Invest Like the Best with Patrick O'Shaughnessy - Bob Pittman - Lessons from Building Media Empires – [Founder’s Field Guide, EP.12]

Episode Date: December 17, 2020

My guest today, Bob Pittman, has had one of the most interesting careers I’ve ever come across. Today, he’s the CEO of iHeartMedia, the country’s largest operator of radio stations and podcasts. Bob also created MTV, was the CEO of Six Flags and 21 Century Real Estate, and the COO of AOL and AOL Time Warner. He’s the Dos Equis man of business. In our conversation we discuss why convenience is king for consumers, his lessons from building MTV into one of the most iconic brands and media properties in the world, the rise of user-generated content platforms, and the future of media. We also discuss what qualities make for a great host, a topic that given my current position, is always fascinating. Please enjoy my great conversation with Bob Pittman.   DocSend is a document sharing platform that enables companies to share business-critical documents with ease and get real-time actionable analytics. With DocSend’s security and control, startup founders, investors, business development executives, and financial professionals can drive business outcomes that have a lasting impact. Start for free at www.docsend.com.   This episode of Founder’s Field Guide is also brought to you by NetSuite. Netsuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly. Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at https://www.netsuite.com/invest.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:56) – (First question) – His personal interest that unites all of his business ventures (4:09) – His philosophy on the consumer (7:43) – Biggest quality mistakes business leaders make (9:31) – Respecting convenience in consumer preferences (11:08) – Founding insight to build MTV             (16:23) – Fred Seibert on Math in Magic Podcast (17:14) – How the music video concept evolved with MTV (22:37) – Role of hosts vs guests in the media world (25:13) – Quality that increases the odds a host works (30:15) – Why everyone needs to know how to tell a good story (31:53) – Peak of his time at MTV (37:51) – Lessons for new media from his experience (43:46 – The largest uncertainty in the media landscape amid the rise of user generated content platforms (49:27) – Where he finds inspiration outside of business             (55:40) – What Other People Say May Change What You See (56:16) – Different ownership structures and how they changed his behavior (59:09) – Finding and respecting your audience (1:02:11) – Lessons from time at Six Flags (1:02:24) – Most interesting thing about podcasting (102:52) – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag  

This episode of Founders Field Guide is brought to you by Doxend. Doxend is the standard for founders to share their pitch decks with VCs when they are raising capital. With Doxend, you control who has access to your fundraising materials and you always know what's happening with your pitch deck after you send it. Did VCs actually open it? What slides did they spend the most time on? Did they share it with others? Founders are using Doxend to fundraise, but also to share investor updates with their board or

to send their sales pitches to prospects for better security and engagement. I personally know a number of successful startups that have been able to raise using Doxent. Check out Doxend.com to start your free trial. If you're curious to hear more about Docsend, stay tuned at the end of this episode where I talk to Doxen CEO, Ross Hedleston. This episode of Founders Field Guide is also brought to you by NetSuite. If you're an entrepreneur, you know how hard running a business is. Don't let QuickBooks and spreadsheets slow you down anymore. NetSuite makes running a business simpler and faster. Whether it's centralizing your multiple payment systems, ditching old spreadsheets and outdated software, only NetSuite gives you

the visibility and control over your financials, HR, inventory, e-commerce, and more in one place instantly. Whether you're doing a million of revenue or hundreds of millions of revenue, join the 22,000 other companies using NetSuite right now to save time and money for your business. Schedule your free product tour right now at NetSuite.com forward slash invest. That's netsuite.com forward slash invest. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Founders Field Guide. Founders Field Guide is a series of conversations with founders, CEOs, and operators building great businesses. I believe we are all builders in our own way and this series is dedicated to stories and lessons from builders of all types. You can find more episodes at investorfield guide.com.

Patrick O'Shaughnessy is the CEO of O'Shaunacy Asset Management. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'Shaun's asset management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of O'Shaunosie asset management may maintain positions and the securities discussed in this podcast. My guest today, Bob Pittman, has one of the most interesting careers I've ever come across.

Today, he's the CEO of IHeart Media, the country's largest operator of radio stations and podcasts. Bob also created MTV and was the CEO. of six flags and 21st century real estate and the C.O.O. of AOL and AOL Time Warner, among many other things. He's basically the Dosecchi's man of business. In our conversation, we discuss why convenience is king for consumers, his lessons from building MTV into one of the most iconic brands and media properties in the world, and the rise of user-generated content platforms and the future of media. We also discuss what qualities make for a great host, a topic that

given my current position is always fascinating. Please enjoy my great conversation with Bob So Bob, it's hard to know where to begin this conversation. You're sort of like the Dosecky's man of business, having run MTV, Six Flags, now IHeart Media, several other recognizable big businesses across different industries. I guess my opening question would just be for you, what unites all of these different things that you've done in terms of your personal motivation and interest? I think when I was a young guy, I described myself as a sociologist. And I think back, I think that it's probably a pretty good description, that I'm only in businesses that are dependent upon the consumer.

I really don't understand B2B, but I do understand the consumer, and whether I'm trying to sell that consumer a house or trying to get them to buy an online service called AOL or getting them to tune in to a new thing called MTV, the consumer behavior is exactly the same. It just expresses itself in different venues. So I've found that moving from industry to industry,

but taking that knowledge of the consumer, not a bunch of formulas for an industry, have served me well, especially in emerging industries where there are no rules and therefore it forces you or maybe allows you to go back to what you should do, which is look at the consumer and build your business from the consumer up as opposed to trying to cram something on the consumer. Let's explore your philosophy of the consumer. And maybe we can go back to the, I'll call it like early insights or aha moments that you might have had about what makes people tick

and therefore what makes good businesses because it recognizes what makes people tick. So what is your philosophy of the consumer generally speaking? My philosophy of the consumer is that the consumer humans are in an eternal quest for convenience. Save me time, make my life easier. And if you can build a product that demonstrably saves them time, gives them more convenience, they'll take your product, and they'll take it over quality. I mean, look at the microwave oven. It doesn't cook nearly as well as the conventional oven.

It's a big hit. Look how few people now have a wired phone line. my mobile phone isn't nearly as good. I traded quality for convenience and people do it every time that make a transaction. It's a little small group of people, maybe about 10% of the people are sort officionados in any segment that don't behave that way. But the vast majority of people behave that way. When I was at Six Flags, our thesis was we were not a destination theme park. We were regional theme parks within a days drive of about 80% of America. So our pitch was, instead of spending all that time going to Disney,

why don't you come out for the day to six flags, save you time? At AOL, it was easy. So easy to use, no wonder, it's number one. When I got to AOL, people said, oh, AOL, don't take it seriously. It's like the Internet with training wheels. And I began to do a little research and said, I will bet it's all about convenience. And it turns out it was. And we described, people said, what is AOL?

I said it's convenience in a box. We're taking stuff you already do, you already like to do, and we're making it easier by using the Internet. And that was the thesis. If you go back to the cable networks, MTV, CNN, ESPN, those cable networks, there were specialized networks, we called them narrowcasting. They were really a precursor to on-demand because what we knew was the consumer didn't want to watch the news when the networks, ABC, NBC, CBS decided to schedule it.

