Bob Pittman

isolated we feel. There are people, you know, you would be identifiable as an extraordinarily successful person, but it's good to know that you are a person to best compliment, I'm going to have thank you. Hello, I'm Mini Driver. Welcome to Many Questions Season two. I've always loved Christ's Questionnaire. It was originally a nineteenth century parlor game where players would ask each other thirty five questions aimed at revealing

the other player's true nature. It's just the scientific method really. In asking different people the same set of questions, you can make observations about which truths appeared to be universal. I love this discipline and it made me wonder what if these questions were just the jumping off point, what greater depths would be revealed if I ask these questions as conversation starters with thought leaders and trailblazers across all

these different disciplines. So I adapted prus questionnaire and I wrote my own seven questions that I personally think a pertinent to a person's story. They are when and where were you happiest? What is the quality you like least about yourself? What relationship, real or fictionalized, defines love for you? What question would you most like answered, What person, place, or experience has shaped you the most? What would be your last meal? And can you tell me something in

your life that's grown out of a personal disaster. And I've gathered a group of really remarkable people, ones that I am honored and humbled to have had the chance to engage with. You may not hear their answers to all seven of these questions. We've whittled it down to which questions felt closest to their experience or the most surprising, or created the most fertile ground to connect. My guest today on many questions is the co founder of MTV and I Heeart Media, where he is the current chairman

Bob Pittman. Bob is a media entrepreneur who feels to me like he's sort of in a league of his own. He's had so many interesting and creative incarnations in a ton of consumer focused industries. Just to give you an idea, Bob has been CEO of a Well Networks, six Flags, Theme Parks, Century to any One real Estate, and a World Time Warner, as well as being CEO of clear Channel, which was what evolved and expanded into the current I

Heeart media. So it's extraordinarily varied. He's one of the most interested people I've ever met, and when you're having a conversation with him, ideas sort of spark off each other, creating this brilliant feeling of forward momentum. And given the scope of his success, it feels like, you know, he could probably sit back and enjoy the extraordinarily diverse fruits

of his labor. But whenever we speak, I always get to see the perspective of a person who is constantly looking forward and is interested in the exploration and unfolding of life, not just business. It feels like a weird time to be asking this first question, but it's always pertinent within peacetime or war, But when and where were

you happiest. I hope that I'm happiest right now. Someone told me when I was a young man, said, you know, most people never live because they're in the past, with their regrets, in the future, with their worries, and they never get right here, right now. And so I try, I, as a human, not always successful, to sort of understand that and try and be happy wherever I am, whatever

I'm doing, and at the moment I'm alive. I've had a lot of happy moments, but I want this to be the happiest moment, and I want to appreciate this moment the most of any moment I could have. Is that part of the contingency of happiness fear is presence and appreciation. It's just a good way to say it, I think so. But it's also I just don't want to think, well that I was happy, then why am I not happy now? I mean to me, happiness is one of those things that I can either choose to

be happy or I can choose to be unhappy. And how do I get myself in a frame where I just look at things and go I'm happy. I'm feeling good. I appreciate it. Yeah, I mean sometimes just saying it. It's tricky with circumstance not lining up with one's expectations. And even though I think that expectation might be the deadliest psychological weapon that we have against ourselves, of expecting reality to conform to what it is we want as opposed to being in the business of what it is,

I agree with you. I think I think one of the worst things we do. And it's gonna sound very weird, and I don't mean it this extreme, and I'm gonna say it this extreme. The worst thing we do is plan. Plans don't come true. Something wonderful can happen. But you know, plan we sort of develop, I think to reduce our fear of the future and our anxiety about the future. But to me, you know, I do I have a plan. Of course, in business, I've got to a game plan

we lay out the year. But it's interesting. Even at work, we have a weekly meeting what we call our strat com and it's the senior leaders of the company, and the goal is to adjust the plan because we know no plan, and even in a week the plan has changed that this plan is not going to come true, and you know, the plans, I hope it's a dream.

