Uber is a $3.5 billion lesson in building for how the world *should* work instead of optimizing for how the world *does* work

Innovation in tech favors the naive and the stubborn. If you are too rational you won't tackle problems that others once failed at.

If there could've ever been a magical time to build an enterprise software company, now is absolutely that time.

There's a lot of pride that business owners have. It's actually really critical that pride and ownership extends to everyone in the organization. I think of everyone is in the same boat in driving the company forward.

My workday begins around 11 A.M., with a cup of black coffee in each hand. If I had more hands, there would be more coffee.

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

Startups often win because it's easier to see what comes next when you don't have to worry about maintaining what came last.