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?

There will be certain points of time when everything collides together and reaches critical mass around a new concept or a new thing that ends up being hugely relevant to a high percentage of people or businesses. But it's really really hard to predict those. I don't believe anyone can.

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

Technology is like water; it wants to find its level. So if you hook up your computer to a billion other computers, it just makes sense that a tremendous share of the resources you want to use - not only text or media but processing power too - will be located remotely.

Qualified software engineers, managers, marketers and salespeople in Silicon Valley can rack up dozens of high-paying, high-upside job offers any time they want, while national unemployment and underemployment is sky high

The great companies get built by their founders

I always had the old-school model that I'm going to work for as long as I'm relevant and focus on for-profit activities and someday when I retire I'm going to learn about philanthropy.