The consumer wants something that's easier. My basic rules is you never fight human nature. The bad part of algorithms is when we use them to get people upset.
Today we're joined by a true architect of modern media. He has been shaping culture and media behind the scenes for decades. He co-founded MTV and today he serves as chairman and CEO of iHeartMedia.
About half of America thought the media dislikes them, hates them, doesn't share their values. I fear we have a lot of other platforms that have emerged that don't have that view. That does trouble me. I hope we never do it.
And I think we're in another era of disruption right now.
If you want to know what the future holds, if you want to know what's working, just look at the consumer.
Hi and welcome to Prime Talks, where we go beyond markets and money to explore the ideas, decisions, relationships that shape the extraordinary lives and enduring legacies of our guests through fairly candid conversations with world-class entrepreneurs, investors, thinkers, and cultural leaders. We unpack not just what they've built, but how they think, what they've learned, and how to use that wisdom to help families and leaders navigate wealth, purpose, and life with hopefully greater clarity. Just as a reminder for everyone, Prime Talks is a project of our charitable foundation, with all proceeds from Prime Talks going towards mental health. Today's conversation is one we've been looking forward to for quite a while, and our guest is the legendary Bob Pittman. But I think his claim to fame is really that he is a dear friend of Sylvia's. And maybe Sylvia, if I could impose on you to share a little bit about Bob.
Yeah, absolutely. I mean, I don't think Bob's claim to fame is that he's a friend of mine. I think my claim to fame is I'm a friend of his. One of my favorite Bob Pittman memories is we were sitting in a restaurant and they were treating him so well because he is Bob Pittman, and he was so surprised by it. He's like, "The service here is so great." And I'm thinking to myself, like, you don't even realize how in awe these people are of who you are. So everybody, welcome back to the show. Today we're joined by a true architect of modern media. Bob Pittman is a name that you've definitely felt even if you don't realize it. He has been shaping culture and media behind the scenes for decades. He co-founded MTV. I am a child of the MTV generation, so much appreciated. And he helped define an entire generation of music culture and storytelling. He's held top roles across some of the biggest media companies in the world, and today he serves as chairman and CEO of iHeartMedia, which is the largest media company in the US. So from revolutionizing how we experience music to shaping how we listen to it today, Bob has consistently stayed ahead of where media is going next. So today we're going to be talking about leadership, about family, about innovation, about risk-taking, and what it really takes to build the kind of career that Bob has built over decades. So it's truly my great honor to welcome you today to the show, Bob. And let's begin.
Thanks, Bob. So maybe we'll kick it off just with, you know, obviously Sylvia shared a bit of your bio and you've had all these media transformations that you've touched and led and shaped over the last 40 years. Is there a thread that connects all the successful ventures that you've been a part of?
Yeah, it is the consumer. I never do B2B. I don't understand anything about B2B. And my job is to understand the consumer and watch them like a hawk because if you want to know what the future holds, just look at the consumer. If you want to know what's working, look at the consumer. And in my career, in my early career, I got them to listen to radio stations, with MTV got them to watch MTV, got them to watch Nickelodeon, got them to go to Six Flags theme parks, buy a house through Century 21 Real Estate, come on the internet in the '90s with AOL when we sort of introduced the internet to the mass market. And obviously with iHeart, getting people on the radio, getting them to podcasting, getting them into our digital products. But it's the same consumer, whether I'm trying to get them to watch Nickelodeon or whether I'm trying to get them on AOL. And so if you understand that consumer and you look at your business through that prism, it tells you almost everything you need to know, and that's what ties it together. And I've always been willing to go with any business that talks to the consumer and where we're dependent upon the consumer for our success.
And what do you think you've done to actually get that deeper understanding of the consumer than others?
Very early on, I was a research guy. I never finished college, but I was on the air as a radio announcer, and I was programming radio stations as a teenager. And wherever I went and got a job, I went to college. But my major was social methods, which is what they used to call research. I mean, I still remember keypunching cards and taking my cards to the computer center to run it. And I was one of the first people in programming to really say, look, the consumer will tell us what we need to know. Forget golden gut. Forget my instinct. Forget I'm a genius—I'm not. And I looked at research very early on, and I still am very data-driven today. At America Online, when half of the traffic of the internet in the '90s came through AOL, we were sort of top dog, and the press wrote about us if we sneezed. So every time we would make a statement, we tested the statement. And we not only tested the statement, we did what we called argumentation. Once we saw the statements that tested well, we then say, "Okay, but critics say," and then we find which ones crater under criticism and which ones survived. And today, obviously, we have a lot more access to data, a lot more understanding of the consumer. But I will caution that at the end of the day, research is not policy making. It doesn't tell you what to do. It conditions your gut and you have to make, at the end of the day, a decision. And when I was at MTV, my head of research, a wonderful guy, Marshall Cohen, came to America Online with me as well. We used to argue about what the research meant. So yes, you see the research, you see the data, but then you have a very wholesome debate about what is it telling us. So when I look at a career, my career is about the consumer. The businesses are secondary to the consumer.