They didn't want to watch cartoons only on Saturday morning. They didn't want to see music on Friday night. They wanted to pick and choose when they wanted to watch it. So the thesis there was we'll have these 24 hour a day networks and you can pick and choose when you want to get your news, when you want to get your music, when you want to get your kids programming, when you want to get whatever. And you put together your own array of programming. Now, they were still linear. The show was in progress when you got on. But it was a step forward in convenience. Probably by the late 80s, the majority of people, majority of viewing was on a cable network, not on the broadcast networks anymore. So I think it's, time after time, it's that. And I think even with I heart, when I got here, we had, we've still reached even back then, 91% of Americans with our broadcast radio stations, but you had to listen to AM or FM. So we went on a quest, okay, our strategy is to be where our listeners are with the products and services they expect for us, convenience. And we're now in 250 devices. Now,

it's 85% AM FM, but it's now 15% other devices. And again, it's people want to get what they want where they want it, they don't want to have to move to where you want to give it to them. But you see it in all these startups, too. Any product that's going after the consumer, I think the key is just look at and say, is it make my life easier or to make it harder? And when I was at AOL, you'd have these eternal debates with the engineers who would say, I got some, it's really great. I said, is it one less click? Well, it's one more click, but it's worth it. No, it's not worth it. It's like quality versus ease. Where do you think people make the biggest mistakes on the quality side? So I doubt anyone would really

fight you, and especially with the caveat of 10% of people being, we'll call them the officinados. I like that term, the select minority few. What are the biggest quality mistakes that you see business leaders make over and over again? Well, look, I think you have to treat the consumer with great respect. So you can intentionally give them inferior product or try and sell it as something more than it is. But I think that in the hierarchy of things, You have to realize that convenience is king and you've got to make it easy. And I can't tell you how many people I've seen build products that either they put some hurdles in there because it makes their job easier to build the product or they service it poorly. So if I've got a problem, now here come the hurdles.

And every business I've been in that's business that's been in existence, I can close my eyes when I walk in there and say, your number one problem is you built your company on operational ease. that every company, and by the way, a group of humans put together, if you leave them for 10 minutes, they're going to start making their job easy, not the ease for their consumer. And often we say, well, that's a lot of work. We've got to work all weekend. I go, yeah, yeah, I guess we've got to work all weekend. That if you sign up to really super serve the consumer and make life easy for them, you have to be prepared to, not have a platitude, but put it there. And that means sometimes you're making operationally much more difficult. Even in our place, we'll say, gee, you know, we can get around.

We can write a piece of software that'll do that, but it's going to take us six months. And right now it'd be a whole lot of people. And I go, well, I guess it's going to have to be a whole lot of people. Because if you're, again, signing up for it, you truly do have to sign up for it. If we were to click one level deeper on convenience, what are some of the second order effects or lessons that you've learned about respecting convenience in consumer preferences? Well, you know, I don't know if there are any second level. It's just, I think it's that prism that I try and put on almost everything, that the consumer is brand loyal, but only to a point.

And if you want to break your brand loyalty, be careful if your competitor has found out how to make there's a whole lot easier, because before you know it, that thing you take for granted is gone. because you didn't respect the consumer and didn't put them first. It sounds so trite because everyone says, we put the consumers first. But I actually think if you analyze most people's actions, they don't. And I do see it in a lot of the, before I came to I heart, I did about eight or nine years of mainly investing.

I thought I was retired. And the flaw I saw in most people's work is that they really were not serving the consumer. They just had an argument that they were serving the consumer or rationalization. that we're serving the consumer. And I just think that super serving almost always wins. I mean, if you think about restaurants you go to, if someone gives you fantastic service, you'll keep going back to that restaurant,

even if the food's not the best. If you go to a clothing store and that person's just all over you and just takes care of everything, hey, I'll bring it down to your house. Come on, your loyalty goes to that, not the best quality. I've never seen it any other way, except again, and I say,

there's an officiato product that you can do, but just going to be small. Those are niche products. I'd love to tell a couple business vignettes. I think it's interesting that in your many examples, so far MTV hasn't come up. And I'd love to just tell that story briefly. Talk us through the founding insight of MTV, what motivated you to start and build that business. And what, as you think back on it many years later, do you remember most in terms of lessons learned? It's funny. I have been in radio, and I've been this so weirdly.

I had this really great career in radio at a young age. I started as a disjockey at age 15, and I left Mississippi at 18 to go to more radio stations. And when I was 19, I talked somebody and letting me program a station at Pittsburgh. They hired me as the midday personality, and then they let me program it, and I had a big success.

And so NBC hired me when I was 20 to go program their station in Chicago. Now, why you'd hire a 20-year-old kid to go program the station. Back in those days, companies could only own seven markets and one AM, one FM in every market. So it was a big deal to go to NBC there. And then by age 23, and I did the AMFM there, had a big success.

And they sent me to New York at age 23 to program WNBC. So I was Mr. Smarty Pants. I mean, I thought I knew everything. And I was recruited to come to this new company called Warner MX Satellite Entertainment Corporation. Cable Industry had built itself basically by delivering distance signals. It was just a big antenna for rural communities. But they started building the big markets like New York, and they realized nobody really is interested in seeing the TV station from Syracuse.

Thank you very much. They're going to have to have some programming. Well, HBO was there. Ted Turner had the super station out of Atlanta, showtime, a couple of others. And so there was this vision. Warner sold half of their cable company to American Express. They formed the company called Warner Amax. And they decided to do a programming company called Warner Amex Satellite Entertainment Corporation.

And they brought me in to be the programming person because they thought that coming out of radio, I knew specialized formats. I understood narrow casting because the radio was all about that. I mean, you find one audience that's very cohesive today. Is it hip-hop? Is it hip-hop? Is it hip-hop? That we understood how to do that.

So they brought me in to do it. And the first network I actually did was called the Movie Channel, which was the first 24-hour-day all-movie service, which was a big hit initially until HBO realized that it was a big hit. We were eating into them, and they started a fighting brand. By the way, never having gone to business school, I didn't know what hell a fighting brand was, called Cinemax.

And they dropped Cinemax on us and slowed our growth. And by the way, we eventually merged that service with Showtime. So they had two services like HBO and Max. There was a Showtime

in the Movie Channel. But after the success in the movie channel, they said, okay, we're ready to do our next network because our job was to build networks. And I had done a TV show on NBC in the 70s

called Album Tracks, which ran after Saturday Night Live because I had a great mentor there, the president of NBC, Herb Schlosher, spotted me young, said, kid, you're going to TV. Here, I need you to do a TV show, get some TV experience.

And so let me do what I wanted to do. And I put together a show that played just enough of video clips so I didn't have to pay rights on it. I could use it as editorial, the music news and looked like the music news segments on the early MTV, and had gotten some experience with it. And there were other people playing around with video clips because they were out there trying to figure out what to do. But I think everybody was trying mechanistically to figure out what to do with a video clip.

So we came up with this idea, said, look, we're going to do a video radio station. And we did that to sort of understand the form of it, because radio stations were all about the image of the radio station, like Kiss FM, Z100. They all had an attitude. TV networks didn't. I like the Cosby show back then, but I didn't know what network it was on. I didn't care. Networks were just sort of this delivery system for programs I had affinity for. And the reason we surmised, we also said, look, music, we had a generation that grew up with rock and roll music, and they grew up with television, but the two had never come together successfully. And the reason, and the two had never come together successfully. And the thesis I have was that they hadn't come together because everybody kept trying to make

music fit the TV form. And we were going to make TV fit the music form. It was going to be about mood and emotion, not about a linear plot line and not about shows. So that was the general thesis of it, and we were going to make MTV the hero, not any show or not any video clip, that the video clips were only going to be program fragments. But the program was a never-ending program called MTV. And as opposed to saying people, I'm going to watch Saturday night live, we had them, I'm going to tune in MTV to see what's going on. And that was our mission. And we put together a group of people who shared that mission. And we all found ways to do it.

