The Exchanges

Q Not at all, but I heard from a little birdie that you started in radio at 15. Can you just talk to me? How did you start in radio at the tender age of 15?

A Well, I was, I grew up in a very small town in Mississippi and, uh, and I needed a job to pay for flying lessons. And I tried every place in town. I tried the men's clothing store. They said I was too young. I tried the high-paying job in town, which was bagging groceries at the Piggly Wiggly. No jobs. And I walked into this little radio station and, uh, asking, I named Bill Jones, who owned the station, if I could have a job. And he said, uh, he said, you know, uh, do you get, you got good grades? I said, yeah, I prefer good grades. He said, do you get in trouble? I go, not really. He goes, Okay, come in this room. Put on a tape. He gave me some wire copy. Back in the days, all the wire came off teletype machines. He tore some off, said, read this. And a minute or so, he came back in and said, that's good enough. Uh, you're hired. And that began my career in radio. And back in those days, technology was such that there was no way to bring in signals from outside your market. So in little towns, they hired high school kids to be on the air. And it's stunning the number of people who got their start doing that. Tom Brokaw, one of the great newscasters on NBC, See started in Yankton, South Dakota as a, as an on-air disc jockey. So, so, so it was a great way to get into the business.

AI assessment note: “that began my career in radio.”

Q What's the best concert you've ever been to, and why them?

A It's either the first iHeartRadio music festival, uh, that we did in Vegas, when we used it originally just to launch the app. That was the way we were going to get the iHeartRadio app. I was going to do the iHeartRadio music festival, and then it was such a hit, we'd do it every year, and the other one was Live Aid, and I sort of modeled the iHeartRadio music festival on Live Aid, because it was this great collaboration of musicians, so many musicians sharing one stage, And in the case of, of Live Aid, we had, uh, the UK and the US, and only one musician played both, Phil Collins, took the Concord, um, and, uh, and the iHeartRadio Music Festival, we do two nights, one stage, but I think having musicians on one stage together, and by the way, when you go backstage, and they're all sort of chatting, and seeing each other, meeting people, is great. And Paul McCartney, when he played at the iHeartRadio Music Festival, backstage said, you know, Can I go out front and, and, and watch that? I never get a chance to really see concerts. And we took him out front, put some security people around him, and he got to sit in the stands and watch the other people perform. And so I think it does something for both the music, the musicians and us, as well as the consumer.

AI assessment note: “It's either the first iHeartRadio music festival... and the other one was Live Aid”

Q of killing things that maybe aren't working or kind of are in between. We're both in the content game. It took me 200 episodes before we got 2000 plays per show, um, and no money, and now we get, you know, hundreds of thousands and millions in some cases, um, but this is eight years in. How do you think about that, like, kill things that aren't material and sizable?

A I'm not saying kill something that's not sizable or material, because I think you kill, there are many things that aren't sizable material, but will be. I think what you kill are things that aren't doing what you initially said. I started tequila with my good friend, Berto Gonzalez, back in 2000, launched in 2009. We deliberately said, let's take a long time. Let's let people, this is going to be a product people discover. So the goal was not to have instant. We weren't pushing to have a 100,000 cases in the first two years. We built a plan to allow it to breathe. So I think, you know, especially when you're doing content, that what you're really saying is I'm going to build this show to reach these people. And then you're probably going to say, okay, you got, let's say, 2000 downloads. Are those 2000 the right people?

AI assessment note: “I think what you kill are things that aren't doing what you initially said.”

Q actually mentioned, you know, obviously you both owning tequila brands, but he said one of his favorite memories from, you know, your relationship is when you told him about how you marketed six flags against Disneyland. And he said, I had to ask this. So how did you market six flags against Disneyland, which was a competitor for context? How did you market And, um, what did that teach you?

A It actually, Disney was not a competitor, but I used them to market Six Flags. That Six Flags were regional theme parks. I had seven of them around the country at the time. 80% of America lived in a day drive of one of the parks, but they were parks that people come out to for the day. Disney was a destination park. People would go there for three days, a week, whatever, and they would stay there. But Disney was, in terms of Theme parks. It was sort of Disney, and then all these regional theme parks. And part of the problem was, and I sort of thought about the cola stuff, you know, when Pepsi did the Pepsi challenge against Coke, they weren't trying to compete with Coke. They were trying to get away from all these others. They wanted to be the other one. So I said, you know what? Disney's that. I want to get into Disney category and be a crummy Disney. That's a win. So people say, You know, say, what do you think of Six Flags? Well, you're not as good as Disney. I win. If they say, you're much better than Dorney Park, I lose, because they've got me in the wrong category. So it's like, you know, Pepsi, they say, wow, you're a lot better than Hojo Cola. Pepsi would not think that was very good. If they say, you're not quite as good as Coke, they go, great, I'm in the right category. So I wanted to use Disney to get in the, in the category of Disney. So I would get that halo of Di…

AI assessment note: “Disney was not a competitor, but I used them to market Six Flags.”

