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

You want to find the really crazy but still somewhat reasonable outliers within the customer ecosystem.

Every single industry is going through a major business model and technology oriented disruption.

If you're in your early 20s and you're hanging out with a bunch of other people in their early 20s, nobody has a sense of the kinds of problems that real 'workers' run into every day. They're running into a completely different set of problems like 'what's the party going on right now that I should be going to?

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.

The best technology is aimed far enough in the future that it stands out, but close enough to the present that it blends in.

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.