How Barry Diller Built Entertainment Empires

When I met Rupert, I had always wanted to start a fourth network because I thought the 3 networks were boring. He said, “Great.”

I said, “What do you mean, great?” He said, “Do it.” I said, “Well, we have to buy these stations. It costs $1.15 billion.” And he said, “Do it.” What could be better?

When I ask around about you, as I’ve done over the last couple of days, lots of mutual friends—the word that comes up in every single conversation is curiosity. Usually “insatiable curiosity” is the term people use.

I loved the part in your book about the time in the William Morris file room, reading everything you possibly could. Where did the spark come from? Is it just innate in you? Has it always been this way?

Curiosity, I absolutely believe, is innate. I guess people could try to make me curious, but I don’t know how you’d go about that. I think you either have the biology or you don’t. So much, to me, is about biology and not necessarily willful direction, but the idea that you can pull it from someplace—I’ve always been innately curious, not voraciously or crazily, just generally.

Luckily, my curiosity is not, like, “I want to understand how unwinged butterflies metamorphosize.” My curiosity is in more general-interest areas, so they’ve somehow resonated in other parts of productive life.

What did you discover in the file room that got you going?

I had always been interested in the entertainment business. That’s why I went there, because I was 19 years old. No one was going to pay attention to me, so I thought, where can I go? Who would want me?

I don’t think anyone wanted me at that time, for sure. But I thought, what could I do? They had a mailroom concept, which brought in young, supposedly sparky people and trained them to be, quote, agents.

I had no interest in being an agent. I would never, ever have thought I was qualified to do that kind of thing, or really had any interest in it. But I was interested in the entertainment business. At the time, the William Morris Agency was 70 years old, and it was the leading agency. So it had the history of entertainment in its file room.

I got lucky enough to be able to wangle my way to basically read it from A to Zed. It wasn’t curiosity; I just read the entire place.

What was it about entertainment that captivated you? It seems like that was the zeitgeist of its day.

I grew up in a little town, Beverly Hills. Almost all of my friends’ parents were involved in entertainment in one form or the other. My parents were involved in construction, building, and finance—things like that—the other world from entertainment.

I was just always drawn to it. It always fascinated me. I was interested in the people; they led definitely interesting lives, to say the least. I was also interested in the mechanics of it. It’s like anything: You’re drawn to something. I was drawn to that.

In the earliest days, when you knew you did not want to be an agent but rather create things, there was this confrontation in your book. I think you were 23 years old, with [likely Charles Bluhdorn]. Can you talk about that fight that you had?

I leave William Morris and go to ABC, and I’m 23 years old. At ABC, there were only 3 networks, and they had 100% of the viewing. Each of these networks was very powerful, but ABC was kind of run like a candy store because it was the youngest of the 3 networks and hadn’t yet bureaucratized itself. If you wanted responsibility, it was there.

I was in the program department, and no one else was doing it, so my responsibility was to buy movies from the major studio producers of movies at the time to put on television. A big diet of television watching then was theatrical movies on television.

[likely Charlie Bluhdorn], this great industrialist of the ’60s and ’70s, had bought Paramount. In order to justify his purchase, he wanted to sell all their old turkey movies. He convinced the chairman of ABC, who couldn’t wait to get rid of the mad Austrian, [likely Charlie Bluhdorn], to buy all these movies.

1. Fearlessness

The chairman called me up to his office. I was the only one on the floor at the time, and he said, “Okay, you do this.” I told Mr. Bluhdorn, after he thought he’d clenched this deal to kind of save his purchase of Paramount Pictures, “I’m not buying any of these movies. They’re all turkeys, and I’m not doing it.”

He fumed. Out of that, we found a way for us to buy some of the movies and for him to create new movies and finance the new movies. So he got intrigued with me.

In that episode, did you discover a fearlessness in yourself?

I had this one big fear about sexuality that kind of obliterated all other fears. So I was not afraid—it turned out, which was a total discovery because I didn’t know it. Of course, I’d never been in such confrontations.

I had no fear of business situations. I had this big fear, and that made me take on—

Weaponized.

Everything else, absolutely. So it was a kind of secret weapon.

It wasn’t a thrill to go through, and I’m not so sure I would advise it, but it was fodder for me. When I came up against this very powerful—and some people are quietly, demonstratively powerful, not in-your-face powerful—he was powerful in all ways and combustible.

He had the biggest conglomerate of the time, again, in the late ’60s and ’70s. He was probably 40 or something—an old man to me. Anyway, I found that I could argue with him, and I wasn’t afraid of him. Everybody else was petrified.

