Bob Pittman: How I Went from Creator of MTV to CEO of iHeartMedia | 20VC #958

1. 0:00 – 1:56

   How Bob Pittman got into Radio

   1. HSHarry Stebbings0:00

      Bob, this is such a joy to do. I heard so many good things, especially from our friend Brad Gerstner before. But thank you so much for joining me today.

   2. BPBob Pittman0:07

      Oh, I'm delighted to be here. Thank you.

   3. HSHarry Stebbings0:09

      Not at all. But I heard from a little buddy 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?

   4. BPBob Pittman0:19

      Well, I wa- 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 Piggly Wiggly.

   5. HSHarry Stebbings0:35

      (laughs)

   6. BPBob Pittman0:35

      No jobs. And I walked into this little radio station and, uh, asking a guy 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 have pretty good grades." He said, "You get in trouble." I go, "Not really." He goes, "Okay, come in this room." He 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."

   7. HSHarry Stebbings1:01

      (exhales) .

   8. BPBob Pittman1:01

      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.

   9. HSHarry Stebbings1:14

      (laughs)

   10. BPBob Pittman1:14

       And it's stunning the number of people who got their start doing that. Tom Brokaw, one of the great newscasters on NBC, started in Yankton, South Dakota as a, as an on-air disc jockey, so, so it s- it was a great way to get into the business.

   11. HSHarry Stebbings1:27

       Can I ask, did you love it from the very first minute or was there a moment where you were like, "This is what I really have a passion for"?

   12. BPBob Pittman1:33

       No. At first, I loved airplanes, and this was a way to get there. What I did love is that I found all the kids in town would call me on the request line, including girls, which age 15 is very important to you, um, and, uh, but it...

   13. HSHarry Stebbings1:47

       (laughs) .

   14. BPBob Pittman1:47

       But I fo- I actually began to fall into radio, and by the time I was sort of 17 or 18, I was just mesmerized

2. 1:56 – 5:28

   Breakout Moments in Career

   1. BPBob Pittman1:56

      by it.

   2. HSHarry Stebbings1:57

      (smacks lips) 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?

   3. BPBob Pittman2:14

      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 15-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's what'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, uh, but that happened.

   4. HSHarry Stebbings2:53

      Why, why, why do you think, why do you think that is? 'Cause I feel the same often. I'm, "I couldn't give a 21-year-old loads of money to invest."

   5. BPBob Pittman2:58

      I, I, I have no idea what they saw in me. And by the way, Charlie Warner, who's the guy who took me to Chicago and then took me to New York with him, uh, is still alive. He's in his early 90s. And, uh, and I've had this lifelong relationship with him. He worked for me for a while at AOL, uh, and I've had him in other capacities. But it just, he said, "You just... Wow, you just impress me. You knew what you're talking about," and there was just something there, and that's why he did it. Um, but, you know, things happen. And then, you know, there are obviously other ones, uh, I went to MTV because my great mentor at NBC at the time, Herb Schlosser, who was the president of NBC, got kicked upstairs and I thought my trajectory's over, so I went over to this cable company that was beginning to form a programming company called WarnerMX Satellite Entertainment Corporation as their head of programming. But at that time, cable was nothing in the US, and everybody goes, "Why would you leave NBC to go to this thing I can't even pronounce?" Um, and so it's sort of dumb luck. And I went with Steve Case at AOL. I, I joined the board in '95, and then, uh, Steve in '96, there were some issues going on and Steve asked me if I would, you know, come down and, and be the president and, uh, and the board, and I was still on the board. And I sort of went as a lark. Um, did not see the great potential of it. And I came here to this company, which I've been at the longest of any place I've ever been, and I came in, in as an investor originally in 2010, and I just thought, "Wow, this company has an asset no one appreciates. Audio is so underappreciated, undervalued. People don't know what it can really do. I do. And by the way, we're gonna take it into digital." I didn't foresee podcasting, but obviously, that was big for us, events, et cetera, and it just seem like this great platform. And so I sort of took a chance on something that was a little crazy. And so-

   6. HSHarry Stebbings4:51

      We get it, we-

   7. BPBob Pittman4:51

      ... big moves have always been when they didn't look like good moves. Actually, when I went to AOL, I had, I, I was running Century 21 Real Estate after Time Warner and Six Flags Theme Parks and, uh, and my friends go, "Why would you leave Century 21 to go to AOL?" That's how unappreciated the internet was and how the potential of AOL was so underestimated.

   8. HSHarry Stebbings5:14

      You said that multiple times, "Underappreciated." We're gonna get to kind of your, uh, insight into new markets. I do wanna t- 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, um, stalked the shit out of you really.

3. 5:28 – 6:35

   What does high performance mean to you?

   1. HSHarry Stebbings5:28

      Um, but, uh, 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?

   2. BPBob Pittman5:38

      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 m-... 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.

   3. HSHarry Stebbings6:25

      Bob, you said about team there. I spoke to someone kind of on your team. Um, I normally have references with other VCs or founders. When, when we were doing the prep

4. 6:35 – 8:27

   Ryan Seacrest asks, “How can you see the future?”

   1. HSHarry Stebbings6:35

      for the show, you gave me Ryan Seacrest. I mean, 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?

   2. BPBob Pittman7:01

      You know, that, 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 keep the trains running. But to keep the business growing, we've got to find those (snaps fingers) , "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 interests, because I'm wildly curious. I, sort of just curious about everything in life. So, uh, when I spot that stuff, I'm, I dig in and, um, um, ask 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. 'Cause I, uh, 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, then I go, and now I know why it's happening. Then I feel much better sort of turning the team toward that.

   3. HSHarry Stebbings8:23

      I, I do want to go to an example. But just first, my question to you that I struggle

5. 8:27 – 14:09

   How do you get consumer insights?