Yeah. And what you're expressing so well is that it's really an art and a science. And you have your own podcast. I think it's called Math & Magic, right? Because it's that—
—combination of both. But when I think about what you're really a master of, it's understanding attention. And the attention economy is maybe the most important economy that exists in the world today. How do you draw in the attention of a consumer and how do you then keep the attention of a consumer? And you've been able to do that through many, many eras of constant disruption. And I think we're in another era of disruption right now. So how do you personally decide how to navigate those disruptions, which disruptions to chase, and how do you look at the disruption that's happening today in media?
Well, it's interesting. I never look at it as disruptions. People have said, "You're a disruptor." And I go, "I never noticed." All I'm doing is following the consumer. And there's one truth about the consumer: the consumer wants something that's easier. When I was at America Online, we actually called AOL sometimes externally, but internally we called it "convenience in a box." All we were doing is doing activities that people already wanted, but making it much easier by doing it on the internet. Instead of going out to a bar to meet people, you could meet them online in a chat room and be in your underwear eating cereal. And it made it so easy to do everything. And there were two areas that I thought were exceptions to the rule, and turned out I was wrong. One of them was I thought, "Well, you won't buy clothes over the internet because you want to try them on and you want to feel the fabrics." I was wrong. Of course, people just ordered and they sent it back. The other one was I said, "Oh, but these big-screen TVs are so big and so great that people are going to want to sit down in front of that." Meanwhile, then I watched my kids pull their phone out and watch their favorite movie on their phone and the screen was black. They wanted convenience. And I've never seen a deviation from that rule. If you can take any product, make it more convenient, you win.
Interesting. A couple of pieces, but I actually want to go back a little bit. Bob, you said you started already on the air, reading the consumer at 17. I'm sure there's been mentors, influences, guides in your life that have sort of shaped how you think about the consumer, shaped how you think about business. When you look back, maybe it was pre-17, maybe it was post-17, but who were those—
Actually, I started at age 15.
Probably not possible today.
So who were those early mentors and guides? Who are the people that you've sort of modeled your philosophy alongside with, and which kind of early lessons do you still carry in that respect?
That's a really good question. On my podcast, I always ask successful people who have a successful career anyway, "What was the improbable jump?" Because there are jumps you make in your career where you say, "Okay, that's logical." And then you see something and go, "How in the hell did that happen?" And the one I think was my improbable jump was I was making $1.65 an hour as an on-air radio personality in Brookhaven, Mississippi, a town of about 8,000 people at the time. And five years later, I was making more money than I ever dreamed of—I mean, multiples of what my dad made—and I was programming and on the air in the afternoon at the NBC station in Chicago.
And it was one man. It was a guy named Charlie Warner. I got a job as disc jockeys did in those days. You had to be in the town to be on the radio because technology didn't allow anything else. So I was in Milwaukee. I was in Detroit. I was 19 years old in Pittsburgh, Pennsylvania. They let me program the radio station there. Why they did that, I don't know—maybe that was an improbable jump. But there at WPEZ, where I had a big success, was a guy named Charlie Warner. And Charlie had been at CBS in New York in the days that CBS was the equivalent of OpenAI or Microsoft or whatever. And he was this elegant Dartmouth grad, well-dressed, looked like a movie star. And he'd fallen out with the guys at CBS, gotten fired, and he wound up in Pittsburgh, which was like a big step down. And he fell in love with me. And I had, by that time, long hair and a beard and t-shirts and jeans—I mean, this was the mid-'70s. And Charlie Warner fell in love with me, and he got fired in Pittsburgh and got hired at NBC in Chicago. So he calls me up and says, "You want to come to Chicago?" And I was 20 years old. "Do you want to come program this?" In those days, it was all AM stations, a 50,000-watt clear-channel radio station in Chicago. And that was the break. And by the way, today if someone told me, "Hey, we're going to hire this 20-year-old program director for our station in Chicago," I'd go, "No, we're not." It was way too risky. Why he took a chance was beyond me. God bless him that he did. And so that's it. I'm not sure Charlie taught me anything about programming, but what Charlie taught me was how to live in this business world. Like he told me, "Okay, you go to New York. In New York, you eat at this restaurant. The media people go here. Here's what time they go. You need to go get a suit from Paul Stuart. You need to go to Côte Basque or La Grenouille, and those are the best restaurants." And, "If you go to The Four Seasons, you go to the Grill Room for lunch and the Pool Room for dinner. 21 Club, all the media people are there at the bar at closing time. You need to be blah blah blah." And he just taught me sort of the code and the ins and outs, which I honestly would have never figured out. And as he explained corporate politics to me, he wasn't particularly good at it, but he was great at understanding it existed and sort of what it was. And for me, I navigated a career at NBC for five years. I was at American Express and Warner Communications, which owned MTV initially, and then we were a public company. And then I went to Viacom. And then I did a deal with MCA after that, and went back to Warner when we were merging with Time to create Time Warner. He gave me an insight that allowed me to feel very, very comfortable in big companies and being entrepreneurial inside a company, which was great for my career. And I have him to thank for that.
