“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.”

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.

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

I think people are always able to achieve more than they think they can. While that’s cliche, I don’t know if managers think about that enough. You have to set your sights extremely high.

The 10% between 90% done to 100% done takes most of the time, causes most of the stress, but is all of the value.

Jeff Bezos is opening a retail store and owns a newspaper. Turns out everything we thought about the Internet is wrong.