Q Bob, that's pretty cool. I mean, I appreciate that a lot. And we had a chat yesterday and Ryan said specifically, Bob has the ability to forecast things that are marketable before they're on the horizon. And so going back to that, people didn't see or appreciate what you did. I want to understand how do you gain an instinct for where the world is going ahead of the world?

A You know, that's a, that's a good question. I don't think I do. I think what I am is I'm wildly observant. I'm wildly curious. I spend a lot of time listening to a lot of people and my ears perk up when something, something catches my ear and I go, well, that's sort of interesting insight. And to me, I think we're looking constantly, if you're, if you're a leader or you're running a company, you're constantly looking for the unique insights and the epiphanies. Most of the stuff we do day to day does nothing except to keep the trains running. But to keep the business growing, we've got to find those, wow, there's something going on here. And that's what I'm constantly in search of. And by the way, it matches my skill set and my interest because I'm wildly curious. I'm sort of curious about everything in life. So when I spot that stuff, I'm, I dig in and I'm, I'm asked a lot of questions. I want to know, I want people to educate me, but I don't think I'm seeing something that's unknown. I think I'm seeing the first glimmer of something and, uh, and saying, wait a minute, this is what's happening. And then I usually try and figure out why, because I, I don't want to chase it if I can't figure out why is that happening? But if I can say that's happening and I go, and now I know why it's happening, then I feel much better sort of turning the team toward that.

AI assessment note: “I don't think I do. I think what I am is I'm wildly observant.”

Q of killing things that maybe aren't working or kind of are in between. We're both in the content game. It took me 200 episodes before we got 2000 plays per show, um, and no money, and now we get, you know, hundreds of thousands and millions in some cases, um, but this is eight years in. How do you think about that, like, kill things that aren't material and sizable?

A I'm not saying kill something that's not sizable or material, because I think you kill, there are many things that aren't sizable material, but will be. I think what you kill are things that aren't doing what you initially said. I started tequila with my good friend, Berto Gonzalez, back in 2000, launched in 2009. We deliberately said, let's take a long time. Let's let people, this is going to be a product people discover. So the goal was not to have instant. We weren't pushing to have a 100,000 cases in the first two years. We built a plan to allow it to breathe. So I think, you know, especially when you're doing content, that what you're really saying is I'm going to build this show to reach these people. And then you're probably going to say, okay, you got, let's say, 2000 downloads. Are those 2000 the right people?

AI assessment note: “what you kill are things that aren't doing what you initially said”

Q actually mentioned, you know, obviously you both owning tequila brands, but he said one of his favorite memories from, you know, your relationship is when you told him about how you marketed six flags against Disneyland. And he said, I had to ask this. So how did you market six flags against Disneyland, which was a competitor for context? How did you market And, um, what did that teach you?

A It actually, Disney was not a competitor, but I used them to market Six Flags. That Six Flags were regional theme parks. I had seven of them around the country at the time. 80% of America lived in a day drive of one of the parks, but they were parks that people come out to for the day. Disney was a destination park. People would go there for three days, a week, whatever, and they would stay there. But Disney was, in terms of Theme parks. It was sort of Disney, and then all these regional theme parks. And part of the problem was, and I sort of thought about the cola stuff, you know, when Pepsi did the Pepsi challenge against Coke, they weren't trying to compete with Coke. They were trying to get away from all these others. They wanted to be the other one. So I said, you know what? Disney's that. I want to get into Disney category and be a crummy Disney. That's a win. So people say, You know, say, what do you think of Six Flags? Well, you're not as good as Disney. I win. If they say, you're much better than Dorney Park, I lose, because they've got me in the wrong category. So it's like, you know, Pepsi, they say, wow, you're a lot better than Hojo Cola. Pepsi would not think that was very good. If they say, you're not quite as good as Coke, they go, great, I'm in the right category. So I wanted to use Disney to get in the, in the category of Disney. So I would get that halo of Di…

AI assessment note: “I wanted to use Disney to get in the, in the category of Disney.”

Q The question I have subsequently, does convenience always equal a great business? And I think about, like, Getty, or you have in the U.S. GoPuff, fantastic convenience service delivering groceries to your door, amazing, respectfully, and, you know, there's no argument on this, margins are really hard, it's a really hard business, probably not a good business, respectfully, again. Does convenience always lead to good business?

