Barry Diller Breaks Down the Battle for Media’s Future 05/21/25
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I'm Andrew Osorkin, and this is SquawkPod. Barry Diller has shaped the media world for more than half a century, redefining television, launching networks, and backing bold ideas long before they were safe bets. Netflix, Amazon, and Apple control the entertainment business. They have, I don't know, what would you say, a hundred times more

the resources of these legacy companies and they're in control they ain't giving it up on this bonus podcast the deals the stories the man barry diller reactions have been i mean they've been incredibly nice and positive and all of those things but i do see in not in the little beatiness of people's eyes but i do see they look at me like i now know you

You're going to hear from my one-on-one sit-down with Diller and from his appearance on the Squawk Box set with me and my colleague, Becky Quick. Squawk Pod begins right now. This week, Barry Diller published a memoir. It tells the life story of a name familiar to the media industry and our audience here on Squawk Box. This is Diller on our TV broadcast 10 years ago. It was for a show celebrating 20 years of Squawk Box.

You know how I hate to be a contrarian. I know how much you hate to be a contrarian. You know, I think the words that we use now, and nothing is, of course, predictable, but the words we use now, broadcast, cable programming, over the top, they'll all be gone.

because now where everything is going to be distributed without question through essentially a data pipe, not a broadcast pipe, not a cable pipe, but a data pipe. So over time, these definitions will no longer be in use. I don't think there'll be anything called broadcast television or cable television.

They'll be brands, if people are good enough to have as much differentiation as they can conceive, or they'll be programs.

At age 83, Diller holds nothing back. From his formative years growing up in Hollywood to the start of his business career, he launched the movie of the week on TV for ABC at the age of 27. In his early 30s, he led Paramount Pictures. He got the Fox TV network off the ground with Rupert Murdoch. So many stories like this are in his new book, Who Knew?

I spoke with Diller last week at the Manhattan headquarters of IAC, the media conglomerate where he is chairman. I asked him what led him to write a book about his life and career. Well, I thought only one thing, which is it's a good story. And it's a good, cracking story, if I could tell it. Who knew is already generating lots of attention. All this closet stuff.

I mean, if I've been in a closet, it has been the most brightly lit closet with a glass door that you've ever seen. I understand kind of the catnip of media, but all this stuff about my sexuality at my frigging age just seems to me

Well, it's kind of, it's obvious and over the top. Diller opens up about his sexuality and his relationship with his wife, Dionne von Furstenberg, the great love of his life. She said to me six months ago or a year ago when I knew I was going to publish, she said, just get ready. I said, get ready? What are you talking about? She said, just get ready. In the book, you talk about having a code. I just said I didn't want to live a hypocritical life. And so I, it was really rules. It was, you know, in a way, rules of conduct.

that I just adopted for myself. Interestingly, when I was like 20, 21, 20, somewhere around that period, I knew enough and I said, "Well, there are things I will do and I won't do, and those are my rules." And it was adopted because I didn't want to be a hypocrite and yet I didn't want to tell anybody anything.

So I said, "I have to have rules for that." And I made them up. Rules for a life he lived in fear. But Diller says that gave him a superpower that propelled his career in business. If you have one great fear, you don't have room for many others. And I think that, in a weird way, as painful as the early development was, I think that's actually a great gift, odd, crazy-ish gift that I was given

that it allowed me to be fearless in so many other areas. What do you think you learned about yourself in the process of this? I've always had a problem living in the moment. And so doing it, actually, it's living in the old moments

since I didn't really live in those moments at the time, was kind of fun for me. And it also, I learned things in the process of doing it that I had never known. Okay, you just said something that's fascinating to me. And I think it's actually true of some of the most successful people in the world, but I also think it's a bit of a prison. You just said you don't live in the moment. Yep. I think that you live oftentimes in the future.

I think you're often, you can be somewhere, but you're thinking about other things that you are hoping and projecting are going to happen in the future. Sure. Is that what's happening? Yeah. For a lot of reasons, I worried that if I lived too much in the moment, it would take things away from me. I thought if I lived in the moment, it would make me cynical. And one of the things I've always tried to hold on to is a certain kind of naivete.

