Startups live at the intersection of existential crisis and everything going perfectly great.

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

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.

The benefit to building a startup is that customers don't have the same kind of friction when they adopt new technology.

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.

If people don't think the odds are against you, you're doing it wrong.

If every customer is using your product "correctly", you'll never learn anything interesting about what to do next.