K-12 Education

Entrepreneurship in Education: Strengthening Community Voices in Chicago

September 9, 2016  • Jennifer Bradley

Key Points

  • Jacob Allen of pilotED explains how his charter school in Chicago prepares students for success by focusing on students' identities and personal narratives.
  • Only about 8 percent of black or brown students in Chicago will finish college in less than six years.
  • The non-profit was built as a response to the challenges facing Chicago students.


This is the third piece of the series “Who Are Urban Innovators?” an effort to show what’s possible when urban innovators and people of color get the capital they need to advance their big ideas. Below, read the exchange between Jacob Allen, CEO of pilotED Schools, and Jennifer Bradley, director of the Aspen Institute Center for Urban Innovation.

Jennifer Bradley: What exactly does your company do?

Jacob Allen: pilotED schools is an identity-based, community hub charter school. We believe that teaching students through the lens of their identity and personal narrative, created by them and by individuals in their communities that they see every single day, will actually drive change further than traditional academics or charters. We use our space as not only a school, but as a place where parents and community leaders come together on a regular basis to talk and take action to better their neighborhood. We are looking to open our first school here on the South Side of Chicago.


Jacob Allen, CEO of pilotED Schools

JB: What’s the problem that you set out to solve?

JA: We consistently saw that students were fast-tracked to college, but by the time they got there they didn’t know why they were there. They didn’t know if their parents and community were on the same page, and they didn’t really know what to do next. We think that partially explains huge dropout rates — right now we only see about eight percent of black or brown kids from Chicago actually completing college in six years.

Listen first and foremost, before you even craft that theory of change for yourself or the neighborhood you are working in…If you don’t listen to the people that you work with and the people that work for you, forget about any impact.

JB: Are you a non-profit or a for-profit?

JA: We’re a non-profit organization.

JB: Where did you get the money to start to develop this idea?

JA: We were originally an after-school program that started out of the pocketbooks of my co-founder, Marie Dandie, and myself, in late 2013. We were just bootstrapping, like most entrepreneurs, but realized the impact we wanted wasn’t going to come from an after-school program. A charter school was the model we wanted to have — a community-centered, charter school. We realized at that point: we needed to raise copious amounts of money. Marie and I met with early individual funders, corporate sponsors, and foundations in Chicago that were willing to take a bet on a charter school that had not opened yet.

“Our curriculum is 180 degrees different than three years ago, because students helped us to develop it. “

JB: So how long did it take you to raise the “copious amounts of money” that you needed?

JA: Well it’s never enough, right? We continually kept crafting our theory of change. We were continually asking ourselves what we wanted to see happen for kids that looked like us, from backgrounds that were similar to us. By early 2015, we could walk into any room and talk to people about what we wanted to see happen.

The second thing we did was build a business plan, to ensure that it could be successful 50 years from now. We don’t have deep networks, but we reached out to individuals. We raised a very small amount of money, but during that process of talking to them, we kept crafting our mission and our theory of change. We eventually got close to organizations, like , an the Urban Education Institute  at the University of Chicago. We realized that they all have funders, and it was from those donor pools that we just started cold-calling, grabbing coffee, and making introductions. Those meetings led to more introductions, and we raised capital that way. Now, in addition to engaging individuals and foundations in the city, we are going to competitions. That includes Echoing Green, NewSchool Venture Funds, New Profit, Camelback Ventures, and foundations that essentially say, “Hey, if you have an idea and you’ve actually done some legwork, come to us and let’s hopefully partner up.”

JB: As I talk to people about access to capital, they usually say that financial capital is only one element; you also need social capital. So, what other support did you need for this venture?

JA: Business acumen: knowledge of what it means to run a profitable, impactful, long-lasting organization. I was a sociology major, as was my co-founder, and we could talk until the cows came home about what kind of world we wanted to see in 20 years, but how to achieve that with a business model was something that we really needed to learn. The year that we were going to get our MBAs, we both lost a student in our own classrooms to gun violence and family conditions while teaching through Teach for America. At that moment we thought, “We can’t spend the time, the money, or the brain power sitting behind a desk at a university. We need to help our kids right now.”

We started tapping into networks at Teach for America and said, “Hey, what is a fundraising plan, what does it mean to raise money, what does it mean to start a charter school?” We started assessing qualities that we didn’t have and noting what we wanted to find for our team. That list was pretty long, but now we’ve found some pretty good players to join our team.

JB: Are there supports that you didn’t have that you wished you had?

JA: A father who ran a successful business, and a mother who put $20,000 in my bank account every year so I could be an entrepreneur, but I didn’t have those. Instead, I bartended on the weekends. I wish I would have had a comfy thing to fall back on, which a lot of other entrepreneurs, specifically in the education space in Chicago, had. My cofounder and I just didn’t have that.

JB: What would you tell somebody trying to start an urban innovation enterprise, which I define as an entity that intends to serve underserved people?

JA: Listen, listen, listen. I see these individuals who think, “Oh, I got this, I know how to engage with people, I know what I’m doing. I’m going to walk into a neighborhood, and bring my solution,” and they just don’t listen. Listen first and foremost, before you even craft that theory of change for yourself or the neighborhood you are working in. So much of where we are today happened after we listened to people running charters, to the community that we work in, and to students. Our curriculum is 180 degrees different than three years ago, because students helped us to develop it. If you don’t listen to the people that you work with and the people that work for you, forget about any impact.

JB: Why should we care about entities like yours having access to capital? What’s lost if PilotED and groups like yours don’t get money?

JA: I can only imagine that if PilotED and all of the other great schools or great non-profits or socially-driven organizations lift up a voice in a group of people who have traditionally not been listened to, we would see huge innovation, new technologies, and educational difference in this nation in the next 20 years. It might take us a lot longer than that, but if it started today, the cars we’re driving would look so different, the streets that we drive on, what people are wearing, individual devices we would have…

JB: Where do you see you and PilotED in five years?

JA: If everything goes as planned, we will be in the fourth year of running our first campus.

I see a community on the South Side, Englewood, that has waited for this to happen for so long. They’ve been at the table with us for the past three years. Before that, they were waiting for a community center or school to open that was with them and for them, rather than an outside source coming in.

I also see us identifying other areas to work in. We already have three other communities with a pretty strong movement of parents and teachers who have come up to us and said, “We want you guys here.”

JB: If you weren’t doing this, what would you be doing?

JA: I was supposed to be in medical school. I had interviews, and MCAT scores, and everything. I just decided that it just wasn’t fulfilling. So if I wasn’t doing this, I would be doing something else that made me want to cry, made me want to smile, made me want to go crazy some days.