Diller's work exploits are legendary. I asked him about his experience launching the fourth TV network, Fox, with Rupert Murdoch back in 1986. When Rupert, who I've always described as kind of the sun god, when the sun god smiles on you, ain't nothing like it. And the way he did me a great good favor when I went to him and said, I want to be a partner in this enterprise I've helped build. And he said, there's really only one principle in

And this is a family company and you're not in my family. And I left. So I want to ask you about that moment because you're right. He says, this is a family company and you are not a member. Yeah. That was the quote. And you wrote that your delusions at that moment about maybe...

Having an opportunity to sit at that table maybe almost as a almost member of the family Crumbled what what did you think I thought I'd prior that I thought I'd been told what I think prior to Prior to him saying that did you think that you know, I think any employee any good employee thinks the company's theirs or should and is proprietary towards it and any good employee acts like it is theirs and

And it is a delusion because it isn't. One of the most challenging times in Diller's career was his court battle with John Malone, whose company Liberty Media sued IAC when Diller proposed his plan to split it up into five companies. I asked him to reflect on that court battle. I was really devastated by it because, you know, first of all, to say the least, control is a big part of my life. And I did utterly, I had a lifetime proxy.

on these shares, which meant I totally controlled the entity. And we were in Delaware court to quote, "take it away." So it went like right to my heart. So tell me when you got the apology what you felt like. I felt a good, decent man reclaimed himself. I mean, he wrote me a lovely note. When it was over, and it was not only an exhale to say the least,

which I felt good about, but what I felt very good about is this person I revered, who I'd been associated with then for 20 years or so, did the right thing in the end. Because by the way, what I didn't say is when John Malone testified, our lawyer said, "It's over." John Malone would not cove to the lies that his executives made. He told the truth. Stand Becky by, stand Andrew by. Three, two, one, cue.

The book really is I just want to say a love story because he does say in the book that he is gay thought he was gay thought that's what was going on in his life meets DVF actually doesn't like her the first time he meets her. And then meets her again.

And as he says in the book, starts making out with her like he's in high school. And it was, I think, a surprise to him that this is what happened. And I think one of the things, and we talked a lot about it, the title, Who Knew?,

really is a double entendre because it's a little bit of who knew and who knew. We talked about how I've known him for 25 years. I never asked him, thought I knew sort of, but I never really knew, but also marveled at this remarkable marriage that they have. And we're going to get to talk to him about all of that and so much more. Look, I think Barry's point that he didn't want to talk about his personal relationships, pretty valid one.

And people don't expect most people to have to disclose everything that's going on in their life at work.

why would he be held to a different standard and I think his rules were pretty appropriate too. Just the idea that he would not take a man to a heterosexual event was one of those rules, right? He had certain rules that I'm not going to pretend. I'm not going to take a woman that I'm not with. I think for him the complication was, and we talked about, for example, Tim Cook who came out publicly about his sexuality and so many others who have over the years and actually he talked about just the courage that some of those people had, but

But for him was more complicated because he never felt that he was the poster boy for one thing or the other given that he was married to DVF and the relationship was as real as any relationship. And I know you know people always sort of is as real as any relationship is as real as any relation. So it's a it's an interesting dynamic because I think there's part of him that you know today says oh you know I I wish I had the courage but

The courage to do what? To say what? Because it's a different situation. We're going to get to talk to Barry about all the headlines and everything that's going on. He's going to be live here at the desk. The book is called Who Knew? There's not a lot of books that I can say this about. It is a brilliantly written book. And it's a fascinating read. And he's right. It is a story. It's quite the story.

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welcome back to squawkpod in 2021 the little island opened off the west side of manhattan its benefactor barry diller who poured hundreds of millions of dollars into the innovative park a public pier built on top of some dramatic pillars i took a walk through the park with diller last week i know you never live in the moment but is there one of these things oh this one that create the most satisfaction for you i'm telling you something as you walk up the bridges these two bridges

As you walk, as I walk on them, and I see people coming, and they're kind of anticipatory, and then I see them leaving, and I see that they're happy, that is living in the moment. That's as close as I'll ever get.

