What were some early leadership lessons after starting Dropbox?

The first thing is having a healthy paranoia for trying to find out what you don’t know that you don’t know. The question I would ask myself — even in the beginning, and I still do today — is, six months from now, 12 months from now, five years from now, what will I wish I had been doing today or learning today?

Reading has been essential. I have always wondered why people put so much energy into trying to have coffee with some famous entrepreneur when reading a book is like getting many hours of their most crystallized thoughts.

What have you done to build culture?

Culture always starts out as the sort of bizarre average of the founders’ personalities. But a couple of years ago, we decided to define our values and make our culture explicit.

There are a lot of ways to think about it, but one of them is, how do you build something that sustains excellence over a long period of time? Or to put it another way, it seems that most companies, most organisms, decay as they get older and bigger, and so how do you inoculate your company from the most common things that tend to go wrong?

So we approached it as kind of an engineering problem — what is the opposite of each of those things? We came up with five: Be worthy of trust; sweat the details; aim higher; “we,” not “I”; and the fifth is just an image of a smiling cupcake, because we don’t want to take ourselves too seriously.

How do you hire?

I’m drawn to people who really love their craft, and treat it like a craft, and are always trying to be better and are obsessed with what separates great from good. And so I’ll ask a lot about those things. Like who is the best in the world at what you do, and who are your influences?

I’ll also ask, what have you learned in the last year? And if you were able to sit yourself down 10 years ago, what advice would you give your younger self? What are the most important lessons you’ve taken away?