And even when you looked at the on-air look of MTV, we wanted the minute you looked at it, so that's not like any TV I've seen. The original name I wanted was TV One. And I was going to put us versus everything else on TV and sharp contrast. And we couldn't clear it. So then we could clear TVM. So we're going to be TVM. And we had the guy who was the driest most, he was the guy who did our music programming.

He was the walk in the group. And he's very dry. And he said, we're meeting. He said, don't you think MTV sounds better than TVM? And you know, right on the spot, we go, you know what? You're right. It does. Yes, it's going to be MTV.

So that's the way it became MTV. And a guy named Fred Seiber and I, and I did a podcast with Fred on my podcast, math and magic about all of this. Fred was just the on-air genius of sort of how we're going to do creatively, the look and the feel. And Fred had never been in TV. I recruited Fred from a radio station, WHN Radio, a country radio station in New York, and he had produced some jazz records. But he had just this great thought process. And he and I went through this whole thing. Now, Fred's a lot smarter about this than I am. So we'd have these discussions. And I'm thinking like

Star Wars is very hot at time. We'll have our Star Wars logo with a big chrome logo coming from space. And Fred said, you know, the problem is, Bob, we don't have enough money for that. And if we do that, it doesn't look cheap. So he said, why don't we do something that no one's ever seen before? And then it'll just look like it'll look different, but not cheap. So that's what we did. And that was sort of the motivation for it. And again, it worked on many levels. I'd love to hear how the early music video concept co-evolved with MTV, because I think one of the most interesting things happening today in media is unique form factor, like a tweet or a TikTok video or a YouTube clip or whatever it might be, where you have this explosion of creativity within a defined container

and lots of different kinds of containers. And I sort of think of the music videos, I remember them so well watching them growing up, was this interesting defined container of new artistic expression. And I would just love to hear how you think the evolution of MTV, the video and music all co-evolved together. They all arrive. at one place for different reasons. When MTV launched, they talk about the second British invasion, as if the Beatles were coming back in the Rolling Stones off. Well, the reason was the second British invasion, because nobody in America made videos, and all the English groups did, because in Europe, you broke music through being on these TV shows. In America, you broke yourself by being your song

played on the radio. So these people didn't want to travel, so they would produce a video of them and send it to the shows. So the videos were pretty much looked like what you would do if you were getting a TV show and doing a performance for the most part. Now, there were some, the buggles I loved, and I saw them actually producing the video before we launched MTV called Video Killed the Radio Star, very clever. And there was some of the creativity beginning to happen with people pushing the form.

So initially, that's what it was. And by the way, if you think about it, remember, before MTV, you didn't know what artists looked like. They weren't really celebrities. You might know what McJagger looked like and the Beatles. But beyond that, you never really got a good look at them because there was no internet. They didn't cover it on TV. They didn't do those celebrity news shows.

CBS, Walter Cronkite wasn't going to cover music stars. If you looked at the album, they generally had some faded pictures, some crowd art. If you went to a concert, they didn't have big screens anymore. Unless you were on the front row seat, you didn't know who was playing down there. So one of the first things, we did is we made the artist, a celebrity. And from the beginning, artists would say, my God, people are stopping me on the street and saying, I saw you on MTV. So nobody's ever stopped me and said, I don't know who you are. So the first thing once we made them celebrities, and that

changed music and changed the music scene and therefore changed the videos to a certain extent. And then American artists looked at MTV and go, wait a minute, I need to be on there. So they began coming along. But simple answer was, nobody was producing videos. Bruce Springsteen hadn't done a video. Most black artists had done a video. And So as this began to develop, we actually were working a lot of artists trying to get them first. Do a video. Forget. Do a better video.

Just do a video. When we launched, we only had 250 videos. And that's not enough for a channel. But the calculated risk we took was that if we succeeded, they would make more videos. And if we didn't succeed, who the hell cared? So that was the risk we made. We launched in August 1 of 81, really about six months too early. we just cobbled together to get it on the air because the record companies were going through bad financial times

and we thought they were going to ax the music video budgets to save money. So we had to launch in August so we could get enough evidence before the budgets at the end of the year. So they keep it in for the next year. I mean, that's how tenuous it was at that moment. And obviously it worked. The record companies began saying, hey, this is a great promotional thing. We were sort of the YouTube or Spotify of that today to get music going. Of course, radio still had the reach and still had the,

bring it home in terms of big sales, but radio played so few songs that MTV could tee up, okay, this is the next one you should play if it was big on MTV, just like today. We'll look and say, okay, if that's big on a Spotify playlist or if that's big on YouTube, yeah, that's probably one will come close to adding, although we've got a lot of sophisticated AI today to help us we didn't have back then. And then the second phase of it was we needed to get artists to do, as you point out, better videos. And so the ones that were good, we tried to give a lot of attention.

attention to. And that was one of the reasons behind the video music award show. Let's start encouraging people. Let's start rewarding it. Let's start highlighting it. And that was a way we pushed it forward. Initially, we actually gave awards to the directors and we would go out and meet the directors and producers of videos and be good friends with them. And then, of course, I think the thing that really put it on its path is we began to have some video artist. And the two that come to mind or Madonna and Michael Jackson. They looked at this new form and go, aha, I need to be something no one's ever seen before. I need to be a performer, a visual performer, visual art in addition to my music. And I think they set a new standard. And now everybody could see what they

were doing. Now I know what you're talking about. And then you began the following. But it took it to the next level when artists like that popped on the scene, which probably may not have happened like that had it not been for an MTV. Had you not seen Michael Jackson's dancing and those moves and seen him as a performer, Michael Jackson may never have been as big as Michael Jackson was. Very talented, but in an album before, bad, it wasn't quite as big as thriller. So those pieces fell in place like that. One piece that we haven't talked about that I think, certainly I remember from God knows how many hours of watching MTV as a kid is the role of the VJs. And And this is an excuse probably to talk about hosts versus guests in media in general, the disc jockey

at the very start of your career. Tell me a little bit about anything counterintuitive about VJs or radio hosts or that side of the equation, which I think is probably underappreciated. It's funny. People think, because all they seem to know is TV and got to spend as much time in TV as I spent radio, so I've appreciated and love it. But this ain't TV without pictures. Radio is not that.

It never has been. It is really about companionship. we're keeping people company. And actually MTV was very radio-like in the beginning in the sense that we were keeping people company. You got nothing to do? Turn on MTV. We'll keep you company. We brought that radio experience to TV, which is why people said, I want to tune in MTV,

not I want to tune in and see a particular show. They didn't even know what show was on. They didn't even know who was on. They knew I can tune in and there they are. And it went in the beginning. Some of the people looking at my budgets, we didn't have much money to spend. And then they say, Bob, why are you proposing to spend the money on these people when it's just the music videos they want? Indeed, my boss was one of those that saw everything as TV and they go, you know, because no one bonds with a thing.

Think about the difference in that point analogy I used. I don't know anymore people know what a jukebox is today, but it's the difference in jukebox and radio. They had favorite radio stations. They felt personally involved with human-like emotions. Jukebox was a thing. and if you don't put people on, it's a thing. And indeed, in the early days of MTV, we would do research because I had to prove the point because I'd stuff my neck out, said, we have to have these people because you have something

to bond to, is people say, I love MTV. Why do you love MTV? I love that Martha Quinn. Why do you love Martha Quinn? I love the video. She's played. She didn't pick those videos. Love that contest.

