Title:Talking with Ted

On living a liberal arts life

This summer Georgetown Magazine sat down with Ted Leonsis (C’77, Parent’14, ’15) to learn about his Georgetown story, talk a little sports, and consider new frontiers for entrepreneurial endeavors. First in his family to attend college, the American Studies major went on to a successful career in technology, and later became owner of several DC sports teams including the Mystics, Wizards, and Caps through his company Monumental Sports & Entertainment. Leonsis received Georgetown’s prestigious John Carroll Award in 2010 and has served on the Board of Directors and Board of Regents. He remains deeply committed to his alma mater, supporting the performing arts and the American Studies program, and becoming involved in growing Georgetown’s entrepreneurship programs.

How has family shaped you?

I’m from a close-knit extended Greek family. I was an only child and my parents were older when I was born. My wife and I spent a lot of time with our two children as they grew up and our household was filled with love. My family is my number one source of joy— every day I count my blessings that we are healthy and contributing to the world. I have four grandkids and a fifth on the way. Grandparenting is the greatest gig ever.

Where did you grow up?

I grew up in Brooklyn, New York. Our rental apartment was across the street from a park in a very diverse neighborhood, a working-class community with Black, Filipino, Swedish, and Puerto Rican friends. It was a positive, unique experience, even though some would say it was underprivileged. It made me relate better to different people, and have more empathy.

My parents got home from work at 6:30, and I’d get out of school at 3. I had to occupy myself each afternoon, which I did with sports. I played basketball, baseball, touch football. Outside the fenced field were benches. The kids who were on the teams with coaches and other players did okay, but the kids who sat on the benches started drinking beer, or sniffing glue to get high, or smoking pot, and then deeper things.

My best friend and neighbor used to play sports but stopped, and ended up on those benches. When I was 16, he and others tried to rob a pharmacy, and he was shot and killed. That was a dramatic moment, and my parents decided to move to Lowell, Massachusetts, where my grandparents had immigrated to work in the mills.

How did you end up at Georgetown?

I needed a job so I went to the library—books are so important to me—and read How to Mow Lawns. I started knocking on doors of houses with big lawns to offer my services. Some people didn’t even answer the door, but one did and he seemed to enjoy my patter. He asked if I’d ever mowed a lawn and I said no, but I read this book and could offer a Wembley cut. He said “Here’s my lawn mower—let’s see how you do.” It took me four hours but it looked great! He hired me to do his lawn every week.

Toward the end of the summer he asked if I was going to college. He gave me a brochure from Georgetown where he went, and later wrote my recommendation. His name was Jim Shannon [C’50, Parent’73, ’74, ’75, ’76, ’79, ’91].

So yes, I had chutzpah. I could go to the library, get the book, and knock on doors. But if he hadn’t been home, or didn’t answer the door and listen to me, who knows how things would’ve gone for me. That’s why I like to spend a little time, give someone a break.

I didn’t say to my dad, “Will you introduce me to someone?” He didn’t know anyone who could help me. He was looking for a job himself at the time. When I knocked, probably 30 people did not answer the door, or they shut it in my face. It only took one.

Why did you choose American Studies for your major?

I went shopping around in different classes but liked Father Joseph Durkin, a Jesuit in his 90s who became my mentor. He explained that if you’re not going to be an engineer or a mathematician, there’s no one clear answer, even on God, like the Problem of God class. That’s why you learn to be critical in your thinking, to take this menu and get a bigger life view. American Studies promised that.

How did you get interested in the tech industry?

My Junior year we did an interdisciplinary thesis. I was working in the library at the time, reshelving. I was behind on starting my thesis so I found a skinny book: The Old Man and the Sea by Ernest Hemingway. I discussed it with Father Durkin and he said, “You’re mailing it in. Go read some of his other stuff,” which I did.

It struck me that The Old Man and the Sea was very different, and I thought maybe he wrote it as a young journalist, but published it later. Father Durkin said we could try proving it using a computer—we had one on campus in the registrar’s office. He introduced me to a linguistics professor and she helped me create an algorithm using the first 5000 words of the book.

Based on measures like how many words per sentence and sentences per paragraph that were typical for a time period, the computer said it was written in the 1940s, not the 1950s. It was a “wow” moment, and I ended up winning a prize for the best junior thesis.

After graduating, I was hired at Wang Laboratories as one of their first liberal arts hires, and began my career in tech. I then created a software directory magazine, and sold that company. I started another company which was bought by AOL, and that brought me back to DC. All roads lead to Georgetown for me.

Did you have other favorite professors or activities?

