The Luckiest Kid in Pittsburgh

In the summer of 1993, a young man was working with children at a drop-in center in a troubled Pittsburgh public housing complex. He received advice from an extraordinary human being, Sister Lynn, who shaped his future when she said: 

Gregg: I know your heart’s in this, but you have a chance. You’re going to have an opportunity in this life to do more systemic things. And you’ve got to get up to the stratosphere so you can start to change systems that affect lives like the ones you’re witnessing here.

I’ve never forgotten that.

Liz: That’s amazing. That’s a huge gift. What was your reaction? Do you remember?

Gregg: I think probably a mix of emotions, right? I think it was probably incredibly affirming because I adored Sister Lynn and respected her so much, and I just thought she was salt of the Earth. Probably a little bit puzzled because I was still a young punk trying to figure out this world and my place in this world and my purpose. And probably some angst, too, right? Because I don’t know, it seems like a big thing to take on systems which seem amorphous and confusing. It’s much easier to work with Will and Wu and to know the kids and to be present in their lives.

Turning that advice into his life’s work, Gregg Behr, the Executive Director of The Grable Foundation has never forgotten what it means to work with a child.  Reminiscent of Mister Rogers himself, Gregg Behr’s smile reflects the profound power of being fully present and authentically yourself. He knows how much it feeds your soul to make a difference in a young life. It keeps you young at heart. As he says, “I am the luckiest kid in Pittsburgh.” He recalls a project that devised “ a way for kids to drive a submersible through the aquariums at the Pittsburgh Zoo. It was fascinating, and I loved it. I got to do it myself. There you are, driving this robotic device. It had cameras on it so you could zoom in on the shark that was right in front of and all other things. You and I laugh about it because you can think of the 100 reasons that went wrong. But actually, I think it sparked so many other things, including elevating the wonder and curiosity of someone today who’s now leading a space company.’

Liz: The fact that you got to drive one… I mean, forget that you don’t get to work with kids anymore. You get to do the things kids do.

Gregg: I told you I’m Pittsburgh’s luckiest kid.

So Sister Lynn was right, Gregg did end up in the stratosphere – in the world of philanthropy, but he maintains a grounded perspective with a heaping dose of wonder usually reserved for children: “I’m someone who believes deeply that genuine change actually happens in lots and lots of little things, being faithful to the little things. The compilation of those little things add up to something incredibly special.” 

This philosophy shapes his approach at the Grable Foundation, where success is measured by the ability “to support extraordinary people and their organizations who in some way are making life better and bringing goodness to kids, to families, to communities in this place that we call home.”

Gregg Behr galvanizes you to do what you can to make your corner of the world better for those around you – especially the children. Starting with something as simple as a pancake breakfast, he has a childlike enthusiasm for possibility that reminds us that the most transformative philanthropy often begins with wonder, curiosity, and the simple joy of asking “What if?” to a gathering of extraordinary people who are working with and for children everyday. 

Gregg: The best things in life happen over food and beverage of some sort, right? When I think back to the very first breakfast meeting at Pamela’s in the Strip District of Pittsburgh that was in so many ways the start of what became Remake Learning. It was a teacher and someone from a museum. It was a multimedia person and a technologist and a gamer. People I had met over the previous months who clearly cared about kids, cared about learning, and were thinking differently about learning. It was just one of those what-if breakfasts. I always figured it’s at least worth the price of admission: a cup of coffee and pancakes.

Bringing together people with a similar passion over pancakes turned into the Remake Learning network of more than 800 schools and organizations. The power of its network is the way it is connecting educators, researchers, and community organizations to fundamentally reimagine how children learn. Remake Learning amplifies the voices of those making a difference for children. Its grant making encourages us to think boldly – to imagine a future different from the one we know in an industry that has barely changed in the past 100 years. 

Gregg: I’m both blessed and cursed. Working in philanthropy, we’re always at 30,000 feet. We’re not the ones doing the work. And yet we have this great perch to see what’s going on, to meet extraordinary people, communities, places, projects, ideas. I don’t know. I think sometimes philanthropy at its best is when it’s simultaneously the R&D and also the connector of people who are doing things. And maybe that’s what I’ve tried to do.

For Gregg, philanthropy exists somewhere “on that continuum between egoism and altruism. It’s never, ever 100% of either.” This balance became profoundly transformed when he became a father.  The disparities he witnessed professionally now struck him at an emotional core he hadn’t experienced before. Each child in an underfunded school or struggling neighborhood was no longer just a beneficiary of the foundation’s work—they became someone’s daughter, deserving every opportunity he wanted for his own children.  It creates an urgency.

Gregg: Becoming a parent, I think you start to see your own kid in so many other kids. You visit communities, and you visit schools, and you visit libraries, and you think to yourself, this just isn’t fair. You start to imagine your own child faced with those conditions, faced with those circumstances, faced with those deficiencies. The work becomes incredibly personal. 