She didn't have nothing to do with the contest. Love that music news. I was collected somewhere else. But they attributed everything to the human being they were bonded with. And, you know, today, I'd liken it to podcasting, which is, like radio, host-driven. And a lot of people that come to it who've come out of TV, and they think it's story and production value-driven, and it's not. People are bonding to that host.

It is a tight adjacent business to radio in the sense of that host-driven, that they bond with that host, they feel the affinity for the host, and you've either got a host that works or a host that doesn't work. And MTV was the same way. and everybody there got the benefit of everything we did on MTV was attributed to that person. Is there any common ground across hosts, we'll say VJs or whatever brand of hosts you want to focus on, that quote unquote work? Obviously, I'm sure there's plenty that just for whatever reason don't share that connection with the audience. And of course, by definition, VJs and every other kind of host are very different from each other.

But is there anything that unites in your experience, either the way they work or how they're introduced to the audience that increase? the odds that they work. It's a really good question and a really good perspective. Of course, if I told you everything, then you'd know everything I know, so I can't tell you everything. Actually, they, I'm kidding. You have to be willing to be honest. Ryan C. Christ, who does this extraordinarily well, says, you know, sometimes he's out with some movie stars or what he calls TV stars, and fans will see them, and they rush up to them,

and they hand Ryan their phone and say, would you take a picture of me with them? that they think of Ryan as their friend and they think of those other people as stars. And Ryan says, you know, if that ever changes, I'm dead. Ryan's the, in addition to everything he does on TV, probably his base and his foundation is his radio show, morning shows on Kiss FM and Los Angeles and then middays all around the country

and American Top 40 and a lot of other things he does on the radio. And I think what's really important to be a person is you have to be willing to talk about things that don't make you look good, but are just honest. And one of the constructs we use in coaching talent is we say, imagine you're riding in the car to work with someone every day and you're sitting in that empty seat. What would you be talking about and what would you be sharing?

Imagine you're sitting on the counter talking to someone while they're shaving. Imagine you're sitting in the chair in their bedroom talking to them while they're getting ready or sitting on the counter in the kitchen talking to them as they're cooking. or in the office when they're doing some mundane work, you're sitting beside them chatting with them. What would you talk about? Would you talk about problems you have in your marriage? Would you talk about problems you have with your kids?

Would you talk about something stupid you did today that's sort of embarrassing? But only the two of you know, you're not telling everybody. That's what you have to do and so few people can do that. Or, by the way, so few people have interesting stories. The truth is that if we look around, there's usually, if you look at a crowd of people, there are a couple of people that are really the friends everyone wants. And they sort of gravitate toward those people. And I don't care.

Give me a group of 20 people and you can still spot those numbers. And there are just some people who are just interesting. And there's some people who are really boring. People say, what did you do today? Well, I woke up this morning and I was getting out of bed. And I thought, well, did I leave a piece of paper on the floor there? And I saw you go, oh, my God, you're killing me. Please.

That's enough. Sorry I ask. And then there are other people you ask that question, too. and it's like they rattle off some great story and you're mesmerized by it. So I can't tell you how to get that part of it. But I can tell you from my standpoint is we look for those people all the time. And when we get them, we promote them. We had a guy who was in pop radio, top 40 radio, CHR, in Austin named Bobby Bones.

We realized in country, we had no great morning personality. We didn't have the Elvis Durant or the Ryan Seacrest in the country and we needed one. And so some of our guys, I didn't know Bobby, I wasn't involved in this, looked at Bobby and said, you know, Bobby could be that. And we moved Bobby to Nashville, put Bobby on a bunch of our country stations. And now, of course, Bobby's all over TV and Big Star, one dancing with the stars, and is untouchable in terms of that morning personality on the radio, on country radio now. But somebody spotted Bobby has that.

And I think that that's what we look for. And given our scale, we can afford to get anyone we need. We re-signed Charlemagne to God, made the news, was all over the news. And Charlemagne had everyone was after Charlemagne to God because he is in the hip-hop world, the Howard Stern, the Ryan Seacrest, whatever, and more. And he wanted to stay with us. And I think one of the reasons is that we help people grow and we coach them and we help people.

We put those shows together. We help promote them. And we get the flywheel effect of our size and scale helps to build a. talent and the talent helps build the size and scale. And I think we treat them with great respect. And my view is it's a talent first company. You know, we started conversation talking about the consumers and you got to listen to the consumer. I think when you start going after the consumer, if this is a host-driven medium, then who do I worship in this company? The host. And I can't be so cynical to say we're going to buy them off. I'll just give them money. They'll be happy.

I started life on air. And for me, it's always helped me in creative ventures because I know how it feels to be on the creative side of things. And by the way, I was not a great talent. Hence, I became programming and management and then running businesses. But I understand it and I understand what it takes. And we do put those people first and really treat them with, I think, a respect they are certainly do. It's funny because this insight and I guess advice or strategy around host used to be probably pretty low utility to the average person. But today, in some ways, everyone is kind of a host, right? Everyone has, at least they have the chance to have the outlet in multiple social media areas to do their own thing with basically no one's permission and with no frictions.

In addition to this authenticity, which I think makes just all the sense in the world, someone that bleeds, are there any other things that you would offer out there even more generally beyond the professionals and some of the personalities that everyone will recognize their names? But just this is a thing that a lot of people care about right now and has you to use the term social status, but it feels like that's a currency of the modern day age. And I just wonder if there's any other advice you have for people that are trying to cultivate something like that, even on a very small scale. You're hitting it just right. I think the secret is you got to be able to tell a good story. And what's a good story? A good story is really about, I got to have a headline that grabs

you. I got to keep it simple. I got to make it understand. Catch people sometimes say, look, don't tell people at the sausage making. No one cares. They don't care what it is. They want the excitement of it. What made that story exciting? Why are you talking to me about it? What's important to me? And I think, again, we go back to, we're talking earlier about just management that people oftentimes get stuck in making the job easier for themselves, not for their customer. I think sometimes when you're telling a story, do you spend too much time talking about yourself rather than what's relevant to it for them? And if you can do that, that makes your story a whole lot better. But I think it is almost 100% storytelling. And you want to be a good host, know how to tell a good story.

As you think back on the MTV days, is there a day or a moment or an episode that you would identify as like the peak of that experience? Maybe where you looked around and you said to yourself, holy shit, we really built something spectacular here. There's some that are good and bad. You want me to cover them all? Please. The first one was we had to prove that we could sell records. So I sent Tom Freston and John Sykes out on the road because MTV was not in the big cities. We weren't on in Manhattan.

We were on some suburb of New Jersey. We were on Tulsa, Oklahoma. Oklahoma City and Tucson and Tom and John hit the road. No internet back then. Phones didn't work real well looking for some evidence. And they called me one night in the middle of the night. I still remember some of my apartment in New York. And they said, we got it. We're at a record store today. And we walked in and the guy said, I'm selling tubes. And nobody's playing it on the radio. Suddenly sold like a box of them. What happened? Everybody's coming in for all these weird songs. So we were able to take that market it to the music

business and say, look, we're selling records. You should love us. So that was step one. Step two was sort of a weird one. MTV suddenly got all this press attention, but it wasn't making any money. As a matter of fact, the sales group had missed their goals. I think we budgeted, we were going to do $10 million in sales first year. We were to half a million dollars. It was a disaster. And by the way, had Steve Ross not been our great protector and Steve wound up in my life, sort of being my great mentor, almost a father figure to me. So Steve was protecting us, but I had this weird experienced. I still was running the movie channel as well as MTV. And my boss came to me and said, you should just run the movie channel. I'm going to get somebody else to run MTV. I built it.