It's an you know, as you say, an expectation. But I think sometimes we get ourselves off track by saying I plan something, and I'm unhappy because it didn't come out as planned. Wait a minute, you made the plan. One, you make another plan. Make a plan work about exactly as you want. It bedevils a lot of people and leads people astray from their own enjoyment of this journey we have called life, you know. And at the end of the day, this thing, it ends the same way

no matter what we do. You know, most business they go, you know, the means, it's not important, it's just the end. What are you gonna do? Life, it's the opposite. The ends the same no matter what you do. So it's all about the journey. And I think if we can begin to get an appreciation of that journey, it not only makes it better for us spiritually, mentally, etcetera, but also even in business, it makes it better because which is realistic about there's so many variables you can't control,

stop trying to control. But if we know these things, why do we persist? Then with the expectation of circumstance, either conforming to the idea that we have about what a good version of that is, like when everything does as we've just seen in the last two years, how

things come apart in an instant. Why are we still so attached as humans to this idea of it working out as we envision it, as opposed to going, let me stay incredibly loose and fluid with the vessel that the things I want is going to come to me, and because maybe it's going to be different. I think

the ambiguity and the randomness makes people very anxious. And I'm comfortable, and I think if they can do a plan and say I've got my five year plan, I've got my one year plan, I have my weak plan, I know what I'm gonna do, I know what's coming for me, it goes ah. I've reduced the anxiety, but

I'm not sure that's healthy. But I will tell you some people criticize me because a year so ambiguous, you know, you're not being clear, And I go, I'm trying to be realistic that there's only so much that's knowable in life. I think is more of a random walk than it is a planned experience. I look back, and you know, even talking about business, I look back on my business career and go, gosh, it's been a series of meteors flying out of the sky and hitting me on the head.

It's that kind of randomness that my career has been about. And when I was a young man and I thought I had a plan, that plan fell apart really quickly, and thank goodness, I sort of opened my mind to say, oh, well, maybe I'll do that. Then if that's popping up, and in my personal life as well, is you know, you think, gosh, I know what's going to be great for my kids. I know what my kids should do. I know what school is, you could do. M Wow. It's like that's

not at all what happens. And if I try and force my kids into my plan for them, I'm not doing them a favor and I'm not doing anything for my relationship with them. It's this idea of how do I do active listening and really try and understand the moment and where they are and how I can support them as opposed to try and get them to conform to my plan. Yeah. I think it's actually the secret

of happiness. In fact, that's what I think happiness is is being able to let go of what you think happiness should be and allow it to be what is and fit yourself. There's a great quote I can't remember who's William James or something about our experience is what we attend to j unit. If you look at something, it can only look like this. And my happiness and my everything, my business, my relationship, my everything is hung

on it looking this way. Well, it's It's also one of those saying as reality is what you perceive it to be. And you know this whole discussion now about is does the universe create consciousness or does consciousness create the universe? I mean you get the very fundamental levels of existence and and so you know, when you get down the happiness is. I think the challenge is to be happy with what we have, when we have it, how we have it, and to accept happiness as opposed

to reject happiness. I agree so eleanor Roosevelt. People are as happy as they make up their mind to be. I like that. I always say that, Yeah, that's a very good line. She was cool. I liked her, Yes, she was very cool. In your life. Can you tell me about something that has grown out of a personal disaster. Sure, when I was six years old, I was at a family reunion and Thanksgiving and a little farm outside of Holly Springs, Mississippi, and one of my uncles put me

on a horse to give becoming. All the kids ride, and the horse reared up, threw me off, stepped in my face, and I lost an eye. Valued lucky the horse didn't kill me, So I'm lucky that all I did was lose an eye. But having a artificial eye growing up made me a bit of an outsider. I was the kid with the glass eye, and kids are not young kids especially can be extraordinarily cruel, not accepting. But I think that experience gave me the feeling of what it feels like to be on the outside, what

it feels like to be an outsider. Gave me a little bit of detachment from being on the inside and allowed me to sort of grow into being myself. Probably helped with my empathy and developing that, and I think I probably wouldn't be anywhere near the human being I am without having had that what you would consider to be a you know, a personal disaster. But ultimately, I think if I look back on my life and say, why am I here at this point instead of somewhere else.