We’re going to talk about the decades more as we go along. But when I read your book, I was captivated and amazed by how clearly you described things in your early life that so impacted you.

The 2 that stood out to me were these. I went to camp and was horribly homesick when I went to camp as a kid. I can remember quaking at the thought of going. You tell this story about wanting your mom to pick you up and her not showing up.

And then everything with your brother. The way that you described these 2 events just blew my face off—that you were willing to be this honest in the book, but also in a way that so many people who have read the book, and I’ve talked to, got them talking about their shit when they were young.

It’s really quite amazing to me. The reason I wrote the book is because I thought, this is a good story. I know story; I know narrative. I’ve been telling stories all my life.

So I thought, it’s a good story if I can tell it true. I thought, well, do I want to? And then I thought, well, if I’m going to do it, why would I not want to? I mean, that would be crazy. So that’s what I set out to do.

What’s really surprised me is how it seems to have emotionally resonated with so many people in ways I would have never expected.

Can you talk about what happened in that camping incident and with your brother, and the impact that those 2 things had on you?

I was at this camp, and I was 7, 8, 9—somewhere in there. As you saw, I didn’t want to be there. The only person in my dysfunctional family that I thought I could have any dependence on was my mother, because I certainly couldn’t depend on my father. My brother was a sadistic monster.

I said, “Come and get me.” She said, “Okay, I will come and get you.” It is an indescribable scene of sitting in a kind of path near the entrance of the campground, near a tree stump, and waiting hours for my mother to come and rescue me.

The waiting became this bitter, sad, sweet moment of me saying, I cannot depend upon my mother, which meant I couldn’t depend upon anyone other than myself. It was a resolve that, from that moment on, I would force the world around me to know that I was dependent on no one.

At that age, it was kind of harsh, but it was a truly revelatory moment of being my own savior.

How did the need for control evolve across the rest of your life?

I think it’s because I’ve thought a lot about that. I’m really not that introspective, but in writing this book, I had to go through that and think a lot about it. I had no control over the biggest issue of my life, which was my emerging and confusing sexuality.

Yeah.

2. Seeing Chat GPT Early

Of course, what I wanted to do was control it. I wanted to say no, turn it this way instead of that way. I wanted that. I wanted this. I wasn’t that obviously argumentative on the subject, but I think we all have stuff that we would like to control and find either our ability to control it or not.

Many things that come up, you can control them. So everything else in my life that I could control, I’d sure want to try.

And has that gone down at all? I mean, you’ve been so successful.

It’s the same as always.

Oh, I think it’s even worse, or more. How does that manifest today? I was reading about the original moment of insight around QVC and the 2-way interactivity, and now—you were with Sam around the time of ChatGPT—another moment—

Very luckily, because Sam Altman was on the board of one of our companies, Expedia.

Right.

So definitely earlier than most, he showed me the magic, which was, to me, magic.

He actually, I think, the first thing he did was say to ChatGPT, “Tell me the biography of Barry Diller in a Shakespearean sonnet.” And it did it. In a millisecond, out of the little iPhone came back—and I’m telling you, of course, again, I had little preparation for what he was doing, but it was freaking magic, and I was just stunned.

How did the two compare? Did it feel like an order of magnitude even greater than the QVC moment?

Well, the greatest epiphany—I mean, my own big epiphany—was when I went to QVC. I’d only known screens—movie screens, television screens—to be narrative formats, meaning that you were passive. They told you stories. That’s what screens did.

3. Creative Conflict

I went to QVC and saw these primitively interactive screens that you weren’t passive with. You said, “I like that product.” At the time, you punched phone codes and ordered it up, and televisions and computers tracked it. I thought, “Wow, screens can be used for something other than a passive experience—narrative.”

Now, this is in ’92, so it’s 3 years before the internet gets used by people. Of course, I didn’t see that, but what I saw was interactivity in screens, and I was dumbstruck by it—probably more so than by ChatGPT, because ChatGPT to me was magic. This was pragmatic. I thought, “I don’t know how, but this is going to change things.”

I was, again, just—so much of life is circumstance and serendipity, moment and whatever. By the time the internet came along 3 years later, I had some fluency about it, so I was able to make it productive.

We’ll come back to the investing chapter of your career, but I want to flesh out some of these components of what I’ll call the Barry Diller model for approaching the world—not that it’s formulaic at all. Some concepts, like creative conflict, maybe starting with that and your love of creative conflict. Talk to me about what that means, how it manifests, and why it’s so valuable.

I discovered fairly early that the best organizational process was to get smart, snappy people in a room who have opinions and get them clanging against each other with their opinions. Out of that conflict, people will say, “Well, I think this about that,” and somebody says, “No, I think that about that,” or, “You’re a dope about this,” or, “That’s an interesting insight,” or whatever.