   1. HSHarry Stebbings8:27

      with here is, naturally when we're so ingrained in work, we surround ourselves with the same people. Often, the people are quite similar in many ways. They all love media, they all love venture capital, they all... And you don't get a diverse set of opinion. And so that unique insight is often quite common thought, because the people and their backgrounds are all the same. How do you think about ensuring that you do actually get the consumer's insights?

   2. BPBob Pittman8:51

      Right.

   3. HSHarry Stebbings8:51

      Not just execs in media or media talents? How do you do that?

   4. BPBob Pittman8:56

      Well, there are, there, there are several layers to that. One is, if everybody agrees on something, it's a bad idea, because that's groupthink and that's media. If it's in the headlines, I'm not going there. There's no upside in that. Uh, the opportunity is to find something that everybody's not doing. And, um, and I also think there are, there are, there are management styles. I, I build a team not of people like me. I've already got me. We need people who are not like me and that are disparate people, but still have enough chemistry to hold together as a team. And we have a couple of things. Look, we, we worship dissent. I want to hear where people disagree. When people throw up an idea and say, "We'll work this out in this way," when they do, I say, "What did the dissenters say?" First time I mention that to people, they go, "Oh, no, we all agree." And I go, "Well, then you haven't really dug in enough," 'cause there's always a dissenting point of view and we need to look at it and examine it. And, and the example I use is John Kennedy. When he announced he was gonna put a man on the moon in the early '60s, he had not told NASA.

   5. HSHarry Stebbings9:56

      (laughs)

   6. BPBob Pittman9:56

      It was 100% a political announcement, and NASA hears about it on the news. Well, as you can imagine, they go batshit. Uh, the, the people from the White House go over and meet with them. And what they did next was really, really change the course of not only the space program, but management in the US, is they said, "Well, why can't we put a man on the moon?" And they start listing out, "No rocket fuel, navigation, no heat shield," blah, blah. They go through this whole exhaustive list. "Anything else?" "That's it." "So what you're telling me, as soon as we solve these problems, we can put a man on the moon?" And they built these teams of people, not general to a private, but people of equal rank, and they just made somebody a team leader. And these teams worked on each one of those problems, and they put a man on the moon by the end of the decade. And I find the same is true in business, that if we listen to the dissent, what they're real... And, and not, not personal say, like, "I hate it." That's not very good dissent. But, "That's not gonna work because of X, Y and Z." The, we need to examine the X, Y and Z and figure out, hmm, we need to make sure we solve X, Y and Z to make this a successful idea. And the dissenters become very important in my process. And, and I think the other thing we do is we also don't expect, uh, everything to be perfect. I could... If you're a genius, maybe you get it right 50% of the time. You're gonna get it right, you're gonna get it wrong most of the time, so just be ready for it. And if you're gonna get it wrong most of the time, then what kind of, what goes along with that? And what goes along with that is quick decisions. Because when you get it wrong, admit it, you made it wrong, and change it and change it quickly. And when you change it quickly, you, the damage of getting it wrong doesn't really hurt. And it iterates till you keep trying, until you get a better chance of getting it right. And, uh, and I think one of the problems too... And so we have quick decisions. We said, we sort of have a-... half-serious rule that we have a 24-hour rule. The problem I have is if you ask people, "When will you have this decision ready for me?" it'll be a long time out. So I always start with, "We need it in 24 hours," and I make people justify why they can't do it in 24 hours, which tends to pull decisions in, uh, by putting that construct on it. And when you push that sense of urgency on it, and we also say, "No study and review." Uh, you're, y- you know, people often say, I say, "When will you make that decision?" They say, "Oh, I'm going to decide next week." And I go, "What are you gonna know between now and next week you don't know right now? And if, if, if you're not gonna know something important in that period of time, why don't you just make the decision right now?" So probably the reason you're putting it off till next week is it's a hard decision. But time doesn't help hard decisions. As a matter of fact, it often hurts them. Um, "So let's make a quick decision and keep going." The third thing I look at is that when we make decisions, these, I'm making these numbers up. Let's say we're making 10 decisions. Two, I'm gonna, I'm gonna make this up, are clear winners. We just go, "Wow, that worked. That was great. Exactly what we expected." Two are clear losers. "Wow, those were stinkers, get rid of them."

   7. HSHarry Stebbings13:04

      (laughs)

   8. BPBob Pittman13:04

      The problem is I got six in between. What do I do with those? The ones that went, they go, "Well, it didn't do exactly what we wanted it to, but it's helping. It's got something that ..." Then we start looking at the good in it, and the decision I always say is, well, if we had said our goal is what it's doing, would we have done this? The answer's almost always no, but it's doing something good. I think the real courageous people kill everything that's not a clear winner. Most people can only kill things that are clear losers. So you figure if there's two on top, two on the bottom, and six in between, imagine what happens to a company if you let everything live that that's gunk in between a clear winner and a clear loser. We call it weeding the garden. So I think, and by the way, and I'm as guilty as everyone else of justifying why something happens. But when we have excruciating honesty at, with each other, we can say, "That's not working. Even though you fell in love with it, even though you're trying to justify, get rid of it." And I think those three things in terms of a management technique help us.

   9. HSHarry Stebbings14:04

      I, I'm, I'm f- I mean, there was so many things, I was writing down (laughs) uh, to, to

6. 14:09 – 16:46

   How do you know what content to kill?

   1. HSHarry Stebbings14:09

      make sure that I can remember. Uh, you mentioned that, about kind of, you know, 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 2,000 plays per show (laughs) . 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 well do you think about that, like, kill things that aren't material and sizeable in long term games?

   2. BPBob Pittman14:36

      Oh, I, I, I'm not saying kill something's not sizeable or material, because I think you kill ... there are many things that aren't sizeable or 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 Alberto Gonzales back in 2000, launched it in 2009. We deliberately said, "Let's take a long time. Let's let people dis- This is gonna be a product people discover." So the goal was not to have instant, we weren't pushing to have 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 gonna build this show to reach these people."

