If you don't go to every level of your company, you distance yourself from the marketplace and from your people.

In an IT lead world, incumbents generally win because they have the existing relationship with the IT organization.

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.

Better to be right about the trend and wrong about the implementation, than the other way around.

If you're waiting for encouragement from others, you're doing it wrong. By the time people think an idea is good, it's probably too late.

Startups often win because it's easier to see what comes next when you don't have to worry about maintaining what came last.

Any time where the delta b/w what is possible and how things work today is at its widest, that's an opportunity to go build new technology.