Sometimes things are the way they are and can't be changed, other times it's because no one ever tried. Your job is to find the latter.

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

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.

Too little process and you can't get good work done. Too much process and you can't get any work done. Most companies never find the middle.

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

It's unfortunate biologically we have to sleep.

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.