“I’d like to have younger people around me and that I’ll be involved with them a lot more now, as opposed to me being the main focal point.”

The normal press cycle is to put a company on a pedestal and then knock it down. It’s much more interesting that way.

Creativity is an infinitely renewable resource – you are not going to run out of it – so don’t be afraid to use it.

In order to succeed spectacularly you have to be willing to fail spectacularly.

Positive culture comes from being mindful, and respecting your coworkers, and being empathetic.

You curate information that you want to receive. It’s a lot different because I’m not asking you if it’s okay, I’m just saying I’m following your updates. That’s why I don’t think of Twitter as a social network.

I’ve seen people twitter in haiku only.

In any leadership position, you’re always going to be disappointing somebody.

Timing, perseverance, and ten years of trying will eventually make you look like an overnight success.

They picked my jacket and when the art director got back to Boston, he wanted to know who designed it and I said, “Me.” He was like, “The box guy?”

We can break news really fast. When an earthquake happens, there are people Twittering about it.

I was kind of showing the art director a thing or two about how to use a Mac. And one day everyone went out to lunch and I jumped on the computer and designed a book jacket and slipped it in the pile to go to the review board in New York.

I never even graduated college. I never finished learning, as it were, and I have a psychological need to be in a learning environment at all times.

Experience and curiosity drive us to make unexpected, offbeat connections. It is these nonlinear steps that often lead to the greatest work.

You can shut down a service, and yet people will find ways to communicate.

Have confidence in your ideas before they even exist.

You can be hyperconnected, then you can take a break for a couple days and it’s fine.