A No, no. And by the way, great products don't lead to a great business. Uh, you have to have a business model. And, uh, you know, I mean, even questions about, I mean, Spotify, great product. People love it. Is it nothing more than a retailer that all the money's going to the record companies, and they're just letting Spotify have just enough margin to stay in business? Is it a great business? Um, I mean, you look at all these delivery services, I can't imagine those are a business. Uh, maybe one day it will be, maybe a smaller subset of the consumers will be willing to make, pay more money, so they'll have fewer consumers paying more money, maybe that's a business, but You know, I, I'm always, um, when you talk about businesses, I always want to see it on an envelope. Like, if you can't show me on the back of an envelope how this, about three or four lines equal the business, I don't think you've got one. And we go through periods in probably the world, certainly in America, where we build up this bunch of things that aren't based on it's going to earn money, and it's going to get a lot of, in the nineties, we're going to get a lot of eyeballs, uh, then it's going to get a lot of traffic, then it's going to get a lot of, Of revenue. Uh, but at the end of the day, all those are IOUs to the investment community for earnings, because when you're saying it implicitly, you're saying…

AI assessment note: “No, no. And by the way, great products don't lead to a great business.”

Q I totally get you. Can I ask then, why, I listened to you on Mini and Mini Driver talk, and I loved it, but you said, like, having a plan Never have a plan. Um, and it kind of flies in the face of almost ghosts, which I love, but I'm going, huh, are they counterintuitive?

A And it depends on what we're calling a plan. I think some people have a plan for their life, a plan of what they're going to do. That plan's never going to come true. Even when we're talking about this ghost, the plan is sort of the tactical level. Since I was at MTV, I've had a weekly operating committee meeting. Senior most eject executives get together. Why? Because we have to change the plan every week because things don't turn out as planned. And, uh, I can't tell you over the years how many people I've offered a job to, and they said, I can't take it because I got a plan of what I'm going to do. Almost to the person, those people can say, boy, I wish I'd taken that job. My plan didn't come true. Plans are something we do to reduce anxiety. About the future, because it's always, it's a little, it takes your breath away a bit to say, I don't, I don't know what tomorrow's going to bring. I don't know what I'm going to do in five years. I don't know what I'm going to do in 10 years. I mean, none of us ever got married thinking, I'm going to get married and then I'll get a divorce. Um, we had a plan of a life together. Things don't always work out. We take a job. We say, I'm going to stay at this job for 10 years. You may stay at the job six months, or you may, in the case of AOL, I told Steve, I'll come down and help out for a year or so. I stayed Eight, seven or eight years,…

AI assessment note: “It depends on what we're calling a plan.”

Q Can I ask what worries you about the podcast industry? I think when I look forward, especially over the next 24 months, but I'm worried about a macro recession impacting podcast, sorry, advertiser sensitivity towards marketing budgets. Um, for me as a media company owner, that's unnerving. What are you worried about, and would you share my concern there?

A No, look, I think podcasting is, of all the businesses we have, is the least affected by the macro, because it has such a fundamental strength. It's growing, it's growing like crazy. Huge engagement on podcasting. People are absolutely listening to, or hanging on every word, You know, when people are watching a TV commercial, most of it's like second or third screen. They don't know what's going on there. They got something in their lap, they're doing their email, they're doing something else. When they're running and they're listening to something, they're actually listening. When they're in the car and they're driving by themselves, they're listening. Uh, they don't have a second screen going on. And so, and, and podcasting is sort of that on steroids. And so I think the impact podcast has The, the, the idea that the audience is just ballooning and also it's the desirable audience, you know, podcast talk radio tends to be older. Podcasting tends to be younger. Um, so you've got this young, interested, engaged audience that you can activate and will act. So I think podcasting is just, I, I, you know, if you say what's your list of 10 things to worry about, podcasting is not on that list.

AI assessment note: “podcasting is, of all the businesses we have, is the least affected by the macro”

Q If you know your children are making a mistake, do you let them make it anyway? How do you know it's a mistake?

A I mean, obviously, getting ready to step in front of a car, I'll pull them back. But things that look like mistakes often turn out to be brilliant ideas. And, uh, who knows? And I'm, I want to be careful that I'm not imposing my judgment of mistake on them, but rather I let them decide for themselves what's right, what's wrong. And, uh, you know, if I thought my kids were gonna commit murder or something, I would probably step in. But beyond that, I think they've got to discover it. And, you know, and they're going to have problems in life, but I can't solve their problems for them. I can support them, and I can be there for them, and I can be a sounding board, and the less judgmental I am, the more they'll use me as a sounding board, and the more judgmental I am, the less they want to use me as sounding board, because I'm not a sounding board anymore. I'm a controller.