This is my baby. I started the whole thing. And it was, you don't know people's vibration, clearly, I think it's killing him that I got all this press attention and all this and none. And I just said, you can do what you want to do, but if you do that, I'm quitting. And sort of left it at that. And one day his boss, CEO of the company came in and said, Bob, did you say you'd be okay with that? I said, no, no, I said, I would quit. He said, I sort of thought that's what you'd say. And about a month later, he left. And about a month later, I took over as chief operating officer at the company. And they came and said, look, can you run the business? I don't only run programming. I was creative guy. By the way, I hated salespeople, those nasty sales people. I was just like,

I'm a purist. I just want the product. And I don't know what I was, 28 or 29-year-old person would say, of course I can. I never, right, I'm not in Vietnam. I'm not a college graduate. And, And so I took over the business. So I sort of knew something it happened when somebody wanted to push me out because they were envious of the attention I had. I realized it was something significant that the company was willing to let me run the whole business. And then the quest was, when do we make money?

I don't know if you remember a guy named Drew Lewis. He was the Transportation Secretary who fired all the air traffic controllers under Ronald Reagan, a really tough guy. They hire him to be the head of the Warner Amex Joint Venture, which is both the cable company, and Warner MX Satellite Entertainment Corporation. The first meeting with him, I say something about the Rolling Stones, and someone is with him says, Drew, do you know the Rolling Stones? He goes, no.

Said, do you know Mick Jagger? He goes, boy, I'm in trouble. He takes me to lunch and he says, look, I don't know what you're doing. So Steve Ross, really loves you and all that. But either you can make money by the end of the year, or I got to shut this thing down. Can't afford to feed it anymore. So meanwhile, I just remember, I just taken over as the COO, and I'm running stuff, and now I'm getting this word that he's going to shut it down.

Well, I think to myself, I can't tell the people that we're close to being shut down because they'll all get bummed out and they're on a high and they're really excited about building this thing. So I got to keep this to myself and the CFO. So we started out just cutting costs. Suddenly, instead of spending $30,000 for a concert, I say you shoot for $10,000. They go, you can't shoot a concert for $10,000. I go, give me the budget. I'll share you. We'll cut that, cut that, cut that.

though I won't look good. And of course, what's interesting is we discovered people found new creative ways to look great if they couldn't throw money at it. So side issue, another point. So we were going through all this, and by the end of the year, we actually made money. So the day I knew we were going to make money, I didn't call Drew Lewis. I called Steve Ross and said, Steve, I want to come see you. And I went over to Steve, and I said, Steve, I have great news for you, said, we've crossed it. We're going to make money.

we're now a money-making venture. By the way, no one had ever made money on a basic cable network. It was thought that that model of advertisers supported wouldn't work. And Steve, and this was a great lesson, too, but also a moment of knock me down a notch on arrival. I'm thinking he's going to say, Bob, you're a damn genius. You're great. You're so wonderful. Instead, he says, great.

Now here's what we can do. And I realized that that moment, one of the great lessons, is that there is no such thing as success or failure. They're just stepping stones. You don't stop. on either one of them. You keep going. But that was sort of the key moment of we had arrived. So there were all those moments at that time that were just dropping one after the other. And of course, at that moment, I didn't realize because I was young, it didn't realize that and everybody. We were sort of the it company. We were cool and hip at a certain point.

We were the Facebook and Google and name any other cool company sort of rolled into one. And so, you know, if we wanted to talk to the president of the United States, we could. We met the president. We met people. They all wanted to know us. If people wanted me to be on their board, it was like, amazing. I was so charming. So we were off and running. And the downside was when we were a scrappy young company, we had to be really smart and convince people who didn't believe in us to believe in us. When we got to this point, it was almost like the dark side of the force.

Everybody thought we were a genius just because we said something. And ultimately, it was probably, I always think back on probably the reason I decided I wanted to leave is I just felt like that's corrupting me. that I no longer have to be smart, good, and do stuff. I just say it and people will leave it. It doesn't sound right. I have to ask about just media more even writ larger and the way that the business has evolved. I don't really know the best way to slice and dice a given media business back then versus today. I'd love to hear how you think it's evolved and sort of what the key pillars are of a given media business. Does monetization and product, do they talk? What is unique about how these businesses are well run relative to other traditional businesses?

Well, first of all, you've got to know what you're doing. What are you trying to do? If you're just trying to sell advertising, good luck, that's not a business. What's your mission? In the case of Iheart, our mission is to give everybody in America a friend anytime, anywhere. It's all about companionship. And if we do that well, we'll figure out how to make money. And I've always thought in every business I've been in is if we can figure out how to be important to the consumer, we'll figure out how to make money.

But if you start from, I got a great scheme to make money, that's what you got. You got a scheme. You don't have a business. you're providing nothing of value. When I was at AOL, the last deal I did was to give Google the search traffic on AOL, which probably in a couple of places we're giving credit for sort of being that catalyst that makes Google Google. But they didn't offer us the most money, although, by the way, we had 10% of Google too bad.

I think it was 10% too bad somebody at Time Warner sold it too early. And we got a lot of money, but it wasn't the biggest check. Somebody else is offering us more money to put another business in there. but we picked Google because I thought it was the best service. And I think you never go wrong by picking the highest quality, the best of whatever you've got there, treat the consumer with respect. And if you do that, monetization is a lot easier because you have a really committed consumer and you have a tight bond.

And I think people will always pay more money for a engaged consumer rather than just there. If you trick somebody into going to a site because your horoscope says you're going to die today, click here, and you click there and you find it something for buying a car. That's not a very engaged consumer. And yet today we see an awful lot of that cynical view of monetization. I'll trick them into coming over here and I'll get some money out of them. I think those aren't long-term models. I think it was a short-term models. You don't have a moat around your castle. You've got nothing that protects you. So I think you start with you build a strong bond with the consumer. And I describe our business model, and I've described this business model for every media business I've ever been in,

is our job is we build a lot of scale, engaged relationships with the consumer, and then we monetize it. We rent that relationship to unaffiliated third parties, and that's what we call advertising. We're renting a relationship is the business we're in. So I'm not selling impressions. I'm not selling spots. I'm not saying I'm renting my relationship, and I have to treat it like I'm renting a relationship. So if I'm renting my relationship to you, I can't let you abuse it. So I have to be careful about what I do in that sales process, what I allow an advertiser to do.

Is it the right advertiser? We just launched the Black Information Network, which is the only 24-hour-a-day news source for the black community. We did it back in the height of COVID right after George Floyd. We'd had it in development, and we'd had it stuck on a shelf, because we need to save money. And executive Tony Coles, who was charged for developing it, called me and said, Bob, I know we don't have an extra penny, but boy, does country need this right now?

And so we launched it. But when we launched it, we decided instead of launching it with ad sales, impressions, et cetera, that if we wanted a really trusted news source, we couldn't have it be about advertising, because then it would be about ratings. And if it was about ratings, it would be about what gets a better rating, getting someone's blood pressure up,

telling them a half truth, gets them all excited. They're what? So we went with the idea, we're going to go and do no more than 10 founding partners, companies that believe in this mission that are willing to support it. And we got companies like McDonald's, Bank of America, Lowe's, CVS, GEICO, etc. But there were some other companies that actually wanted to invest. And we go, you know, then I write for it. They don't want to come with the purity of the mission of really supporting this. And we said no to them.

