I think people are always able to achieve more than they think they can. While that’s cliche, I don’t know if managers think about that enough. You have to set your sights extremely high.

Tip: Take the stodgiest, oldest, slowest moving industry you can find. And build amazing software for it.

In the enterprise you want to start intentionally small.

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.

Do things that incumbents can't or won't do because it's economically or technically infeasible.

I interned at Miramax and subsequently at Paramount because I was really curious about the future of entertainment - how were we going to get films online? While the inspiration for Box didn't come from that experience directly, it was very obvious that bigger businesses had a lot of slow processes and cumbersome technology.

That's already been tried before only means the first attempt got it wrong.