Invest Like the Best with Patrick O'Shaughnessy - Barry Diller - Building An Entertainment Empire - [Invest Like the Best, EP.441]

Episode Date: September 23, 2025

My guest today is Barry Diller. Barry is the former CEO of Paramount Pictures, Fox Broadcasting, and the founder of IAC. He has been at the center of every major media transformation over the past five decades, from creating the Movie of the Week format to building the fourth broadcast network to executing 150 internet-era deals. Barry reveals his "creative conflict" philosophy - pushing smart, opinionated people past their endurance point to generate breakthrough ideas. He also shares stories of working alongside media titans like Rupert Murdoch and Bill Gates. We discuss his current portfolio strategy, innovation in media, and how personal struggles can become professional superpowers. Please enjoy my conversation with Barry Diller.  For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:02) Early Career in Entertainment (00:06:33) Defining Moments and Fearlessness (00:09:18) Personal Reflections and Family Impact (00:12:37) The Magic of Interactivity (00:14:44) Creative Conflict and Instinct (00:19:24) Breaking Down Complexities (00:21:35) Innovations in Television (00:23:37) The Fox Network and Murdoch's Gamble (00:29:37) The Value of Money and Motivation (00:30:17) The Leap to Independence (00:32:28) QVC and the Internet Revolution (00:33:37) The AI Opportunist Approach (00:36:55) The Rise of Match.com and Tinder (00:38:57) The MGM Investment and Future of Entertainment (00:41:21) Negotiation Lessons from Lou Wasserman (00:43:47) The Simpsons: From Doubt to Success (00:44:25) The Changing Landscape of Media (00:51:53) The Kindest Thing Anyone Has Ever Done for Barry

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To see what happens when you eliminate the busy work, check out Ramp.com slash Inverc. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review along with all of our podcasts at join colossus.com. Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions, expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of positive sum.

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of positive sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc. A guest today is Barry Diller. Barry is the former CEO of Paramount Pictures, Fox Broadcasting, and the founder of IAC. He has been in the center of every major media transformation over the past five decades, from creating the movie of the week format to building the fourth broadcast network investing in 150-plus internet-era companies.

In this conversation, Barry reveals his philosophy of creative conflict, pushing smart, opinionated people past their endurance point to generate breakthrough ideas. He also shares stories of working alongside media titans like Group of Murdoch and Bill Gates. We discuss his current portfolio strategy, innovation, and media, and how personal struggles can become professional superpowers. Please enjoy my great conversation with Barry Diller. When I ask around about you, as I've done the last couple of days, lots of mutual friends, the word that comes up in every single conversation is curiosity.

Insatiable curiosity, maybe is the term that people use. And I love 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. People could try, oh, make me curious.

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, metastas, metastasize, my curiosity is in more general interest areas.

They've somehow resonated in other parts of productive life. What did you discover in the file room that got you going? I would always been interested in the entertainment business. So 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? It was kind of a mail room concept, which they brought in young, supposedly, sparky people and train them to be, quote, agents. I had no interest in being an agent. I would never

ever think I would be qualified to do that kind of thing or really have any interest. But what I was interested in was the entertainment business. And at the time, William Morris agency was 70 years old, and it was the leading agency. So it had the history of entertainment in its file room. And I got lucky enough to be able to wangle my way to basically read it from A to Z. And in there, I just read the entire place. What was it about entertainment that captivated you? It seems like that was the AI of its day, all the top talent. In a little town, Beverly Hills, where almost all of my friends' parents were involved in entertainment in one form of the other. My parents were involved in construction and building and finance things like that.

