“If every customer is using your product “correctly”, you’ll never learn anything interesting about what to do next.”

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

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

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 don’t use many apps. I use naps.

Better to be too early and have to try again, than be too late and have to catch up.

Your product should sell itself, but that does not mean you don’t need salespeople.

Companies have never won. You’re always either fighting for survival, or fighting for relevance.

Startups live at the intersection of existential crisis and everything going perfectly great.

I’m obsessed with speed. I’m always asking myself, ‘Why can’t we do things faster? Why can’t it happen more efficiently? Why is this requiring three meetings instead of one?’

Listen to your customers, but don’t always build exactly what they’re telling you. This is a really key distinction around building enterprise software.

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

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.

The chance of failure is almost always better than the guarantee of never knowing.

You’ll learn more in a day talking to customers than a week of brainstorming, a month of watching competitors, or a year of market research.

What happens to the Microsofts, Oracles and IBMs of the world is that when they get big enough, they don’t think they need to bring that same level of focus and energy to the end-user experience.

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