Founding Reflections

An Interview with John Simon

Co-Founder, The Steppingstone Foundation

John Simon

When John Simon looks at the sweep of what Steppingstone has accomplished across three decades, he can’t help but be inspired.

Thinking back to its early days, he remembers how his cofounder, the late Michael Danziger, would often talk about the power of “high expectations, high results.” The two friends believed wholeheartedly that Scholars could “achieve great things.” So, too, could their fledgling nonprofit.

“High expectations can be self-fulfilling,” John reflects, echoing the words of his visionary friend, whose influence lives on in so many ways at Steppingstone today.

Shortly after meeting as students at Oxford in the mid-1980s, the pair had already worked together to plant the seeds for another nonprofit. John had been moved to try to create an inclusive sports program like the Special Olympics in the UK, and he rallied Mike and others to the cause. Today, those seeds have grown into KEEN, an international nonprofit.

As John reflects, “we came away thinking we could create something special together again.”


Once back in the States, that “something special”—The Steppingstone Foundation—was born. The idea grew from the devotion of the 20-something roommates to find a way to create more just and equitable educational opportunities for underserved students in Boston. As John recounts, they’d both had the good fortune to benefit from incredible schools. “When someone’s given you a gift, you have that sense of personal responsibility to give that gift to others.”

Rather than “reinvent the wheel,” they sought to learn from and build on approaches that had shown time-tested results. They dove into researching and evaluating models and impact, looking at about 50 different programs nationwide. After one organization’s founder generously gave them his “playbook,” John and Mike pored through the data and immediately began to see the potential for adapting it to the educational landscape of Boston and having a similar impact.

At some point, “a switch flipped for us,” as John puts it. They decided they could no longer keep talking about it. They needed to act. They saw how much was being lost by children and their families as well as by the city and wider world from the untapped potential. They knew some students in historically marginalized communities were falling a year or two behind grade level, despite their ability and desire. Undaunted by the challenges, they felt with the right support that “the sky’s the limit.”

John Simon and Mike Danziger


As “young and green” as they were, they presented their concept to a group of heads of several leading independent schools. While the group could easily have been dismissive, they took an encouraging and open-minded stance. That was a pivotal moment.

In retrospect, John realizes how blessed they were by so many others “who put their arms around our shoulders and made it happen.” That included the leadership of Mass College or Art, which opened its doors to the summer classes.

Having just graduated from Harvard’s Ed School, Mike committed to teaching and running the program full time. “I had never seen Mike teach,” recalls John, “and I couldn’t believe how charismatic and creative he was.” While John had a full-time job, he assisted in the classroom on Saturdays. He quickly learned “teaching is exhausting,” and he’d fall asleep when they got home in the afternoon.

Together, the two did a bit of everything, though sometimes things didn’t go as planned. John still remembers one of those times: getting hopelessly lost while driving Scholars home after classes in a school van that they’d rented. Thankfully, Morenike Adams Shelton ’91, “Nike” to her classmates, took charge and guided him through what seemed like 20 turns, navigating from one student’s home to the next with an uncanny, GPS-like sense of the city’s streets.

He’ll never forget that inaugural class of “bright, engaging, enthusiastic” Scholars who with their families took a leap of faith and signed on.

He also vividly remembers when he and Mike first saw the Scholars’ test scores, and “the results were off the charts.” Admission officers began telling them how amazing the students were. “We knew that already,” he says.

“The rest is history,” he adds with a laugh.

Inaugural Class of Scholars with Co-Founders


Creating something is just the start. Sustaining a vision over time takes building a team that will continually infuse it with “new waves of energy,” John reflects.

“You need to believe it can always be better,” he contends, adding that “the leadership team is infinitely better today.” From the staff to the Board, everything keeps getting more and more diverse and “stronger and stronger and stronger.”

In his mind, being results-oriented has also been a key to success. “We have a heart and a soul, but we also look at all kinds of data,” he notes. Measuring performance has gone hand in hand with “thinking we can continually improve.”

Steppingstone has also inspired John to grow and do more. As much as it has transformed others’ lives, being part of it has transformed him, fueling a “call” to find new ways to make a difference.

Along with his groundbreaking work in the investment world, he’s gone on to co-found the Greenlight Fund. The nonprofit has had an impact on nine, soon to be 12, cities across the nation by bringing one desperately needed solution for an unmet need impacting lower income children and families and life outcomes to each of its cities every year, year after year. More than a dozen additional cities have sought to be considered in the future. This process is similar to, and deeply informed by, the one Mike and John followed in bringing Steppingstone to Boston.

To him, “Greenlight is one little ripple effect from Steppingstone,” he says. “There are thousands of ripples from Steppingstone in the world, many of which we may not even see.”


In celebrating Steppingstone’s 30th anniversary, “it’s a time to look back and be thankful, and to look forward and think about the next 30.” He still sees it as “a family,” and he’s stayed engaged on the Board of Directors and as all-around champion. In the years ahead, part of what excites him is the potential for Alumni to become dramatically more involved as they get older and more established in their lives and careers.

At the start of any venture, “you have a certain horizon, and it gets pushed out farther and farther,” he reflects. Over time, “Steppingstone has never been content with the status quo,” he adds. “The horizon isn’t fixed.”

When John thinks about its future, “what excites me most is the piece of the horizon that I can’t quite see—yet!”