And that was when you're starting a business, can you imagine saying, know to somebody who's got money in their pocket. I say that just illustrate the point that I think it's very important when you monetize that you are really respectful of that relationship with the consumer. They've given you their trust. If you blow it by selling it off in some irresponsible way, it may not affect you today. It may not affect you next year. It will affect you eventually. I'm old enough to be one of those people that I've seen jerks in business. And I say, you know, good people are the ones who win. And they say, what about so-and-so? Look how well they're doing. And back then, I didn't have an answer for it. Today I do, which is, no, their career's not over. And I've seen

almost no examples of a lifelong jerk who really has a lifelong career, that at a certain point, it all comes back to them, and it all is relevant. And they have to pay for not treating people with respect. I think that's so true with consumers and products. And I think sometimes when we just let the engineer decide what you're going to do. It's not what can we do. You also need that hyphen and what should we do. I'm a great believer. Look, I may be old fashioned, but I do believe, having been in this business for 50 years, that I've got a long enough road to see that actually you can't abuse people forever that they eventually are found out, or what you've done is you've created an opening for a competitor to slip in and say, you know what? They didn't treat you well.

I will. In that point, they're not even more convenient. They're more trustworthy. What do you think is the largest set of uncertainties or uncertainty in the media landscape today? And maybe as part of this question, I'm just curious how you think about the role of centralized traditional media companies versus, I'll call it user generated content companies. Anyone can publish a podcast, right? They may not have the I-heart distribution, but anyone can try. How do you think about uncertainty today and sort of the way the internet and permissionless creativity is affecting that landscape? I don't think of the example you used as matters because you can still be user-generated content, YouTube, and still be a part of the major monetization machines. When you think about uncertainty, I don't think there's any greater level of uncertainty than there ever has been. I think there's always been the ability of a talent on TV who is working.

in Des Moines, Iowa to suddenly be the nighttime anchor. Tom Brokaw is a good friend. You should listen to his story. Actually, I think I covered on one of my podcasts, The Math and Magic. He's in Omaha. He gets a call from Atlanta, the big time to come. And then when he's in Atlanta, it gets called from NBC, the network to come. You could be discovered anywhere. And I think the people doing user-generated content, what they're really looking for is they don't want to have 10 listeners or 10 viewers. They want to be the next big star. And so they have. have a shot to do that. And I think that's good and great. And by the way, we have algorithms which help find them and other things as well. But I think the process is probably the same.

When you get to certainty, I think everything's uncertain. I actually think plans are sort of funny because I think we invent plans to reduce our anxiety about the future. But I've run for, I can't remember the first company I used it. I do a weekly operating. committee and we used to meet every Monday and the purpose to adjust a plan because I find even a week sometimes is too long before we adjust a plan if we wind up hitting our numbers for the quarter we probably did it in the way we didn't intend to at the beginning of the quarter if you're really going to run a business you've got to run the business which means understand that because you planned it doesn't mean it's going to come true I'd love these strategy groups that say and here's your

plan of how we're going to do I go good luck with that pal Like I was there when Steve Jobs went back to Apple and had conversations with him when he was describing to me what his vision of Apple was. And when the big revelation would sound silly today is he said, instead of the modem being an application on the computer, I think the computer is a part of the internet. And it's a way to use the internet. And I'm going to do the IMAQ and build the modem into it. That was the innovation. Or Jeff Bezos, building a book retailer. That was just the beginning.

if either one of those geniuses had stopped at the original idea. So I did it, we'd never have this success as we had today. So I think plans are silly in a sense. I think you have to build them. But I think it's better of just saying, look, this is the best guess I've got it right now. But if you wait until tomorrow, I'll have a better guess. And if you wait until next week, I'll have a better one. But I think the best managers, the best creative people really look at this as it's always changing.

There are way too many variables for us to ever be predictive. And so when I look at the media business, here's what I know can get them in trouble. You got to look to the future. When I came to this company, it was a radio company and outdoor company. It's not that today. But people were selling spots and they looked at how Facebook and Google were selling and go, huh, that's interesting. And my point was, you know what, that's where it's going.

We've got this big and able audience. What holds us back? Not that we got a big and able audience. Who wouldn't want that? but that we're selling people spots instead of selling them these enabled relationships defined by the data we have and letting them see what kind of results we're getting through attribution. So we need the data and analytics that everybody else said, we're going to have to catch up. So I think you've got to keep your mind open that things change and not only in terms of what you are, but how you're going to sell it. It's silly to think about if you have an opportunity to say, okay, I can either do search for cookies.

And when it comes to cookies, I can say, try Tate's cookies. They're great with a little line in the box. And I'll go to the website maybe, and I'll get a couple of people click on it. Or I have Elvis Rand say, wow, have you tasted these Tate's cookies? You know, it came from this shop out in the Hamptons. And Danielle's going, yeah, I've been eating them too. My kids love them. Yeah, I promise you that.

I always think about as marketing, it's the name of my podcast, is math and magic. I need to know the analytics about it. And by the way, all the digital people are spectacular at that and do it better than anyone. Facebook and Google and Amazon deserve enormous credit. But when you get to the magic level, there are very few people to do magic better than radio, getting people excited about something. They are IHart Radio Festival, the new IHart Radio app. How do we get to be the number one podcaster?

How did as IHart this big brand? We just talk about it on the radio all the time. So the magic's great. So for me, and you know, the example here is that I think we have to say, okay, there's a math that's being applied to all this that we weren't doing. We have to do it. So we spent the five or six years and the hundreds of millions of dollars to be able to do that now. And so I think every plan people have, you've got to be willing to throw that plan out. I got to be willing to throw the plan out that we sell spots. The plans don't matter. It matters what's right today that's maybe different

than yesterday. And by the way, none of us are no Stradamus. I'd love to talk about magic and creativity and how those two things interrelate. I'm a big believer that creativity is in many ways about collecting useful or inspirational experiences and information. And I'm curious for you personally, what are some examples of things that you found maybe outside of business, other things that you're interested in that you find inspiration in? And how do you think that relates back to the creation of magic and business?

I think the biggest problem we all have are the blinders that we put on. when I was in MTV, we had a self-serving and half-serious joke that no one over the age of 30 has any good ideas. And I think there's a certain truth to that. I think in our 20s, we have our best raw creativity because we don't know enough. If I had known what I know now, I'd never been able to create MTV. I would never been able to build Nickelodeon into this tweens network. I saw it because I didn't know what I wasn't. I wasn't encumbered by knowing too much and knowing all this other stuff. So I think when you think about creativity, the question is how do we keep the blinders from killing us? And I'm always looking for the new experience. I retired at 49 once.

And I retired thinking I wanted to go see the world and do all this stuff because I didn't go travel Europe as everybody else did when they were in college because I was working full time. And I said when I stopped working, I always had to say no because I didn't have any time. I said, I'm going to say yes to everything that I can now. My first answer is going to be yes. And I went to Burning Man for the first time. And I went to Burning Man. I walked out on that desert on the playa one night and saw all the fire and all this stuff. I go, what?