The more that conflict forges hearing interesting things, if you’re a good listener—and I’m lucky, I can listen—you can pick out of that something that’s not hidden. It’s just a truth or something that you can roll with, something that makes sense to you. You can say, “Whoa, huh, that’s a good idea,” because I’m always searching for an idea, and the definition to me of an idea is: is it a good idea or a bad idea? That’s obviously editorializing by instinct.

I have always thought that the best arrangement for that is a group of people who are in conflict with each other, usually past their point of endurance. I found over time that when you push people somewhat past their endurance—when they say, “Oh, please, can I go home?” and you won’t let them go home—interesting things happen after that.

The notion of spark and edge being things that you were searching for in the people who might be in that room really interested me. Spark, I think I understand. How would you think about edge? What was an edgy person?

Edge is someone who is edgy. Someone who has some coarseness—and I don’t mean coarseness in the pejorative sense. I mean someone who is like sandpaper, that creates a spark.

Someone who’s got some—I wouldn’t call it original thought—but someone who’s willing to be on the edge of things rather than the common center of things.

And is that related to this notion of discontented and willful that you’ve talked a lot about?

Discontent is—I mean, Robert Woodruff was the chairman of the Coca-Cola Company in its great formative years. Once—I mean, it’s kind of obvious, but it wasn’t obvious to me when I heard it—he said, “Only give me the discontented. Those are the people I want in our organization.”

4. Instinct vs Data

It so resonated with me. Yes, of course, if you’re not discontented—and I think if I had grown up in a different environment, and I wasn’t in this dysfunctional environment that I was in with all these other issues, I’d probably end up a shoe clerk. That’s not a terrible thing, but it’s a little more interesting this way.

Is there a room of creative conflict that most stands out in your memory, where some idea came out of it?

Oh, no. They’ve just been—it’s just my life.

If you think about this notion of instinct and acting on instinct, not based on data or research or things like that, why has that proven so powerful to you rather than the alternative?

If you say relative to data and research, it’s good, of course, when there’s a factual base. Research, of course, can give you the deepest and broadest factual base. But when you’re dealing with editorial matters or new ideas or things that aren’t yet there, there’s no research that can help or guide you. It can only mislead you, because it will essentially tell you what the past factual base has delivered to you, which has no relevance to a fresh idea.

All it can do is say, “Well, here’s why it won’t work,” based upon this, that, and the other thing. It ain’t never going to tell you why it will or should work, because it’s not knowable. It’s not researchable. It’s purely instinctive.

If that’s the realm in which you want to live the productive life, then you really have to try very hard to keep those instincts of yours as fresh and clean as you can. That means you have to fight cynicism. You have to fight being sophisticated. You have to hold on to a certain form—even if you make it up—of naïveté, because it’s only when you’re in that state that your instincts can be applied to determining what is interesting or not interesting.

One of the things I loved hearing in the story was how, once you decided to do something, you would drill all the way down to the bedrock foundation and the essence of something, and then build back up from that understanding.

But you know, the thing is—which still amazes me—is that it’s me. There are really people so much smarter than me who get stuff so much quicker. For me, I have to go all the way down. It’s not like I want to; I have to go all the way down, because until I can get to the first little building block, I don’t understand it.

There are some areas that, even if I try now—certain obvious areas that defy me—I just don’t have the capacity. But in the areas that I lived in, I had to break everything down to its base-block DNA, where I could have the basic understanding. Just tell me, yes, okay, 2 + 2 is 4. But I have to really, as dumb as that sounds, get down to those basics before I can figure out a very complex transaction.

If you give it to me midway or 2/3 of the way, with all the jargon people use to confuse people with everything, you never get to understand it. I can tell you, actually, one of my first revelations was this. This was when I was in my, I don’t know, probably late 20s, early 30s, and I had at the time a kind of business manager who took care of things outside my career life.

5. Entertainment Innovation

I had some capital, and he would be investing it in real estate transactions. He would come into my office every 4 or 6 months, whatever, and go through something. I was so bored with it because I didn’t understand what he was talking about. He would give me this thing about this deal, and I didn’t understand what he was really talking about; he was just using language I didn’t understand. I would basically say, “Yeah, yeah, yeah.”

A couple of years later, he was doing it to me, and I thought, “You know what? I’m really a total bimbo.” I said, “I want to understand this transaction. So let me now understand it.” I forced him to explain it from the very base of it. He got about halfway through it, and I said, “This is stupid, and I’m not doing it,” and I fired him.