AI assessment note: “beyond that, I think they've got to discover it.”

Q Can I be really direct and ask if you were to do those three to four lines on iHeart, just so I get an understanding for what sort of thing that would look like, what would you say the three to four lines on iHeart is?

A The iHeart is revenue minus expenses Equals a bottom line, EBITDA, our earnings. And then I take it one step further and say, how's our free cash flow? And what else did I invest? And how did I use the cash? How much do I have left? Um, and to me, I think every business ultimately boils down to free cash flow. And for me, I'm always looking at, okay, and if I'm going in a new line of business, what's the margin going to be on that? We've, we've done the podcasting business in the US, which was an adjacent business to radio in my mind. And we are now, uh, the size of the next two podcast publishers combined. And we prime, so we got the more, more downloads than anyone else by a mile. We've also got more revenue than everybody. But what we really have is we're probably the only podcaster that has real profits. And we may be 20 or 25% of the revenue of the podcast business. I'll bet we're probably 90% of the Profits of the podcast business because we refuse to do deals that aren't profitable. And there are plenty of people, we got to get in and we'll buy our way in. You don't buy your way in by doing unprofitable business. It never gets profitable. Um, you know, you may buy your way in because as you pointed out, you'll start small and do 2000 to 5000 to 10,000. But you know, when you hit 20,000, you'll make money. Or when you hit 50,000 and you can see a pure path to get there. B…

AI assessment note: “The iHeart is revenue minus expenses Equals a bottom line, EBITDA, our earnings.”

Q But we've been very successful in your career. When you think about your relationship to money, How do you think about and describe your relationship to money today?

A Look, I have never in my life, I'll take that back. I took one job in my life for money. Uh, every other job I've taken because it just sounded like great fun. And it was a grand adventure. And I happen to make some places more than others, a lot of money, or at least a lot of money for me. I've never chased money. I've never worshiped money. Uh, I don't think money ever defines me. Uh, I am try to be very careful that I don't hang out with just people who also have money. Uh, but that I also have a great variety of friends and that keep me grounded in what's really going on in the world and give me an interesting life. And, uh, I think, you know, money, money doesn't give you happiness at all. Uh, if you don't have a certain amount of money, you might not be happy, but above a certain amount. It's like when I tell kids about, you know, give them career advice, I go, look, you're going to spend more time at work than you are at Spending the money you make it work. So do something you'd love to do and find something that you can't wait to get to work in the morning. And at the end of the day, you're sad you have to put it away. And when you're not working, you're thinking about it and it's challenging to you and it's satisfies your curiosity. And then as long as you make enough money and pay the bills, um, you're a winner. And, you know, sometimes you get lucky and make a whole …

AI assessment note: “I've never chased money. I've never worshiped money. Uh, I don't think money ever defines me.”

Q I totally get you. Can I ask then, why, I listened to you on Mini and Mini Driver talk, and I loved it, but you said, like, having a plan Never have a plan. Um, and it kind of flies in the face of almost ghosts, which I love, but I'm going, huh, are they counterintuitive?

A And it depends on what we're calling a plan. I think some people have a plan for their life, a plan of what they're going to do. That plan's never going to come true. Even when we're talking about this ghost, the plan is sort of the tactical level. Since I was at MTV, I've had a weekly operating committee meeting. Senior most eject executives get together. Why? Because we have to change the plan every week because things don't turn out as planned. And, uh, I can't tell you over the years how many people I've offered a job to, and they said, I can't take it because I got a plan of what I'm going to do. Almost to the person, those people can say, boy, I wish I'd taken that job. My plan didn't come true. Plans are something we do to reduce anxiety. About the future, because it's always, it's a little, it takes your breath away a bit to say, I don't, I don't know what tomorrow's going to bring. I don't know what I'm going to do in five years. I don't know what I'm going to do in 10 years. I mean, none of us ever got married thinking, I'm going to get married and then I'll get a divorce. Um, we had a plan of a life together. Things don't always work out. We take a job. We say, I'm going to stay at this job for 10 years. You may stay at the job six months, or you may, in the case of AOL, I told Steve, I'll come down and help out for a year or so. I stayed Eight, seven or eight years,…

AI assessment note: “it depends on what we're calling a plan.”

Q consumer product adoption, messaging and storytelling is, is so crucial. I spoke to so many and they said you are the best in the business when it comes to kind of packaging and messaging, especially around consumer products. And so I just want to kind of open up with a broad question of how do you think about what makes great messaging, Bob? And what is great storytelling to you?

