The Copycat Saint

Five years in, GreenLight is still finding its legs, and it's not always easy to see immediate results from some of its programs. The sort of 12-year mentorship that Friends of the Children is built on doesn't offer the instant impact of a soup kitchen or a shelter. Nor will results in Portland grab headlines here. But what GreenLight's initiatives do have is the performance of their predecessors in other cities, which, for the kinds of supporters GreenLight targets, is usually more than enough. "We do our due diligence on organizations and invest in them in a way that just resonates with people who work in the VC and private equity worlds, and the entrepreneurs," says Hall. "They've been through that process. And they recognize it as one that turns out well-vetted organizations."

It's a market GreenLight aimed for consciously. Hall talks of a "change in the gravity"—a shift away from a philanthropic landscape once dominated around here by a few honchos at a few corporations, and toward a terrain with clusters of moneyed innovators. By unlocking a whole new type of donor rather than hitting up the same sources as everyone else, GreenLight eases some of the competitive pressure in a city that doesn't suffer from a shortage of nonprofits. Of course, the old-guard charities have also taken notice of the new paradigm: The United Way of Massachusetts Bay, in a bid to appeal to this emerging class of results-hungry benefactors, recently rolled out a plan that puts a fresh emphasis on charting progress.

"John is at the very cutting edge of a trend that is continuing to grow quite a bit," says Andrew Wolk, a senior lecturer in social entrepreneurship at MIT's Sloan School of Management and founder of Cambridge's Root Cause, which consults with nonprofit groups. "All of the people who have had the benefit of a very successful economy in the past 10 or 20 years are all shaking their heads as they get to be philanthropic at a younger age and saying, ‘What is this? This is not what I know.'" GreenLight, then, is a wake-up call for the rest of the nonprofit world. "If the sector wants to attract a group of people who have made a fairly large amount of money in their chosen careers," Wolk says, "it's going to have to operate in a more performance-based way."

Throwing a decent bash every once in a while doesn't hurt, either. Jeffrey Glass, a serial entrepreneur and now a partner at Bain Capital, has been involved with Simon's fund since the beginning, and he and his wife have recruited others to the burgeoning scene. "Part of it, frankly, for us, is the social aspect," says Glass, who's made a lot of friends at GreenLight events. "We can have a good time and we can feel like we're contributing to something that makes a real difference to kids' lives here in Boston—what's not to like?"

After all the number-crunching and fundraising appeals, this is what GreenLight really looks like: bright orange and royal blue walls surrounding a group of kids and mentors at the year-old Friends of the Children office in Jamaica Plain. A headshot of John Simon, smiling a crooked smile and as uneasy in the spotlight as ever, hangs among photos of mentors and kids with their missing-teeth grins. The children are taking turns reading about Martin Luther King Jr. A fourth-grader from Dorchester struggles over the name of King's Atlanta church. Ebenezer—that's a tough one. His mentor prods him along encouragingly.

Like the rest of students in the room, this boy was invited to Friends after teachers, counselors, and principals determined that he'd have a hard time succeeding without some extra support. Friends matches kids with their full-time mentors, who are paid about as much as a starting teacher and who work with eight children for at least four hours a week. The long-lasting relationship, which will stretch through high school, is meant to provide the student with the sort of cool aunt or uncle type that helps them with homework or takes them to get pizza.

The nonprofit also offers a separate program called Family Friends, in which 25 volunteer families spend some quality time with at-risk students. These interactions, says executive director Imari Paris Jeffries, are eye-opening for the struggling students. "When are these kids ever going to have the experience of going on a 70-foot yacht out on the Cape?" says Paris Jeffries, whose site now works with 60 children. "Maybe that kid sees the ocean for the first time and decides, I'm gonna be a marine biologist." It also works the other way around: When the kids from the suburban day schools go apple-picking with the kids from Hyde Park and Southie, Paris Jeffries says, "it's an education for everyone." That's the feel-good version, anyway. Because Family Friends also has another value to the cadre of well-to-do suburbanites who are the very donors Simon is relying on to help him hold philanthropy accountable: It gives them a chance to have a hand in the hard work of protecting their investment.