I’ve read your amazing background story that talks about how you overcame such adversity. When you were growing up did you ever see yourself as an entrepreneur or owning a nonprofit such as Homeless to Higher Ed?
I have always been a writer; I have journals from those years that I wrote, knowing I’d help kids like me one day. I have three life dreams: work in television, open a nonprofit for homeless kids, and bring Mr. Hero to the West Coast. (Mr. Hero is my favorite sandwich shop back home in Cleveland.) I honestly thought I would become a very successful TV show runner, and sometime in my 50s, use some of my wealth and power to start a foundation for homeless kids like me. I’d create films and television that spoke to those experiences in a realistic and compelling way, and I’d make a bunch of money and then solve the problem. And somewhere in there, I’d bring Mr. Hero to California. So, yes, I always thought I’d be an entrepreneur, and I always thought I’d lend my experiences to a charity one day. I just didn’t know it would be right after my 34th birthday. I didn’t realize that my storytelling skills would lead to it. This all started because James[Ward] let me share his story and I produced a campaign that connected with people around the globe. It’s all so exciting, and despite my plans I do feel I am exactly where I’m supposed to be.
What was the big “aha.†moment that helped you to realize Homeless to Howard was more than just a one-time initiative?
I was advised to incorporate as a nonprofit because otherwise, this amazing gift that the world gave to James would have been taxed away as income, rather than scholarship, and he wouldn’t have had enough money for all four years! I figured we’d just run a small scholarship fund, not much of a time commitment to find a structure for raising money and doling it out.
But then, I realized James still needed mentorship. He still needed me. I started keeping track of the challenges he faced, and the resources he was unaware of, and I began to require weekly check-ins. I filled in some skills he hadn’t picked up before arriving at college. I also was researching the climate for homeless kids in college, and saw the problems: 56K homeless students in American schools in 2014…but nine out of 10 will fail to graduate in six years. Also, the single most reliable predictor of college success is whether or not one’s parents went to college. What if we could fill in all of those gaps for as many of the 56K as we can find, and get them out in four or five years, ready to live on their own and break the cycle of generational poverty?
I now mentor four young people in our pilot program. I’ve got 20 times that asking for help that we simply don’t have the resources for right now, both in financial and human capital. On the money side, most of our micro-donors think this ended with James’s education being fully funded back in 2013, but that’s not true. We’re still all working as volunteers, with the first floor of my house serving as our base of operations until we get major funding or corporate sponsorship.
What did this new and significant venture mean for you as an entrepreneur? How has it affected you personally?
I was ill-equipped to launch a nonprofit, as I had no experience in the sector. However, after years of producing, I know the value of building a team of brilliant specialists united in a common goal. Building the H2H Team is no different. Once the adrenaline wore off from the whirlwind of #HomelessToHoward, I questioned myself, if I could see this through. That’s normal, to doubt yourself when embarking on a startup. But I didn’t see the connection between crewing a show and building the H2H team at first, so I spent a lot of time doing too much by myself. I pressed pause on a lucrative career 20 months ago, and there are significant financial consequences to that decision; no regrets per se, but if I could do it all again, I’m not sure I would have been so arrogant to think a scheduled production hiatus would be enough time to build something as effective as I want H2H to be. Also, I would try to find a way to steer two ships at the same time, to reduce the financial consequences. But, I can’t do it again, so here we are.
What are your biggest fears as you pursue this venture and how do you plan to overcome them?
I’ve overcome the fear of telling my story, and the fear of losing my anonymity. I was always the one behind the camera, but now people want to hear my voice, and it is still fairly surreal to know people I’ve never met know so much about me. That’s a huge adjustment.
I fear failure, and I fear returning to poverty. I always have. The nonprofit sector will never be as lucrative as the entertainment industry (not that it should be), and I fear my educational debt will never be repaid.
I hate turning away potential clients most of all, and fear we won’t get the funding we need to be able to increase our impact. The kids are so brave to come forward, and to have to say, ‘We can’t help you right now but we’re working on it,’ well, that makes me fear I’m casting a shadow on young people who need all the light they can get.
What’s next for Homeless to Higher Ed?
I’m going to keep talking about homeless college kids, and I’m excited for my growing platform to do so. I’m going to keep working with homeless kids. My team will keep working to find major funding so we can increase our enrollment in the pilot program. It’s all so exciting. On the public access side, we’ve got some fun things coming up this summer, including our first major funding drive since #HomelessToHoward. We’re working on some really great storytelling-based outreach efforts that we hope will appeal to all the homeless kids in college out there, so they reach out for help from us, from their schools, and from their communities. We want these resources available at every college and university in the United States, and we want every homeless college student to feel safe enough to access them.  In the meantime, we’ve also got some great people working together to create a self-service resource guide for our website.