If you think you can execute a previously failed idea, you just have to be able to show that now is the time.

The advantage of the consumer businesses is they tend to be much broader-based, much larger number of customers, that tend to over time be a lot more predictable. The advantage of the enterprise companies is they are not as subject to consumer trend, fad, behavior.

All's fair in love, war and ride-sharing.

Breakthrough ideas look crazy, nuts. It’s hard to think this way — I see it in other people’s body language, and I can feel it in my own, where I sometimes feel like I don’t even care if it’s going to work, I can’t take more change. O.K., Google, O.K., Twitter—but Airbnb? People staying in each other’s houses without there being a lot of axe murders?

Health care and education, in my view, are next up for fundamental software-based transformation.

Almost every dot-com idea from 1999 that failed will succeed.

It was a joke, okay? If we thought it would actually be used, we wouldn't have written it!