CLAY: We are joined now by media giant — I’d like to be referred to that one day — radio industry veteran Jeff Smulyan. He has done an amazing job as the CEO of Emmis Communications. He’s got a brand-new book, Never Ride a Rollercoaster Upside Down: The Ups, Downs, and Reinvention of an Entrepreneur. And I love this, Jeff, and thank you for coming on with us. You say there’s a fine line between a genius and an idiot. Uh, some people would say we walk that line — sometimes straying in both directions — on this radio program every day. What have you found in business about that fine line?

SMULYAN: Well, I’ve said, you know, that there is a fine line, and I’ve been on many sides many times, both sides. And I, in the book, I have a chapter “Idiot to Genius,” which is the start of WFAN, which is the first all-sports radio station. And all of our guys said it was the single stupidest idea of all time. Jim Lampley called it the Vietnam War of Emmis, and it was kind of a disaster. And since it was my baby, I got needled about it. They called it Smulyan’s Folly. And then one day it turned around.

We put Don Imus on the air. We had Russo and Francesa. And the next day it was a national success. And I went from idiot to genius. And then after that, we bought the Seattle Mariners and I was kind of the boy wonder out there, and I was signing autographs and doing all sorts of interviews, and everybody loved the marketing and the new look of the team. And I was a genius. And then when it didn’t work, I became an idiot. I always said, “There’s nothing worse than being an idiot in front of 40,000 people every night.” So that’s life.

BUCK: Go ahead. Go ahead, Jeff.

SMULYAN: No, I just said that that’s what I’ve learned about life. That’s why it’s a roller coaster. Sometimes you win, sometimes you lose. You’ve just got to, you know, grit your teeth and smile through all of it.

BUCK: If someone’s coming up to you and they say, “You know, I think I want to either start a business or take a big risk,” you know, an expansion. So, some form of entrepreneurial shift or elevation. If someone’s like, “I want to do this –”

SMULYAN: Yeah.

BUCK: How do you advise them? Because I know we get a lot of people listening who maybe already have a business or are thinking about starting a business. And they might sit back and say, “Oh, I don’t know. Should I really do this?” What do you say when people come up to you as somebody who have tried things and had big successes but also taken big risks?

SMULYAN: Well, and that’s why I wrote the book. I think… Listen, I think if you believe in something and you love it and you’re willing to, you know, put it on the line and have that kind of passion, I think you can be successful. You aren’t always successful. But I think, you know, if you want to do something, you care passionately enough about it, you’ve got to do it.

CLAY: You started sports-talk radio —

SMULYAN: Right.

CLAY: — and people out there listening know that I came from the sports talk radio universe. You also owned the Seattle Mariners at one point.

SMULYAN: Right.

CLAY: I’m curious. Buck and I were just talking. This DeSantis versus Trump battle reminds me of Alabama versus Auburn. It reminds me of Ohio State versus Michigan. Conversations that can take place depending on those marketplaces every single day — Yankees-Red Sox is another good one — where that rivalry is so passionate, it fuels the conversation all the time.

SMULYAN: Right.

CLAY: What did you find about sports, talk radio? And a lot of people dream about it, but what was it like owning a pro sports franchise?

SMULYAN: Well, one of my favorite lines is somebody once said, “Every man in America once owned a major league baseball team except the 28 guys who do.”

CLAY: (laughing)

SMULYAN: But I loved it. We made a lot of friends. I was proud of the work we did in Seattle. I always said we weren’t rich enough to own the Mariners. I joked and said, “You really had to be a billionaire on the Mariners or the Kansas City Royals,” but if you had a good paper route, you’d get on the Yankees or the Dodgers. You know, it was just… The economics were wildly different in those days, but I loved it. I’m really proud of some of the things, the stuff we invented in the ballpark — situational music, movie clips and contests and games — you see everywhere now. But it was absolutely revolutionary then.

BUCK: We’re speaking to Jeff Smulyan, and he’s the founder and CEO of Emmis Communications. His book is Never Ride a Roller Coaster Upside Down — good advice, by the way — The Ups, Downs, and Reinvention of an Entrepreneur. Jeff, what are the trends that you see right now in media? I mean, we’re talking to you right now on radio stations across America, but we also have a website, ClayAndBuck.com. We’ve got podcasts going. We’ve got streaming video. You know, Clay built a digital sports business at OutKick. We both do hits on TV at Fox. What do you see as the trajectory right now? Streaming is a big part of the conversation. Subscription service is a big part of the conversation. Where do you see it all going?

SMULYAN: Well, it’s all fragmented so much. And I think, you know, the biggest challenge of streaming is can you find enough subscribers? Can you find an economic model? It’s easier with talk than it is with music because you have giant music royalties, which is why Spotify went into podcasting, you know, so they didn’t have to pay the royalties. It’s a fragmented world. If you follow the streaming services in video, there’s a big question as to whether the regional sports networks can survive because so many people have cut the cords.

We have, you know, 300 and what, 40 million people and everybody’s got, you know, fragmented places they go. And it’s hard to know how it will shake out, only that it’s totally different, and you have to sort of be flexible enough to adapt. I think you guys have done a brilliant job, you know, putting your content in a lot of different places. It may work in some places. It may not be profitable in others. But I think we’re in an era where you just have to experiment with a lot of different things.

CLAY: We get the question a lot, Jeff — and I appreciate you coming on and the book sounds really fascinating. If you were talking to a young person today and Buck said, you know, you’re interested in entrepreneurship. But if you were interested in moving into media —

SMULYAN: Right.

CLAY: — what would you tell them is the most important thing they should be learning in order to train themselves going forward?

SMULYAN: Well, again, I think there’s two things. I think, number one, the most important thing is your word. When you work with somebody, if they know your word is good and they trust you, that helps you an awful lot in any enterprise. I don’t care whether it’s starting a job or being married or having kids or having friends. I also think, again, you have to have the passion. I tell people starting out when you get a new job, volunteer for more stuff. The more people can count on you and the more you are willing to go out and do things, the more you move up the food chain.

CLAY: No doubt the book is fabulous. We need to have you on maybe somewhere down the line. Again, we appreciate all the support you’ve shown for this show. And we would encourage everybody out there to go make sure that they check it out. The book again: Never Ride a Rollercoaster Upside Down: The Ups, Downs, and Reinvention of an Entrepreneur. On the way out, I’ll let you say this. You obviously have an incredible uplifting sort of mindset about you. How much of your success do you think is internal based on the energy that you put out into the world for everybody out there in terms of their own lives?

SMULYAN: Well, I think it’s internal because I think you have to have a spark. Although I’ve said… Somebody said, “What does it take to be an entrepreneur?” I said, “Look, we’re all the entrepreneurs of our own lives.” You know that… We really are. I think part of the internal part of it is I’ve been fortunate to work with people my whole career who I just love and who make me look smarter that I am every day, and that helps a lot.

CLAY: No doubt. Jeff Smulyan is the author. We encourage you to go check out his book. Thank you for the time today, sir.

SMULYAN: Thanks. Thanks, guys. It was great.

BUCK: Thank you.

CLAY: No doubt.