We are joined now by a very special guest this morning right here on the set. We're going to talk about the state of the media, dealmaking, and so much more in the life so well lived by Barry Diller, chair and senior executive of Expedia and IAC, and the author of the book, Who Knew?, which is available today. You've been not on a book tour because the book, this is just the beginning. I don't know that there is such a thing as an actual tour. But my tour has been like within the 12 square miles of the city. But how have you been feeling about all of this? Exposed.

weird a bit i mean i've never it's weird to be the product if you've been making products all your life to actually be the product is a kind of odd thing to feel so i'm feeling it and i don't know it makes me feel well you know i wrote this book and and i should have known since i'm telling the story of my life that my life would be exposed well here i am surprised that it is

why do you think why are you so surprised because i'm a dope because i i i have a great ability to compartmentalize and i just even though my wife said to me get ready i said oh no no no one will care please no no no anyway yes so what has the reaction been have people reached out to you no the reactions have been i mean they've been incredibly nice and positive and all of those things but

I do see in, not in the little beadiness of people's eyes, but I do see they look at me like, "I now know you." That may be you imagining stuff, though. Of course it is. Yeah. All of this is imagining. How could I complain? It's very nice, actually. I mean, to do it is one thing, and then you never, or at least I almost never thought I would publish this, and it was only relatively recently that I said that I would.

that like 10 year or so period of trying to write the thing and You know once you do that then you press the button the rest is kind of auto it just What's the most surprising phone call you've gotten so far? I'm in my car a few days ago Coming off something and I get a no caller ID and I don't you know We probably none of us answered no caller ID, but you do but I some I I

I can't do the voice. Hi, this is Bill Clinton. And he had just, he said, I've stayed up all night. It was so incredibly sweet of him. He said, I've stayed up all night reading your book. And then he just went on about it. I kept trying to like say, gee, thank you so much, et cetera. All right, stop. It's making me run into a wall. Okay. We're going to talk about all sorts of deals that are in the headlines now, but I have one question about deals in your book.

Was there any of the deals that you talk about in the book something that you didn't want to talk about? Was there any that they had afforded? What do you mean didn't want to? Well, was there anything in the book where you were like, I'm not... Because remember, there were parts of the book I think you weren't sure you were going to publish. Oh, yeah, for sure. I mean, I don't think there was any... I think when I approached talking about probably the... Well, the third Paramount little try, I actually took out of the book. Why? Why?

Because I thought, why should I put another thing in that I didn't do rather than the things that I did do?

while we were in there for three or four months. Which is the third try? Is this the most recent try? Yeah, yeah, yeah. You mean around the Skydance situation? Yeah, around that one. Well, here we are then, so let's go for it. It's kind of the book. We can do it here. Well, no, it doesn't matter. We were in there for a few months, and I realized that it was more about duty than desire. Duty in the sense that it would be a great way to end a book, given that my life was paramount.

kind of twice. But in the end, I thought, I just don't want to do that. And so we dropped out. We would have lost anyway, because who wants to be in an auction with someone who has a better balance sheet? And Larry Ellison has a better balance sheet than I do. Didn't want to do it in the sense that it didn't make business sense from the financial side of things? No, no. By the way, I think it makes enormous business sense. I think they bought it abominably cheap. And so no, I absolutely think it...

It's there for the doing. And so, no, I think it's a perfectly legitimate economic transaction. Okay, let me ask you a more complicated one. What was that? That deal is not closed yet.

And there is a real question about whether it will close because it sounds like it'll close. Well, maybe it will. But the question is, I mean, what what Sherry Redstone and that team is going to ultimately have to do. Yes. Well, they have to effectively placate the administration you saw just yesterday. They effectively fired the head of CBS News and they pushed out the head of 60 Minutes a couple of weeks earlier. What would you do if you were in that situation?

Oh, I hope I brave it through. I hope I would. But I didn't have a guillotine at my neck as Sherry Redstone has, because for her, if that deal does not go through, I mean, she was in technical bankruptcy. So I guess you do what you have to do. But even saying that is kind of seems like wish not.

What I think is heinous is that for a stupid lawsuit, there is no one who thinks this lawsuit has any merit. At least I ain't heard anyone, maybe a plaintiff's lawyer, but even that would have to cock his eyes. So it is utterly frivolous. So you ought to think, fine, go through, sue us. But the idea that the FCC...

actually says that is then a standard for holding up the transaction. - Look, we've seen this before though. - I mean, what have we come to? Where have we seen this before?

with the AT&T deal in the first Trump administration that was put upon and put upon and put upon before you had to put everything together before it was unspun again. Yeah, and by the way, of course, eventually it happened because there was nothing to stand in its way. But it took so long to go through that process. The idea you can't fight city hall. There was nothing to stand in the way that's legitimate of this deal. Nothing. Whether they settled it or not, I don't know. All right.

