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

You intentionally start small, because you will not be able to compete with an incumbent... because the incumbent is always going to go for the full solution.

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

Start with something simple and small, then expand over time. If people call it a 'toy' you're definitely onto something.

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.

Everything about the enterprise, and then by definition the software the enterprise uses has changed - just in the last 5 years.

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.