Freston has several missed opportunities under his belt.

Question: What was your biggest mistake?

Tom Freston: Oh gosh, there are so many I don’t know where to start. I don’t know whether I want to admit them. I never ranked them in terms of the biggest, but you make a lot of mistakes. I don’t wanna seem real arrogant and say, “Oh, I don’t know what they are.” But as I . . . You know I guess you could always say you make mistakes in certain people that you’ve hired; certain . . . You know someone in my case with, you know, people that you’ve hired or opportunities to start things, make things, buy things that you passed up later. I mean that happens to everybody. You know when you’re in a (33:18) creative business, let’s face it. All the record companies passed on Madonna. Half the record companies passed on the Beatles. You don’t know a lot of times what’s gonna turn into, like, you know, some great hit. So when you’re in the . . . in the pit stage, it’s very easy to, you know, pass on a project thinking . . . You know someone will go . . . Everybody passed on the Lord of the Rings in Hollywood. And one studio, New Line, tripled down and said, “No, I’m not even gonna do Lord of the Rings. They’re gonna make three of ‘em at once. So they’ll all be made and in the can before the first one even comes out.” Most people in Hollywood said, “That’s the dumbest thing I’ve ever heard of,” and yet they went on and had the biggest movie franchise of all time. So there’s that certain roll of the dice like in a crap game that in the entertainment and media business I think people always find appealing – where the long shot, the think that people never thought would work can actually, you know, emerge as some huge hit.

Recorded On: 7/6/07