Other world from entertainment. And I was just always drawn to it. I was fascinated. I was interested in the people. They led definitely in colorful lives, to say the least. I was also interested in the mechanics of it. 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 Charles Bluorn. Can you talk about that fight that you were? had over something. After I leave William Morris and I go to ABC and I'm 23 years old, ABC at the time, there were only three networks and they had 100% of the view and each of these networks were very powerful. But ABC was kind of run like a candy store because it was the youngest of the three networks. It hadn't yet bureaucratized itself. If you wanted responsibility,

it was there. And anyway, so I'm 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, because that was a big diet of television watching then was to watch theatrical movies on television. Charlie Bluador, 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 in a meeting where he couldn't wait to get rid of the mad Austrian Charlie Blutorn to buy all these movies. And the chairman called me up to his office. I was the only one on the floor at the time and said, okay, you do this.

I told Mr. Bluorn after he would thought he'd clenched this deal to save his purchase of Paramount Pictures. And I said, I'm not buying any of these movies. they're all turkeys and I'm not doing it. And he fumed at the ears. And out of that, we found a way for us to buy some of the movies and him to create new movies and to 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 obliterated all other fears. It turned out, I had no fear of business situations. I had this big fear and that made me, Take on. Weaponized you. Everything else. Absolutely. It was a 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. So when I came up against this very powerful, and some people are quietly, demonstratively, not at face power. He was powerful in all ways and combustible. Charlie was quite young. He had the biggest conglomerate of the time. in late 60s, 70s, he was probably 40 or something, an old man to me. I found that I could argue with him. I wasn't afraid of him. Everybody else was petrified of him. We're going to talk about

the decades more of that to come, 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 two that stood out to me where I went to camp and I was horribly homesick. When I went to camp as a kid, I could just remember quaking going to it. And you tell this story about wanting your mom to pick you up and her not showing up. And then everything with your brother and the way that you described these two events, it 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 that I've read the book that I've talked to

got them talking about their shit when they were young. It's pretty quite amazing to me. The reason I wrote the book is because I thought, this is a good story. I've been telling stories all my life. I thought, it's a good story if I can tell it true. And then I thought, well, do I want to? And then I thought, well, if I'm going to do it, why would I not want? 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 two things had on you? I was at this camp and I was seven, eight. 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. So I certainly couldn't depend on my father and my brother was a sadist monster. I said, come and get me. And she said, okay, I will come and get you. It is a describable scene of sitting part to the entrance of the campground near a tree stump

and waiting hours for my mother to come and rescue me. and the waiting of it became this bitter, sad, sweet moment of me saying, I cannot depend upon my mother, which meant I can't depend upon anyone other than myself. And it was a resolve that from that moment on, I would force the world around me that I was dependent on no one, which was at that age harsh, but it was a result. a truly revelatory moment of being my own savior. How did the need for control evolve across the rest of your life? I've thought a lot about that.

I'm really not that introspective. But in writing this book, I thought a lot about that. Because I had no control over the biggest issue of my life, which was my emerging and confusing sexuality, and of course, what I wanted to do is control it. I want to say, no, turn it this way instead of that way. I want that. I want this.

I think we all have stuff that we would like to control and find our either ability to control it or not. Now, many things that come up, you can control them. So out of that desperation to control the uncontrollable, everything else in my life that I could control, I'd want to sure try. Has that gone down at all? You've been so successful in so many ways. 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 two-way interactivity. You were with probably Sam around the time of chat GPT. Very luckily because Sam Altman was on the board of one of our company's Expedia, definitely earlier than most. He showed me the magic, which was to me magic. The first thing he did is he said to Chat GPT, tell me the biography of Barry Diller in Shakespeare Sonnet.

And in a millisecond, out of that little iPhone comes back. But I had a little prep about what he was doing. But it was frigging magic. And I just was stunned. How did the two compare? Did it feel of an order of magnitude even greater than the QVC, moment of shock. Well, the greatest epiphany was I'd only known screens, movie screens, television screens, to be narrative formats, meaning that we were passive. They told you

stories. That's what screens did. I went to QVC and I saw these primitively interactive screens that you weren't passive with. You said, I like that product. You at the time punched phone codes and you ordered it up and televisions and computers. tracked it. And I thought, wow, screens can be used for something other than passive experience, narrative. Now, this is in 92, so it's three 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. Because that wasn't magic. Chat GPT me was magic. This was pragmatic. And I thought, I don't know how, but this is going to change things.

