The Power of Lunacy

As I prepared for my interview with Jason Calacanis--the subject of this issue's cover story--I had no idea what to expect. After all, this is a guy who's been referred to both as a "tyrannical overlord" and "the rare successful entrepreneur who's a nice guy and maintains balance in his life." Or, if you prefer, "the moral compass of the Internet" and "the most hated individual in the blogosphere."

I was hoping the nice guy would show up.

As it turns out, Calacanis was the ideal interview subject. His answers were thoughtful and refreshingly candid. He was quite engaging, as anyone speaking passionately about a topic tends to be--and few people are as passionate about anything as Calacanis is about the Internet.

Above all, I found him to be exceptionally optimistic. For example, we spoke about the dot-com era. Instead of parroting the standard bleak description of a time marked by ridiculous overspending and a foolish emphasis on growth over profits, Calacanis's take was this: "Sure, people are critical of this overspending, but it led to many of the huge breakaway hits that became global brands. People saw the potential of the Internet and bet big. And for some companies, it worked out." Calacanis sees it, in part at least, as a period of great innovation, which helped propel the U.S. to the forefront of e-commerce.

Perhaps the most interesting part of the conversation was one that isn't even included in the story (see "Musings of an Internet Maverick," beginning on page 10). But yet it perfectly captures the optimistic, irrepressible spirit responsible for Calacanis's entrepreneurial success. "When I'm considering an idea for a new business opportunity, I start by assuming that my crazy idea is going to work out beyond my wildest expectations," he says. "Then I double it in scope. Then I double it again. It's a totally lunatic, assume everything works out' approach. But when you just assume that everything is feasible from a technology or operations standpoint and focus on the idea, you can get to some pretty interesting places. And it's been my experience that eventually your technological capabilities will catch up. Then, while everyone else is still debating whether something can or can't be done, you're making it happen."

I think many of us could benefit from a little of this lunacy. I know I could. So often in my business and personal lives, I look at opportunities with a hypercritical eye. Thinking I am being prudent, I try to poke holes, to find weaknesses. And usually, they're pretty easy to find, and I'll end up passing on the investment, the career opportunity, the summer home--whatever it may be. Perhaps I'm making sensible, level-headed choices. Or maybe I'm being small-minded and timid.

Next time I'll hold off for a little while before looking for weaknesses. Next time I'll allow myself a little lunacy.