   3. HSHarry Stebbings15:19

      Mm-hmm.

   4. BPBob Pittman15:19

      And then you're probably gonna say, okay, you got, let's say, 2,000 downloads. Are those 2,000 the right people?

   5. HSHarry Stebbings15:26

      Yeah.

   6. BPBob Pittman15:26

      And do those 2,000 people like it? And if you say, "Yeah, those are the right people and they do like it," then say, "Okay, then our issue is scale." Now we go from, "We did a show, but now how do we scale it?" Or they say they liked it, but they didn't like it because of X, Y, and Z. Okay, I'll change, I'll adjust that. Um, I make, I, I think, you know, the, the back and forth dialogue is so important with a consumer. But it's, it's also important in terms of, what's my goal and am I hitting my goal? And part of it is you can't have unrealistic goals. Like, if you want something and you say, "I'm gonna have 200,000 downloads to the episode," well, that's probably a stupid goal. Uh, unless you have some secret sauce like you've got 10 million social followers or you've got $10 million in advertising to put behind it, or somebody's gonna cross-promote you on another hit. So there are ways to do it, but I think it's a matter of understanding realistically what you're trying to do. And sometimes it's hard. By the way, sometimes you can start big and say, "Wow, I got a million downloads," and you go, "Yeah, but you know what? People don't like it." Um, "They don't look like they're gonna come back. The show stinks. We can't sell advertising in it." Get rid of it. So there is no s- Things aren't a success or failure based on big numbers. Success or failure are based on what you're trying to do. And part of it is precisely know

7. 16:46 – 20:34

   GOST Goals Objectives Strategy Tactics

   1. BPBob Pittman16:46

      what you're trying to do.

   2. HSHarry Stebbings16:47

      When should you change your goal?

   3. BPBob Pittman16:50

      Well, you know, I, I think when you change your goal is when you're ready to change your business. Um, I find, I use a process in budgeting called GHOST, which is goals, objectives, flowing to strategy, and then tactics. And I, you know, so I think you sort of start with, "What are we trying to accomplish here?" Um, and then you'll have some strategies to do that, and then you'll develop your tactics. Your tactics are your operating plan, and those will usually be your key KPIs. And I find over the years, my goal rarely changes. My objectives change sort of year to year, 'cause that's how I'm gonna, you know, have a million dollars of revenue or $2 million or $10 million. And you know, there are, uh, there are external factors that affect some of that. But the strategy to get there is almost always the same. What changes radically are tactics. And tactics change day to day. And I think that the key in, in a business is focus on, uh, on those tactical solutions if you have the right goals and strategies. But if you're having to change your goals and strategy, you probably don't have a good plan and you probably don't have a good business.

   4. HSHarry Stebbings17:58

      Can I ask you, what's the difference between a goal and an objective? They seem the same to me.

   5. BPBob Pittman18:02

      A goal is, what am I trying to do? I'm trying to give everyone in America a friend anytime, anywhere, using my ... It's more your mission statement. Or, by the way, "We're going to make," in the case of AOL, "we're going to make the internet as essential to people, as important to people as their telephone or television." Those are the goals, big real goals. The objective is, "Okay, and we'll make $10 million this year and $12 million the next year, and we'll do a profit of $2 million this year." So now there's a quantifiable output of the goal, and then the strategy is how we're going to get there.

   6. HSHarry Stebbings18:37

      I totally get you. Can I ask then, why ... I listened to you on Mini, in 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 Ghost, which I love, but I'm going, "Huh. Are they counterintuitive or why do you still-"

   7. BPBob Pittman18:54

      Yeah, and, and look, and, 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 gonna do. That plan's never gonna come true. Even when we're talking about this Ghost, the plan is sort of the tactical level.

   8. HSHarry Stebbings19:06

      Uh-huh.

   9. BPBob Pittman19:07

      Since I was at MTV, I've had a weekly operating committee meeting. Senior-most eject- executives get together. Why? 'Cause 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 'cause I got a plan of what I'm gonna do."

   10. HSHarry Stebbings19:29

       (laughs)

   11. BPBob Pittman19:29

       Almost to the person, those people come to me and say, "Boy, I wish I'd taken that job. My plan didn't come true."

   12. HSHarry Stebbings19:33

       (laughs)

   13. BPBob Pittman19:33

       Then I think plans are something we do to reduce anxiety about the future because it's always, it's a little, (gasps) it takes your breath away a bit to say, "I don't, I don't know what tomorrow's gonna bring. I don't know what I'm gonna do in five years. I don't know what I'm gonna do in 10 years." I mean, none of us ever got married thinking, "I'm gonna 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 gonna 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," so I stayed eight, seven or eight years. Um, that plans are not the reality. Now, when we're talking about a, a company, the operating plan is what is that thing we're operating from? And, uh, and I think when we call it the plan, you better be prepared to change it and change it often. Uh, because nothing, and I don't think we go a week without changing the plan because there's something that's better, something that's worse, and, or some external variable has sort of shifted the world, and,

8. 20:34 – 25:54

   Messaging and Storytelling

   1. BPBob Pittman20:34

      uh, and you gotta take it into account.

   2. HSHarry Stebbings20:36

      I love that in terms of hiring people and then them coming back to you saying, "It didn't go to plan." Um, when, even when you're hiring people or when you're, you know, addressing consumer product adoption, messaging and storytelling is, is so crucial. I, I spoke to so many and they said you are the best in the business. When it comes to kind 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?