Let me ask you about a different deal. Yeah. I don't know what you thought of the Charter and Cox getting together just this past week. Inevitable. Inevitable. Absolutely. And you think that deal will go through? Sure. They don't compete with each other. Why wouldn't it? And what ultimately happens then to, for example, parent company of this network, at least currently, because it's a spinoff. But I think long term people... You are all in such great shape. God bless you. By the way, let it go out.

buy the stock, which will probably trade at a very low multiple. It'll be money good really quickly. It's a great... From your lips. Why? What's the street missing? Because right now, everything linear is being discounted. Everything. What will happen, just like happened in the record business, which is you had this great deaccessioning. And then, because people wanted records...

old term, and streaming came along, it got resurrected. What will happen to these linear channels is they're going to all get reconnected into a bundle. This is not going to be a world of a la carte. So eventually, all that stuff gets reconnected, not necessarily the incredible high price points that it was, but legitimately enough to pay the bills with a lot left over. So

It's just a matter of time. Do you feel that way about all of these businesses? I mean, there's this business, then David Zaslav potentially is going to be pushing off some of his linear channels, including maybe CNN. I mean, you're going to see, you might see a lot of this. Yeah. What an opportunity. And so how long does it take to get resolved? Oh, you mean for it to...

Come back. Well, first of all, by the way, we're sitting here in five years. Wait a second. Wait, wait, wait. These are all very profitable businesses. The ability of Warners to spin this off is because it can take an awful lot of debt with it because they're legitimate businesses that have billions of dollars of cash flow. It's totally reasonable. By the way, I wouldn't spin them off.

You wouldn't know why because I think they're enormously valuable even if you're Brian Robertson you hold of voting control in the spin-off company - well No, look, I think again I think keeping them is probably better but if you're gonna spin them off and you can keep control of them which is vital because what you don't want is someone to come in and cobble them up for scrap and

if they're out there with no protection. Having Brian, the best steward, having voting control over it, protects it for the time it'll take for it all to get reconnected, which I say is three to five years. But what do I know? There's another, there is a lot. There's another question, though, about in the media business right now, which is just how valuable what people think of as the most valuable parts of these businesses really are anymore, which

which is some of the streaming businesses. So, you know, how valuable ultimately is HBO Max or, by the way, Peacock and NBC? Or you can go down the line, meaning the businesses, there are certain businesses that are being split up. I get the point. You get it. Here I go.

The businesses are all okay. They're just never going to be, they can't really be big growth businesses anymore. The old, you know, the hegemony has passed from the Hollywood quote studios. They will no longer dominate things. Everything now is dominated by the tech overlords because they really control it. Netflix, Amazon, and Apple control the entertainment business. They have, I don't know, what would you say, a hundred times, uh,

of resources of these legacy companies

And they're in control. They ain't giving it up. Doesn't mean these other companies can't survive. They will survive. They'll just be smaller entities. It reminds me of Fox coming along and shaking up the three networks, primarily that were there, and then seeing, like, football, being CBS and going to Fox. Because they could pay more because it made more sense for them. When Fox came, there were three channels, then there were four, and then there were 400 a few years later. That had real effect. However...

The old companies, the legacy companies, ended up like they did with every new technology up until streaming. They subsumed these companies and bought them in. So they still controlled everything. It's only when Netflix came in

and really ripped it away. And then Amazon came in with a completely different business model. The business model of people in the entertainment business is people come and pay you directly for your product. The business model of Amazon is joint prime. We don't really care what you watch, whatever. I mean, like you watch good stuff. But it's another business model. How do you compete with that if you're just out there making good television? We're going to take a break in just a second, but distribution.

Yes, sir. So there's Charter. John Maloney, you worked with for a very long time. Yes. There's Brian. There's others. And for a very long time, cable owned the train tracks, right? There was one set of train tracks, and that was it. Now there's Elon Musk, who has satellites in the sky. Amazon may be putting satellites in the sky soon. Obviously, the cell phone companies. Yes, what about this all? So what happens to the values of the whole sort of distribution ecosystem? Well, the...

