Whatever you're selling, storage or networking or security, you're going head to head with the incumbent players.

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?

If there's been a crisis in a market, you don't tend to have a new crisis in that market until the people who went through the last crisis aren't in the system anymore.

Out of ten swings at the bat, you get maybe seven strikeouts, two base hits, and if you are lucky, one home run. The base hits and the home runs pay for all the strikeouts

Start-ups should be based on radical ideas. There should be a high failure rate for start-ups, because if there isn't their ideas aren't bold enough.

There are people who are wired to be skeptics and there are people who are wired to be optimists. And I can tell you, at least from the last 20 years, if you bet on the side of the optimists, generally you’re right.

No one should expect building a new high-growth, software-powered company in an established industry to be easy. It's brutally difficult.