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"I hadn’t planned on working in venture capital as my next step, but as I got to know City Light, I was delighted to find an investor group that was really a team of entrepreneurs..."

Greg Gunn

Education Expect

Personal Story

Two passions have driven my career — education and software development. As a teenager I made my spending money by tutoring older kids for their SATs and by developing software and databases for local businesses. As a middle-school teacher after college, I became fascinated with the possibility of using software to support the learning process.  

In 2000, I co-founded Wireless Generation, an educational software company, as a way to fuse my interests in a single venture. We created software tools to transform the way in which teachers analyze student needs, and then use that information to create highly effective learning experiences for K-12 students. Over a span of ten years, we built a successful business reaching tens of thousands of schools and millions of learners. In the process, I found that I enjoyed the work of designing a scalable organization as much I had already enjoyed designing useful software.  

Despite the success we were having in getting our software into many schools, I became  increasingly troubled by patterns of student progress in the districts we were serving. Despite the introduction of data into the teaching process, many schools — especially those in underserved communities — were not succeeding in adapting to the needs of learners and producing growth. As an African-American, I grew especially frustrated and angry that so many students of color were not enjoying the rich educational experiences they deserved despite our efforts.  

It became clear that the educational software community needed to get better at understanding the operational realities of schools — and then delivering smart technologies, tools, and algorithms to unlock the ability of teachers to serve a wide range of learners well. We had the ability to be part of a project called School of One, an important experiment in fundamentally reorganizing a school (with the aid of both instructional and operational technologies) to serve learners individually.

By the time we successfully sold Wireless Generation in 2010, I found myself asking new questions about the educational technology field as a whole: What new technologies were on the horizon that could dramatically improve the learning and lives of students? How could I find promising young companies doing this work and help them reach millions of learners? What creative work could be done to make the whole industry better?  

I hadn’t planned on working in venture capital as my next step, but as I got to know City Light I was delighted to find an investor group that was really a team of entrepreneurs – each of whom was asking the very same questions about the sectors in which they had built their careers. And I was impressed to see the team spending as much effort analyzing the social impact potential of a business as they did the financial return potential, and bringing thoughtful approaches to the ongoing work of helping CEOs deliver both kinds of return over time.  

I knew that this would be the right platform for my next stage of work. I’m now enjoying building the kind of investment firm that I would have valued years ago as an early-stage entrepreneur, and that could have helped me and my industry serve all stakeholders even better. I welcome investors and innovators who want to join us in this mission.  

Investment: StraighterLine


About Greg

Greg is an Education Expert at City Light Capital, where he focuses on early stage investments in educational software and services companies.

In 2000, he co-founded Wireless Generation, a leading educational software company now serving more than 3 million children with groundbreaking assessment and instruction products. As President, Greg created and led the product development team, shipping the award-winning mCLASS® handheld
formative assessment platform. He took over and revamped the company’s sales division, landing key state and district sales and tripling the company’s revenue in 18 months. As Chief Scientist, he designed highly effective professional development techniques and created the company’s analytics and data mining division, turning raw data into new insights about student learning progressions. The company was sold to News Corporation in December 2010.

Greg holds a bachelor’s degree in physics from the University of Chicago, an MBA and Master's in Computer Science from the Massachusetts Institute of Technology, and was a Rhodes Scholar. He currently is a trustee of the Nellie Mae Education Foundation and of the Center for Excellence in Education, and was named one of Fast Company magazine’s “100 Most Creative People in Business” in 2012.

He serves as an expert-in-residence at Harvard University’s Innovation Lab and coaches entrepreneurial students at the Harvard Graduate School of Education.