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.

As a kid, I always idolized entrepreneurs. I thought they were cool people in the way that I thought basketball players were cool people. It's cool that some people get paid to dunk basketballs, but I'm not one of those people.

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’d never managed anyone before, so I don’t have a lot of experience. But I’m lucky - I have a lot of team members who have a really honest relationship with me.

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

I kind of think of engineering like the chefs at a restaurant. Nobody's going to deny chefs are integrally important, but there's also so many other people who contribute to a great meal.

Most people generalize whatever they did, and say that was the strategy that made it work.