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.

Innovation in tech favors the naive and the stubborn. If you are too rational you won't tackle problems that others once failed at.

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.

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

Look for new enabling technologies that create a wide gap between how things have been done and how they can be done.

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 have a lot of faults. I often interrupt in meetings. I talk too loud. I talk too fast.