You've reinvented yourself so many times across the decades. When you think about that ability to reinvent yourself, what is the skill or the mindset that you think has been most attributed to your ability to do that?
You know, I actually don't think I ever reinvent myself. I just think I'm constantly flowing and growing. What attracts me? I've never taken a job for money. Actually, I took one job for money: Century 21 Real Estate. But nothing else for the money. I've taken it because it's just fascinating. And by the way, even at Century 21, I got fascinated with the business and the opportunity. And it's at Century 21, actually, that I said, "I know nothing about real estate. Online is becoming important, and we ought to be online." No real estate company is online. And I went to see a guy named Steve Case at AOL and said, "I'd like to be your real estate area on AOL exclusively, and I'll pay you $1 million a year." Like, "Wow, that's great. I got it." And before the lunch was out, he said, "Do you want to be on my board of directors?" So it's interesting that Century 21 was my—I was on the board for a year, and then went in to run the company with Steve as the president and COO. So even the one I didn't take for money turned out to be a critical step to getting to probably what was the biggest opportunity I'd ever had, because we were inventing a whole new world, in addition to a company that created an enormous amount of value. So that's the way I look at it, Sylvia. I've never consciously thought about, "Oh, I'm changing or I'm evolving." It's just like times change, situations change, and I just sort of flow with it. I was one of those kids in school that hung out with every crowd. I never sort of declared. And it was always interesting to me: I'd hang out with that crowd, and that crowd, and that crowd. And I still like to do that. I am thankful that I have the ability to do that. But what that allows you to do is as something new pops up, you go, "Wow, I never heard of that." Someone took me to Burning Man when I was 50 years old, many years ago, and I was like, "What's Burning Man?" And I go, "Wow, look at this." New things pop up, and I think I have a bias towards saying yes, not no. Almost every job I've taken, people thought was this terrible move. Like, "Why would you do that move?" And then we build it into something worthwhile. And so for me, it's just looking for opportunities to have something stimulating, enjoy my curiosity, meet new people, do new things, and it's that constant journey of life. Life's just a journey. We're not going anywhere. We're all going to the same place.
Yeah. And before we turn the conversation towards media and a couple of the current trends that you're seeing, Burning Man—what did you learn from Burning Man? Did it shape you? Did it—
I mean, I go every year. I've been going for 20 years or more. And I think what it did was it opened my eyes. I think the biggest problem we have in life for any of us is the longer you live, the more the blinders come on, and you see your group, your path, what you do, you see your world, you think that's the most important, and before you know it, you're down to this. What Burning Man did for me was you go in there and the blinders swept. It opened the blinders. And I encourage a lot of people to go, and I go, "It's healthy for you to open your mind." It's a great way you look around and go, "What is this? Who made that? Who thought that up?" And it's an event in which most people are sort of in costume, so you can't recognize the symbols of who's got money, who doesn't, who's successful in business, who's not. It's just a bunch of people. So you just go, "Okay, that's an interesting way to look at life." So I still love going. It sort of rejuvenates me. In the turn of the last century, if you were Christian or Jewish, you probably went to a summer retreat for a week or two to renew your spirit. Both of them are very famous for having all these camps and communities, etc. I think Burning Man is sort of one of those where you go to renew your spirit for a week every year.
Wait, maybe there's a Burning Man in your future.
Oh, you know, I'm sold. Yeah, you had me at "I've been going for 20 years," so hopefully I have a few years ahead of me to capture that. But I do want to come back, because I was thinking when you said, "I haven't really evolved as drastically; I've just kind of gone with the flow." And I'm wondering how you're finding this moment, because this moment is almost unlike any moment in time where the rate of change and the number of things to just be curious about seems to be staggeringly faster and more abundant and more vast than anything that we've experienced before. So how are you navigating this moment in time?
They always say that. When the cable revolution came, you'd go, "What? I'm not constrained by three networks deciding what I can see and hear? I can get 30 channels of TV? What?" Pay-per-view came along, home video. Remember, you couldn't see movies unless you went to the theater or you waited for one of the broadcast networks to run it sometime. It was sort of like, "Wow, it's changing the world." And I wrote an op-ed for the New York Times which was a very popular one called "The TV Generation," and how the TV generation was different from everybody else, and oh my gosh, it's like a whole thing. Well, then we go to the internet in the mid-'90s, and what—I mean, I worked in business before there was the internet. I would get a stack of mail this high on my desk twice a day. We had the guy coming around with a cart multiple times a day to take memos and we'd move them around. I look back and go, how on earth did we do business? And it said, "Wow, the rate of change—it's changing everything." And then we had social, we had mobile, and now we have AI. And yes, it always looks scary and crazy on the front end because you don't know where it's going.
I want to ask you a question as a parent, right? Because I hear what you're saying and I like to think of myself as an open-minded person and somebody who's not putting on her blinders. But when you're raising a teenager in today's environment, I am the old person looking at how they engage with media, especially TikTok, and it doesn't feel okay to me. I'm like, gosh, that feels like—and then I think, but that's what they used to say about kids going to Elvis concerts back in the '50s. So I just became that old person who doesn't understand where we're headed.