This interview, which was condensed and edited for clarity, was conducted at Portland House of Music on February 8, 2019.

What was your childhood like?

I was one of seven children. The first five of us were born in five years, which is an odd and cruel thing because my mother says she doesn’t even remember the 1960s. Both of my parents were educators. My mother taught kindergarten. My father taught high school, and then went back to school. I remember being in the audience when he got his doctorate at Boston University and seeing him in this red robe was quite a moment, and he then became a college professor – and, ultimately, became a university president over time. My parents worked extraordinarily hard, not just in raising us but in challenging us in all kinds of ways. My father often held three jobs at a time. My grandmother took the bus to be with us each day to watch us. It was just part of our life.

Talk about your path in high school.

Baseball was my favorite sport in high school and maybe the only one that I was reasonably good at, and I was looking forward to playing that year. My English teacher tapped me on the  shoulder and said, “I want you to think about a possibility that there’s a job opening with the Massachusetts Department of Education. I think you’d be really good at this.” I’m thinking I’ve got to play baseball. And she said to me, “Do you think you’re going to play professional baseball?” I’m like, “I’m not sure I’m going make the team, actually. But I might, I might.”

It was a good moment to think about trade-offs in life. I took that job. For the next three years, I worked every day after school, I traveled around the State of Massachusetts, going out into schools, helping to train teachers and counselors and others. You know what? I’m a 16-year-old kid doing this, so it gave me a very different kind of sense of myself and a deep immersion in issues around policy and legislation.

I try to do that now, when I see people who have potential, and give them that tap on the shoulder at the right moment and say, “Maybe here’s a way forward for you.” When people walk through that door that you’ve opened for them, it can change their lives. And that’s what happened for me.

And now you do have a lot of degrees.

In graduate school, I did a lot of work in econometrics, and in looking at different types of research methodology, the power of data analysis, asking questions in sophisticated ways, and using powerful tools to answer questions. This is something that is part of my life every day. Learning the way that you ask questions is probably more important to me than the substance of things that I learned. It’s a way of approaching problems on a day-to-day basis, and having the confidence to be able to do that. I think that’s probably made a bigger difference for me than anything else.

What was your first job?

We used to grow rhubarb in our yard. We would cut it and sell it door-to-door for a nickel for a couple of stocks of rhubarb. It turns out, people don’t really like rhubarb. It’s kind of sour and like dental floss. I learned a lot about rejection selling rhubarb.

How did the opportunity with Colby College come up?

Through a phone call. As most of these things do. For college presidents at the kind of top places, there are a handful of search consultants, and most of their offers just were not very interesting to me. The Colby one got my attention. I knew Colby, and I knew what an extraordinary place it was. I knew how important it was for great liberal arts colleges which are distinctly American institutions to continue to thrive. The chair of the board at the time calls me up, and says, “David, I want tell you, I want you in the search. You’re my guy.” I’m like, “How many times have you said that on the phone today? How many people did you call and just say that to?” And I still like it. He was a good recruiter.

Tell us more about your work at Colby and your commitment to making it more affordable.

People talk about the cost of education, and rightly so – it’s expensive. A year at Colby is about $70,000 a year. That’s a lot of money. At Colby right now, if you attend and you have an income of $60,000 or less for a family income, you can attend with zero family contribution and no loans.

This year we had a great gift that allowed us to create the Fair Shot Fund. It’s aimed at families who are middle-income that are totally squeezed out by the expense of a private education. For families with up to $150,000 income, parents will contribute no more than $15,000 to their kids’ education at Colby, for room, board, and tuition.

We’re working very hard on affordability and making sure that students can come to Colby no matter their financial background. If they’re talented, they’re hardworking, they’re deserving, and they’re going to make the most of the kind of education that we can provide, we want to make sure that we’re opening the door to them.

Tell us about Colby’s investment in Waterville.

Colby started there in 1813, but by 1929 Colby had outgrown its campus, and the infrastructure was starting to crumble. The campus was hemmed in between the Kennebec River and the train tracks. Colby would have had to move from Waterville to continue to grow. Instead, the people of Waterville got together, raised $107,000 – no small sum at the time – and bought land on the top of Mayflower Hill and deeded it to Colby College. An extraordinary moment for a community to come together. Colby, over the next three decades, built out the picture postcard of a campus that’s there right now. The campus totally changed our fate, and Colby took off and became one of the great liberal arts colleges in the country over time.

