she wants to go to the bathroom.
X: What did you want to be when you were a kid?
I think on a practical level I wanted to be an attorney. On a non-practical level, I wanted to play professional football. I played college football, but I’m not a big person so that was never going to happen. When I was young, I just knew I wanted to be the boss. That sounded fun to me—and it’s not. I tell people, ‘Everybody wants to be a CEO until they are the CEO. Then they’re thinking, ‘Damn, this stinks.’ You have all the bad stuff to deal with; you spend 70 percent of the time doing things you don’t like, or things you’re not especially good at.
X: What’s your biggest failure as an entrepreneur?
So, I would answer this a couple different ways. My biggest failure that people would say is my biggest failure, which I don’t consider a failure, is that I passed up on being the head of the US for Skype before it launched. I was with the guy who created it. I was with this thing called Morpheus; they were literally jumping from city to city in Europe because they were being chased by the US government, which was trying to sue them for copyright infringement. I was traveling around Europe after I left Morpheus; I met them in Copenhagen. I thought it was going to be at least three years before people would use VOIP. I thought Skype was the dumbest name I ever heard. I said, ‘You’re going to get sued because people will use it for music.’ It took three years for the technology to grab on; nobody was doing VOIP for three years, and I think they did get sued for copyright.
The first company I worked for sold for a ton of money in eight months. The first company I ran had 110 million customers quickly. My error was thinking that three years was a long time. I was 22 years old. I had no idea.
I consider it part of the learning process, not a missed opportunity.
My biggest entrepreneurial failure … that’s really hard. I’ve never had, knock on wood, a big failure, never had a company that I’ve built that didn’t work. But that’s because I’m really risk-adverse inside of an entrepreneurial mindset. I don’t usually start a company until I’ve got customers, something in place to make it work.
