The companies that I really admire the most are the ones that have a deep visceral understanding of why people use their service, and they figure out ways of making money that are completely consistent with how people are feeling and what they are doing at the time.

I look around my neighborhood, and I see people hailing a cab or ordering their food and then paying for it all with their phone. I've read about that stuff for a really long time, and now it's starting to become commonplace.

People say doing a startup is like a marathon. It's actually a roadtrip at night with no headlights. You think you're going to Toledo but you're actually going to Miami and you might not have enough gas so you might need to buy gas from someone who might take you out if you aren't driving well

What you collect says so much about who you are.

I was obsessed with this idea that these things that you collect, they just say so much about who you are. I can't say it came from hard-nosed business analysis... It was just something I really want to see built.

I used to wake up and look at our analytics and think, “What if yesterday was the last day anyone used Pinterest?” Like, everyone collectively decided, “We’re done!” Over time I got more confidence.

I always read about these stories of entrepreneurs - it’s like they’re in the desert with no water, and they’re the ones that survive. But I’ve been really fortunate to have people on my team who are optimistic about the future and who know that if you work through hard times that there’s usually something good at the end.