I have to attribute a lot of it to what I got out of being the kid with one eye. Wow. Were there any other children that you grew up with who had either a disability or had some other challenge that they were dealing with or were you Were you really isolated in that experience? I was probably the kid with the problem. I mean, I think today we would

probably identify some of the kids as having dyslexia. You know, dyslexia was undiagnosed back then, and you know, you had these kids that were thought to be dumb that we're not all done. They were brilliant, but they had dyslexia, and so the issues like that that I look back on now and gosh, it's very clear what was going on, But at the time it was more physical. Do you have an arm, a leg, ni or something missing? It was isolated, but it was also allowed me to build

who I am, and I certainly wouldn't trade it for anything. Now. Yeah, what person, place, or experience, most of all to do your life my mom and dad. I couldn't have asked for a better childhood. If you know, there's a parental lottery I certainly wanted. And you know, I lived in a house where the words you couldn't say was hate. We don't hate anything, honey, And it really set me

on the course. I'm not saying I've lived up to all those expectations, but I have them at my core, and I I am very grateful for him, and I think that certainly shaped me. I also think I have to say I was shaped by I grew up in Mississippi in the fifties and sixties, which was segregated. When I started school, there were black and white schools. There were colored only bathrooms and white only bathrooms. When I graduated from high school, our school was about fifty fifty white, black.

So everything happened in that period. I was going to school in the Civil rights move But so you know, everybody's influenced I think by whatever, that big thing that overhangs them in their childhood, and that probably for me was the one that hit me the most. And so as a result, I sort of still see that in society and and look forward and notice it. Did you talk about the civil rights movement with your parents, like did they address it with you or was it more experiential.

Oh yeah, and my family, it was a big issue, and everybody there was working on it, at least the people I knew, working and trying to work for change. My dad was a Methodist minister, and in Mississippi they had a Black They have conferences in the Methodist Church, and they had a Black conference and a White conference of the same geographic area. And my dad made it his mission to integrate the two and to combine them,

which meant the Ku Klux planking. After my dad a few times when I was a little young to sort of understand the impact of that when that was going on, and then after they merged that, my dad was in the by that time in the acutive branch of the church and worked on trying on what he called reconciliation, is trying to get people to join together and sort of you know, move past it, and you know, mentors some of the black ministers as they went into some

predominantly white churches and really tried to change the tenor of things. But there are, you know, awful stories to

go with it too. My mother's first cousin, who she was very close to it or like a brother, was the school superintendent Philadelphia, Mississippi, and he had thrown some clansman's kid out of school for harassing a black child, and they came one Friday night, shot up his daughter's bedroom, and my mother's cousin want up committing suicide and just sort of couldn't see a way out, felt torn between

doing the right thing and protecting his family. And they're awful stories like that, and you know, certainly, you know that pales in comparison to the stories that the black community suffered through and the horrors that they dealt with and the degradation. I think for all of us who were there. My mom and I were watching them mpr

s along the Civil rights movement in the nineties. We were in New York and watching it together and my mother turned to me with tears and just go she said, For the life of me, I can't imagine how we let that go on. And I think there's something in that. When you grow up in things a certain way, at what point do you look around and say, hey, this isn't right. And the lesson I've tried to take out of it that goes beyond this is what am I

seeing today that's not right? But I'm just not noticing because it's quote unquote normal, and I think there's probably a lot of them I'm not even seeing right now, but I at least try to look for those. And as we look in the world, is what is happening that's not right? What moment do you notice it? And then when you notice it, what do you do about it? But I think as human beings, we all have that obligation.

