Alright – so today we’ve got the honor of introducing you to GREG DEEGAN. We think you’ll enjoy our conversation, we’ve shared it below.
Hi GREG, thanks for joining us today. The first dollar your firm earns is always special. We’d love to hear about how you got your first client that wasn’t a friend or family.
I had actually started Teaching Cleveland as a part-time activity. As a high school social studies teacher, I realized how little I knew about Cleveland’s history and I soon realized my students knew little as well. I became interested in providing educator professional development to help teachers understand more about our city and its history. First, I found another educator who was doing what I was doing, and together we began providing professional development experiences and we worked with educators to help them develop curricula and place-based pedagogical approaches in the classroom.
Then, we found two other educators through our professional development offerings, and the four of us built our Teaching Cleveland Student Challenge — a program for high school students to learn about the history of current issues that leaders were discussing. We did this for about 10 years, and one of our clients had been the Cleveland Teachers Union. It turns out that the professional development we provided them was so well-received that years later, the Cleveland Metropolitan School District called and offered us a major contract to teach every single employee of the district — about 7,000 — the social history of Cleveland to help people understand how we got here today. It was this contract that finally took the part-time organization into a new era, with me leading it on a full-time basis.
GREG, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I grew up in a sheltered, middle-class, almost all-white and Catholic suburb on the east side of Cleveland. I attended St. Ignatius High School, and on my daily commute on public transportation across the city I realized my connection to place was mostly limited to my love of Cleveland’s sports teams. I started wondering about the larger city and its history, and that curiosity brought me into publishing books about the city’s history, teaching about it, and now working with students, educators, and others to help them understand better the community that we inherited.
Cleveland — and Ohio, too — has seen its population stagnate or drop over the last 50 years or so. Ohio is also third in the nation in the percentage of adults living in the same state where they were born and raised (73%). And, when we ask our audiences how many remember learning about their community’s history in any formal way — few people raise their hands.
So, we are not going anywhere, our population isn’t growing, and we’re not learning about what shaped the community we’ve inherited, and we’re supposed to be the authors of our future? It strikes us that there is a disconnect and an opportunity to figure out ways to educate are residents about our history in ways that help provide insights for the work they do today. It’s about a long-term brain gain to plant and nurture the seeds of greatness that we think are already here in our community.
We’re trying to create a love of place from kindergarten to career, and we want to make Cleveland a model for how a community learns about itself, has conversations with each other about our shared past, and moves into its future engaged and interested in creating a shared prosperity for everyone. We find that when we provide opportunities for students, educators, area employees and others to share conversations about their own histories and insights — they shrink the city in meaningful ways and expand their “universe of obligation” — the circle of people they care about. When the more than 2.3 million people who call themselves Clevelanders start thinking about themselves in relation to each other and to their city — they change. Our data suggests that more people want to learn more, are more likely to volunteer in organizations, and more likely to change their narrative about the region. Corporations are hiring us to help onboard employees, and more corporations also see us as partners in employee retention efforts.
Any stories or insights that might help us understand how you’ve built such a strong reputation?
We started in the educator professional development space, and the four people who built the high school programs and educator workshops all had deep teaching experience. So I’d say we were generally well-received by those audiences because of our experience. As a public school classroom teacher of 21 years, I know that sharing my experiences helped other educators see me as someone who had a pretty good sense of what they were experiencing. Same goes for my colleagues who began the program with me — Arin Miller-Tait, Pam Crossman, and Jen Forshey.
We did our work for years on a part-time basis partly because we all loved teaching. During that time, we were experimenting in the classroom with approaches that would become staples of our educational work. We were all deeply impacted by Facing History and Ourselves, a national education organization that helps teachers teach through the lens of personal choices. That approach changed my teaching life. So, we always said internally — let’s make the high school programs or educator PD so good that participants would spread the word. I think that’s what happened to build our reputation as a group of people who was providing quality programming.
The trick was moving from the education world into the corporate and nonprofit world. How do you sell a program about appreciating our shared experiences to employees whose primary orientation isn’t learning history? How do you make the case that learning history helps them to be better employees and more engaged community members? How do you measure that? That’s the space we’ve been moving in for the last few years.
Has your business ever had a near-death moment? Would you mind sharing the story?
Almost a year into jumping into Teaching Cleveland full-time, our initial capital investment was nearly depleted. We had been making headway and had contracts, but money was coming in slowly. I distinctly remember a conversation with our board members. It was a January. I told them we had enough money for one or maybe two more payroll runs, and that I thought I should start putting my resume together to go back to the classroom.
We knew relying on school and school district contracts was tough, because schools are usually under such budget crunches, and as I like to say — they operate as “closed systems.” They are so busy doing the work and addressing all the challenges that outside organizations like ours are difficult to get into their world. We had had focus group conversations with local foundations and corporations about their needs, especially as it related to onboarding, recruitment, and retention. So we were moving into the corporate space but it was slow going.
Somehow, inexplicably, within two weeks of that board meeting, we received a major amount of funding that set us on the course we’ve been on since. It seemed like a miracle. We have not looked back since, and it feels like we are starting to really move in the right direction. We’ve expanded our revenue streams, connected with more organizations and have reached more students than we had been reaching before the close call.
Contact Info:
- Website: https://www.teachcle.org
- Instagram: teachcle
- Facebook: Teaching Cleveland
- Linkedin: Teaching Cleveland