So much of life is circumstance and serendipity, moment, and whatever. By the time the internet comes along three years later, I had some fluency about it, so I was able to make it productive. 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. But some concepts like creative conflict, maybe starting with that, and your love of creative conflict. Talk to me about what that means and 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 opinion and get them clanging against each other with their opinion. And out of that conflict, because that can be conflicting, because people will say, well, I think this about that. And then somebody says, no, I think that about that, or you're a dope about that. or, oh, that's an interesting insight or whatever, whatever. So the more that conflict forges hearing interesting things, if you're a good listener, and I'm lucky, I can listen,

I can pick out of it a truth or something that I can roll with, something that makes sense to me. I 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 it a good idea or a bad idea? And that's obviously editorializing by instinct. And I have always thought that the best arranging room for that

is a group of people who are in conflict with each other, usually past their point of endurance, meaning the longer you push it, 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 that might be in that room really interested in me. Spark, I think I understand.

How would you think about edge? What was an edgy person? Edgy. Someone who has some coarseness. And I don't mean by coarseness in a pejorative sense. I mean like, I don't know, a scratch paper that creates a spark. somebody who's got some, I wouldn't call it original thought or whatever, but someone who's wielding to be on the edge of things rather than the common center of things.

Is that related to this notion of discontented and willful that you've talked to a lot about? Robert Woodruff, who was the chairman of Coca-Cola company in its great formative years. It wasn't obvious to me when I heard it many decades ago, probably 40s, 50s, 60s. He said, only give me the discontented. Those are the people I want in our organization. And it so resonated with me that, yes, of course. 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, and that's not this terrible thing. A little more interesting, this right. Is there a room of creative conflict that most stands out in your memory? where some idea came out of it? Oh, no, it's just my life. If you think about this notion of instinct, acting on instinct and not based on data or research or things like this,

why has that proven so powerful to you rather than the alternative? Because I think, if you say relative to data and research, it's good, of course, when there's a factual base that research, of course, can give you the deepest draft of that factual base. But when you're dealing with editorial

matters or new ideas or things that aren't yet, 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. That's all it can really 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, then you really have to try very hard to keep those instincts of yours as fresh and clean as you can, which 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 naivete, because it's only when you're in that state that your instincts can be applied to determining what is something interesting or not interesting. One of the things I loved hearing the story was how once you decided to do something, you would drill all the way down to like bedrock foundation

and the essence of something and then build back up from that understanding. There are really people so much smarter than me who get stuff so much quicker. For me, 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. And there are some areas that even if I try now, certain obvious areas that 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 basis understanding. Just tell me, yes, okay, two plus two is four. I got to get down to those basics before I can figure out a very complex transaction. If you give it to me midway or two-thirds of the way, all the house names people use to confuse people with everything, you never get to understanding. And I can tell you, actually, my first revelations is this is, this is when I'm in my late 20s, early 30s, and I had at the time a business manager. And I had some capital, and he would be investing it in, like, real estate transactions. He would come into my office every four or six months, whatever, and he would go through something.

I was so bored with it, because I didn't understand the fuck of what he was talking about. And he would give me this thing about this deal and whatever, and I would just basically, yeah, yeah, yeah, yeah, yeah, yeah, yeah. And a couple of years later, he's doing it to me, and I thought, I'm really a total bimbo. I said, I want to understand this transaction. I said, so let me now understand it. And I forced him to explain it from the very base of it. And he got about halfway through it.

And I said, this is stupid. And I'm not doing it. And I fired him. And it was my revelation, which is not that I didn't really know it, that's the only way I can function. If you think back to the entertainment days at Paramount and Fox, you're part of so many of them. What innovation 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 The Week, which changed television at this time.

