What do you do today to make a living?
It's complicated; I do a few different things. First and foremost, I have groups of people who make stuff that can create a profit. The groups are comprised of writers, designers, developers, hackers, artists–whatever. We then work together to create something that'll either earn money or garner attention and PR.
When I'm not doing that, I freelance in advertising and creative as a copywriter. I've worked for a ton of ad agencies from Droga5 to BBH. It's fun, I mostly just sit in a room and think of ideas all day.
I also have my own fashion line, events company, and a small startup. And I teach all that to kids who want to do what I do at a graduate program in Brooklyn.
Describe the worst moment of failure in your creative/entrepreneurial career.
I don't know if I ever had a 'worst failure.' I've had projects I hoped would take off and get more attention than they did, I had projects that didn't go through, I had projects that a client changed until they were nothing like they were intended. But I'm proud of all of them, I put everything I had into each and every one.