   3. BPBob Pittman21:04

      I, you know, I 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, and I have a podcast called Math & Magic 'cause 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 gotta 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 the kid with the glass eye. So, and being an outsider is great because what the outsider does is I learned to read people, I learned to watch people. And by the way, I was a skinny little kid in a bullying Old South, uh, and I had one eye. And, and we moved two or three times during my childhood, which really makes you an outsider again. But I learned to just watch people and listen to people and think about, so what I think, and you say, what's an innate skill I have? I have a pretty good skill of saying, "Ugh, that's a cringe-worthy message," or, "Ooh, that's a cool way to say it." Um, and sometimes I come up with a line, sometimes I don't come up with a line, but I'm a really good editor. When I hear the line, I go, "That's the line. Let's go with that." And, uh, and there's not a lot of indecision. There's not a lot of hand-wringing. I worked for a guy named Henry Silverman once, who's a great pal and great thinker, and Henry always talked about study and review is the greatest insult. We're not study and review people. Just make the damn decision. And, and I think in the creative process of messaging, it can't be committee decision. It's, there's a keeper of the vision of every product. Uh, when I was at MTV, I was the keeper of the vision. I was not saying, "Is this a good idea, bad idea?" I'm saying, "Did it fit MTV or not?" It's a great editor. When Graydon Carter edited Vanity Fair, he wasn't making a decision about this is a great article or bad article. He'd say, "This fits in this issue of Vanity Fair." It's the, the vision of what's going on. When, and when we had Nickelodeon, the keeper of the vision at Nickelodeon was Jerry Laybourne in my day. That there's always the keeper of the vision, and I always step in as sort of...... you know, if it's not obvious, I'll make the decision about what we're trying to do. Um, I did a podcast, Math & Magic, with one of the guys who did the on-air look for me, Fred Seibert. And Fred is a brilliant guy, and he talks about how we came up with this idea of the look of MTV, and we're sort of pushing it. I sort of told him this sort of outlandish, radical idea of what a, a logo could be and what our animation would go. He goes, he goes, "Okay, great, I'm there. I'm with you." That, you know, you say a couple of things and people begin to frame what it is and understand it, and I think that's important in a message. But I usually start with, is there something I can say that's so important that you, w- that that alone will sell it? Like instead of four clicks, it's one click. "Oh, I like that." Uh, or, "I'll send it to you in the mail," or, "I'll deliver it tomorrow." Uh, something that's radically different from what you have today. If you've got something like that, say it. If it's more subtle, you have to convey it with messaging, with sort of image and, and, and concept. And I think that's what you, you sort of wrestle with. And, you know, the creative process often works, the people, I think, that do it best. And, and they, by the way, David Eagleman says this is sort of the way the, the brain works. Sort of my, one of my favorite books. And, and, you know, you sort of look at everything you need to know, you think about it, you fill your head full, and then you forget about it, and you let your subconscious do the work. And then one day when you're in your most meditative state, mine happens to be a 15-minute hot shower in the morning, suddenly I go, "God, I got it. Where did that come from?" And I've got the answer. And your subconscious has been ruminating and working it. And almost everyone I know who does, is in the creative side of the business, their, their decisions come to them like that. And, uh, so I think that's sort of tee it up and be that way, and don't think there's an MBA approach to, and we're gonna rigorously develop the message,

9. 25:54 – 27:45

   Messaging Gone Wrong

   1. BPBob Pittman25:54

      'cause I rarely happens that way.

   2. HSHarry Stebbings25:56

      Can I ask, Bob, have you ever got the messaging wrong? Have you ever embraced a project, done the messaging, and it's just flopped? And, and did you learn anything from that?

   3. BPBob Pittman26:06

      You know, I must have. But mine is, I don't ever think I'm there. I think we're always moving. So whatever was wrong is just a reason to do more. Um, I, I, I talk with my kids about decision-making and s- failures and successes, which they're in their early 20s, which it means, my younger kids, which, you know, that's very important in, in that stage. And I think a failure and a success is exactly the same thing. It's a stepping stone. What we call a failure is one of the stepping stones we make a turn on. We go left or right. And a success is when we goes forward. But all of them are just stepping stones. We're constantly moving. Nothing ever gets there. It's not finished. Uh, and when you think about it's just constantly moving and it's a journey, then you don't keep track of 'em. People say, "Well, you had a great failure." I go, "I don't know. I don't keep track of 'em." I don't keep track of, I don't have a ledger of failures and successes. It's just all a process to try and get to the right place. And by the way, what's the right place today could be the right place tomorrow. When I was at MTV, we used to have the, you know, Neil Armstrong landing on the moon, planting the flag, and we originally were gonna have "one small step for man, one giant leap for mankind," and then Neil Armstrong said we couldn't use his voice, so we never had the voice. And then when the space shuttle came out, we changed it. And we did this, we changed the animation to being the space shuttle taking off and the space shuttle delivering the MTV satellite, and it was great. And then Challenger blew up. Um, so we would go, "Whoops, wrong icon, wrong..." And so, you know, external factors can come into play which change what you're doing. That was

10. 27:45 – 32:02

    Six Flags vs Disney Land

    1. BPBob Pittman27:45

       obviously a radical example.

    2. HSHarry Stebbings27:47

       Can you talk to me about... I, I love that in terms of successes and failures being the same. Uh, (laughs) on that note, um, I spoke to Joe from Human, um, who actually mentioned, you know, obviously you both own 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 have to ask this." So how did you market Six Flags against Disneyland, which was a competitor, for context, how did you market it, and, um, what did that teach you?

    3. BPBob Pittman28:18

       It actually, Disney was not a competitor.

    4. HSHarry Stebbings28:20

       Huh.

    5. BPBob Pittman28:20

       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 within 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 in the 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, 'cause 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." Uh, 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 Disney on Six Flags. And then we also, we managed to sell it as c- what could be the advantage of a day trip versus the, the vacation? What we knew from the research was that dads are stingy bastards, and they're selfish as hell, and they only wanna do what they wanna do. Moms always look to the kids to say, "What do kids wanna do? That's what I wanna do, what the kids wanna do." So we had to make sure... So we began to play a little bit to Dad. So we said, "You know, uh, you can go, come to Six Flags, and you can come for the day."... uh, you can be home in time to feed the dog. Uh, we began to say, and so the dads go, "This is great. I can just take him out to Six Flags for a day, and I don't have to frickin' fly to Orlando for a week." Um, so it began to be a way also to begin to position it as, and there's one thing that really matters in all consumer products, which is convenience. We managed convenience. You don't have to get on a plane and go somewhere. You can just go out for the day and come back. That's more convenient. And convenient always has a huge advantage in any consumer decision.

