Photo by Richard Howard

At the time, Elyse Cherry ’75 wasn’t sure it was a good idea. But it was 1984, she was a second-year associate at her law firm, and a group of friends wanted to create a community loan fund in Boston. “When we started, we only had $3,500,” Cherry says. “None of us had the good sense to realize you couldn’t do much of anything with that.”

Since those humble beginnings, however, the fund has grown into Boston Community Capital, a nonprofit enterprise which has invested more than $1 billion in underserved communities—financing affordable housing, creating jobs in low-income communities, preventing foreclosure-related evictions, creating community childcare facilities, and more. And Cherry has moved from combining a law career with working on the fund to serving as chief executive officer of a growing multifaceted organization. Boston Community Capital now incorporates the work of the original fund with several other initiatives to help communities not just in Boston, but in states from Massachusetts to Florida. And although the company has grown significantly from a single business line to six, one thing hasn’t changed: the core mission. “Our mission is to help build healthy communities where low-income people live and work, and that mission has not changed since the beginning,” Cherry says.

Although that core mission has resonated throughout her career, a few other things have changed for Cherry over the years. A political-science major at Wellesley, she always envisioned the law in her future, but she didn’t jump right into post-graduate studies. “I knew that I needed a few years just from a financial perspective and to get grounded in the world before I went back to school,” Cherry says. So, after Wellesley, she worked for a year as an AmeriCorps VISTA volunteer in Tennessee. “[It was] a great transition year, where you could learn a lot of stuff, and be in a different part of the country, and create some new networks and relationships, and do some good, and generally kind of figure out where you were going,” she says.

And it was during that time that Cherry developed an interest in labor and labor history. She went on to spend the next several years working as a labor relations examiner at the National Labor Relations Board, learning about contract negotiations and labor issues. “I went to law school fully intending to be a labor lawyer,” she says. “But that, of course, did not happen.”

After earning her J.D. from Northeastern University, Cherry had to readjust her thinking to what the market was offering. “My goal had been to do plaintiff-side labor law, [but] by the time I got out of law school, there were no jobs,” she says. Boston was undergoing a real-estate boom at the time, however, and there were some opportunities in that arena. “As a VISTA volunteer, I had done a ton of urban planning and public planning and trying to figure out how to get community facilities bills, so I was familiar by then with the concepts of real-estate law,” Cherry says. So she joined the real-estate department at what was then Hale and Dorr (now WilmerHale). “[It] was a great way to get on a rocket ship in terms of learning and responsibility very early in one’s career,” she says. The firm also had a long history of pro bono service, which appealed to Cherry. “I was able to go there and build not just a commercial practice, but actually an affordable-housing practice,” she says. “What I discovered was that the two really played off each other.”

As Cherry built a commercial real-estate finance and development practice, eventually becoming a partner at Hale and Dorr, she continued to work with Boston Community Capital. “It was a pretty engaged relationship right from the very beginning,” she says. “I served on the board of directors and wound up being the strategic vision and voice of the organization.” Then the real-estate market hit a serious downturn in 1992. “There were days when I was spending the morning explaining to members of bank boards why it made no sense to sue my developer clients who were defaulting on their loans, and then I’d spend the afternoon insisting that whoever it was that owed Boston Community Capital, then Boston Community Loan Fund, was going to pay,” she says.

That downturn gave Cherry the opportunity to consider where she wanted to go next in her career. “The challenge is that lawyers inevitably pursue someone else’s agenda,” she says. “I got to the point where I wanted to pursue my own agenda.”

With her background as a transactional attorney and her experience negotiating, Cherry took her skills to the business side and joined the Plymouth Rock family of insurance companies. “[I was] running the insurance services side of the business, about which I knew nothing,” she laughs. “If you’re going to do more than one thing in your life, you can’t really go up the mountain and come back down and go all the way back up again,” Cherry says. “Once you go up, you have to jump from mountaintop to mountaintop.”

After four years with Plymouth Rock, Cherry jumped again. She decided to try the entrepreneurial side and started to work with a group trying to bring environmental technologies to market. But soon, Boston Community Capital came calling, asking her to run the organization. “I was pretty reluctant to shift gears,” Cherry says. At one point during her conversations about the move, she determined that she could write down 20 reasons why it wouldn’t work. “So I wrote down the 20 reasons, but the problem was, by the time I got to the bottom of the list, I had solved 18 of them,” she says. Her two remaining big challenges were: She wanted the organization to grow, and they needed to find a source of capital for that growth. “Everybody was on board about growing, and I realized I could figure out where to find the capital,” Cherry says. “And then there really weren’t any excuses.”

Cherry became chief executive officer of Boston Community Capital in 1997, and she hasn’t looked back since. “We were at about $30 million then, and we’re well past the $1 billion mark now and on our way to $2 billion,” she says. “It has turned out to be the most interesting, most challenging, most rewarding work I’ve ever done, and the ability to lead a values-driven life and to really blur the edges between work and civic leadership and life has been one of the great privileges of my life.”

