He says so himself in a Q-and-A about the Internets in this month’s Vanity Fair:
I really did grow up as a nerd. In high school I really did have thick black glasses taped together. I really did wear a plastic pocket protector. This is not an exaggeration. And I felt left out all the time. Nowadays, I remember that feeling, and I want everyone to be included, and that’s something we work on every day on the site.
Of course, the left-out nerd in high school grew up to be one of the savviest entrepreneurs in the history of the Web. Here’s what he told The Observer in a Q-and-A in March 2007:
In New York, real estate is a blood sport. It has always been that way.