It was my revelation—not that I didn’t already know it—that this is the only way I can function.

6. Movie of the Week Success

If you think back to the entertainment days at Paramount and Fox, what innovation—you were part of so many of them—stands out as the thing you’re most proud of, to the extent you are proud of something?

I was very lucky. The first real responsibility that I had was to make these original movies every week called The Movie of the Week, which changed television at the time. I was 25. Everyone thought this project would fail, and it was my project—an original concept—and the risks were very high. Because everybody thought it would fail, I got to do it myself.

I built up the fluency to do it, and then we did it, and it succeeded gigantically.

Is there any better feeling than owning something end to end like that?

It was just fantastic. It was fantastic because you can kind of—I can drill to the moment when I, at that time, well, you got ratings, which were the initial scorecard for whether you were succeeding or failing. At that time, they came overnight, at 7 in the morning, and I stayed up all night waiting for this rating.

When I heard it in my ear—and, by the way, it was so big that it was like, “Oh, my freaking God.”

We did it, and that was fantastic.

Do you remember how many people it was? Do you remember this stat?

7. Working with Murdoch

Yes. Yeah, I do. It was a 34-something, so I call it a 35 rating. Now, this means that there were 100 million households, and this meant that 35 million households were watching this one little program.

Which does not happen today.

No, no, no, no. See, it's not—I mean, yes, actually, you'll get—

I guess someone will watch a TikTok.

A mega-event will do that, but that's incredibly rare.

A movie every week seems logistically impossible.

Everybody thought it was logistically impossible. We made 25 the first year, 40 or so the next year, and by the third year, we were making 75 of these a year.

This is, like, impossible. Do you think people should do more of that—set impossible goals and then thrive in the constraint?

Of course. Yes. I mean, I don't know. The world will only handle so many.

I'd like to zoom to the Fox days.

Oh, sure.

What was it like working with Murdoch when he was facing hard challenges?

Well, he always faced hard challenges because he threw everything onto the middle of the table in order to challenge those challenges. He did it in Australia, he did it in the UK, and then he did it in the US. He was the biggest risk-taker that I know or have known—a kind of hard-ass risk-taker who would courageously absorb whatever risk and grimly go through it.

Rupert was, and is still at 94, a joyous risk-taker. I was lucky enough—and again, all my life's serendipity and circumstance and moment—that when I met Rupert, it was when he bought an interest in the company that I had just become the CEO of, 20th Century Fox. I had always wanted to start a 4th network because I thought the 3 networks were boring, and I thought there ought to be an alternative to them.

I got the opportunity, and literally in about an hour—less, realistically—I told him the concept of doing this 4th network, and he said, “Great.”

I said, “What do you mean, great?”

He said, “Do it.”

I said, “Well, we have to buy these stations. It'll cost $1.15 billion, and then it'll cost, I don't know, $150 million, $200 million.”

“Do it.”

What could be better? There was a moment when The Simpsons and Home Alone together effectively saved his bacon.

That's true.

What happened then? What was going on? Why was there so much risk? Why did those things save his bacon?

Well, what happened is, like a gambler—an industrial gambler, and someone who keeps trying to change things—Murdoch had overextended himself because he had taken on a huge amount of debt to start satellite broadcasting in the UK. He'd taken on debt to buy TV Guide, which at the time was like America's Bible and is now, of course, kind of irrelevant, and he paid $3 billion for it, which ended up some years later to be relatively worthless.

So he had overextended himself, and the banks didn't want to renew. It literally was the renewal of his entire loan package, and there were 50 banks, I think, that were involved all over the world. Some of them had very little exposure. The big banks with big exposure all said yes, but the smaller ones said no: “You're too much. You're too much of a gambler. It's too dodgy, and we're not going to renew.”

For about a year, it literally teetered on whether or not they'd renew these loans. Since there was no more credit, and because of the debt repayments and all, cash became extremely important—literally to keep my lights on.

Home Alone, which was this giant hit at the time, poured cash into the company. We were very cash-positive at Fox at that time. So it wasn't The Simpsons yet. The Simpsons later delivered huge returns, but it was the cash, basically, from Home Alone that kept the company from going dark before he could refinance his loan package, which took place about a year later.

What was he like in that?

I have so much admiration for Rupert. I have some issues that are not admirable about his conservatism, but during that period he never complained. He suffered enormously, but his character was that he would not show it, and he wouldn't complain, and he wouldn't blame others. He took full responsibility for it—no favors, no whatever. And that's a great demonstration of character.

How much did you and he care about money as a motivator?