A You know, I'm a southerner, and Mississippi had great storytellers, and I had a bunch of uncles who were great storytellers, and the family was always about storytelling. So I think that part is sort of you culturally come to it or genetically come to it. Um, but I think what makes a great story is what is interesting to people. What's the sort of sense of tension or discovery in that? What makes it exciting? And whenever I develop messaging, I use them. I have a podcast called math and magic because it's sort of what I live by that. I think there's the math of marketing, which is who are the people? What are they like? What are they looking for? And then once I know that, that doesn't make it interesting. I just sort of know where they are. Now I have to have magic. I've got to have something that sort of Brings them in and captures their imagination. And a lot of the messaging is what's the attitude? What's the mood? What is the image I'm trying to convey? Uh, at MTV, we were trying to convey the image of we were not TV. We were throwing TV out. We were spitting on TV. We're the new TV. We're the rebellion. So everything had to reflect that kind of attitude. And I've been, you know, we all have a personality type and I'm probably much more of an empath. Uh, I lost an eye when I was six years old, have an artificial eye. You can imagine as a kid, you're the outsider. You're th…

AI assessment note: “I think there's the math of marketing... Now I have to have magic.”

Q The question I have subsequently, does convenience always equal a great business? And I think about, like, Getty, or you have in the U.S. GoPuff, fantastic convenience service delivering groceries to your door, amazing, respectfully, and, you know, there's no argument on this, margins are really hard, it's a really hard business, probably not a good business, respectfully, again. Does convenience always lead to good business?

A No, no. And by the way, great products don't lead to a great business. Uh, you have to have a business model. And, uh, you know, I mean, even questions about, I mean, Spotify, great product. People love it. Is it nothing more than a retailer that all the money's going to the record companies, and they're just letting Spotify have just enough margin to stay in business? Is it a great business? Um, I mean, you look at all these delivery services, I can't imagine those are a business. Uh, maybe one day it will be, maybe a smaller subset of the consumers will be willing to make, pay more money, so they'll have fewer consumers paying more money, maybe that's a business, but You know, I, I'm always, um, when you talk about businesses, I always want to see it on an envelope. Like, if you can't show me on the back of an envelope how this, about three or four lines equal the business, I don't think you've got one. And we go through periods in probably the world, certainly in America, where we build up this bunch of things that aren't based on it's going to earn money, and it's going to get a lot of, in the nineties, we're going to get a lot of eyeballs, uh, then it's going to get a lot of traffic, then it's going to get a lot of, Of revenue. Uh, but at the end of the day, all those are IOUs to the investment community for earnings, because when you're saying it implicitly, you're saying…

AI assessment note: “No, no. And by the way, great products don't lead to a great business.”

Q Can I ask what worries you about the podcast industry? I think when I look forward, especially over the next 24 months, but I'm worried about a macro recession impacting podcast, sorry, advertiser sensitivity towards marketing budgets. Um, for me as a media company owner, that's unnerving. What are you worried about, and would you share my concern there?

A No, look, I think podcasting is, of all the businesses we have, is the least affected by the macro, because it has such a fundamental strength. It's growing, it's growing like crazy. Huge engagement on podcasting. People are absolutely listening to, or hanging on every word, You know, when people are watching a TV commercial, most of it's like second or third screen. They don't know what's going on there. They got something in their lap, they're doing their email, they're doing something else. When they're running and they're listening to something, they're actually listening. When they're in the car and they're driving by themselves, they're listening. Uh, they don't have a second screen going on. And so, and, and podcasting is sort of that on steroids. And so I think the impact podcast has The, the, the idea that the audience is just ballooning and also it's the desirable audience, you know, podcast talk radio tends to be older. Podcasting tends to be younger. Um, so you've got this young, interested, engaged audience that you can activate and will act. So I think podcasting is just, I, I, you know, if you say what's your list of 10 things to worry about, podcasting is not on that list.

AI assessment note: “No, look, I think podcasting is, of all the businesses we have, is the least affected”

Q If you know your children are making a mistake, do you let them make it anyway? How do you know it's a mistake?

A I mean, obviously, getting ready to step in front of a car, I'll pull them back. But things that look like mistakes often turn out to be brilliant ideas. And, uh, who knows? And I'm, I want to be careful that I'm not imposing my judgment of mistake on them, but rather I let them decide for themselves what's right, what's wrong. And, uh, you know, if I thought my kids were gonna commit murder or something, I would probably step in. But beyond that, I think they've got to discover it. And, you know, and they're going to have problems in life, but I can't solve their problems for them. I can support them, and I can be there for them, and I can be a sounding board, and the less judgmental I am, the more they'll use me as a sounding board, and the more judgmental I am, the less they want to use me as sounding board, because I'm not a sounding board anymore. I'm a controller.