I'm 25. Everyone thought this project would fail, and it was my project. It was an original concept. The risks were very high, and 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 then it succeeded giantly. Is there any better feeling than owning something end-to-end like that? It was fantastic because I can drill to the moment. At that time, you get ratings, which was the initial scorecard you got for whether you were succeeding or failing.

And at that time, they came overnight, like at seven in the morning. I kind of stood up all night to wait for this rating. And when I heard it in my ear, 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 the stat? Yes, yeah, I do. It was 34.

Something, which I called 35 rating. Now, this means that there were 100 million households, and this meant that 35 million household for watching this one little program. Which does not happen today. I mean, yes, actually, you'll get... I guess someone will watch a TikTok. I'm a show. I'm a mega event.

We'll do that, but that's incredibly rare. A movie every week seems logistically impossible about that kind of constraint. We made 25 the first year, 40 or so the next year, and by the third year we're making 75 of these a year. You think people should do more of that, set impossible? goals and then thrive in the constraint. Of course. The world will only handle so many.

I'd like to zoom to the Fox Days. 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 U.S. is the biggest risk taker I've known. And he was a hard-ask risk-taker who would curmudgeonly apportioned risk whatever and grueling go through it.

Rupert was a joyous, and is still, 94, a joyous risk taker. And I was lucky enough, and again, all my life's serendipity and circumstance and moment, that when I met Rupert, which is when he bought an interest in the company that I'd just become the CEO of, 20th Century Fox, And I had always wanted to start a fourth network because I thought the three networks were boring. And I thought there ought to be an alternative to them and got the opportunity. And literally, in about an hour, that's less realistically. I told him the concept of doing a fourth 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 a billion 150. And then it'll cost, I don't know. 150, 200. And he said, 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 was going on then? Why was there so much risk? Why did those things need to have a gambler, 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 America's Bible, 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. And some of them had very little exposure. Big bank, big exposure, all said yes. But the smaller ones said, no, you're too much of a gambler. It's too dodgy. And we're not going to renew. And it literally, for about a year, it teetered on

whether or not they'd renew these loans. And since there was not more credit, and because of the debt repayments and all, cash became extremely important, literally to keep the lights on. Home alone, which was this giant hit at the time, and poured cash into the company. At that time, we were very cash positive fox. It wasn't Simpsons yet. 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 period? 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, took full responsibility for it. He has no favors, yes, no whatever.

And that's a great demonstration of character. How much did he care about money as like a motivator? He adds better than I do. For me, part of the fun of being in the movie business is I love process. Another difference between us is he don't like process. He wants basically he has an idea. 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. And usually when it's more difficult, the movie has come out better. A happy set is a boring set. When you make a movie in olden times before streaming, you open it on a Friday night. And by Saturday, Sunday, this is, again, before a lot of predictive stuff comes along that can tell you what the end gross is going to be. You literally understand every theater in the U.S. and you get one by one the results from these theaters as to how it's doing on its first showing,

its second showing, it's third showing. That process, which either you're building yourself into a success, into a hit movie, because people are going to see it or not, that's a iterative process-y thing. I love that. The rhythm of it was worth the candle of making the film. I can't remember one of the early days of Foxwood's,

Rupert, I think we were talking on a Sunday of some movie. That was diehard. And I'm getting these hourly figures, whatever. And I think, Rupert comes, how's it doing? And I said, well, it's doing really well. And 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 make? He said, well, no, no, no.

Let's take the data of this and the data of that and multiply it by whatever. And what will be the final amount that it'll make? And it was like, fuck if 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, give me the final amount so I can take that amount and invests it somewhere else. Did you ever care about money?