It's no longer their lunch to eat every day. It does not mean that they can't survive. They will, but their margins are going to be affected, of course. If you have competition, what's going to happen? You're going to have to compete on price, which they will. It's not a disaster. It's just the great days when you had one railroad track that one group controlled,

Those days is over. Netflix, whatever happens after this, Netflix won. They won more than five years ago. End. The end. Well, it's not the end of the interview. We're going to come back in just a minute. The book is called Who Knew? We're going to get into more of that and so much more with Barry Diller right after this. Do check out this book. I said it's a love story, really, but we'll talk about that maybe as well. Okay, fine.

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This episode is brought to you by Schwab Market Update, an original podcast from Charles Schwab. Join host Keith Lansford for this information-packed daily market preview delivered in 10 minutes or less, including projected stock updates, monetary policy decisions, and key results and statistics that may impact your trading. Download the latest episode and subscribe at schwab.com slash market update podcast or find Schwab Market Update wherever you get your podcasts.

We are speaking with the one and only Barry Diller. His new book is out. It is called Who Knew? And it's out today. And we've been talking about I think this is actually one of the it's a great business book, but it's a love story. Can we just talk about that for a second? Sure. What do you want to know? Well, I do want to I do want to know when you did the title, what you actually thought the title was supposed to mean. The title came to me one day. You know, these things do, you know, celestially into my head.

It came, who knew? It wasn't who knew with a question mark. It was who knew. That was what came into me. And then I started playing around with it and I thought, well, yeah, okay, there is a question mark. But in some cases, but more, it's like, it's to me, this double play of both a question mark and an assertive statement, who knew?

I just thought it was a good time you knew and by the way to me One of my big advisors said you can't have that title It sounds like a Henny Youngman joke and the Catskills and it's disrespectful to a very, you know, whatever Serious book and I said, yeah, I guess that's true, but I like it. So anyway, that's it. Do you think? You knew meaning that like this whole success was gonna work out the way worse not I don't even know now

it's true i mean it sounds like noise but it is true i've never thought that one of the things you said to andrew earlier was just this idea that having one big secret kept you focused and and scared of one thing and not of anything else i think it's again i'm not saying how because it was it that it's hard to have and particularly 50 years ago god i'm sold 60 years ago to have this big secret and to have to keep or

feel that you had to have this big secret, which is a cruel thing to do for someone to feel. But it does have, like many things, like many things that you have to burden, live through, plow through, do whatever through, it did have the effect, since I had one huge secret and one huge risk, everything else was riskless. So it enabled me to do things that most other people wouldn't do because they had normal risk. What did you think was going to happen if people knew? Nothing.

That's the myth. Well, it's not completely true. Well, first of all, mine was also confused. I wasn't absolutely certain, but of anything. Of course, I knew that I had basic instincts, basic desires and all of that stuff. But when you really examine that, I think that's true of so many things. Your great fear is

usually is it will dissipate out there and nothing bad will. But at that time, there were consequences. Look, there are consequences today, of course, if you have same-sex sexuality. If you're an adolescent, it's the last thing. You just can't not even risk it. You want to be one of the bros, your guy. You want to be part of the group. And if you're not part of the group,

That robs you of adolescence, which I think is cruel. How did you feel in this book, Disney War,

You remember that? Oh, no. I was just going to ask how you felt, though, in that moment. Because in the book, it outed Barry in the book because Michael Eisner wrote actually a very lovely thing about you, suggested he become the CEO of Disney, but said that because of his sexual orientation, you need to overlook that and wrote them a memo. This whole thing about outing.

