85. Greg Gunn

Entrepreneur in Residence of City Light Capital, How To Reinvent The Education System

85. Greg Gunn

Greg Gunn’s goal:

Find effective practices in one school that can be replicated across the system. That’s his role at this VC fund, which invests in early-stage companies that target social problems. Previously, he cofounded Wireless Generation, an educational software company that serves 3 million users.


His favorite tool:

The “mind map.” “I often use mind maps for fast, flexible brainstorming when there are a lot of different ideas in play at once; you can get the ideas out quickly and figure out the structure and connections as you go,” says Gunn.

What this one maps:

“I made this after visiting many schoolsí«í_in an attempt to organize, describe, and create a design language for what happens in the chaos of a regular school day. My objective–which I hope to achieve within a year–is to bring design language and tools into an online community so that schools can share operational practices and moves with each other. The goal is to help schools work as a system, to more effectively benefit learners.”


As an example, he cites Boston’s Match charter school; it uses donor and AmeriCorps funds to hire tutors and house them at the school–drastically increasing one-on-one instruction at no cost to the school system.


  • 1980

    Learns to program in Basic and 6502 on his school’s Apple II+ computer

  • 1984

    Runs a software development business and a tutoring business while in high school

  • 1992

    Wins Rhodes Scholarship to study at Oxford University

  • 1997

    Marries fellow Rhodes Scholar and educator Lisette Nieves

  • 2000

    Starts Wireless Generation, an educational software company

  • 2004

    Wireless Generation user base reaches 1 million students across the US

  • 2005

    Birth of son Gabriel, who will soon upend all of Greg’s theories about the learning process

  • 2010

    News Corp acquires Wireless Generation

  • 2011

    Joins City Light Capital and the Harvard University Graduate School of Education