What is the art of what you do?
"The art of what I do is really about listening to people - and out of that comes sometimes new ideas, sometimes a regurgitation of old ideas, and sometimes an adaptation of old ideas. When I was a young guy someone told me that being a radio programmer - which I started out as a young kid, and it’s ironic I’m back here again - is the marriage of math and magic. The math tells you who the people are you’re trying to reach - what they’re interested in and how they behave. But it’s magic to capture them. And the magic is that spontaneous idea, the look, the aesthetic, the attitude that captures them to say 'I want to join that, I want to be a part of it.' "
So is magic an epiphany?
"I think magic is something that suits a situation but was not derived from the situation. There is no structure to create magic. I think in the creative process you load your head up with what you're trying to do and then you forget about it. And one day you have a vision. One day it pops into your head. Whether it’s writing a line for a commercial or dreaming up an art piece - designing a new house, a fashion design, a speech - I’ve written so many speeches running out of a shower with my hand dripping wet, trying to keep the paper from getting soaked, just to begin to write all the stuff that flows out of my brain. There's a wonderful book: Incognito - The Secret Lives of the Brain. It talks about how you're really two people in there. One is this conscious person and there's this other thing going on all the time that just sends the consciousness some cues once in a while. But it 's calculating and looking and thinking about everything all the time. If you believe all the brain studies — and this book was just full of them — life is about tapping into the subconscious to find out as they say, 'who else is in here with me? Who else is thinking in here with me - calculating and devising and only giving me stuff occasionally?' "
What is the math?
"The math is the research - the math is: who are these people? At iHeart Media we have 250,000,000 radio listeners a month. Who are those 250,000,000 people? What segments are they in? What are they thinking, what are they feeling? What do they like, what do they respond to? These things tell me who they are, but that’s not going to make the product that they like. Now we have to have the magic. So ok, for those people, what would be the magic? My son was just with us at Burning Man. Went out a week early and he was one of the temple builders with David Best - who’s a fabulous artist that does the temples every year and burns them. And it was wonderful for my son to experience that - seeing it built, you see what people are bringing to it. People with problems in their lives, joy in their lives, tragedies in their lives - it’s a healing experience, it’s an expression, it’s something different for everybody. And the temple was the embodiment of all those feelings and emotions. I think that ultimately human beings are wired to create. We can call it art, we can call it business - whatever it is. The purpose of humans is to create. Whether it’s to create another human being, or to create a sculpture or to create a business or a temple — it’s about creation."
You're at the head of an empire. Do you find that you’re still able to mix in the magic or do you spend most of your time dealing with the math?
"I hope I embody both. I’m sort of a math mind who has always thought somewhat unconventionally. When I was a young guy I had much more free-flowing ideas because I didn’t know enough. Today I’m formed by the body of work I’ve done in the past so it’s kind of hard to escape that. I’m one of those people that when I look at anything I see proportions, I see math, I see relationships. So when people throw numbers up I say 'what does that mean?' I’m looking for patterns, I’m looking for correlations. As I talk, I’m often looking at pieces of a puzzle, but I don’t know the whole picture yet. What I’m trying to figure out — I’ve got all these pieces, what’s the whole picture? We’re looking for those aha moments - that to me the world is about when you’re doing anything - it’s about two things - epiphanies and insights. Epiphanies come to you in the middle of god-knows-where -- you wake up in the middle of the night and go 'I have it' or you’re taking a hot shower or you’re meditating— or you're on the treadmill and it pops in your head — 'I’ve got it.' Those are the epiphanies. The insights are 'oh, now I see how it works...'
So my role is - 'ok we know this, now what are we going to do about it?' Do I throw around ideas? - absolutely. But at my age I’m probably a better editor than I am a creator -- although occasionally I have an idea that survives. Often I can take ideas and move them and stretch them and make them fit what we have to do."
What are your thoughts on the broad generalization that artists make terrible business people?
"Depends on what you define art as and what you define business as. Why on earth would someone who’s creating for the sake of creating even be interested in business? It’s such a different idea."
To pay rent.
"Well then they’re in it for something other than a pure expression of themselves. The thinking becomes 'I want to express myself and have someone value it enough to pay me money for it.' I once went to see this lady I think her name was Miss Mohamed, who as a folk artist from Belzoni Mississippi. She had been in a Smithsonian Exhibit on folk art. I went to visit her, she was an older lady, and she ran the general store in town. I talked to her about selling her art and she said 'sell it? I sell boots at my store - that’s what I sell, I make my art.” She had no intent to sell her art, though there are plenty of people who would pay for it. So there are a lot of blurry lines around art and commerce and it depends on what you want out of life. If your goal is free self-expression then you can’t put money into the calculus. If you want money then you have to think that what you’re doing is a very deliberate act of commerce."
So is it really art if you’re thinking about money?
"I think again, everyone has their own definition. There’s no way or purpose to get everyone to agree on definitions of things. What’s the saying ‘art is what you perceive it to be?' Whatever is art to you is art. Andy Warhol sold off all his cookie jars and suddenly everyone rushed out to buy cookie jars."
What role does art play in your personal life?
"I have always loved looking at things, and building my environment. Art does that. It also reminds you of who people are. I have two paintings by the same artist. One done by him in the 1920’s on one wall and one done by him in the 1950’s - 25 years later - on the other wall. The one done by the young man was very meticulous, very studied. The old man painting is very freehand and flowy and you can feel it and see it."
