The Copycat Saint

At his home in Wellesley, Simon, 45, sits at the dinner table pondering the question of why a man with more than enough to keep him busy—two kids, a wife, and a 80-hour-a-week job as a partner in a venture capital firm—spends his extra time tinkering with schemes to save the city. He runs through a list of reasons that don't convince even him. "I don't know, maybe altruism…maybe personal goals—it's just a mix of things, I can't explain." His eyes wander to the framed painting on the opposite wall. It shows a farmhouse with mustard walls and a red roof. "Sometimes you just see something. Like if that painting was hanging sideways, there's just an impulse that says, ‘You gotta do something about that.'"

Growing up privileged in Chestnut Hill, the son of Harold Simon, chief of radiology at Newton-Wellesley Hospital, Simon was always made aware of his advantages. It was at Harvard that he first became engaged, volunteering to read to a blind student and working for the Special Olympics. "When I was lucky enough"—a frequently deployed preface that characterizes Simon's uniquely genuine humility—"to win the Rhodes Scholarship and go over to Oxford, I knew wanted to do something." That "something" took the form of a weekly tennis group for a few children with disabilities; by the time Simon's studies ended, it had served some 100 youngsters. Today, Kids Enjoy Exercise Now (K.E.E.N.) has 11 programs in the United States and Britain.

Simon returned to Boston dead-set on what he wanted to do for a living. "I made the determination that ‘Gee, if you like starting things, maybe the venture business is a good one to get exposed to,'" he recalls. Simon landed a position at Charles River Ventures, eventually following a group of colleagues to the newly formed Highland Capital Partners in 1988, where his job was to sniff out promising investment prospects. In 1990, at the age of 28, Simon formed a medical device company called UroMed that would ultimately make him his fortune.

While at UroMed, Simon, then still a bachelor, was living in the South End. He shared a small apartment in the steeple of a converted church with his buddy Mike Danziger, who'd worked with him on K.E.E.N. while at Oxford and was set to graduate from the Harvard Graduate School of Education. Looking for a place to invest some volunteering time, they stumbled onto an approach that still informs GreenLight's tactics now.

The two grew impressed with a New York program called Prep for Prep, which offered willing fifth-, sixth-, and seventh-graders afterschool and weekend instruction, with an eye toward getting them into some of the city's better private schools. Simon and Danziger studied the program closely, paid it a few visits, and figured it could work equally well in Boston. But they wanted to be sure. So they met with principals at public schools. Then the headmasters at the private schools. Then they went to the teachers. Then to the funders.

There was a little hurdle: Boston already had a group doing pretty much the same thing. The program, called IndePrep, had good financial backing and a board made up of the headmasters of top schools. "But John and I thought that we could do better," says Danziger. "The point was how effective [the program] was for the kids—not how great the funders or the board were. We thought that if we brought more resources—both human capital and money—that we could do a better job."

Their organization, which they'd call the Steppingstone Foundation, would have full-time employees (in contrast with IndePrep's part-timers). It would have revenue projections and a formal growth strategy. "I remember early on saying to John, ‘This is becoming like a business,'" says Danziger. "And he said, ‘No, this is a business. If we don't run this as a business—not like a business—we won't be in business any longer. We have to have a plan.'"

In 1990, Steppingstone's founders rock-paper-scissored for the titles of chairman (Simon) and president (Danziger). Simon made the budgets and organization charts, and Danziger put together the curricula. And they both fought hard against the idea that two rich white guys couldn't understand how to help the children of Hyde Park and Mattapan. "There was incredible skepticism," remembers Danziger. Potential backers, other nonprofits, the schools—everyone had doubts.

Seven years later, after sending 175 kids to places like Boston Latin and Milton Academy, Simon and Danziger decided it was time to fill gaps elsewhere. To take Steppingstone to other cities, the pair enlisted the help of board member Luis Ubiñas, now the president of the Ford Foundation and then a director at the elite management consulting firm McKinsey & Company. Ubiñas assembled a pro bono McKinsey team to figure out where it made the most sense for Steppingstone to set up shop next. The resulting report was several inches thick, and recommended 15 cities. Philadelphia, where some of Simon's partners had nonprofit connections, also had the benefit of being relatively close. It seemed like an easy place to start before taking the concept national.

Everything Simon and Danziger had done in Boston to get Steppingstone rolling had to be done in Philly, this time without the benefit of knowing the terrain. It took five long years to get their new offshoot performing up to their standards. Suddenly, the thought of going through this 14 more times seemed like madness. What they wished they had was a group in Detroit or Kansas City that already knew the lay of the land there, a collection of smart people who knew which donors to hit up and how to avoid the local political pitfalls. What they needed was somebody interested in importing Steppingstone. That's when, for Simon, the light bulb went off.