And unfortunately, unfortunately I have something in my past that was so horrible and the fact that my mother looking at me at that time, I mean I still remember that and saying, yeah, my mother grew up in and sort of didn't see it, didn't sort of see what was possible and uh, and then did take an action

and they could have people have seen it earlier. Do you look today and do you feel whether it's a similar or maybe it's akin to the ground swell of change that is hopefully happening in some of the systemic ship that exists in our world. Like having seen things really shift in the sixties, do you think that that's playing out now? You know, present world collapse? Yeah, you know what I think we're finding. You know, there are things that are falling apart, and there are things that

are growing and blossoming. My dad used to talk about and I talked about somebody did something terrible. He says, well, I believe in the redemptive power of love, and he was talking about forgiveness, that we should all have an open heart to forgive, because if somebody says something wrong to someone, hey, here's what's wrong with that, and give them the chance to say, wow, you're right, I'm sorry,

and sorry means something. Apologies do mean something. I mean, I love the old things, slow to blame, quick to forgive. I think there's always a room for them, and always room for love and our hearts to accept that people. Basically, I think most people want to do good. I think

most people want to do the right thing. There was time at which, you know, and I'm sure we've all had it, which I've been in a meeting, someone says something and it's off, and after the meeting, I'll say, you know, I know you maybe didn't realize it, but you said this, And almost always they're horrified. They're mortified. They go, I didn't even realize that. I didn't see it that way. I feel so badly, and so I

think that's actually most people's feelings. And at work, I try and push upon our people that don't be afraid of the mistake because we learned from it. I forget who it was said I either win or I learned something. And I preached to my kids that, you know, a failure and success are the same thing. They're just a stepping stone. They're not the end. And what we call the failures, I step on that stone and I go

another direction on what we call it success. I step on that stone and keep going in the same direction. But those aren't the ends. They're just merely a step on the journey. And I think if we can wrap our heads around the fact that we're constantly moving, we're constantly growing, we're constantly changing, then it allows us to be a little more gracious with our forgiveness and our understanding. Being a preacher's kid, always remember vengeance as mind say

of the Lord, Wait, what does that mean? Vengeance's mind? That God was like, only I can have vengeance. Don't have vengeance. That that's not for humans to have, that's not for you people. Yeah, yeah, God, I wish he'd I wish you'd given us a proper list. This is really not your cast out because he ate from the tree of knowledge. I want a really specific list. It's why I do this podcast because I like very specific questions, so I can have very specific answers and try and

understand the meaning of everything. What relationship, real or fictionalized, defines love for you? I think it has to be a mother child relationship, which is one of the most beautiful, pure relationships I've ever seen. I mean, I'd love to say it's dad gile because I love my kids and I hope they love me as much as I love them.

But I actually think there's something about the mother and child childbirth with a child, I mean, that experience that just sort of indescribable bond I think is pretty polperful. It's sort of hard to imagine love could be any deeper and impurer than that. Was that observable because you were there at the birth of your children, or because you've observed their relationship with their mother. I think both, and also the relationship with my mother and watching other

people with their mother. I have a close friend who was the victim of just a awful abuse as a child,

and I said, how do you cope with it? And she said, I think about that abuser as once was just a baby and their mother loved that person, and I try and take it back to love as opposed to what they became, and I go, wow, that is like so advanced, because I'm not sure I could ever bring myself to do that, but I do think this idea, and it was one of the ones that sort of keep me in and sort of focused me again on

that mother child old love. It being so pure that it's what we sort of all aspire to in some form or another. That's so interesting. I mean, I think you're right, like there is it's unadulterated, you know. It is the version of unconditional. Yea completely unconditional, and it may turn into something that gets distorted over time, but at that moment, it's this sort of truly unconditional love.

I hope what we all can achieve and strive for. Yeah, the sure looks like some people don't want to strive for that, or they don't know the power of it, you know, you see, unconditionally except for and no, no, there's not no except for Look, it's easier for me to talk about it because I had that for my mother and I know people that didn't have it from their parents. It's a much more difficult experience for them. You know, it's the regret of parenting issues. But if

you've got it, you can always call upon it. And it's that sense that it's always there omnipresent gives you this security to go through your life with sort of a base. And I think people who have not been even that gift have a lot of work they've got to do that. Fortunately I don't have to do. So I'm not judgmental about the issues they deal with because I understand that they're going through something that I can't

totally relate to. It's funny, I think about a lot, maybe since Mom died, the love for a mother and the love for my child. It's like, what's it cooled? Is it a double helix? The shape of the DNA keeps going, Yeah, So what quality do you like? Least about yourself? Lack of patience? I run things too quickly. I want to move too quickly through things. I don't sometimes take the time. We're just talking about active listening, etcetera.

