Portrait photo of Greg
Greg Gunn
Connecticut & Oriel 1992
Born in Chicago in 1970, Greg Gunn grew up in Stamford, Connecticut and attended the University of Chicago before reading Psychology and Philosophy at Oxford. He returned to the US and worked in educational technology startups, going on to co-found Wireless Generation (now Amplify), a leading educational software company. Gunn is also the co-founder of Lingo Ventures, which makes early-stage investments in education and workforce technologies. He serves in a wide range of philanthropic roles and is a particular supporter of entrepreneurs of colour. This narrative is excerpted from an interview with the Rhodes Trust on 26 March, 2024.
‘From as early as I can remember, I was always obsessed with science’
I spent the better part of my childhood in Stamford, Connecticut. My family is African American, and my father’s family was all from Alabama. He grew up there, picking cotton and working in the fields, but was one of the first of his family to go to college. He actually had to sue to get into state college in the 1960s. So, he was he was part of that generation that had to desegregate education to be able to participate in it. My mother was from Champaign, Illinois, and she and my father ended up meeting in Chicago, in the church choir up there. I had a younger brother and sister as well and by the time we were living in Connecticut, my father was working in banking and then corporate finance, and my mom was a homemaker. We just had a pretty nice, peaceful life in the suburbs out there.
From as early as I can remember, I was always obsessed with science: dinosaurs, space, technology, everything. I was a very early reader and so, when I got to school, they skipped me out of kindergarten into first grade. I remember in the school library, they would only let the first graders go in the fiction section, not the non-fiction section, and that made me really mad. So, I made them let me go over to non-fiction too. I had early thoughts about being an astronaut (I saw the movie 2001: A Space Odyssey when I was four years old) and then later, when computers came along and I first got to touch one, it was the idea of working with computers or building technology that started to captivate me. In high school, I also started a side job tutoring kids in math. I did it to make money. I got excited about that and entrepreneurship, and I also got excited about teaching and learning too.
I went to the University of Chicago because they gave me a full scholarship, and also because it’s where my father had been studying when I was born. I majored in physics and minored in mathematics, although fairly soon, I discovered that I’m actually an engineer. In college, my most influential teacher was a professor named Paul Sally, who was head of the math department. He was brilliant, and a really intense teacher, and I ended up bonding with him because he ran one of the most innovative after-school enrichment programmes in math for neighbourhood kids in Chicago. It was really with him that I started to get deeper into my interest in teaching and learning and also connect my interest in teaching and learning with my ambitions around race. Paul Sally was white, but we were largely working with black students, so that’s when some different things started to connect for me. Being in Chicago also gave me the chance to spend time with my grandfather, and that was very important, because he just had such a different set of experiences in his life. He was a judge, and his whole life had been as an activist. Through him, I started to learn more about what it meant to fight for causes through different channels.
On applying for the Rhodes Scholarship
Applying for the Rhodes Scholarship is not something I ever thought I would do, but in college, I had a wonderful advisor and she encouraged me to apply for both the Rhodes and the Marshall. I remember going to the event the night before the Rhodes interviews, where you meet all the other candidates, and everybody seemed so much smarter than me, so much better read. It felt like they had already done world-changing things, and I was, like, ‘Why am I even here? I don’t even belong in this room.’ Anyway, I ended up getting both the Marshall and the Rhodes, and I went for the Rhodes, and the whole world looked different from there.
Oxford was disorienting for me at first because I had never been out of the country before. Also, it rained my whole first term! The whole educational model threw me too, and I never really got used to the tutorial system. At the same time, I was meeting wonderful people, both Rhodes Scholars and other international graduate students in my college. In that first semester, I met Lisette (Lisette Nieves (New York & Corpus Christi 1992)), who would later become my wife, and also Larry Berger (New York & Lincoln 1991), who would go on to be my co-founder in starting my company. So, it was a great social time, and I also had the chance to travel and to explore ideas around faith and belief. My world was just expanding in all these different ways.
‘A different kind of fire lit in me’
After Oxford, I went on to MIT, and that was the richest intellectual experience of my life up to that point. I felt like all of my interests were firing at the same time. Just before, I had spent time working for the Carlyle Group and learning about finance and investing. At MIT, I began to combine that with my interest in the science of learning. This was when the internet boom was really getting going, and I went to work with another Rhodes Scholars, Mark Lundstrom (Washington & New College 1993), who was starting a web company. From there, I worked with Larry Berger and we set up Wireless Generation.
For the first part of my career, my interest in education was mostly technical. It was only later that it started to tie into my sense of social mission, particularly my mission around race. I had always been uncomfortable with the fact that when I was back in school and I was in the gifted classes or honours classes, I was often the only black kid in there. Later on, I worked in a school that was explicitly designed to start going against those mechanisms, and that’s when I really started to connect the dots and understand that what I had experienced was not just unfortunate, it was actually a structural injustice. At Wireless Generation, I was looking at data across thousands of schools and saw how sharp these inequities were at a national scale, and that’s when a different kind of fire lit in me.
I think building Wireless Generation has been my greatest career accomplishment. It’s had positive impacts on kids and on the future of educational technology, and it’s also created good livelihoods for people. Now, I invest my own money as an angel investor, and I’m spending most of my time advising black and Latino entrepreneurs, for profit and non-profit, all mission-driven, all tech-enabled.
‘Those were the first people I thought about the future with’
The Scholarship had huge impacts on my life. It brought me two of the most important people in my life – my wife and my business partner. It also gave me the chance to see the world. But most of all, I had never spent time with so many people for whom changing the world was just part of how they woke up in the morning and decided what their day was going to be about. That helped me make sense of and further articulate those qualities in myself. I suppose you could say those were the first people I thought about the future with.
I’m a futurist by mindset, and I’m also mostly an optimist, about the future of technology and the future of society, as well as an optimist about the future and opportunities for black folks. The last ten years of my career, if not more, have been about making sure that more black people are in the driver’s seat on the future of technology and on the technology, businesses and economic models that are shaping our society. In the past, too often, we’ve been cut out of the shaping roles of that. We’ve been the worker bees of it, but we haven’t been the shapers of it. That’s why I support black tech education.
At the moment, we’re watching the world seemingly fray into division and become less and less anchored in anything that can be thought of as shared truth or shared reality. If there’s one thing we need now, it’s people with the perspective that Rhodes Scholars are supposed to have so that they can figure out how to unfray this mess. And I have to say that when I meet new Scholars or recent Scholars, they’re all as impressive as hell, so I have high hopes! As to advice, I think the only thing I would say is something small: just keep following your curiosity and break any rules you need to, to do so.