AI assessment note: “things that look like mistakes often turn out to be brilliant ideas”

Q Can I ask Bob, I always think careers have inflection points, big break moments, where for some reason you're given more opportunity chance than maybe one should at a young age. When you think back over your career, what would you isolate as a big break point in your career where you really scaled trajectory fast?

A Well, you know, I've had a lot of those actually, but most of them were by accident. Um, I was, uh, I was, I mean, how did I go from being a fifteen-year-old disc jockey in Brookhaven, Mississippi, to programming the NBC station in Chicago when I was 20 years old? At the moment, it didn't seem like that, so it's so unusual. I look back, and by the way, I went to program WNBC in New York, flagship, when I was 23. I go, how does that happen in an eight-year period? So clearly there were some people along the way who really believed in me. And gave me a shot and, and sadly they gave me a shot. I might not give a kid. I might go, that's a kid. I can't give him a shot like that. Um, but.

AI assessment note: “programming the NBC station in Chicago when I was 20 years old”

Q Can I ask, does human psychology change around messaging, do you think? Easy, you mentioned there. Stingy bastard dad's cost. Easy in cost today. Isn't that what, 90% of great brands they're built on?

A I'm going to tell you, I, I've only done consumer services business. I never do B to B. Uh, and I will tell you the one thing that all, only one thing matters, convenience. When I was at AOL, we described AOL to the business community. As convenience in a box. What we were in the business of doing is taking everything you did in your life and make it easier by doing it on the computer. And, uh, and, and, and it's interesting. The one thing I really got wrong was I said, yes, I know it's more convenient to look at something on the phone, but people are going to want those big screen TVs. You know, years later, I see my kids sitting in front of a big screen TV turned off, looking at their laptop or looking at their phone, watching a TV show. Convenience beats quality. And, and, and it's, you hate to say that loudly because people think I'm a, I'm a horrible guy and don't like quality. I appreciate quality, but if quality won, everyone would still have a wired line instead of a mobile phone because the quality is a lot better. They would have never used a microwave oven because the conventional oven cooks so much better. Uh, but convenience is the winner, not quality. And when you understand that, then you can just bake everything down to is more convenient. We were talking to engineers at, at AOL in those days. Sometimes they come in and say, man, we've got a great new feature. A…

AI assessment note: “only one thing matters, convenience... Convenience beats quality.”

Q What's the best concert you've ever been to, and why them?

A It's either the first iHeartRadio music festival, uh, that we did in Vegas, when we used it originally just to launch the app. That was the way we were going to get the iHeartRadio app. I was going to do the iHeartRadio music festival, and then it was such a hit, we'd do it every year, and the other one was Live Aid, and I sort of modeled the iHeartRadio music festival on Live Aid, because it was this great collaboration of musicians, so many musicians sharing one stage, And in the case of, of Live Aid, we had, uh, the UK and the US, and only one musician played both, Phil Collins, took the Concord, um, and, uh, and the iHeartRadio Music Festival, we do two nights, one stage, but I think having musicians on one stage together, and by the way, when you go backstage, and they're all sort of chatting, and seeing each other, meeting people, is great. And Paul McCartney, when he played at the iHeartRadio Music Festival, backstage said, you know, Can I go out front and, and, and watch that? I never get a chance to really see concerts. And we took him out front, put some security people around him, and he got to sit in the stands and watch the other people perform. And so I think it does something for both the music, the musicians and us, as well as the consumer.

AI assessment note: “It's either the first iHeartRadio music festival... and the other one was Live Aid”

Q do want to kind of start at the top there in terms of your leadership. I spoke to so many of your friends, your colleagues before the show and stalk the shit out of you really. Um, but my question to you is when we think about leadership in particular, when I say the words high performance, what do they mean to you having, having led so many different organizations?

A Well, look, I, you know, I think the key is at the end of the day, there's something we're trying to do. There's a goal, there's an objective, and I think it's just being religiously focused on that goal and objective and being sort of pretty open to any way to get there within reason and also to always do it as a team. Uh, I've never, ever been successful without a great team, and so for me, I'm constantly looking around who are the people I want to be in the foxhole with, who can do stuff I can't do, Uh, and by the way, if they've got a big weakness, as long as somebody else on the team can cover the weakness, who cares? We're looking for that combination of people who gel as a team, work as a team, respect each other as a team, and, uh, and I've never seen, by the way, big success without it.

AI assessment note: “being religiously focused on that goal and objective and being sort of pretty open”

Q Can I be really direct and ask if you were to do those three to four lines on iHeart, just so I get an understanding for what sort of thing that would look like, what would you say the three to four lines on iHeart is?