For me, part of being in the movie business, part of the fun of being in the movie business, is that I love process. Another difference between us is that he doesn't like process. He basically has an idea, and he wants to get to the conclusion of the idea so he can move on to the next idea. I love process.

So you make a movie; it's not an easy thing to go through. Usually, when it's more difficult, the movies come out better. A happy set is a boring set. Anyway, when you made a movie in olden times, before streaming or whatever, you opened it on a Friday night, and by Saturday and Sunday—this is again before a lot of predictive stuff came along that could tell you what the end gross was going to be—you literally understood every theater in the US, and you got, one by one, the results from these theaters as to how it was doing on its first showing, its second showing, and third showing.

That process—you're either building yourself into a success, into a hit movie because people are going to see it, or not—is an iterative, process-y thing, and I love that. The rhythm of it was worth the candle of making the film.

I can't remember when, in the early days of Fox with Rupert, I think we were talking on a Sunday about some movie. It was Die Hard, and I'm getting these hourly figures, whatever, and I think Rupert asked, “How's it doing?”

I said, “It's doing really well.”

He said, “All right, well, so if it's doing this, how much will it make?”

I said, “What do you mean, how much will it make?”

He said, “Well, no, no, let's take the data of this and the data of that and multiply it by whatever. What will be the final amount that it'll make?”

It was like, “Fuck, I know. I don't want to know right now. I want to enjoy the process of learning about it as actual human people are coursing through and sitting in those seats.”

All he wanted to know was, “Give me the final amount so I can take that amount and do something else and invest it somewhere else.”

So did you ever care about money? Was it ever a motivator?

Never. Ever. Ever. Now, I'm an odd character, obviously, because there are definitely some of us. Although, weirdly, people who have grown up with wealth seem to be very concentrated on wealth, and money means a lot to them, even if they've got it.

In my case, because it was never an issue to me, I never cared about it. I had no practical necessity. It was probably about other things, too. Since it never mattered to me, do I like it now? Yeah, sure. But I have no interest in it. I have no nominal interest in it because it's never been a marker for me.

At the end of your executive run in entertainment, you're 50-ish or so in the early 1990s. There's this amazing line in the book that basically said you were thinking about wanting to own and control this thing, to be independent. There's a line: “Either I am or I'm not.” It's just incredibly simple. What was that leap like?

I was very successful, had been very successful in multiple iterations of it, but I'd always worked for companies. I was a corporatist. I worked for the mother church, in a way. When you do that, if you're a good employee, you think it's yours. You do have an illusion that, oh, it's mine. It is an illusion. It is not clearly yours. And that illusion can be alive forever, and who cares? It's nice. There's nothing bad about it in any way.

For me, when I realized that it wasn't mine, but I acted like it was mine, I thought, “Am I capable of actually having something that really is mine, that is independent of the mother church of the corporation?”

Over a period of time, I didn't want to leave Fox. I was doing very well. I was very happy. I was challenged. I was still doing interesting stuff. But I thought, “I'm either capable of being independent or I'm not.” And I got this thing in my head of this binary: You either are or you're not.

8. Internet Opportunist Era

I couldn't turn away from it. I mean, as much as I tried—I don't know how much I really tried—but as much as ideas or convictions do dissipate, the “you are or you're not,” I could not accept that I wasn't. That was what it came to. I didn't want to go. But once I realized this binary, “you are or you're not,” it forced me into action I did not want to take.

And then everyone hated QVC, right?

Oh, yes. Well, then—but then, of course, I did leave, and I left by design with a blank piece of paper because I didn't want to repeat myself. Then I did go to QVC, which everyone thought I was insane.

You described yourself as being an internet opportunist, not a visionary. You did something like 150 deals and investments coming out of QVC. I want to hear about how the hell you managed to do all those deals. But starting with QVC, what was so hard about it and the Home Shopping Network, which followed soon thereafter? What was it like getting the flywheel going?

It wasn't hard, actually. Oddly, we created this business model that was not full-blown at the first hour of the first day; nothing with me ever is. We created this kind of conglomerate that was an anti-conglomerate because we've spun off 11 public companies over the last, I don't know, 15 or so years.

But it was very iterative, again lucky in that I had this primitive understanding of convergence and the coming of the internet. The internet came in 1995. There were so many possibilities, so many ideas—the good from the bad—and we picked more good than bad. They just came one after the other; the ground was just so fertile. That was maybe the second revolution, and now we're embarking on the third revolution.

If you want to be an AI opportunist, is the lesson from that chapter that you should do a lot of things? That you should just be biased to action and say yes, rather than be nitpicky about it?

