I grew up in a highly overachieving family.

"I grew up in a highly overachieving family. Both my parents are MIT faculty. All four of the boys went to MIT. My brother is now very high up at the Red Sox. Another brother is high up at Amazon. Another brother is high up at Lockheed Martin. I'm the youngest. It was constant achievement all around me. It was just expected that we were going to be successful. I was good at math as a kid. My teachers were always trying to convince me to be on the math team. I went to one meet. I really enjoyed it. But I was like, "No, this is lame." And I never went back. There's obviously a social stigma there… says the guy who couldn't shoot a basket to save his life. But I think it was one of those things where I didn't want to try as hard as I could and find out that I wasn't the smartest person in the state at math. I could just tell myself, ‘Yeah, no. I would obviously win all those competitions if I tried, but I don't.’ No one wants to not be the best, right? It was easier to imagine that I wasn't achieving greatness only because I wasn't bothering to try. I've learned now that a cheat code is to say to myself like, even if I just completely fuck everything up, it's horrible, at least I learned something. Hopefully I won't fuck up in the same way next time. It’s better to have tried and failed at something then to hold yourself back."