What is this? Who thought of this? How did they? And you look at these ideas out there and you go, where did that come from? And I have tried to say yes to things just to see stuff I've never seen before. And I think that helps your creativity a lot. It's just open your mind. Assume it will work until you know it won't, as opposed to start with it won't.

You know, that's that creative process which people use, which is you put all the ideas on the board before you start evaluating them. Don't evaluate them as you go, well, I'll never work. Don't allow your stuff. Say anything won't work to put everything up on the board. And I think that process works a lot better. But it also works better if you get some wow cards in the thinking process. because I find as an old man now, what I'm really good at is I don't have quite that just out of left field idea. My ideas tend to be something that I've seen somewhere before, some pattern or something I've seen,

but I'm really good at helping somebody who's got a really raw idea shape the idea. Because I go, okay, I'd never thought of that. That's a great idea. Now let me tell you how we put it together to make it work. And so I think the hardest part often is that magic. But you also want to inform the magic against something. What is it we're trying to do? And so random ideas probably is not good, but say, look, here's what we need to accomplish.

You've got to figure out a way to do this. And now you start unleashing people. And I find the creative process works for me. And as I talk to other creative people, I think this is the way it works for most people, is I think of all the stuff I need to know, I think of all the information I have about it, and then I forget about it. It is not an MBA kind of process. I forget about it.

And the moment at which I'm in my most Zen state, which for me is about a 15 or 20 minutes shower I take every day where I'd sort of just go into the zone, suddenly the idea pops in my head. It might be a speech. I just have writers block on and suddenly I got it. It might be a slogan we need. It might be a structural thing. It might be a new product. It just pops in my head. I don't have any idea where it comes from.

And so when I used to work with ad agencies, I would tell them I'm not interested in your process. please don't bring your account people and research people and lay this out as if it's some process that we're going through. I know how it really works. What I want you to give me is three creative teams that don't talk to each other. I want them to go away and come up with the best ideas they can. I don't want anyone to evaluate them. I don't want you guys to go through before you show them to me. And I just want you to come in raw and tell me those groups from three because by having three different groups on it,

I'm going to maximize my odds that one person has the idea. So easy to use. No wonder it's number one. which was the AOL line, came from a briefing memo that Stone Roberts brought to me. And they were reading it says, so easy to use the known. I said, that's the line. They go, no, no, no, that's not the line. That's just with a briefing we're using so we can develop the line.

I go, no, no, that's it. I want my MTV was part of a spot, which Dale Pond and George Lois did. We had a problem as cable companies didn't want to put MTV on. And they wanted us to pay them to put it on per month, per subscriber. and there's no way we'd ever have that money. So he said, I'm going to take a small fraction of that amount of money, and we're going to buy TV advertising, and we're going to do the first consumer pull in cable.

We're going to get the consumer to demand the product. And so they have one that's America's becoming a land of cable brats and cable brats, blah, blah, blah. And in there it's saying, I want my MTV. So I hear this, and it's Fred Seiber and Tom Fresner with me and go, you know what? I want my MTV. And we reformed that spot as I want my MTV. So somebody just has that flash of an ID.

And it's not that the idea is fully formed, but when they've got the right idea, again. So what you have to have is you have to have a good editor. I think I'm a pretty good editor. So, okay, I may not have the idea, but wow, I know the idea when it hits me. That's the idea. Let's move it around. And I think that's the process through this. And I think the best people open their minds to anything's possible, and they listen really hard.

And by the way, the great idea is just as likely to come from a production assistant is your president of production. By the way, your kid or a friend of theirs or a cab driver or anyone else, listen hard and value every experience you get. Really neat idea. And I would all remember it as like if you don't have unique inputs, you're not going to have unique outputs, which sounds obvious on the face of it, but everyone seems to consume the same inputs all the time. There was a story in the New York Times, Science Times years ago. It was about they did a study of people and they looked at a picture and looked at what they saw in the picture. Then they took part of those people and they showed them something they had never seen before.

Of course, it's always in my mind imagining, oh, I went to the Burning Man, showed them something they'd never seen. Then both groups looked at the picture again. The people who had been shown the stuff they'd never seen before saw all sorts of other things in that picture, and the control group did not. So I think what it does is opens up when I see stuff I've never seen before. it opens me to thinking about and being open to a lot of other ideas. You've had a really interesting set of experiences that probably not many have where you've spent time investing. You mentioned for that long period. You've been running companies that were publicly traded companies, privately owned companies, probably companies that just you owned.

Just say a little bit about that overall perspective, maybe first as an operator, the notable differences between the different kinds of ownership structures and how it affected your behavior. It's much easier to run a big company because when you need something done, you have the money to do it and the people to do it. When you run a tiny little company, you've got to say, who can I convince to do that for me for free? Or how am I going to get that done? So it's more of a struggle. Also having an impact. I love something like I heart because we reach more people in America than even Google and Facebook more than anyone else.

So we can have an impact. So for a creative standpoint, it's great because we can actually create stuff. We don't have to wait until the market leader creates something and then we have a little side opportunity or side hustle somewhere. And in terms of monetization, we're big enough that it matters to companies so we can actually go have a conversation with decision makers as opposed to people who really don't have the authority to make any decision other than what they've been instructed to do. On the other hand, I find that some of the small businesses have been some of the most interesting.

And for me, when I was doing investing and I had a pilot group, I did things with company I call whiteboard with them. And I would say, look, let me invest with you. And I'm going to be your coach. And we'll do a whiteboard session once a week, once a month, once a quarter, and which we just sort of talk it through. And I've had this privilege of working with some brilliant people like Ben Lair, who was coming out of college and we financed Thrillist and use some of the expertise that we picked up from Daily Candy from Danny Levy and her gang. That, you know, it's just this very interesting groups of people. So I find in some of the smaller, more entrepreneurial companies, I got an opportunity to really deal with people who are new and

fresh to it, which has a certain reward in itself. I think on the bigger companies, I've had a chance to have perhaps more impact, whether it's a Time Warner or AOL or what MTV became. And MTV sort of went through all those stages for me. And certainly with Iheart, they each scratch a different itch with each of them. And I've been lucky enough to be able to do them all. And even that, I'm a major investor and still on the board of Casa Dragonus, which I was a co-founder of, and that was an idea that I had just sitting in my house of Mexico where I used to spend a couple of months a year when I really wasn't working much and hit upon this idea of the sipping tequila and found Berta Gonzalez, who actually knew what she was doing and it ran Jose Cuervo or North America.

And so we rolled this thing out, and I still play with that too. I love having these other things to touch and feel because what gives my life purpose and joy is this sort of creation process. It's great excuse to ask a couple closing question. The first of which is you've given us so many interesting stories and examples of what I'll call identifying and respecting an audience. And I think many people make the mistake of overdefining their audience as too big or not narrow enough and therefore they're mediocre to many versus great to a few. Any closing advice you would have for people on audience selection and the respect that the creator has for their audience?

I think they go hand in hand. It's a mistake to say, I have my audience. What you really have is you have a coalition of a lot of small segments that have come together to give you a big audience. And if you fail to understand the segments and the tension between the segments and among the segments, you're talking to no one. If I've got someone 20 years old and I've got someone 40 years old, it's a mistake to say my average user's 30. You actually don't have any 30-year-olds. And it's a mistake I hear all the time. People talk mean scores. all the time. And I say, give me the distribution, will you? Tell me who your people are. And when they say, well, these people love this, I go, everybody couldn't love that. Who loves this and who loves this and how do we do? It's interesting on radio stations. If we build a radio station that's got a pretty broad audience, let's call it a CHR station, C100 New York, Kiss FM in Los Angeles, there's not one audience. That station encompasses probably four or five audiences that really behave differently, but they behave enough that we can put them together under one brand. But you got to know which one.