9. Bill Gates

We were very picky because, unlike most people at the time who just thought getting attention—almost everyone in the early internet wanted to go after volume, meaning eyeballs—we thought, no, we treat revenue importantly against expenses. We didn't do those Webvan-y things that were good but were very much before their time, and not just simply an aggregation of eyeballs.

I would approach this next super-period in the same way, which would make me very wary of what now seems to be the cat's meow, which is huge expenditures in areas in which there is no known revenue, or no known big revenue, to relate to hundreds of billions of dollars of investment. Tell me how that's actually going to return. Now, of course, some of it will, whatever, but I would be dodgy about that.

In this chapter in the ’90s, a whole new cast of characters enters the scene. There was this amazing Larry Ellison interview on Charlie Rose where he quotes you talking about Bill Gates, which I found from way, way back when. It was around the whole Ticketmaster thing, which certainly relates to the AI copyright stuff today—kind of a similar episode, history repeating—and you said something very funny, which was, “He’s young, he’s mean, and he’s not tired.”

All of those things definitely were true. Actually, that's not fair to Bill, who I like very much and respect a great deal. Usually, I think people do not grow. I think they kind of, by the time they're—

Sentient, they're relatively fully—

Gates has grown enormously in so many areas—empathy, but he was mean and relentless. He is no longer that. He's a solid citizen of today and tomorrow.

Did you ever see anyone more competitive and aggressive than him in his heyday, at that time?

He was truly ferocious, and he understood leverage. Anybody who's in any world of commanding or revolutionizing a world—which Gates certainly did—has got that quality.

Many people would love to be the person that you were in the internet era for this AI era. You did these 150 deals. What was that process like? What was the team like that found them? How much of it did you just do yourself?

We never had a lot of people, but we had a lot of stimulants, and anybody who had an idea was a good idea. You can't do good ideas until you ratchet through a lot of rotten ideas.

I've always thought you've got to tolerate stupidity, because in any kind of argument about what to do, what not to do, the future, whatever, you've got to be stupid before you're smart. You've got to go through that process of allowing dumb stuff to come out, because in the dumb stuff alongside of it is some little smart thing. If you can tease that one out and act on it, you've got a shot.

Was there a defining early transaction, other than QVC and HSN in those days, that you think back on?

There were the early obvious ones, but Match.com Personals was also something that, at that time, was very early-stage and primitive, and again, just a good idea. There were players around it that we had kind of rejected, but then we came upon this tiny little company in Texas called Match.com, and we bought it. Then it just spawned everything.

One thing spawns the next thing, and out of little Match came all sorts of different personals brands, and then along came Tinder.

This was the definition of an idea that, with no investment—I don't know, I think the investment in Tinder was nickels—but absolutely virally just shot to the skies.

You've got this interesting setup with IAC now. You've spun out all these businesses. You've been this amazing capital allocator. One thing that's so remarkable is that Buffett's observed this lots of times: Usually, amazing executives get to the promised land, which is tons of free cash flow they can do something with, and now they have to be an allocator, and they stink at it. You had the opposite experience—arguably a better allocator even than executive. You're an allocator again. It's amazing that you're still doing this through IAC. How do you think about that job in this world?

I think I'm no longer qualified for it. That's what I think. I think I'm irrelevant to it.

Why?

10. MGM Investment

Because I don't want to do it anymore. It's really for others to do. I also have this whole thing about dodging every aspect of age and thinking about it and conceptualizing it, which I think is a horrible thing to do, so I stay way away from it.

But the one thing I am aware of is that I still have a lot of curiosity, but this world we're entering is too much for my curiosity load to relate to.

I don't think I've ever conceptualized that.

Well, by the way, this is why one of the things that interested me: We own 24% of MGM. Why does that appeal to me? Because you can't disintermediate it. You give me any AI equation, and I will tell you, “Irrelevant to this.” No one's going to get between going to an MGM resort—let's put it particularly in Las Vegas, in which we have a huge share of Las Vegas. We have 11 properties in Las Vegas. No tech is getting between that and a human.

I'm actually—it's maybe going, you know, it's like The Flintstones. I'm going back to the—

I was going to say, yeah—

—to the dark ages. But I think that, to me, because it is so unlike everything else in the world that I see—almost everything else is able to be disintermediated by this, that, and the other thing, and this isn't—it fascinates me.

I certainly understand how a visit to a place, a concert, or something live in person can't be. What about betting, though? Polymarket and [likely Kalshi], and these markets—people are glued to their phones. A $10 million valuation today or yesterday?

I think that's crazy.

Do you think that's a major threat to MGM?

No.

Because people want to go.

People want to go. The gambling part of it is certainly an important part of the revenue, but it's not the most important part.