    6. HSHarry Stebbings30:40

       I'm just trying to, like, think. So I totally get that in terms of your-

    7. BPBob Pittman30:42

       And by the way, and our line was, "Bigger than Disneyland, closer to home." Um, so we played the convenience angle of closer to home, and tied to Disney with the bigger than Disneyland. I mean, we're just looking for an excuse to hang on. By the way, did sort of the same thing at Six- at, at AOL. We were s- uh, so easy to use, no wonder it's number one. Um, so again, we're like size-wise, everybody always likes number one, but if you say "I'm number one," you sound like you're bragging. So you have to have a reason to mention that you're number one. And then easy was the winning strategy. But the, at the time, you were early talking about groupthink. The groupthink was AOL is the internet with training wheels. It's not sophisticated. It's not really the internet. That's not what consumers thought. That's what the tech industry thought. And, uh, the consumers said, "Ooh, this is very complicated. Make it easy." So we did spots with kids saying, "It's so easy, even my dad can do it." People saying, "That's none of that computer mumbo jumbo." And we were all about easy. And we weren't the best. We weren't the whatever, but we were the easiest, and we owned easy. And in my day and Steve Case's day at AOL, half of the traffic of the internet came through AOL in the US. So it was a smashing success. But again, in terms of the marketing, sort of similar thing. You know,

11. 32:02 – 33:49

    Convenience Beats Quality

    1. BPBob Pittman32:02

       play to what you know about the product.

    2. HSHarry Stebbings32:04

       Can I ask, does human psychology change around messaging, do you think? Easy, you mentioned there, stingy bastard dads, cost. Easy and cost today, isn't that, what, 90% of great brands today are built on?

    3. BPBob Pittman32:18

       I'm gonna tell you, I, I've only done consumer services business. I never do B2B. Uh, and I will tell you, the one thing that all, only, uh, 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 gonna 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, uh, 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 the 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 bo- bake everything down to, is more convenient. We were talking to engineers at, at AOL in those days. Sometimes they'd come in and say, "Man, we got a great new feature." And you say, "Is it one less click?" They go, "No, it's one more click." I said, "I don't wanna hear it." If it's not one less click, it's not more convenient. And no c- nothing you can say about quality is gonna justify more, uh,

12. 33:49 – 35:39

    Does convenience mean a great business?

    1. BPBob Pittman33:49

       uh, clicks, less convenience.

    2. HSHarry Stebbings33:51

       The question I have subsequently, does convenience always equal a great business? And I think about like Getir, or you have in the US GoPuff, fantastic convenient service, delivering groceries to your door. Amazing. Respectfully, and you know, there's no arguing 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?

    3. BPBob Pittman34:17

       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, there are even questions about, I mean, Spotify, great product. People love it. Is it nothing more than a retailer that, uh, all the money is 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 have fewer consumers paying more money, and 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, then 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 gonna earn money. And it's gonna get a lot of... Um, in the, in the '90s, it was gonna get a lot of eyeballs. Uh, then it was gonna get a lot of traffic. Then it's gonna 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 one day that will turn into earnings. But if it's not gonna turn into earnings,

13. 35:39 – 42:24

    iHeartMedia’s Business Model

    1. BPBob Pittman35:39

       you don't have a business.

    2. HSHarry Stebbings35:40

       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?

    3. BPBob Pittman35:51

       Oh, the iHeart is revenue minus expenses equals, uh, bottom line, E-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, and 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 a- always looking at, okay, and if I'm going in a new line of business, what's the margin gonna be on that?... we, 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 pri- um, 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 going, "Well, we gotta 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 2,000 to 5,000 to 10,000, but you know when you hit 20,000 you'll make money.

    4. HSHarry Stebbings37:12

       Right.

    5. BPBob Pittman37:12

       Or when you hit 50,000 and you can see a sure path to get there. But it, for us, we, I, I just always demand that things are really profitable. I don't believe in phony stuff. Uh, and there are times in my life in which I'm out of phase with the world because there's great value in businesses that are never gonna make any money, but I've never seen it last. And I think the lasting part is the, is the key.

    6. HSHarry Stebbings37:35

       I, I, I totally get you. Can I ask, when you think about the business that you have today, how do you think about the split between like, you know, original content that you, you own and package yourself and it's pure iHeart, versus that which you buy? And the ones you own and ... Like, how do you think about the different economics between the two? I'm fascinated as a podcast-

    7. BPBob Pittman37:53

       Well, there, there, there, there are several... There are gradations of that. Um, you know, we start on the radio and we really don't have content in terms of shows. We really have... We're keeping people company. We're companionship. And by the way, we're... I would argue we're that in podcasting as well. It's very host-driven, just like radio. And what people are really doing is they got a friend to hang out with. It's like when people say, "Aren't you competing with Spotify?" Because Spotify is not even close to being a competitor. Spotify replaced Apple downloads, which replaced CDs, which replaced cassette tapes. Um, that, that... There's always a symbiosis. I listen to my music collection when I wanna escape the world. I listen to radio when I wanna hear what's going on in the world. By the way, 70, 80% of Spotify, Pandora, et cetera listeners, the main way they discover new music is FM radio. Uh, these are their pals. That's Ryan Seacrest they ride to work with every day. Uh, it's Steve Harvey, it's, uh, Charlamagne Tha God, it's Elvis Duran, it's Bobby Bones. It's these friends they have, Ellen K, that they know and trust. And so that's the business we're in. When we go to podcasting... And so by the way, on the radio, we have all variations of deals. We have some people who make probably union minimum wage, and we have people who make fortunes, uh, on the air. Some of them are guaranteed. Some of them are revenue split. We're sort of look at any deal that economically makes sense and works with them. And when we go to podcasting, we're sort of the same thing. Some of our podcasts we come up with the idea, we produce it in-house, and somebody just voices it. By math and magic, we have no profit participation. They don't pay me anything. Um, and then you've got some that go up, but we refuse to do one where anybody makes so much money there's nothing left for us. And we also say, "What do we contribute to it?" What we contribute is, we can get traffic for podcasts, hit podcasts more than most people can.

