[...] HOFFMAN: So how did you apply your blank page, your process, to the starting of your Internet businesses?
DILLER: The first one is always the first, and then since I’m always up for anything, I really want to keep scrubbing it so that I’m open. But by the fourth or fifth, I said, “Yes—this is what we do.” In a world where nobody really knew anything—I always think nobody knows anything about anything, including me. But where very few people knew anything, we had actually built up some expertise in knowing some of the basics of both product iteration and distribution.
And so it was very natural. We started businesses, we invented them, we bought them at various stages, and we got used to it.
HOFFMAN: This is a high-stakes game, buying companies and figuring out how they work as you go. You can imagine how this portfolio might collapse in a cloud of mismanagement. But Barry, once again, has a competitive advantage: He may be a novice in all of these fields, but so is everyone else. Remember this line?
DILLER: I always think nobody knows anything about anything, including me.
HOFFMAN: There’s a lot of wisdom packed into that statement. First, he knows that so long as no one has figured out how to run these businesses, he has as good a shot as anyone.
Second, he knows what he doesn’t know. And this helps you to continually embody a beginner’s mindset — where you’re curious, nimble and open to new ideas.
And finally, he has the confidence of a lifelong learner — and this sort of confidence can’t be faked. You can’t just declare yourself an infinite learner. You have to do the hard work of both deep learning — and quick unlearning — before you can place bets on so many industries. If you go in with too many preconceived notions about how a business should run — it’s a liability.
DILLER: The more you know, the worse it is. In fact, it’s relatively simple—is it a good idea?
When an existing company—an acquisition—if you spent too much time on it, and you learn too much about it, you will inevitably be talked out of it. And I’ve seen it happen so many times in my company,
Hindsight is hindsight—but you go back a year or two later and say, “What was wrong?” You know, we’ve got teams of analysts and—same thing you’ve got. And you get too much data in that, as against a good idea, and you come to the wrong conclusion.