Is it ever a motivator? Never, ever, ever. I mean, I'm an odd character, obviously, because there are definitely some of us. Although, weirdly, people who have grown up with wealth, they 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. Since it never mattered to me, now, do I like it? Yeah, sure. But I don't know, nominal interest in it. 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,

and there's this amazing line in the book that said, you're thinking about wanting to own and control the next thing to be independent. And there's a line either I am or I'm not. Just incredibly simple. What was that leap like? Maybe more interesting is that I was very successful, had been very successful in multiple iterations of it, but I'd always work for companies.

I was a corporatist. I worked for the mother church in a way. And when you do that, I think 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. That illusion can be alive forever, and who cares?

It's nice. 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, well, 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.

It was challenged. It was still doing interesting stuff. But I thought I'm either capable of being independent or I'm not. I got this thing in my head of this binary. You either are or you're not. And I couldn't turn away from it. As much as I tried, I don't know how much I really tried, but as much as ideas or convictions do dissipate,

you are or you're not, I could not accept that I wasn't. I didn't want to go. But once I realized this binary you are or you not, It forced me into action I did not want to take. And then everyone hated KVC, right? Oh, yes. Well, 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.

And then I did go to QVC, which everyone thought I was insane. This next chapter you described as being an internet opportunist, not visionary. You did something like 150 deals investments coming out of KVC. 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 the getting the flywheel going life? It wasn't hard, oddly. We created this business model.

Nothing with me is ever full blown at the first hour of the first day. But we created this 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. It was very iterative. Again, lucky in that I had this primitive understanding of convergence and the coming of the internet. And the internet came in 95. There was so many possibilities, so many ideas, the good from the bad.

And we picked more good than bad. And they just came one after the other. The ground was just so fertile. That was 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? You should just be a bias to action and to say yes rather than being picky about it? No, I think we were very picky because unlike most people at the time, who just thought getting attention,

meaning almost everyone wanted to go after volume, meaning eyeballs. Exactly. More eyeballs, you could aggregate a dis-economic cost. often. We thought, no, we treat revenue importantly as against expenses. And so we didn't do those vanny things that were good, but very much before their times and not simply 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 expense. in areas in which there is no known revenue or no big revenue to relate to hundreds of billions of

dollars of investment. Tell me how that actually is going to return. Now, of course, some of it will, 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 Allison interview on Charlie Rose, where he quotes you talking about Bill Gates, which I found from like way, way back when it was around the the whole ticket master thing, which relates certainly to the AI copyright stuff today, kind of a similar episode, history of 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 I respect a great deal. Usually, I think people do not grow. Gates has grown enormously in so many areas. empathy, but he was mean and relentless, but 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? Unlikely, at that time, he was truly ferocious. And he understood leverage anybody who's in any world of commanding, 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? 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. And I've always thought you've got to tolerate stupidity.

because in any kind of argument about what to do, what not to do is future, whatever, you've got to be stupid for 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. And if you can tease that one out and act on it, you got a shot. Was there a defining early transaction other than QBC and HSN in those days that you think back on? There are the early obvious ones now. Match.com, Personals, which was something at that time that was so early stage and so primitive.

Again, just a good idea. And there were players around it who we had kind of rejected, but then we came on this tiny little company, Texas called Match.com, and we bought it, and then it just spawned everything. If you start in a good arena, one thing spawns the next thing. And out of match came all sorts of different personal brands. And then it got to a large category. And then along came Tinder, just definition of an idea that with no investment, I don't know. I think the investment in Tinder was nickels, but absolutely virally just shut to the skies.

You've got this interesting setup with IAC now. You've spun out all these businesses. is you've been this amazing capital allocator. One thing that's so remarkable is 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. And you have 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. I think I'm irrelevant to it. Why? Because I don't want to do it anymore. I have this whole thing about dodging every aspect of age and thinking about it and conceptualizing, which I think is horrible a thing to do.