The thing is, we have these resorts that, if you just look at the depth and breadth in Las Vegas, we have 490 restaurants. We have 125 performance venues, from 25,000 seats down to a few thousand seats. We have so many ideas of things and places to do and to go and to be and to enjoy and to entertain, and all of those things. Gaming's over here, but that's the plotting and pleasure of it, to me.

The other person that I would argue built the modern media world with you is John Malone, who just came out with the book as well.

Yes.

What was it like being around him, being with him?

11. Best Negotiation Advice

Malone was, and is today—I talk to John frequently—the smartest one in the room. There's just no question. He brings to it, again, people's ingredients and their history and whatever. John's an engineer by training, but he has such a pure ability to analyze almost any situation because he brings this engineer's frame with an absolute rounded understanding of every technological possibility that could possibly happen. He can mix all that—

Both horizontally and vertically.

And so when you're talking to him, you're really talking to a master. He's a master craftsman.

What did Lou Wasserman teach you about negotiation?

Lou Wasserman was the legendary chairman of MCA, which started as a talent agency and became Universal Studios and other kinds of things. I grew up with his daughter as my friend, and so I knew him when I was very young.

But then, when I was in my 20s and negotiating movies, I went to his office to close one deal. Of the 60-some-odd units we were buying, because we were paying a big price, I said to him, “Can you just give us one less?” And he just looked at me. He said, “No.” I said, “What do you mean, no?” And he said, “No.” He kind of said, “That's it.” We got up and walked out the door.

He said to me, “So, let me tell you something. When you're in a negotiation, you better be prepared, if I say no, to blow the deal, or you're never going to get what you want.” It was the greatest lesson in leverage and in organizing in your brain how far you're prepared to go. You must figure that out up front. You draw a line, and you must demonstrate that beyond that line, you will never go.

That's how I learned to negotiate. How did you produce so many people that have gone on to great things? Eisner, Katzenberg, Kilar.

I don't produce them. They grow up in your environment, and I like environments where, in all those cases, just like me, I was totally unprepared and had no reason for anyone to give me any responsibility—no experience about anything, right? But I got dropped in the deep end of the water, and I kind of figured out how to swim.

12. Simpsons Origins

I like people coming into any orbit of mine without any experience, particularly without any necessary expertise, without having been “made” at kind of the earliest stage. Then you give people more responsibility than they qualify for, because in that forge you find out who swims and who doesn’t. If you have that kind of environment, out of it are going to come pretty good people.

What made Eisner so special?

Oh, Michael is just this big guy whose brain is so creative and whose mind is so fertile that it just outspins stuff faster than his mouth can do it. Stuff comes out a little like, “That’s goofy.” But the next thing is absolutely brilliant. It’s actual original thought, and he is capable of that.

I lost track of The Simpsons, which I think is maybe the most profitable show ever in history—probably the longest-running.

Yeah. Well, it’s that, but it’s also probably the single most profitable entertainment product ever invented.

What was it like at its origin?

Everybody thought it was stupid.

Patrick O’Shaughnessy

Yeah.

And they thought it was stupid because it was a cartoon.

Patrick O’Shaughnessy

You just liked it?

Well, Jim Brooks, who is the creative force of this along with Matt Groening, and I were in this screening. When you’re making things, and particularly comedies, and you’re in a room with other people and you’re involved in the making of the thing, you laugh harder at things. You kind of want to create laughter so that other people will laugh, so you’re overengaged.

And so Jim and I are laughing. We had, by the way, long stopped laughing at this stuff because we’d seen it 100 times. We’re laughing to create, with these 12 suits, some laughter in the room. They’re just solid hunks, not even moving. It was so sad.

Afterward, they said, “Well, you know, we’re not successful enough to just write this off. I don’t know what you’re going to do with this. You certainly can’t put it on the air.” And, of course, like many things, from the first hour of the first day that it went on the air, it was a smash.

Patrick O’Shaughnessy

I mean, it’s been running ever since, and it’s the most profitable thing ever. How, through the lens of The Simpsons, do you think about the world of entertainment today? There just seems like nothing—it seems like nothing like that will ever happen again.

Oh, no. I don’t know that that’s true. I just think that now—I mean, by then, some cable networks had gotten successful, but that was a time when there were fewer options. There were still a reasonable number of options. Today, the options are so unlimited. There’s just so much out there, whether your time is spent on TikTok or Instagram or watching television programs and streamers and this and that.

If you make an entertainment product, a movie or a television series, the amount of people who see it is your revenue stream. There’s your reaction. You go back to the olden times of today’s times—rarely, but in theaters—people come into the place, sit in seats, they like it, they pay their money, and you see them and they leave, and they come and they leave and they come.