A The iHeart is revenue minus expenses Equals a bottom line, EBITDA, our earnings. And then I take it one step further and say, how's our free cash flow? And what else did I invest? And how did I use the cash? How much do I have left? Um, and to me, I think every business ultimately boils down to free cash flow. And for me, I'm always looking at, okay, and if I'm going in a new line of business, what's the margin going to be on that? We've, we've done the podcasting business in the US, which was an adjacent business to radio in my mind. And we are now, uh, the size of the next two podcast publishers combined. And we prime, so we got the more, more downloads than anyone else by a mile. We've also got more revenue than everybody. But what we really have is we're probably the only podcaster that has real profits. And we may be 20 or 25% of the revenue of the podcast business. I'll bet we're probably 90% of the Profits of the podcast business because we refuse to do deals that aren't profitable. And there are plenty of people, we got to get in and we'll buy our way in. You don't buy your way in by doing unprofitable business. It never gets profitable. Um, you know, you may buy your way in because as you pointed out, you'll start small and do 2000 to 5000 to 10,000. But you know, when you hit 20,000, you'll make money. Or when you hit 50,000 and you can see a pure path to get there. B…

AI assessment note: “The iHeart is revenue minus expenses Equals a bottom line, EBITDA, our earnings.”

Q What's your biggest lesson from the Casa Dragones journey?

A God, there are so many of them. Uh, one is that passion really does matter. Uh, two is that it's possible to let, because I'm in the business of using, I got to grow fast. Every business I'm in, in Casa Dragones, we said, we're going to let it grow at whatever pace it grows, because we want it to be authentic, and we want it to just roll out in a way that we own the tequila connoisseur. And so, and, and we let it go. And that, that was hard for me because that's so different from me as normal business person. Uh, but we had the luxury to do it. And, and for me, Casa Drugs was great because my, my thought was, I, it was a win-win. I either have a successful business or have all the tequila I ever need for the rest of my life.

AI assessment note: “one is that passion really does matter. Uh, two is that it's possible”

Q do want to kind of start at the top there in terms of your leadership. I spoke to so many of your friends, your colleagues before the show and stalk the shit out of you really. Um, but my question to you is when we think about leadership in particular, when I say the words high performance, what do they mean to you having, having led so many different organizations?

A Well, look, I, you know, I think the key is at the end of the day, there's something we're trying to do. There's a goal, there's an objective, and I think it's just being religiously focused on that goal and objective and being sort of pretty open to any way to get there within reason and also to always do it as a team. Uh, I've never, ever been successful without a great team, and so for me, I'm constantly looking around who are the people I want to be in the foxhole with, who can do stuff I can't do, Uh, and by the way, if they've got a big weakness, as long as somebody else on the team can cover the weakness, who cares? We're looking for that combination of people who gel as a team, work as a team, respect each other as a team, and, uh, and I've never seen, by the way, big success without it.

AI assessment note: “religiously focused on that goal and objective and being sort of pretty open”

Q Bob, that's pretty cool. I mean, I appreciate that a lot. And we had a chat yesterday and Ryan said specifically, Bob has the ability to forecast things that are marketable before they're on the horizon. And so going back to that, people didn't see or appreciate what you did. I want to understand how do you gain an instinct for where the world is going ahead of the world?

A You know, that's a, that's a good question. I don't think I do. I think what I am is I'm wildly observant. I'm wildly curious. I spend a lot of time listening to a lot of people and my ears perk up when something, something catches my ear and I go, well, that's sort of interesting insight. And to me, I think we're looking constantly, if you're, if you're a leader or you're running a company, you're constantly looking for the unique insights and the epiphanies. Most of the stuff we do day to day does nothing except to keep the trains running. But to keep the business growing, we've got to find those, wow, there's something going on here. And that's what I'm constantly in search of. And by the way, it matches my skill set and my interest because I'm wildly curious. I'm sort of curious about everything in life. So when I spot that stuff, I'm, I dig in and I'm, I'm asked a lot of questions. I want to know, I want people to educate me, but I don't think I'm seeing something that's unknown. I think I'm seeing the first glimmer of something and, uh, and saying, wait a minute, this is what's happening. And then I usually try and figure out why, because I, I don't want to chase it if I can't figure out why is that happening? But if I can say that's happening and I go, and now I know why it's happening, then I feel much better sort of turning the team toward that.

AI assessment note: “I think what I am is I'm wildly observant. I'm wildly curious.”

Q My question is, both of these elements, not having really seen it or felt it before, and then also just the danger to my business, it makes me feel very insecure. Honestly, Bob, you're a, you know, seasoned, wise, wise leader. What are you insecure about in leadership today?

