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

Entrepreneurship: 10% coach, 20% player, 30% cheerleader, 40% waterboy.

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

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.

I think because of the iPhone and the fact that we now have a ubiquitous internet, our creativity in the startup space is 10 times different. Every single industry, every single market, is going to be technology-driven in some way. There's an infinite opportunity for startups because now you can go and solve problems that previously looked like they had nothing to do with technology.

My downtime tends to resemble my uptime. Weekends are workdays, but toned down. Over the whole weekend, I may have five meetings, as opposed to six on a weekday. I used to play piano for 30 minutes at night, but I had to pull that out of my schedule. I don't have time for nonwork stuff.

The IT model of the enterprise has become a lot more user lead.