How do you deal when the business model, instead of being the audience reaction to it, is to take a subscription to Prime, whose business model is to get you to buy products on Amazon, where they offer you, on the side, amazing movies, movies and television programs? They could not care less whether 1 person or 9 billion people see it. It’s just whether or not we get more Prime subscriptions. Or the Apple environment, which is to keep you in the closed circle of Apple rather than any 1 thing that you want.

So, if you’re a maker of these things, or if you’re in the vineyard of trying to create this stuff, it’s just dismaying that the business models are so vastly different. It’s not the best environment for making work.

Patrick O’Shaughnessy

If you add Netflix into that category—

Well, yes, of course Netflix is in that. Netflix is the leader of it. Hollywood is irrelevant. No, I mean, it’s not. People yell at me for saying that. First of all, it used to be that all these companies did was make movies and television shows, from the top of their executives to the bottom. Now, making the product is the 68th or 78th division inside very large enterprises. So it’s just so down on the totem pole of stuff that it makes the process—

Look, the fun of it is mostly as an organizing process. The fun of it is gone.

Patrick O’Shaughnessy

Is glamour gone too?

Gone. It’s just now in other areas.

Patrick O’Shaughnessy

Where is that? Where is glamour?

Certainly not in Hollywood, where it was. But that’s—you know, now it’s dispersed. Of course, now it’s probably on Instagram. It’s in other things, but it’s not that. The whole hegemony has now been transferred to the world of big tech.

And is this going to be true—and this is probably the biggest question of AI—because it is possible that our entire worlds will be subsumed by further advances, AI advances of big tech, in which case, in the end, we’ll all be a simulation anyway. And as one of my friends said, maybe we’ll have a happy ending.

Patrick O’Shaughnessy

I saw these amazing photo spreads from Sun Valley in, like, the ’90s, when entertainment was in its complete ascendance and blooming. You’ve been to these conferences, these sorts of conferences, your whole life. Does it now just feel like the center of gravity is entirely shifted to tech, away from the entertainment people?

13. Publishing In AI Era

Completely, completely shifted. And, after all, it is true, the cultural stuff aside—and maybe it’s just an old dog talking—but the fact that it has dispersed so that there is just so much now, there’s so much optionality, everything comes and goes so quickly.

It used to be there was a cultural event. Take one of the great cultural events of this era, which was Roots, the seminal thing that went for 11 nights and captured 45% to 50% of the population of this country and lived in the cultural environment for months. You do good work today, it’s here today, it’s gone in the next hour.

Patrick O’Shaughnessy

So, you’ve got IAC, Dotdash Meredith, which has People?

Yes.

Patrick O’Shaughnessy

Talk about that business. In print—it’s print media, in many cases—how have you made this such a strong business? It feels like an anachronism, and yet it’s a really strong business.

Yeah. Well, we’re doing it, I hope. I spent, actually, just before I got here, 2 hours with Travel + Leisure, which is doing extremely well. And yet publishing—all publishers—what’s happening with Google is just—it is going, you know. They say it goes slow and then it goes fast. It’s going fast. I mean, it really is.

If you depend on your traffic from Google, from search, you’re going to be close to extinct if that’s what you do. And that’s a huge issue. But directly to the question, we were talking, and this one magazine of ours is doing very well: 1 million subscriptions, extremely strong digital life, whatever. Nevertheless, it’s got this Google paradox, which is direct searches are dying.

So I said to the creative people, “Don’t you have to kind of invert your business? You create content, from People magazine to Food & Wine to all these areas—this incredible gold mine of content, of ideas and of subject areas, et cetera. And you publish them in both print and make 10 million copies a year. It’s more than that. Anyway, whatever. We still have a print business and a big digital business, and they’re doing really well at it—certainly far better than their competition.”

But I said, “Back up 4 years ago, 5 years ago, and you’re Travel + Leisure. So you know something about the travel business, and you know that lure. How come you didn’t create The White Lotus? How come it didn’t come out of you? Because think of what would have happened if it did come out of you. And there’s no reason it didn’t, other than you have not inverted your business.

“We own Food & Wine. Why didn’t, if you’re in the food and wine business, liquor business, or the whatever-drinking business, and you know a lot about that—you know where trends are and you know what’s happening—how come you didn’t do Casamigos?”

So, if you think about our businesses that way, then you succeed and fail, but you come up with hundreds of things to pursue that, if some of them work out, you build a giant company anyway.

Patrick O’Shaughnessy

So, the media becomes the marketing.

Exactly.