So I can play a song for one segment, but I can't play two songs for that same segment because I'm alienating the others. I got to start saying one for this segment, one for that segment, one for that. And this group's the most alienating everybody else. I only play that one every three times. And you begin to figure out that balance of that audience. I mean, if I look at Walmart or Amazon, there are many different audience segments. and the secret to it is not merging them together and say the average is why and talk to that. I hear people say, I imagine I have one person and I'm talking to that person.

I think those people are making a terrible error. I think you better understand that whole array of people you've got out there. Imagine it's your whole family. My son wants to hear something different or see something or buy something different than my daughter than my wife than I do, my friends or other partners I've got. You've got to understand each of those people and figure out the tradeoffs you're willing to make. and what's fair and what's respectful for each of those groups. So I think it ties in the same thing. It's really understanding people not coming up with a data point

and thinking your data point is an audience, data points, not an audience. A data point's a poor reflection of who that is. Before my traditional closing question, same question I ask everybody, it's a testament to our conversation that like we literally even haven't even talked about six flags or some of these other iconic brands. We haven't talked about podcasting. Everybody wants to talk about podcasting.

That's used in the number one thing. How did you get to be number one in podcasting? Let's do it. Two lightning fast round questions on those two topics, just so that we can say we cover them. What's one lesson you take from your time at Six Flags? I think it is respect for the consumer, super service to the consumer, understanding how the consumer works and being willing to do whatever it takes to make them happy. Podcasting. What is the most interesting aspect of it in your opinion today? I think what's most interesting is that young people actually do want to hear talk shows and that they really do. do want to hear, not see, that people have run out of time for their eyes, but they got time for

their ears. And they still enjoy a good story. They still enjoy information. They still enjoy a good discourse. And they love it when they can just listen, as opposed to also having to find time for their eyes. So now I have to ask you my traditional closing question, and that is to ask for the kindest thing that anyone's ever done for you. God, I've got too many of them. I've got abundance of riches, but I would say probably it has to be parents, right? The kind of thing they've ever done is give me unconditional love. I didn't grow up rich. I grew up poor. I grew up a parsonage. My dad was a Methodist minister. We lived in the church's house. But I had the richest life you can imagine because my parents never made love come and go. They always loved me,

even if they were disappointed in actions I did. And I think having that foundation for my life has allowed me to have a rich and a beautiful life. And hopefully I'm able to do that for my kids and my friends and others I come in contact with. Well, Bob, when we first talked, I think the first thing I said was I was worried that a lot of time was too short. I feel that way, yet again, here today. I so appreciate all the interesting stories and perspective and lessons from your fascinating career. Thanks for sharing this all with us. I love it. This is great fun, and congratulations in all you're doing. This episode was brought to you by Doc Send. In this four-part mini-series, I sit down with DocSend CEO and co-founder Russ Hedleston to hear the origins of Docsend,

the problems it's solving and what the future may hold. In this week's episode, Doxent CEO Russ Hedleston and I discuss why PDFs are so cumbersome and outdated in how Doxent is a step function change to solve them. I was thinking about this conversation earlier this morning and I checked my email and I had like 15 emails from the weekend that had some sort of PDF attached to them. It made me start to think about PDF as like the sending of information without any sort of real feedback loop. So maybe talk about the difference between that core action.

that just happens all over the business world all the time and why Doxan represents a step change up in functionality. Yeah, I can't believe people still send so many PDFs, it's especially ironic when it's a PDF that says confidential on it because, you know, there's no controls, no security. Our Series A investor, our Hartenbaum invested because he thought that Doxan would kill the attachment. He's like, there are still attachments. Docson's going to get rid of the need for attachments. And that's really been the journey we've been on. But key difference is you send an attachment. Once you hit send, it's gone.

And this is like my fundraising journey for my first startup where it got sent to a competitor. I never heard anything back. If I had a new version, I'd have to resend the attachment. And PDF is the state of the art because if I send you a keynote file, you might not even be able to open it. Or if I share a Google Doc with you or Google slide, then you might need to create a Google account and you're not going to do that. So DocSend is a way to send a link, not an attachment, that gives you per page analytics. It's always a unique link so that link can be tracked when it's forwarded. And then as a sender, you can put controls on top of it saying, only these emails can access, only these domains can access.

I can dynamically watermark it. I can authenticate your email. It's just a whole list of different features in there that depending on what you're using us for are really just big game changers. Like if you take even the example of I sent you my pitch deck, I then have to update my pitch deck. The question is, do I need to resend my pitch deck to you? Because that's just awkward. And then, you know, I send it to you and then we talk about it. I might have to start the conversation saying, Patrick, which version did you look at?

You're going to be like, I don't know which version. What was different? And suddenly, I look bad from the get-go versus with Docsend. I can see that you haven't looked at it yet. I can update that link. You never even know they updated it. And that just immediately makes me the sender look more professional. I'm more prepared.

I just have more information. And that's just, it leaps and bounds better than sending a PDF attachment. We all know that PDFs and PowerPoints are ubiquitous in business, right? it's just a key part of communication and sales and kind of everything these days, even internal team meetings. Who are the key personas that use Doxend the most? Is it people raising money? Is it people selling? You know, what are your key stakeholders on the client side? They all have similar workflows, but they all carry very different job titles. So like a CFO is very different than a banker, is very different than a founder, but they all are sending documents, as you point out, and they all would like

control and they'd all like to know who read it and how long and where'd they go and they as senders want to look professional so we talk about there being multiple different workflows but there's deal sourcing so you're sending out a PDF to like 30 people and trying to figure out which of them is most interested there's deal management which is the data room side of it I need to collect all these items behind one link and give you access control that there's relationship management which can be I have a relationship with my investors all the board material in one spot or you as an investor have your LPs and you need to keep all your investor updates in one spot. And finally, there's deal execution. That's the e-signature part the Doxon also covers where you actually need to get a

signature done and get a deal done. And we explicitly don't target internal use cases. So you mentioned kind of the collaborating on a Google Doc. That's not what Doxend is for. The mission statement for our company is to combine common workflows for sending documents externally into one intuitive solution, which shockingly is there's not really another company that's viewing the world and solving it that way. You mentioned something at the end there, maybe that might surprise people, which is e-signature, and sort of often that's the very end of all of these processes. Someone has to sign something.

What have you learned there? What got you into that space? The way we got into e-signature was that for the financial use case for Docsend. There are a lot of NDAs that need to get signed. I'm sure you've seen these. And what people asked us for our users is they said, I just want to checkbox so someone has to sign the NDA before getting into the document or into the data room. And we said, okay, that makes sense. We can add that. To add that, you actually have to build out e-signature legally on the back end for it to be binding. And so we released a very

lightweight version of e-sign along with the one-click NDA functionality. And people just started using it. And we were really surprised. And so we talked to these people and we realized we don't need to rebuild all of docuSign. There's just a few different things we need to build out. And I think the next iteration of e-signature, I think it's you combine e-sign in with all these other. workflows. So as you point out, all these deals end in any signature. Why switch and use an entirely different system for that? If you can have that be bundled in with the system you're already using. To find more episodes or sign up for our weekly summary, visit investorfield guide.com. Thanks for listening to Founders Field Guide.