A You know what, what am I insecure about? I guess I'm insecure about what I don't know, but I think at this point, you know, the, the beauty of being old is that you get really comfortable with all of this, and I probably am not as passionate or as fiendish as I, just like maniacal as I was when I was younger, but I'm also a lot more chill. When people have a bad crisis, I always say, look guys, you know what, enjoy this one, because when we get the next crisis, you'll wish you had this one back. Um, I mean, we'll get through them. It just, you know, it's not getting all worked up. I'm going to help us solve it any better. Some of it's within our control. Some of it's not. And, uh, it's just a matter of trying to figure out, okay, whatever it is, what is it? Let's diagnose it. And then let's do all we can to, to respond to that diagnostics. But I think very important on this stuff is to diagnose it correctly.

AI assessment note: “I guess I'm insecure about what I don't know”

Q Can I ask Bob, I always think careers have inflection points, big break moments, where for some reason you're given more opportunity chance than maybe one should at a young age. When you think back over your career, what would you isolate as a big break point in your career where you really scaled trajectory fast?

A Well, you know, I've had a lot of those actually, but most of them were by accident. Um, I was, uh, I was, I mean, how did I go from being a fifteen-year-old disc jockey in Brookhaven, Mississippi, to programming the NBC station in Chicago when I was 20 years old? At the moment, it didn't seem like that, so it's so unusual. I look back, and by the way, I went to program WNBC in New York, flagship, when I was 23. I go, how does that happen in an eight-year period? So clearly there were some people along the way who really believed in me. And gave me a shot and, and sadly they gave me a shot. I might not give a kid. I might go, that's a kid. I can't give him a shot like that. Um, but.

AI assessment note: “programming the NBC station in Chicago when I was 20 years old”

Q How do you think about bringing up, you know, you have three children. How do you think about bringing up your children, uh, who have, you know, more money than maybe you did growing up, um, and make sure that they have that humility and hard work ethic, despite having money in childhood?

A You know what? I, I think it's hard. Um, I think it's hard to have The total influence on your kids. I think you can be an advisor. I think you can set a tone. Um, I, I think, you know, you go through a period from sort of 1516 to sort of mid to late twenties in which I'm an idiot. Um, and then, but some of the things I told them later in life, they go, you know, I remember you told me that and that's, you know, so, but it's later on, but they have to build their own life. And I think the hardest problem, uh, that we have as parents is not to do too much. Um, I let them find it. What worries me to death about the world today is when I grew up, I would go outside and I would get on my bike. My mother had no idea where I was. Uh, she didn't know who I was with. She'd be home by dinner. I would be home. They called it supper then. Be home by supper. I was home by supper and, uh, and she had no idea. When I moved away from Mississippi, when I was 18, I moved to Milwaukee. My parents had no idea what was going on in Milwaukee. There was no information source from Milwaukee unless they subscribed to a newspaper, which would come probably a week later. Um, the long distance phone calls were very expensive, so we talked once every couple of weeks, and I saw them in person once or twice a year. And, uh, so I was completely independent, and I was able to build me. I, I worry about my kid…

AI assessment note: “I think the hardest problem, uh, that we have as parents is not to do too much.”

Q Final one, I promise you, and then we'll do a quick fire. I love children and I want to have children, but I also work my fucking ass off and I'm terrified about losing any inch on performance. How do you think about being there for your children in the way that you want to be, but also being a rockstar CEO and bluntly leading 100,000 of people?

A I, I, I retired once in my life when my little kids were young and took about eight years as just sort of an investor, part-time investor. And I'm a pilot, so I flew all around the world. I had them in 50 countries by the time they were 10. I, I fed my curiosity and fed them and hopefully helped them develop some of theirs. Um, but I believe in, I, I think life work balance is hard. I think life work integration is easier. Uh, and it's a matter of how we all sort of, you know, do it together. I wouldn't hold myself up as being the greatest parent in the world. I try as hard as anyone does. But boy, is it hard work, and I think when you get to kids, you don't do the kids for you, you do the kids for them, and you do, you're right. I'm willing to, just like I want to contribute some of my money to charities which are important and help them, I want to give the world some more human beings that I think are good human beings that I helped raise, but it's work. It's a lot of work, and it's a commitment, and, uh, and I love every minute. I adore them. But it is, uh, and I learned a lot. I learned as much from them as they, as they learned from me. And, you know, you asked me, how do you keep in touch with ideas, et cetera? Is my kids open, open the world to me ideas they have and interest they have. I would have never had their ideas would have never occurred to me. And if I listened…

AI assessment note: “I think life work balance is hard. I think life work integration is easier.”