    8. HSHarry Stebbings39:45

       Mm-hmm.

    9. BPBob Pittman39:45

       Because our radio s- group alone reaches 90% of Americans every month. Only two companies come close to that and they don't surpass, it's Facebook and Google. Everybody else, the biggest TV network in the US reaches about 35% of Americans. Biggest cable network reaches less than 20%. Spotify, Pandora, Sirius XM reach less than 20% of America. Uh, so we've got this huge asset of this 90% reach. We advertise podcasts on the radio and make them a hit if they can be. I mean, you can't make something not a hit, a hit. But if it's gonna be a hit but four people can't find it, we can solve the problem. We also have so many hit podcasts that we can cross-promote with the other podcasts.

    10. HSHarry Stebbings40:26

        Right.

    11. BPBob Pittman40:26

        Um, we can take... We have 270 million social followers to iHeart and all of our products and brands and people. So we can push it through that as well. When we do the iHeart Music Awards, we get twice, twice the social impressions of the Super Bowl or the Grammys. Uh, people talk, 'cause it's back and forth. That's what people are doing with us. They think it's a friend, they think they're talking with us. So we can make podcasts that... And the other thing we can do is we can monetize. We have the biggest, uh, uh, audio sales force. We have about 1,500 sellers. We have now with Triton and some of the other pieces we have, we have this terrific ad tech platform as well. So we... And by the way, we do about four times as much ad revenue as the next largest audio player, uh, in audio ad revenue. So we're able to plug people in that system and maximize it. So it gives us an advantage, and because we're so big, almost everybody who's got a great idea comes to us first. The ones we don't take are the ones that aren't economic. Um, and so by definition, the other folks are getting, as you go down the list, the less and less economic deals. And I'm just... I think when you're the leader, what you don't do is you don't cave on economics. It's either a business or it's not a business. Can love the idea, can love the people, but if there's no economics, then I go, "That's great, but it's not for us."

    12. HSHarry Stebbings41:48

        Can I ask, do you see an 80/20 distribution in the revenue generated on a podcast basis? The hits pro-

    13. BPBob Pittman41:55

        Meaning what?

    14. HSHarry Stebbings41:55

        Meaning that the 20% of hits produce 80% of the revenues.

    15. BPBob Pittman41:59

        Oh, it's probably more than that. It's probably, you know, given how many podcasts there are today, it's gotta be 1/99. Um, because-

    16. HSHarry Stebbings42:07

        For you, though? Within iHeart.

    17. BPBob Pittman42:09

        Oh, no, not within iHeart. Within iHeart we're hundreds of podcasts, and you know, maybe it is 80/20 or 10/90. But the big ones always make most of them. Uh, but the same is true on radio too. Our biggest stations, our biggest talent make a outsized,

14. 42:24 – 46:55

    Why Podcasting is Not Affected by Macro

    1. BPBob Pittman42:24

       uh, proportion of our, of our overall ad revenue.

    2. HSHarry Stebbings42:27

       ... can I ask what worries you about the podcast industry? I think when I look forward, especially over the next 24 months, partly I'm worried about a macro recession impacting podcast... or sorry, advertiser sensitivity towards marketing budgets. Um, to me as a media company owner, that's n- unnerving. D- how... What are you worried about? And would you share my concern there?

    3. BPBob Pittman42:48

       No, look, and I think podcasting is, of all the businesses we have, is the least affected by the macro-

    4. HSHarry Stebbings42:54

       Huh.

    5. BPBob Pittman42:54

       ... because it has such a fundamental strength. It's growing. It's growing like crazy. Huge engagement on podcasting.

    6. HSHarry Stebbings43:02

       Yeah.

    7. BPBob Pittman43:02

       People are absolutely listening to or hanging on every word. K- k- you know, when people are watching a TV commercial, most of it's, like, second or third screen.

    8. HSHarry Stebbings43:11

       Yeah.

    9. BPBob Pittman43:11

       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 a car and they're driving by themselves, they're listening. Uh, they don't have a second screen going on. And so... A- and podcasting is sort of that on steroids. And so I think the impact podcast has, the, the, uh, idea that the audience is just ballooning, and also it's the desirable audience. You know, podcast... Ta- talk radio tends to be older.

    10. HSHarry Stebbings43:38

        Hm.

    11. BPBob Pittman43:39

        Podcasting tends to be younger.

    12. HSHarry Stebbings43:40

        Yeah.

    13. BPBob Pittman43:41

        Um, so you've got this young, interested, engaged audience that w- you can activate and that will act. So I think podcasting is just... I, I... You know, if you were to say, "What's your list of 10 things to worry about?" podcasting's not on that list.

    14. HSHarry Stebbings43:56

        What is number one?