So I stay way or away from it. But the one thing I am aware of for me is that this next period, 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. By the way, this is why one of the things initially we bought 24% of MGM, and why does that appeal to me? Because you can't disintermediate it. Because 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, particularly Las Vegas, in which we have a huge share of Las Vegas,

because they have 11 properties in Las Vegas. No tech is getting between that and a human. It's like the Flintstones. I'm going back to the dark ages. But that to me, because everything else in the world that I see is able to be disintermediated by this, that, and the other thing, that isn't. And so it fascinates me.

Certainly understand how a visit to a place, a concert, something live and in person. What about betting, though? Polymarket and Kalshi in these markets, people are glued to their phones, $10 million valuation today or yesterday. Do you think that's a major threat to MGM? No, no, no, no. Because people want to go.

People want to go. Gambling part of it. It's 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. thousand seats, now and 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, all of those things. Yeah, gaming's over here, but that's the

plotting and pleasure of it. 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. What was it like being around him? I talk to John frequently. He's still the smartest one in the room. And there's just no question. John's an engineer by training. But he has such pure ability to analyze almost any situation because he brings this engineer's frame with an absolute ground understanding of every technological possibility that could possibly happen.

And he can mix all that both horizontally and vertically. When you're talking to him, it's really you're talking to a master, Craftsman. What did Lou Wasserman teach you about negotiation? Lou Wasserman was the legendary chairman of MCA, which started a Stalin agency and became Universal Studios and other kinds of things. I grew up with his daughter as my friend, and so I knew him was very young. But then when I was in my 20s and negotiating movies, I went to his office to close one deal. And I said to him, of the 60-some-odd units we were buying, because we were paying a big price. I said, can you just give us one less? And he just looked and he said, no. I said,

I didn't mean no. And he said, no. He kind of said, that's it. And we got up and walked to the door and he said to me, so let me tell you something. He said, 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. And it was the greatest lesson in leverage and in organizing in your brain how far you're prepared to go, then you must figure that out up front. You draw a line and you must demonstrate 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, Dara, Dillers, Killers, as they go on. I don't know. I don't know if they don't produce them. They grow up in your environment. I like environments

where, in all those cases, just like me, I was totally unprepared and I had no reason for anyone to give me any responsibility. They had no experience about anything. But I got dropped in the deep end of the water and I figured out of swim. I like people coming into any orbit of mind without any experience particularly, without any necessarily expertise, without having been, quote, made. And then you give people more responsibility than they qualify for. Because in that forge, you find out who swims and who doesn't. And if you have that kind of environment, out of it's going to come pretty good people. What made Eisner so explosive? Michael is this big gokey, gawky guy. His brain is so creative and his mind is so fertile

that just outspin stuff faster than his mouth can do it. Stuff comes out, 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 before, which I think is the most profitable show maybe ever in history. Longest running. Well, it's that,

but it's also probably the single most profitable entertainment product ever invented. What was it like at its origin? Well, it's origin. Everybody thought it was stupid. Yeah, yeah, yeah. And I thought it was stupid because it was a cartoon? Well, because, yes, the last cartoon, and the Flintstones before was like, I don't know, 20, 30 years before we put The Simpsons on.

So, you're going to start, are you crazy? You're going to do a half hour cartoon about these characters, The Simpsons. The first screening we had was with a bunch of suits, executives from Fox. And they said, well, you can't put this thing on the air. I mean, you're actually nuts. And you just liked it. Well, Jim Brooks, who was the creative force of the Senate along with Matt Grinning, 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're wanting to create laughter so that other people will laugh, so you're over-engaged. Jim and I are laughing.

We, by the way, had long stopped laughing at this stuff because we'd seen it 100 times. And we're laughing to create with these 12 suits of laughter in the room, and they're just solid hunks, not even moving. It was so sad. And afterwards, they said, 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 went on the air, it was smash. It's been running ever since and most profitable thing ever. Through the lens of the Simpsons, how do you think about the world of entertainment today? It just seems like nothing like that will ever happen again. I don't know that that's true. By then there's some cable networks around and it had gotten successful.

but that was a time when there were fewer options. There were still 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 Insta or watching television programs and streamers and this and that. The optionality is so much, the record keeping.