Dr. Emmet Curran and Dr. Dorothy Brown, who taught history, and Dr. Hugh Cloke, in the English Department. At Georgetown, I got involved in everything, because I was paying for it. My roommates sometimes would oversleep and not go to class. I was working three jobs and I had loans, so I went to every class.

How do you stay connected with Georgetown today?

Georgetown is very meaningful in my life and career, to my entire family. I work with entrepreneurship at the business school: Bark Tank, Venture Lab, all of that continues to have deep ties to what we do here at Monumental Sports and my philanthropy with the family. It just seemed like a natural outgrowth of work that we’ve done and work that we’ll continue to do.

Why is entrepreneurship important, and how is it evolving at Georgetown?

When I came to Georgetown in the mid ’70s, there was no entrepreneurial movement. Your career path was pretty much set: law or consulting. There wasn’t an established tech or venture community. My first venture-backed business at Georgetown was a snow cone vending business. My roommate, Laurance Armour (SFS’77), funded my idea. We started Snoco Loco Inc during America’s bicentennial celebration in 1976. “Be a patriot, eat a snow cone.”

Small business entrepreneurs are the lifeblood of the economy. The great leaders are the ones who are taking risks, who aren’t afraid to fail. They start their company, hire lots of people, try to create wealth for lots of people.

Our responsibility is to think differently and go into established businesses and change things up, make them more relevant to a new generation. The church needs entrepreneurs, charities need entrepreneurs, even universities need entrepreneurs! We can’t keep doing the same things we’re doing in the same way. Look at how every industry is changing dramatically—you either play defense or you play offense. Entrepreneurs play offense and we should embrace that, we should lead that.

Georgetown has created an atmosphere to be the East Coast’s best startup entrepreneurial enterprise in academia. I’m very proud of that.

You know, Jesus was an entrepreneur. He had to go out and sell a new way to look at the world.

Entrepreneurship should be one of the big outcomes of a liberal arts education: how to see the world uniquely and differently, dreaming it and seeing it, but then doing it. How do we mentor students to look at the world critically and be able to leave it better than we found it?

I’m Greek Orthodox. Both the Greek Orthodox and the Catholic churches are struggling. Both need reinvention. It’s hard to change institutions unless we have a new generation, new ways of thinking, and can overcome the antibodies in a long-term institution that fight change. If you don’t do it, you go into irrelevance. We need “intrapreneurs” who engender change within organizations.

We need to build entrepreneurs in politics, in religious institutions, in philanthropy. And Georgetown does this. Our students define themselves with more focus on changing the world versus how much money I’m gonna have at the end of the day. That’s why most people come to Washington: to change the world. That’s what Georgetown does, and we should never lose that.

What message do you share with students in the entrepreneurship programs at Georgetown?

We celebrate that it’s good to be able to birth something. And also communicate how difficult it is. There’s a lot of failure. In baseball, you get up to the plate 10 times. You could strike out seven times and hit three home runs and you’d be in the hall of fame.

Some of the greatest entrepreneurs didn’t finish college, and that’s leading to a mindset that we need to fix. I want people to know that my experience at Georgetown was the most important thing that ever happened in my life. Georgetown’s different because it focuses on critical thinking and development of your emotional maturity, responsibility, communication skills, and connecting the dots, which is what entrepreneurs have to be able to do. How do you take something from science, from the arts, from religion, business, politics and bring it all together? Every single day, I’m living a liberal arts life.

How is philanthropy part of your work?

Philanthropy sometimes is misunderstood—it’s much more than writing a check. We have hired, provided internships for, and mentored hundreds of Georgetown graduates. We’ve invested in companies created by the Georgetown community. We look at our collective work as a family and our company: how does it uplift everything?

I continue to be supportive of the university because sincerely, it changed my life. When I arrived on a Greyhound bus, it was the first time I’d ever been in Washington, DC, and I was like, “This is the greatest place I’ve ever seen.”

The journey for me started when I walked on campus and met my mentor, Father Durkin. He gave me confidence. The people I was hanging out with had gone to prep schools. I didn’t have that background: my dad was a waiter and my mom was a temporary secretary. You can have incredible imposter syndrome when you get to a campus with that environment.

Georgetown had much higher expectations of me than my family did, than I did. And so my mission has been to leave more than I take. I’d like to be able to find other kids like me and support them because without that mentoring, that pushing, that confidence building, this uplift doesn’t happen for the community.

I’m interested in how we are helping the basketball teams, how we are helping the student body, how we are hiring people, how we are investing in the community. And that adds up to a much, much bigger leaveback than just writing a check.

Chris Enochs contributed to this interview.