Boston Community Capital has grown significantly under Cherry’s leadership, and more than just monetarily. In addition to the community loan fund, which lends money for affordable housing and community facilities like health-care centers, the organization also encompasses a number of other ventures. “Effective institutions change to respond to the changing needs of their communities and constituencies,” Cherry says. “We’ve developed over time.” To that end, the organization added a venture capital fund that invests capital into businesses either serving low-income communities or run by low-income entrepreneurs, as well as a program that helps low-income communities gain access to solar energy, a utility benchmarking company, and more.

In fact, after the real estate and financial crisis hit in 2007, Cherry drove the launch of the Stabilizing Urban Neighborhoods (SUN) Initiative, a foreclosure-relief program which buys mortgages back from the foreclosing lender at the current market price and then issues a new mortgage to the original homeowner. “We understood something about how to make good loans and about how to work with borrowers long-term, so that we took into account not just the monetary side of the transaction, but the human side of the transaction,” she says.

The program has been heralded by many in the housing community, including Barry Bluestone, founding director and senior research associate at the Dukakis Center for Urban and Regional Policy and a professor of public policy and urban affairs at Northeastern University. “Boston Community Capital, under Elyse’s direction, played an important role in helping people stay in their homes and find ways to avoid foreclosure,” Bluestone says. “When somebody gets foreclosed out of their home, not only have they lost their housing, but they often lose the community they were in. The work that she’s done with Boston Community Capital is to not only help individual families but to help entire neighborhoods.”

The SUN Initiative is now operating in seven states, and Cherry estimates that they have done about $150 million in lending to help stabilize roughly 800 families. “I would like nothing more than to be put out of business,” she says, but they are still seeing demand for foreclosure relief, despite what has been hailed as a significant recovery. “I sometimes describe this as a tale of two recoveries,” Cherry says. “If you live in a middle or upper middle class community, your housing prices are just fine … but if you live in a low-income community, you’re often still underwater because the recovery has not been uniform.”

Paying attention to what communities actually need has been a goal for Cherry and Boston Community Capital since the beginning. “We really set out to understand what is was that the communities we were serving, the populations we were serving, needed and then to really figure out how to take these downtown techniques, if you will, the same kinds of techniques that build wealth for the folks in the middle class, Wall Street, rich people, and apply them to the issues of low-income communities and people,” she says. “To be able to say we’re going to bring these downtown experiences and these downtown techniques and combine them with the idea of communities driving their own future—that, in some ways, was really an innovative idea.”

It was just one of the things that drew Cherry to working with Boston Community Capital. The organization also encourages civic leadership as part of its strategic plan. “If what we want to do is build the world we want, then we not only do that through our work here, but we can also do it by pursuing civil-rights issues, by serving on the boards of nonprofits, by participating in town government,” Cherry says.

“From the beginning of my career, it was clear to me that I wanted to build a for-profit life and a nonprofit life, and I didn’t think it made sense to say, ‘I’ll wait.’ … What I really tried to do was build them both together.” Which means that whether Cherry was working at a law firm, or an insurance agency, or Boston Community Capital, she was also engaged in a variety of other pursuits. She was board chair and director for MassEquality during its historic fight for same-sex marriage equality in Massachusetts; she served as director and chair for the Massachusetts Cultural Council; and she is currently serving as co-chair for the GLBTQ Legal Advocates & Defenders (GLAD) One Justice Fund.

Carol Rose, executive director of the American Civil Liberties Union of Massachusetts, met Cherry in 2003 when they were both working for marriage equality. “We were really shoulder to shoulder in the trenches on probably the greatest civil rights victory of the last 20 years. Elyse brought to the struggle for equal marriage rights the kind of creativity and doggedness that was necessary to really see it through,” Rose says. “There were some very thin margins that we won by here in Massachusetts, but Elyse never lost focus. She never hesitated.”

Her work with other nonprofits informs her work at Boston Community Capital. “People have come to understand that issues for the LGBTQ community and for communities of color and for women and for the economically disadvantaged are all really tied together,” Cherry says. As CEO, she provides leadership and strategic vision for the organization, and for that, she needs to be “in the traffic of ideas,” she says. “I really think that the most interesting place to stand is at the intersection of many communities.” One of the challenges of leadership, she notes, is to stay away from the driving needs of the day-to-day business and to be able to look forward. “So the more perspectives you can develop, whether it’s by travel, or wandering through a variety of communities, or cultivating a variety of friends, or being in a variety of industries …the more complex the mosaic, the more accurate the view in the long run, the more able one is to look around the corner and try to make a decision about where to go.” She’s currently working on several new initiatives for where to take the organization next, including one about the future of work and one about financing a path to citizenship.

“At a time when we have people in the White House and Congress who would strip away rights for undocumented people, who would strip away rights for gay people, women, people of color, and poor people, Elyse Cherry isn’t going to be satisfied with mere resistance. She’s going to push forward with a vision of where she wants to see the world,” Rose says. “She doesn’t have time to tear things down. She’s building.”

While Cherry and her organization’s initiatives do help erect actual buildings, more importantly, they create opportunities. “The work that we do at Boston Community Capital, at the core, it’s really about trying to build the world we want,” Cherry says. And although she may have been unsure at first, it seems like it turned out to be a pretty good idea after all.