-- As told to Jeff Bercovici
You founded Groupon at 27 and got fired as CEO at 32. How did the company change you?
When I was in grad school for public policy, I thought I had the world figured out. I knew what was right and what was wrong, and it was just a matter of convincing everybody else. But then, as a CEO, you have to have a more open mind, because you care about getting it right more than anything else.
Any regrets about getting fired?
No, because it wasn't bad--it was basically like getting let out of jail early. The bad part was leading up to getting fired. Recently, I dreamed that I'd been brought back in to run Groupon, and I spent the whole time going around saying, "How the hell did I agree to do this?"
You had the idea for Detour, which makes apps for travelers, before you started Groupon. Why revisit it after all this time?
It turns out you can't have good ideas after you've achieved financial independence--you no longer have real problems that need to be solved. All of my ideas since Groupon have been like, how do I press a button and get something to appear before me right now without moving? So I have to go back to when I had actual problems and work through those remaining ideas, and then, once I work through those, I'll basically have expended my life as a useful entrepreneur.
You created an equity structure at Detour designed to reward more employees in the event of another Groupon-size success. Should other founders consider this?
There's something so obviously absurd about being in Silicon Valley. We get to do something that's so creatively satisfying and that we love to do, and then we get so outlandishly financially rewarded for it. And yet there are all these people who have worked as hard as I have and are as passionate about the company as I am; they might have a nice payday, but it's not going to be anything near the same. You can't help feeling a little bit guilty about that. But it's really kind of an indulgent thing, an almost obscene problem to be thinking about: What if I become too rich?