This is my experience too. I have said many times I worked on creating a school where my children would thrive. You could call me the most selfish mother in the community, I guess. I was asked to consider the position of Head of School two years before I accepted it. I turned it down at first because I was trying to adopt a baby and didn’t think I had the bandwidth for the responsibility of leading a school. Over the course of the following two years, I visited almost every elementary school in the tri-state area as a supervisor of student teachers. I would return home to pick up Grace from Universal Preschool and silently commit that school would be better for her than what I experienced that day. When I couldn’t find one, I knew I could lead one. 

Gregg: I remember When Catheryn was born, I had said, I hope she doesn’t graduate from a brick and mortar high school like I did. I wasn’t naive to think high schools were going away. I mean, schools are central in kids’ lives. But now, referring to Mister Rogers, Fred himself understood that schools were central in kids’ lives, but he also understood that there’s a great big neighborhood where kids can learn and have experiences.

Fred Rogers—Pittsburgh’s most beloved neighbor—emerges as a touchstone in our conversation and in Gregg’s life. “Being a Pittsburgh kid, I find relevant modern wisdom in the work of Mister Rogers, whom I loved as a kid and have come to love even more so as an adult.” A black and white photo of Mister Rogers sitting on the steps of his trolley hangs next to Gregg’s desk. Of course it does. In its simplicity it evokes innocence and hope and a way to be transported to a child’s world even as an adult. Fred’s legacy reminds Gregg that the most meaningful education happens when we honor children’s natural curiosity and connect them with diverse experiences and people who care deeply about their wellbeing. 

Gregg’s admiration for Fred Rogers’ educational philosophy ultimately inspired him to co-author with Ryan Rydzewski When You Wonder, You’re Learning: Mister Rogers’ Enduring Lessons for Raising Creative, Curious, Caring Kids. The book emerges from a series of lightning bolt moments that indicated the time had come to elevate and amplify the great work happening in schools and neighborhoods in and around Pittsburgh. These experiences manifest Mister Rogers’ seemingly simple messages as profound wisdom about child development and learning. By writing this book, Gregg and Ryan transformed their personal inspiration from Fred Rogers into a resource for parents and educators, demonstrating how the beloved TV host’s simple approach remains powerfully relevant in today’s complex educational landscape. The book reflects Ryan and Gregg’s commitment to “curating examples” rather than prescribing solutions—highlighting Mister Rogers as “a master educator whose work should inspire us in the things that we’re trying to do.”

When we push ourselves to notice and wonder about the people and the things right around us in our own backyard as Gregg puts it, “you start to notice that excellence and how you can be part of it, how you can cultivate it, how you can advance it.”  Excellence, in this view, is inextricably linked to acknowledging the full humanity—including the doubt and resilience—of everyone involved in the work, even ourselves.

Liz: I think the hard part for people in the work we’re in is you never feel like you can do enough because the problem is so big, the profession is so noble. How do you deal with that?

Gregg: I’m always feeling that “never enough.” Sometimes I notice that I’m trying to do too much and I pull myself back. Sometimes I notice I’m asking others to do too much. I think I’ve garnered at least a little wisdom over the years to know how to pull back. But I often quote Arthur Ashe, and I’m not sure that he originated this phrase, but in many places it’s attributed to him. Start where you are, use what you have, do what you can. I say that to myself a lot. I think it’s in part why I use phrases like “this corner of the world.” I’m just at this point in the world with whatever skill or privilege or luck or whatever it is that I have, what is it that I can do? Trying to know when that’s enough, I think it’s probably a continuous lesson.

Honestly, I feel like that’s a lesson I learn repeatedly. But I think that’s partly the challenge of being human, isn’t it?

Liz: So when you say you have to learn it repeatedly, do you kick yourself? Oh, my gosh, I had to learn that lesson again. Or are you forgiving of yourself?

Gregg: That’s a hard question. Forgiveness is not my first instinct, but I think I do come to forgive myself.

Liz: There’s no timeline.

We walked for just over an hour through Gregg’s neighborhood. It rained the entire time. It was February. I was wet from my toes to my hips. Like another beloved neighbor, he invited me in.  “Hot tea?” he asked. 

The funny thing is I remember that afternoon as being warm, welcoming, and inspiring. I don’t remember it as the only walk I’ve taken in the rain.  The gentle patter of raindrops created a natural soundtrack to this walk. The rain made ordinary streets glisten. Trees appeared more vibrant. The local school took on a dreamlike quality as it was reflected in surrounding puddles. Or… maybe that is just what it is like when you are lucky enough to walk with Gregg Behr… the luckiest kid in Pittsburgh. 

Sister Lynn would find that to be true.

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