If you make an entertainment product, movie or a television series, the amount of people who see it is your revenue stream, or your reaction. Go back to the olden times, today's times, fairly, but in theaters, people coming into the place sitting in seats and they like it and they pay their money and whatever, 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 one person or nine billion people see it,

it's just whether or not we get more prime subscriptions or the Apple environment, which is keep you in the, closed circle of Apple rather than any one thing. 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 just so vastly different. It's not the best environment for making work. If you had Netflix into that category? Well, yes, of course, Netflix. This is the leader of it. Hollywood is irrelevant. worse than death.

Yes. And 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. It's just so down on the totem pole of stuff

as an organizing process, the fun of it is gone. Is glamour gone too? Never gone. It's just now in other areas. Where is glamour now? It's certainly not where it was. Now it's dispersed, of course. Now it's probably an Instagram. It's the whole hegemony has now been transferred to the world of big tech.

Is this going to be true? This is the probably 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, we'll maybe have a happy ending. I saw these amazing photo spreads from Sun Valley in the 90s

when entertainment was in its complete ascendance and blooming. You've been to these conferences your whole life. Does it now just feel like that center of gravity is entirely shifted to tech and the entertainment people are? And afterthought, they are. It is true. The cultural stuff aside. And maybe it's just an old dog talking, but the fact that it has dispersed so, there's just so much now, there's so much optionality that everything comes and goes so quickly.

It used to be there was a cultural event. Take one of the great cultural events, which was Roots, which was the seminal thing that went for 11 nights and captured 45, 50 percent 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. I want to go back to the Flintstones portfolio. So you got MGM.

dot-dash Meredith was just renamed to people. Talk about that business and print media. How have you made this a strong, it feels like an anachronism and yet is a really strong business. How did you do that? Well, we're doing it, I hope. I spent actually, just before I got here,

a really great two hours with one of our magazines is Travel Leisure, which is doing extremely well. And yet, what's happening with Google is just, it is going, they say it goes slow and then it goes fast. It's going fast. If you depend on your life 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, this one magazine of ours doing very well as million subscriptions, extremely strong digital life. But nevertheless, it's got this Google paradox hardly, which is direct searches are going. 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 and wine. And all these areas, this incredible goldmine of content, of ideas and subject areas, et cetera. And you publish them in both print and 10 million copies a year. You still have a print business and a big digital business. And it is there doing really well at it, certainly far better than a competition. But I said, back up four years ago, five years ago. And you're a travel and leisure. So you know something about the travel business, you know that's Lord.

How come you didn't create 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 and wine. If you're in the food and wine business and you know a lot about that, and you know where trends are and you know what's happening. How come you didn't do Casamigos?

If you think about our businesses that way, you succeed and fail, but you'll come up with hundreds of things to pursue that if some of them work out, you'll build a giant company. So the media becomes the marketing. Exactly right. For the product. Two closing questions for you. At the end of the book, there's this beautiful line where you got money and fame

and all that good stuff. But your life has mostly been about building and building and then your family built you into something resembling a person, quite a powerful closing line. What constituted that? What did your family do to build you up? They defined me. They became the fabric of my life.

They became the reason. My children, grandchildren, soon great-grandchildren, that's the fabric of my life. I didn't seek it. Certainly I did seek it in some way because I got it. But without it, I'd just be pathetic and lonely. The closing question I ask everybody is the same. What is the kindest thing that anyone's ever done for you?

The kindest thing anyone has done for me is to give me the security that they love me. Beautiful. Very, thanks for doing this. If you enjoyed this episode, visit join colossus.com where you'll find every episode of this podcast, complete with hand-edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at join colossus.com slash subscribe.