I keep wanting to jump to a conclusion and jump to an action, and jump to the next step and not sort of savor at the moment, take the time to sort of let it all unfold and blossom. So patience is not a virtue of mine, but I work hard at trying to compensate. When you're impatient, what are you impatient to get to? That's exactly the point. Nothing. There's no reason to have that impatience. I can take

a beat, I can listen a little longer. I think a beat between the last thing someone says and what I say. I can think about it a second. I tend to move too quickly to action, and again I try and modulate it. I have some degree of self awareness that may have self control, and I do work on that. Going back to the point about happiness, it

does interfere with my happiness and others happiness. If they feel like I'm not listening to them enough and I have taken the time to truly consider everything they have, it sounds like I'm moving too quickly to a conclusion. Uh, it's harder for them to be happy, and it's harder for me to be happy. Do you think there's anything other than catching oneself in the moment of doing these things that we would like to change? About ourselves that when you're doing it and having an awareness of it

is how it evolves. I can have some self awareness and began to control it to a certain degree. I stopped working in two thousand and two completely, and I've been working full time since I was fifteen years old, probably never taken more than a two week vacation ever in that period of time, and my vacation was like long weekends or something, and always thinking about work. And when I stopped working, it took me about two or

three months to come off the adrenaline addiction. And then I discovered that it's actually possible to be bored, and I began to enjoy boredom and go, Wow, I'm bored right now. I'm just gonna wallow in this boredom. And I think that my patients got a lot better because I just sort of wallowed in the moment and accepted whatever it was as interesting. Boredom was suddenly interesting. Wow, this is a great sensation boredom, and get excited about whatever life threw me at that moment and not feel

like I had to quickly do something. You know, when I first stopped working, if I went to the beach, if I was lying on the beach. I go, what am I gonna do now? What I was lying on the beach, and then at a certain point I began to go, Wow, this is great. I'm just lying here. And it was a real transformation and gave me an insight that I can still use even though I've gone back to my adrenaline addiction and I did go back to work, and my impatience is still a problem for me.

I can call upon this time I had to go boredom is good, and I should look for a little more of that and a little bit of that ah time where I don't have to process anything, I don't have to have an opinion. I can just let life drift over me a little bit. And that's sort of the opposite of impatience. Yeah, it's interesting. We spent a lot of time being bored when we were kids, because I was you know, obviously they want cell phones and computers, and my son sometimes I say, put the phone down

and stare out the window and see what happens. And he does and he's like, it's so weird. You kind of go into a trance. And I was like, yeah, that was like my whole childhood. Well, you know, in my childhood, my parents had turn off that TV, turn off the radio. Oh, which is funny because you the went and put the radio on television with MTV. So there's always something that kids would occupy themselves, whether people

will rather than just enjoy ourselves and our space. And it's hard sometimes to feel comfortable with yourself in that space because you really have to confront your space and you have to live with you. There's nothing to distract you, there's nothing to keep you busy, there's nothing to drive your ambition. But I think it's wildly helpful. And when I can have those moments to recharge my batteries, I'm so much better at all this other stuff that I

think is better if I keep working. But I discover again and again it's actually better when I recharge myself a little bit and then come back to the task. And I find that if I'm working on a problem or trying to come up with a creative solution, even looking for a line in an advertising campaign, that the best thing I can do is sort of okay, low myself.

I'll understand and then forget about it. And at that moment where I'm in my most zen moment down in my alpha state, which for me is about a fifteen minute hot shower in the morning where I just like zone out. Suddenly the answer just pop in my head. And I have run out of the shower so many times with a pen and a wet piece of paper writing a speech, writing down something because it comes to me. And I think there's a great lesson in that, which is it's not going to come when you try too hard.

