of income. We succeeded, but every year you start over.”

He says the Board of Trustees and the Advisory Board have been invaluable during his tenure, and have helped him immensely with this difficult task.

When asked what advice he would give to his successor on the fundraising front, Flanagan states, “I urge whoever replaces me to network, and become part of as many organizations as possible.”

But HEP has also faced another, unexpected challenge: “There’s a very scary movement in our country to criminalize homelessness.” In 33 major cities in the United States, for example, it’s illegal to give food to homeless people, whether you’re an individual or an organization. And Flanagan says these kinds of laws are becoming more prevalent.

Even in Boston, there have been more attempts to “sweep the homeless under the rug,” he says. When the city chainsawed park benches to prevent homeless people from sleeping there, the city claimed it had nothing to do with homeless people. But “I don’t believe that for a minute,” says Flanagan.

The third major challenge for the paper’s future is to appeal to young people, and he realizes that social media is a big part of this effort.

He recounts a recent visit to a local university, where he asked how many of a class of 30 had heard of Spare Change News. “Only two raised their hand,” he says, and that’s when he realized that the organization needed to start an initiative to reach out to the younger generation. “High school, college, just out of college — they’re our future readers.”

Vincent Flanagan with out Editor-In-Chief, Sam Baltrusis (left).

When asked where he would like to see the paper in five years, Flanagan immediately responds. He wants it to be a weekly paper, he says, and to have a larger sales force and a wider reach. “I think we should have people in every corner of Cambridge, Somerville, Boston, and all of the surrounding communities.”

When asked where he himself wants to be in the future, he isn’t so sure of the specifics. But he is sure of one thing: “I want to continue to work for homeless causes.”

“Dreaming?” Flanagan continues, “I’d like to see New York have a street newspaper again. And I’d love to be part of making that happen. Is it realistic? I don’t know.”

In the long run, Flanagan is a cautious optimist when it comes to societal progress on homeless issues. When asked about Mayor Walsh’s new plan to end chronic homelessness by 2018, or a hypothetical plan to end all homelessness in the city in ten years, Flanagan chuckles. “I think it’s an ambitious goal, but I think it can be achieved,” he states. But only with a “drastic realigning of our priorities” as a society.

It’s a question he’s obviously thought of before, and he has a very clear idea of what needs to happen to achieve it. He states that a partnership between businesses, nonprofits, citizens, and the government is imperative to make it happen; nonprofits — or the government — can’t do it by themselves. “If the will is there, it can be done,” he continues. Affordable housing should be the number one goal unquestionably, “but people have to accept the fact that this is going to cost money.”

In the end, it comes down to citizens. “We have to use our vote to put into office people who will [budget] money that way.”

But voting is not the only way we can make a difference. “Everyone should be doing something about [these issues],” he concludes.

Underlying much of his career, it’s Flanagan’s unshakable sense of duty — to his community, to his society, and to his fellow man — that sets him apart. Though we are sorry to see him go, we know the city of New York will be better with him working tirelessly for its people.






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