Innovation in tech favors the naive and the stubborn. If you are too rational you won't tackle problems that others once failed at.

You intentionally start small, because you will not be able to compete with an incumbent... because the incumbent is always going to go for the full solution.

You want to find the really crazy but still somewhat reasonable outliers within the customer ecosystem.

Focus too much on the near-term and you won't get tomorrow's customers, focus too much on the long-term and you won't get today's.

There's a lot of pride that business owners have. It's actually really critical that pride and ownership extends to everyone in the organization. I think of everyone is in the same boat in driving the company forward.

All we're really doing is repeating technologies that were tried 10, 20, 30 years ago... it's just that it was too expensive, too unusable, and we didn't have the enabling technologies to make it possible.

My co-founder Dylan Smith and I left our junior year of college to move to the Bay Area. To the horror of our friends' parents, we actually had two other friends drop out of college to work on the product. The four of us were just working non-stop growing Box.