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.

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.

What happens to the Microsofts, Oracles and IBMs of the world is that when they get big enough, they don't think they need to bring that same level of focus and energy to the end-user experience.

The business models in enterprise have changed pretty dramatically. A huge problem with enterprise software traditionally has been usually you sell to the customer and then they adopt the technology. The great thing about 'freemium' and the new way enterprise software is being sold is you get to try it first and then buy it.

I think I'm the kind of person who would be very difficult to employ - I'm pretty annoying, but driven.

Better to be too early and have to try again, than be too late and have to catch up.

I tend to not discriminate when it comes to people I can learn from. Basically, if someone has built a meaningful business in software, technology or media, faced disruption and adversity, and overcame underdog status, I want to know how they did it.