We have an obligation we have to the city that partnered with us and picked us up when Colby needed it most. Waterville needs it now. It’s our turn to be able to invest in the city and make sure it thrives.

Talk about your partnership with the city and how you figured out together what was needed.

My sense is that any great city has a strong, vibrant core. Bringing back what once had been a really bustling, vibrant downtown is a priority for us. We’ve worked together with the city to attract new businesses and build new buildings. We put 200 students downtown this year for the first time, with a group of faculty who live there, and those students totally changed the energy of downtown. We’ve got a hotel that’s in the works right now, an arts center and a new technology center downtown. And the exciting part is, people from all over are now investing in Waterville.

Now let’s talk about bringing employers to Waterville. Peter DelGreco of Maine & Company told me the story that you literally camped out in the office of a CEO to get him to bring jobs to Maine. So how long were you actually camped out there?

It was like getting a new Apple phone – you’ve got to stand out there. It was a Massachusetts-based company that does software development and software consulting. They were going to put 200 jobs somewhere. I went to visit them, but I called ahead first.

I said, “Just hear me out a little bit. You need to come take a look at Waterville.” And they said, “That doesn’t really look like it fits with what we’re doing. We’re pretty set on where we are.” I wouldn’t take no for an answer from them. I just kept saying, “No, you really need to take a look at this.” They checked it out, and said, “No, this really isn’t for us.”

That was the wrong answer. I told them, “You’ve got to imagine what this Main Street is like because we’re going take this old turn-of-the-century Waterville Savings Bank and turn it into a technology hub for you.” It was different then what any other city was doing. We created a set of incentives for them to move a company to Waterville for 200 jobs, and it worked. That company got bought out by CGI and they’d like to grow to 300 to 500 jobs over time which would make a huge difference.

Let’s shift to your leadership principles and talk about your management style and your team.

There are certain things that are important to me as a leader. I’m kind of a roll-your-sleeves-up type of person. I believe in doing the work and leading by example. I care a lot about the folks who work with me, and I care about their path and what they’re trying to do in their lives. I want people to know Colby can be a place where they can really make a difference.

I tell people who come to work with us, “You’re going to work harder than you’ve ever worked. The bar is going be set higher for you than you’ve ever expected in your life.” But to do that, I need to know them and support them. I can help them in various ways by giving them different professional opportunities.

I’d say is one of our principles at our work is, “Begin with yes.” When somebody comes to you with something, start with yes. I’ll have to tell you, I learned that as a waiter at Legal Sea Foods. They had a rule that you couldn’t say no as a waiter. “Do you have skim milk?” And you’ll be like, “We have 2% milk. Would that be okay?” I learned to speak in a very different way.

For me, the other piece, is authenticity in leadership and being true to who you are as a leader. Colby’s a small community, a place where people know you and where everybody can sniff out a phony. And I thought when I came here, for good or for worse, I’m going to be myself. When you can do it in a way that you’re real and you’re true and you’re enjoying yourself and your work, it feels entirely different.

Our leadership team is I think by far is the most diverse, from race to gender to background, including where people have come from, their backgrounds, and their experiences. I want a group that really is going challenge one another. So far it has worked extremely well.

By the way, people told me you can never recruit great people up to Maine, to Waterville, Maine. Total lie. We have extraordinary people who have come to work with us at Colby, so I just don’t believe that at all.

And you’ve said that right now, your near-term horizon is to stay closer to Colby because more recently you spent a lot of time on the road.

That’s my goal, and I keep failing at it. We’ve launched what’s the largest fundraising campaign ever for a liberal arts college in the country. That’s a tall order for Colby. I don’t think anyone believed that Colby would be a place that could raise more money than any other liberal arts college, many of which have demonstrated capacity that goes beyond what we have.

But we’ve raised more in the first few years than any other college of our kind has done. It does mean a serious amount of work on the road. The good news is, I enjoy it. Meeting Colby alums is not hard work. They are extraordinary people. And hearing about their lives and what’s important to them is one of the great joys of what I do.

Now what’s the best piece of advice that you give to people?

I don’t know if I ever give good advice to people. When students ask me what’s going to make a difference for them, I tell them: Be the hardest worker in the room all the time. Everybody wants to be with a person who works harder than everybody else. Second, always be a great student, always be learning. If you do those two things, and if you’re always learning, and you’re working super hard, you’re going to grow and develop, and good things will happen.