You know, I was never, I truly, once I was in my 20s, I was a kid, kid, I was hiding everything. But once I was in my 20s and living my life, I wasn't hiding anything. I just wasn't making declarations. And so I think this whole idea of actually officially outing somebody, I always thought that was terrible because I thought that was pulling someone's privacy away from them for decades.

whatever. I understood the movement and all that. But by the time that story came out, I guess it was in a book that Jim Stewart wrote in the 90s or 2000s and whatever. I mean, forget about who knew. Who cares? But I did think I did think it was a kind of cheap shot.

barry one of the things that you mentioned in talking with andrew too was just this idea of rupert murdoch it was like being with a sun god when he shined on you when he shot when he shined his light on you and you said some very nice things about john malone just how you completely um adored him and and loved him like a mentor as of this moment he's always been and he really is the smartest person in the room

And he is still at this moment, as you can see with this recent transaction, he's as he says, the phone's open 24-7 and he's answering that phone. And he's he is the master. If there is a master of media, it is John. But you are so kind to so many other people. I

do you realize how many people feel that way about you like the legions of people who we've had come through here and talk about it everybody from bonnie hammer uh to dara kashra shahi there's so many people in business who you have played that same role for i don't know if i played a role like like dr jean i i mean no whatever anyway do you think about mentoring i don't like the word i think it's too official i think natural you know natural mentoring

The word I just think is bimboish. But you get very lucky if you're in the orbit of somebody who takes a strong hand with you. You're just really lucky. And the examples of that, of course, are almost everywhere. Everybody's got somebody who took an interest in them in some way that profoundly affected their lives. And always for the better.

let me ask you a different question one of the things i didn't realize it was not sean whatever his name is that would have been an example not for the better not sean the one who's right now in jail being arrived did he yes yes um

Let me pivot off of that for a second. I don't know how, but I was going to say one of the things about this book is the, I would say first half of your career is super well documented. And I think you give short shrift, frankly, to the second half, which in many ways you've probably had arguably even more success. True. Probably. Yeah, I guess so. I mean, yeah.

You know what it is? It's the fatigue of writing. I was going to say that. You got sick of it. It's absolutely true. By the time I got there, I thought, oh, God, when is this going to be over? And then I knew it, and I came back to it many times to try to make it live more and give more detail to it. Right.

I did the best I could. It ain't good enough. It is not good enough. But it is your voice. Yeah. And the writing is so good. Oh, thank you. The excerpt and the rest of it. I mean, Andrew said this before. He would put this in the Pantheon with Shoe Dog. Which I think is one of the great... Your voice, your storytelling. You put yourself in this. I love Shoe Dog. That's a great book. What do you think? I was going to say, I think your best deal in the second half is Expedia. But I'm curious what you think. Oh, yeah.

Oh, well, Tinder is pretty good. Tinder from zero to a thousand miles an hour in about two months. I've never seen viral adoption like happened with Tinder. And Tinder, you know, we did pay fair money when we bought Expedia when it was losing money from Microsoft. But Tinder cost about $700,000, literally,

Literally, it was simply what did it cost to build that little product. We never spent a nickel on marketing. And Tinder valuation, I don't know what it is now, but it was about $15 billion at one point.

What did you think when you bought that company? Which one? Tinder. Do you have any idea? We didn't buy it. We developed it. In-house. In-house, but I thought you bought some people in. We bought nothing. We had a little innovation team in-house, and they created Tinder. And like anything, as soon as you saw it, you said, wow, this is just great. This kind of hit or miss.

that concept of finding someone you wanted to do something with. Okay, if you were going to start your whole career all over again right now, and you were 21 years old, what would you go do? What would I do? Well, I'm kind of... We are doing that at one of the companies, at IIC, which is essentially an incubation company to put its capital into things. So there are all sorts of things to do. You just wake up in the morning, you get a group of people together, you...

You have contentious, creative conflict discussions, and out pops an idea of something. I mean, there's no... Look, today, if you were choosing a track, what track would you choose?

I mean, I certainly probably would think that you've got to do something that has the chance of not being disintermediated. And don't you think in a world of AI, it's going to disintermediate everything or not? Not everything. Of course not. But as many things will come as will go. But but.

But, again, best look for things that technology is not going to be your overlord. Your overlord. Meaning that it can't disintermediate a good idea. The book is called Who Knew? It's a great one. Thank you for coming in this morning. Nice to be with you. Appreciate it. Congratulations, Barry. Thank you, thank you, thank you.

And thank you to you for listening to this podcast. Today's episode was produced by Jacqueline Korba, Katie Kramer, and Zach Valise and edited by Julie Tross. SquawkBox on CNBC weekday mornings at 6 a.m. Follow SquawkPod on your favorite podcast app platform and listen anytime.

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