    15. BPBob Pittman43:58

        The macro. I mean, how much money are people gonna spend on advertising, and, uh, are they gonna pull back? And, and it's... A- a- and by the way, clearly everyone said, you know, what began as a very robust year, we've said on our earnings call has turned out to not be so robust. But it's probably doing better than we expected. And the question you ask yourself is, why is it doing better than we expected? And I think there the reason is that we just had a downturn two years ago. Normally, it's about 10 years between downturns, and the people making the ad decision have forgotten all the lessons from the last one. And the most important lesson to learn is, and you learn it the hard way, is if you cut back during the... uh, uh, during an ad recession, you... when you wanna restart after, it costs you more money than if you kept advertising through it. And, uh, there was a study done during the last... uh, in the pandemic, that I... and, and I may have my numbers wrong but is directionally right, companies that cut back their advertising saw about a 17% drop in, in sales. Companies that advertised through the pandemic saw about a 17 or 18% increase in sales. Huge delta. And I... And I talk to people who say, "God, I wish I'd just kept going. Do you know how expensive it is to try and capture that customer back that I lost because I didn't advertise? Or worse, my competitor advertised and got them, and I've gotta try and fight them and, and win them again." And so the people... Because it was two years ago, the people making the ad decisions today are the same people who made the ad decisions then. So, if... this is fresh in their mind, and I think that's why we're seeing a moderating effect in terms of, of an ad downturn. I could be... By the way, I could be completely wrong. Maybe this thing's gonna fall off a cliff somewhere. But I am, uh... I think that's what's going on, and, um... and, and I'm... and I'm sort of fascinated by it. You know, you talked earlier about human nature.

    16. HSHarry Stebbings45:47

        Hm.

    17. BPBob Pittman45:47

        And I think human nature gov- governs everything. You know, just bet on human nature every time. And human nature is, if you've had a recent painful experience, you will learn something from it. If it was really long ago or it was a lesson in the history books, you didn't learn any lessons.

    18. HSHarry Stebbings46:03

        Can I ask... Uh, t- you mentioned two things which make me feel very insecure. One is, like, an unknown about advertiser willingness to pay. As I said, run a business that relies on it. And number two is, not really seeing it before. You said about the ad recession two years ago. Respectfully, I didn't really feel that. It was short, it was... For me, it was short, it was brief. Didn't feel that '08.

    19. BPBob Pittman46:22

        But podcasting, our podcasting business and our digital, if I looked at numbers, I wouldn't have known there was a recession. Traditional advertising fa-... uh, I think in the month of April of 2020, advertising revenue dropped 40%. I've never seen anything so precipitous in my life. Uh, it was, you know, a terrible year for us overall, and, uh, and so I think podcasting and digital were a little immune from it, uh, then. I think now that they're bigger and they're more sizable, they probably have less immunity they had then, but

15. 46:55 – 48:01

    What are you insecure about?

    1. BPBob Pittman46:55

       I still think they're, they're much better performers through a downturn.

    2. HSHarry Stebbings46:58

       My, 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?

    3. BPBob Pittman47:15

       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, 'cause when we get the next crisis, you'll wish you had this one back." Um, mean-

    4. HSHarry Stebbings47:43

       (laughs)

    5. BPBob Pittman47:43

       ... we'll get through them. It just... You know, it's not getting all worked up isn't gonna 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, 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

16. 48:01 – 49:43

    Relationship to Money

    1. BPBob Pittman48:01

       very important in this stuff is to diagnose it correctly.

    2. HSHarry Stebbings48:04

       Bob, you'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?

    3. BPBob Pittman48:13

       Yeah. Look, I have never in my life... I take that back. I took one job in my life for money. Uh, every other job I've taken 'cause it just sounded like great fun, and it was a grand adventure. And I happened to make, uh, 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's- 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... And it's like when I tell kids about, you know, give them career advice. I go, "Look, you're gonna spend more time at work than you are spending the money you make at work. So do something you love to do and, uh, 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 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 lot of money. It's usually luck. It's usually accidental, um, unless you go into finance. Um, but it's, uh, that's sort of the- the game we play. And by the way, and if you do happen to make a lot of money, then be generous with people who didn't make a lot of money and provide

17. 49:43 – 56:09

    Advice to Parents

    1. BPBob Pittman49:43

       for a lot of other things that help the world.

    2. HSHarry Stebbings49:46

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

    3. BPBob Pittman50:00

       You know what? I- 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 15, 16, to sort of mid to late 20s 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, and let them find it. I- I... 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 say, "Be home by dinner." I would be home... Uh, 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, they... 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 kids and I try to resist this temptation, but I have them on, you know, the FriendFinder. I know where they are at all times. Uh, I text with them constantly every day, running f- you know, uh, running family text. Um, I see them all the time. We fly everywhere together. It's like, how are they gonna build their true independence? How are they gonna be independent from me? Forget money, but independent from me in terms of their own thinking and their own... Who do they want to be? And I think they're... I look, I got three kids, all of them have very different personalities, all of them want to do different things, and what I really hope for them is they do that. And I- I try not to give them advice, uh, because my parents used to tell me, they'd go, "Why don't you get out of that radio business? You're just wasting your time. Just finish college." Because I was going to college and on the radio. And they would go, "Just..." And then I- I moved to the next job, and they'd say, "Why'd you leave them? They were so nice to you, and- and, you know, don't you feel bad about..." And then when I was about 30, my parents go, "God, I sure am glad we didn't listen to us."

    4. HSHarry Stebbings52:26

       (laughs)

    5. BPBob Pittman52:26

       Um, and- and I remember that. It's a great parental lesson, is don't listen to me.

    6. HSHarry Stebbings52:31

       (laughs)

    7. BPBob Pittman52:31

       Uh, listen to yourself. And the only thing I would ask you, have you examined it well? Have you thought it through? And if you've thought it through, whatever decision you come up with, I'm supportive. I'm- I'm- I'm- I'm behind you. I want you to do what you want to do to build you.

    8. HSHarry Stebbings52:45

       If you know your children are making a mistake, do you let them make it anyway? Because it's a lot-

    9. BPBob Pittman52:49

       How do you know it's a mistake? I mean, obviously, if they were 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- 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- if I thought my kill- kids were gonna commit murder or something, I would probably step in.

    10. HSHarry Stebbings53:18

        (laughs)

    11. BPBob Pittman53:18

        But beyond that, I- I think they've got to discover it. And, you know, and they're gonna have problems in life, but I can't solve their problems for them. I can support them, and I can be for- 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 a sounding board because I'm not a sounding board anymore, I'm a controller.