It's gonna come in your most relaxed moment, in which you're just letting things drift over you. That's an enormous amount of trust that is required to let go of, I think, being into control. It's interesting when I was a young man, I would give speeches, and I would write the speeches and slavishly read them, and at a certain point I realized I could do a much better talk if I just got up and talked. So I would have maybe three points scribbled down, a little note

and get up and start talking. The scary thing when you do that is you have to go on to your point about trust trust yourself, because suddenly I'm standing in front of all these people and I've really thought of nothing except a couple of things I want to talk about, and I just go with the flow. And I find when I do that, it's much better. It's much more of what I really want to say. I think people enjoy it more. It's more relevant to them.

And even sometimes we're doing a you know, I'm doing a speech for the company or something, and I've got to do that inspirational closing. I don't have any idea what I'm going to say, and I just step out there and start talking. And that's one of the ones where you really have to just trust that it will come to you. But boys, it's scary at that moment. Now I've been doing it long enough that I probably

not scared enough. But it's just to sort of relax, go out there and whatever is in your mind, your heart, let it start coming out, and just trust that it will be the right thing. As opposed to them, I said the wrong word, I stumbled on a word, or I said no one cares about any of that. I think here about your message, well, I wholeheartedly agree, I really do. I think that so much is about letting go untrusting, and we don't do that. We don't because

I think I think it goes back to planning. We think you have to have a plan, you have to have a script, but you have to have a preordained idea of what you're doing, when, like you said, it's a random walk life. It's not prescribed. And yet I honestly think it's fair of death. I really do. I really think that the distraction and the planning and this idea of control is because we know, like you said,

where this ends, this is where it's going. But if we actually lived with that idea, there is a clock ticking. Don't waste a single moment. What worrying about the moment not looking like you think it should? I think it is mortality. I agree with you. I think that is a big consideration for people, and it drives us more than we recognize. I didn't realize until my mom died that it was a huge consideration. It's actually incredible. It's actually in an extraordinary moment because you can use it

like rocket fuel to just be that. I'm no longer available to judge whether this looks like how it should. In fact, the words should I've said this before and this podcast. My mother used to say, the words should should be buried in a big hole in the backyard. Your mother was very enlightened. I think the loss of our parents does something to us. All. My mom died in her sleep, and so I didn't get a chance

to be with her as she died. My dad was dying and died slowly, and my brother and I sat with him the day he died and held his hand as he died in this weird way. It was such a beautiful experience to be able to share that moment with him. Because I think we're so afraid of it, we want to avoid it. But I went on the journey with my dad. I'm still here, but it was you know, it's a lot of talking to my dad. It's okay, you know you can, you can let go.

We love you, and sort of all the reasons why he had a wonderful life and why we love him so much. And with my mother, I sort of missed that moment, although I had a great relationship with her and felt very close to her, and even after her death that's I still feel her presence. But I think you're exactly right. It were sort of fearful that we

want to run it away. I had a house of Mexico for about twenty years and I got to know Day of the Dead there, which is turned out to be one of my favorite holidays because it is so contrary to what we do in America. And in this little town, Sam Miguel, day and day there was a ex pats cemetery and there was a cemetery for the locals. And on Day of the Day, it's so sad because there's no activity in the cemetery for the ex pats.

It's dark, and in the other they're celebrating the life of those people and they have their food out, their favorite songs. They're acting as if they're still alive and still a part of them. And I just thought such a beautiful experience to accept death and to sort of put it into your life, as opposed to, as you point out, spend your whole life trying to avoid the existence of it. Bob is not only a wonderful podcast guest,

but he is also a wonderful podcast host. You can listen to his own podcast, Math and Magic wherever you listen to your podcasts, and while you're at it, check out the i Heart Radio app for radio stations, music, and more podcasts. Many Questions is hosted and written by Me Mini Driver, Supervising producer Aaron Kaufman, Producer Morgan Lavoy, Research assistant Marissa Brown. Original music Sorry Baby by Minni Driver, Additional music by Aaron Kaufman. Executive produced by me Mini Driver.

Special thanks to Jim Nikolay, Will Pearson, Addison No Day, Lisa Castella and a Nick Oppenheim at w kPr, de La Pescador, Kate Driver and Jason Weinberg, and for constantly solicited tech support, Henry Driver,