You’re in a unique position to be around a lot of successful artists. What do you in them that propels them forward?
"I think some of the best artists in the world are people who do not have the control button - the button that keeps us all as functioning members of society saying 'well I shouldn’t do that.’ It makes us inhibited. As a result many of them are self-destructive because they don’t have that button, but I think the button lets things free-flow out of them onto canvas, songs, fashion - but they are sometimes messes as people. Moving from the rational to the instinctual and this free-flow is often what makes a great artist. Some of the greatest performers and artists I know are pretty self-destructive, I wouldn’t want to be them. But I sure like the output of what they do."
If you could go back and see yourself as an 11 year old what advice would you give yourself?
"Well, I just sent my 17 year-old son away for his senior year and the one piece of advice I gave him was: 'Whatever you do, be intentional. If you’re going to do something, intend to do it. Don’t get dragged along and do something that somebody else wants to do and you’re just along and you didn’t intend to do it. Don’t say something that you didn’t intend to say. If you're swearing make sure that you really intend to say those swear words. They didn’t just come garbling out of your mouth. If you’re going to miss a test, intend to miss it - don’t just accidentally miss it. Whatever you’re going to do, do it with intention.' If you do it with intention, you own it, it’s you and you have the responsibility and the honor of having done it.
Its hard advice to follow. The one thing I drive to is to be intentional because if we’re not careful, our whole life will be gone and we’ll realize that it just sort of happened - we weren’t intentional about anything. You'd end up saying 'I wound up with a girlfriend -- I just sort of fell into it'- or 'I’m in this job 20 years because I never got around to finding something that I really wanted to do - it was just something I did.' Life will pass us by. The only resource we have that is truly limited is time."
What are you passionate about?
"Life, experiences. One of the bad things about getting older is you lose your passions. But it's replaced by an incredible tolerance and acceptance and a lot more even keel about everything, along with a broader view of the world. When you're 20 years old there are two types of music; good music and bad music. Everything you don't like is bad music. When you get to be 60 you say: 'This is sort of interesting, and that's interesting too.' You become more tolerant of things that are different and of different view points. I'm coming to the realization that this is the gift of aging. I'm a lot closer to being dead, but we’re all close to being dead at every second. It's sort of like making plans - we have a construct of the future to reduce our anxiety but the chances of the plans coming true are about the same as a random walk. How on earth can you plan on anything? I think about my career - how could I have planned to be at MTV? — there was no cable tv. How could I plan to be at AOL? - there was no internet."
Did that just happen?
"Things fall -- like a meteor. I think life is a random walk. It’s hard to accept the fact that we have no control and all we really have is right now. The next thing we do is jumping off a cliff. Closing our eyes, jumping off the cliff and hoping for the best. We put a construct of a plan on top of it. But all the plan does is reduce anxiety. I’d rather not reduce the anxiety and just know that I have no clue. We’ll see. I’ll have an intention about what I would like. I know what I would like the outcome to be. I know my moral compass. But we’ll see. And I’m prepared. I have a friend - he’s a young guy. I don’t know how he’s so astute on this. He said to me 'the bad experience is still great experience. It’s a worthy experience.' He said: 'I value those as much as I do my good experiences.' If you get your mind around that then when you’re in that bad experience you’ll be able to deal with it a whole lot better. Somewhere along the way I learned that I had a plan for myself, I was going to do something the plan got derailed and I was so disappointed. A year or so later I’d say: Oh my god, I’m so glad that didn’t happen, I wouldn’t be here. “ So I think when something bad happens you can get yourself in the mindset to say “well I wonder what BETTER is going to happen” than what I had expected or wanted. And I’m going to let it come to me. And you see so many people just butt their head against the wall trying to MAKE that thing come true.
You can’t always tell what those moments are. When I went to AOL I was at Century 21 Real Estate and I had this very smart business person call and say, I know why they want you, I don’t know why you’d want them. Why are you leaving Century 21 for AOL? But it turned out to be big. And often you can’t see it at the beginning - you can only see it in hindsight. "
Bob is an American businessman. Currently Chairman and CEO of iHeartMedia, Inc. (formerly Clear Channel), a global media and entertainment company, Pittman led the team that created MTV (eventually becoming its President). Pittman joined Clear Channel in November 2010 as an investor and the company’s Chairman of Media and Entertainment Platforms, was named CEO ofiHeartMedia (formerly known as Clear Channel Communications) in 2012 and was named Chairman in 2013. Clear Channel became iHeartMedia, Inc. in September 2014. Pittman has also been the CEO of MTV Networks, AOL, Six Flags Theme Parks, Quantum Media, Century 21 Real Estate and Time Warner Enterprises, and COO of America Online, Inc. and AOL Time Warner.
Pittman has also been a radio and TV programmer, marketer, investor and media entrepreneur who has had multiple careers in a number of consumer-focused industries. According to Sean Parker, Pittman is the only media mogul who’s genuinely an entrepreneur. In giving him its first-ever 'Media Visionary" award, advertising publication Adweek  referred to him as a "jack of all media" and former MTV executive Tom Freston referred to him as "the wonder boy of branding."