A number of people in the United States, almost everyone, is using plastic cards to pay for things, but it's extremely difficult to accept these cards. So let's make it's easy and take more and more of the friction out as we can.

The strongest thing you can cultivate as an entrepreneur is to not rely on luck but cultivating an ability to recognize fortunate situations when they are occurring.

It's empowering to be asked to look at what's possible, not told how to do it.

Twitter was around communication and visualizing what was happening in the world in real-time. Square was allowing everyone to accept the form of payment people have in their pocket today, which is a credit card.

I spend 90% of my time with people who don't report to me, which also allows for serendipity, since I'm walking around the office all the time. You don't have to schedule serendipity. It just happens.

I loved couriers. You had this transfer of physical information happening throughout the city and the world. Someone picking up the package, putting it in a bag, going somewhere, taking it out of the bag, giving it to someone else. I thought that was so cool. I wanted to map it, to see that flow on a big screen.

Amazing what people make up based on what they choose to see.