    12. HSHarry Stebbings53:42

        Final one, I promise you, and then we'll do a quick fire. I- I love children and I- 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 rock star CEO and bluntly leading hundreds and thousands of people?

    13. BPBob Pittman54:01

        I- I've- I've- 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, uh, 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 re- 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 of it, I adore them, but it is, uh... And I learn a lot. I learned as much from them as they, they, as they learn from me. And, you know, you asked me, "How do you keep in touch with ideas," etc.? Is my kids op- open the world to me. Ideas they have and interests they have, I would have never had, or ideas would have never occurred to me. And if I listen to them, I go, "I, I got... They gave me something." And often their, their critique of my behavior, their critique of my clothing, their critique of my businesses, there's often a real, something to the idea. Even when they were very young kids.

    14. HSHarry Stebbings55:40

        Final, final one, I promise. What's the hardest part of being a parent?

    15. BPBob Pittman55:44

        Control. Loss of control. Uh, the hardest part of being a parent is you can't will things to happen. Even if you work really, really hard, even if you spend every penny you have, you can't guarantee outcomes. That this is, it's scary. Uh, it's scary to be in that position, and, but at the same time, it's very rewarding.

    16. HSHarry Stebbings56:04

        Bob, I'm gonna move into a quick fire round, otherwise I'm gonna take all of your day. Um, I say a

18. 56:09 – 56:33

    Favorite Memory from MTV

    1. HSHarry Stebbings56:09

       short statement, you give me your immediate thoughts. Does that sound okay?

    2. BPBob Pittman56:12

       Fine, let's go.

    3. HSHarry Stebbings56:13

       So what's your favorite memory from the NT-, MTV journey?

    4. BPBob Pittman56:17

       Probably the best journey or the best memory was when we did a meeting with Steve Ross, who was the CEO of Warner Communications, and Jim Robinson, who was the CEO of American Express, and we had to ask them if we could do the idea and they said yes. So that has to be the

19. 56:33 – 58:09

    Best Concert Ever Attended

    1. BPBob Pittman56:33

       best idea, uh, the best moment, uh, in the, in, in all of MTV.

    2. HSHarry Stebbings56:37

       What's the best concert you've ever been to and why then?

    3. BPBob Pittman56:41

       It, 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 gonna get the iHeartRadio app, was 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 Concorde. 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 and meeting people, it was great. And Paul McCartney, when he played at the iHeartRadio Music Festival, backstage he said, "You know, could I go out front and, and, and watch?" He said, "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.

    4. HSHarry Stebbings57:52

       I love that. Who's the best board member you've sat on a board with and why?

    5. BPBob Pittman57:56

       God, that would be too hard. I couldn't, I couldn't say that because then I would be, uh, shortchanging all of them, because I think almost every person I've sat on a board with, I've learned something from, and, uh, and continue to sort of

20. 58:09 – 58:48

    Bob Pittman’s Legacy

    1. BPBob Pittman58:09

       use lessons I learned from them.

    2. HSHarry Stebbings58:11

       Wow, we sit on very different boards. Um, (laughs) what do you want your legacy to be, Bob?

    3. BPBob Pittman58:16

       I, and I don't believe in legacy. I don't think any legacy, I don't think there is a legacy. Uh, you know, it's funny, I worked for Steve Ross who was, took his father-in-law's two funeral homes, turned it into Time Warner. Couldn't have been a greater entrepreneur. I say to people today, "Steve Ross," and they go, "The guy who owns the Miami Dolphins?" I go, "No, no, not that Steve Ross." Or I go, "Lew Wasserman." They don't know who Lew Wasserman is. They don't know who Bill Paley is, he started CBS. There are no legacies. Uh, unless you put your name on a building and then they think you are the building, um, but have no idea who you are. Um, na- na- legacies don't matter. I mean, you should do what you want to do

21. 58:48 – 59:41

    Casa Dragones Vodka

    1. BPBob Pittman58:48

       and I think anybody who's trying to build something for legacy is kidding themselves.

    2. HSHarry Stebbings58:51

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

    3. BPBob Pittman58:55

       God, there are so many of them. Uh, one is that passion really does matter. Uh, two is that it's possible to let... 'Cause I'm in the business of, I gotta grow fast, every business I'm in. At Casa Dragones, we said, "We're gonna let it grow at whatever pace it grows," 'cause we want it to be authentic and we want it to just roll out in a way that, that we own the cons- 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 businessperson. Uh, but we had the luxury to do it. And, and for me, Casa Dragones was great because my, my thought was, "I ei- it was a win-win. I either have a successful business or have all the tequila I ever need for the rest of

22. 59:41 – 1:00:48

    What consumer habit are you most excited about today?

    1. BPBob Pittman59:41

       my life."

    2. HSHarry Stebbings59:41

       (laughs) I love that. Uh, penultimate one. What consumer habit are you most excited about today?

    3. BPBob Pittman59:48

       You know, that's an interesting one. I think it's, um... I think it's probably, uh, I mean, the consumer habit's the same, which is convenience. I think, uh, the ability of, to reach the consumer quickly and to get a, a retail response from a reaction quickly has been great. But I'm not sure the consumer, uh, behavior has changed much. It expresses itself differently when they're watching this screen than they're watching NBC, but at the heart of it, it's still the same desires.

    4. HSHarry Stebbings1:00:23

       Final one for you, Bob. Five years' time, we're gonna do another show. It's gonna be 2027. Um, where will you be then?

    5. BPBob Pittman1:00:30

       I hope I'll be alive.

    6. HSHarry Stebbings1:00:33

       (laughs) I mean, you are the only person to have given me that response. Bob, I cannot thank you enough. Honestly, I so love doing this show. So thank you so much for joining me.

    7. BPBob Pittman1:00:42

       Thank you, and congratulations on the show and thanks for having me on.

Episode duration: 1:00:49