Entrepreneur Highlight: Clyde Cole

This is my 30th year in education. My career began in entrepreneurial fashion.

The Journey of a Social Impact Leader is Never Linear

I was fortunate to be given the chance to be a founding teacher of a small Jesuit middle school for Boys in Harlem right out of college. What made that even more special was that it was also a dual homecoming for me. I was able to come back to New York City after attending Northwestern for 4 years and the new school was going to be at the site of the place where I had done Christian Service as a senior in high school.


We had very little money for books and no funds for professional development, so I created curriculum, scope and sequences, and learning materials from scratch. This was a big task for a brand-new teacher. It was even bigger because I had to do it for both Mathematics and for English Grammar. I learned so much those first 6 years. In addition to school design, curriculum design, and classroom management, I learned a ton about being a teacher, a mentor teacher, a basketball coach, and a leader. 

Having a Mentor is Key

I was blessed to have two amazing mentors: two Jesuits who have continued to do great things in education. One is doing the same work, leading a small middle school for boys, this time in Buffalo, another urban district in New York that is under-served in many ways. The other is currently the leader of a national network of junior colleges designed to serve poor and working-class students who otherwise might not have continued their education after high school. I am lucky to still have them as colleagues and friends.

I left Harlem with one of the teachers and founded a youth center one block away from where I grew up in Crown Heights, Brooklyn (homecoming #2). The two of us worked well together: he took care of fundraising and I took care of programming. At that point, I felt like a veteran when it came to starting from scratch.

Slowing Down Can Reveal Next Steps

I kept that same energy when I went to New Haven, CT to co-found a charter middle school. That was a rough year. We were well-resourced, especially as compared to my stints in Harlem and Brooklyn. We had a smart and hard-working teaching and administrative staff. The kids and parents were very good to us too. And while we had great academic gains in that first year, I think I ran out of gas somewhat. Three startups in a row might have taken their toll. Having a dual role as teacher/practitioner and as leader/administrator for a third time was also tough. Being away from home, though not far, didn’t make it any easier.

So, on the advice of one of my mentors, for the first time I decided to work someplace that existed before I got there. Those two years as “only” a high school Math teacher and freshman basketball coach were ones I will never forget. Ironically, I learned much more about leadership there than I thought I would. The principal was an amazing leader, role model, and practitioner. He was a man of faith. He was seemingly omnipresent. And he never forgot a name or a face. I left that school to pursue my master’s degree in educational administration and it was mainly because of him. Interestingly enough, he was disappointed that I was leaving even though it was sort of his fault.

Currency Comes in Many Forms

When I think of what I’ve experienced since – founding assistant director of an academic enrichment program for academically gifted, poor and working-class middle school boys in Manhattan, founding principal of a 6-12 public school for boys in Brooklyn, leading professional development for teacher-leaders, principals, and principal supervisors around the country, holding two district leader positions in New York State, founding a nonprofit for boys and young men focusing on social-emotional development, and founding Impact.Ed – I cannot help but think of all the ways I have learned to value all 8 forms of currency. I will admit that it is easier to see and appreciate other forms of currency when you aren’t always making a lot of money, but I can mostly credit the people, both adults and children, I have met along the way.

As an educator, one might think I place the highest value on Intellectual Currency. That would be right. I greatly value people who can build on knowledge because that demonstrates the capacity to grow. I value those who can share knowledge because that shows the ability to give. I value people with ideas, because it means they are connected to those around them and seek to fill a need or solve a problem. I value innovation because all good ideas need action behind them and the courage to execute.

Live by Your Own Mantra

However, I firmly believe that Intellectual Currency is at its greatest value when combined with Social, Cultural, and Experiential Currencies. I’m at my best when I’m connected (Social), when I’m respectful of and building on history and tradition (Cultural), and when I’m unafraid to take risk because I look forward to what I may learn (Experiential). 

I have also come to be more Spiritual (which is different than “religious”) over the years, especially recently. My spirituality helps keep me connected, respectful, and courageous. Without it, I would be a very different version of myself. 

I used to have two sentences in the footer of my e-mails. The first was “Be excellent every day.” The second was “Learn something from everything.” When I stick to doing both, I am at my best, for myself and for others.