Joel Hollander is the former Chairman and CEO of CBS (NYSE: CBS) Radio Network (formerly Infinity Broadcasting). Hollander succeeded the legendary Mel Karmazin at Infinity/CBS, the longtime home of Howard Stern. Previously, Hollander served as CEO of Westwood One. Hollander is currently the President of 264 Echo Place Partners. Along with his wife, Joel Hollander is the founder of the CJ Foundation for SIDS.

I recently had an opportunity to talk with Hollander about the future of Howard Stern and the future of radio.

In this excerpt, Hollander talks about the difficulty in replacing the Sirius XM (Nasdaq: SIRI) radio icon. This transcript has been edited for clarity.

Mac Greer: In 2006, shortly after Stern started on satellite radio, CBS sued Stern for misusing CBS broadcast time to promote his satellite radio show. Now, that suit was settled, but I think it's fair to say that CBS, your then-company, and Howard Stern had a pretty bad breakup. Looking back, are there things that you would have done differently?

Joel Hollander: It's hard to say. The bottom line is Howard left for two reasons. He couldn't do the radio show that he wanted to do because of some FCC constraints. We never really got to the batter's box even to take a swing to renew him. He was the highest-paid personality by a country mile already, at the company and in the industry. And Sirius gave him a deal that was just not to be duplicated, obviously, by anyone. He was a pioneer in something that was new, and he has proven again that he has done very well in mining that business.

Greer: And Joel, CBS Radio has tried some other things since Howard Stern, and no one has achieved anywhere near his success. In hindsight, do you think CBS undervalued Howard Stern?

Hollander: No, no, no, no, no, CBS didn't undervalue Howard Stern. Howard went in a different direction. I was in the seat at the time, and it was like replacing Babe Ruth; it isn't so easy. There are a lot of talented on-air personalities and people and media, but Howard is one of a kind. But life goes on, and CBS is doing well. They have changed a number of formats, but the talk radio format and the sports format are doing quite well on a lot of the radio companies.

Greer: And let me ask you about Howard Stern today. He's got a smaller audience now on Sirius XM, and for the first time, he has no boundaries. He doesn't have to do that dance that he does with the FCC. From a programming perspective, do you think Howard Stern needs boundaries? Do you think he needs something to rebel against to be at his best?

Hollander: You know, those types of questions are really vanilla and chocolate. Some people like vanilla. Some people like chocolate. What I mean by that is, Howard wanted to go and do something else. He got paid an incredible amount of money to do it. Was his show different on terrestrial radio? Absolutely, because there were constraints. Was it different in a different time? Yes. Five years ago, you just didn't have the choices that you have today, whether it be music or online or pay radio or sites like Pandora. We are living in an on-demand world, so it's very hard to compare what happened then and what happened now.

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