Re: PG and Jessica
A few times a year, I end up in a conversation at a party where someone tells a story about how much PG changed their life—people speak with more gratitude than they do towards pretty much anyone else. Then everyone else agrees, YC founders and otherwise (non-YC founders might talk about an impactful essay or getting hired at a YC company).
What did they do? They took bets on unknown people and believed in them more than anyone had before. They set strong norms and fought back hard against bad behavior towards YC founders. They trusted their own convictions, were willing to do things their way, and were willing to be disliked by the existing power structures. They focused on the most important things, they worked hard, and they spent a huge amount of time 1:1 with people… When YC was very small, it felt like a family.
When I did YC in the summer of 2009, PG asked me during the batch what made me want to do YC. I told him it was because I started reading his essays in high school (Why Nerds Are Unpopular). I was always into the hacker subculture (hack the planet!), but this was an interesting mix of hacking, art, intellectualism, philosophy, capitalism, contrarianism, and pragmatism.
I was curious what my cofounders thought about this question, so I asked them. PG and Jessica both came up in conversation. I thought doing YC was contrarian, but it turns out, doing startups was the contrarian thing to do in 2009. YC was just the no-brainer thing to do if you were going to start a startup. YC helped us take care of everything in terms of getting incorporated, fixing edge cases like 83b elections, and provided access to the top investors.
When I thought back on it, I remember my first interaction with PG and Jessica was emailing them after we received an exploding term-sheet from a different investor. YC generously and quickly flew us out for early interviews and we got in before that other term-sheet expired. We also had other investors offering us better terms when they found out YC made an offer. But YC provided the best terms out of the gate, and treated us fairly from the start. That matters a lot—to the degree that I am talking about it 11 years later with the guys I started that company with.