On with Kara Swisher - Barry Diller Unfiltered: on Family, Fortune, Elon, Trump & AI

Episode Date: May 19, 2025

Barry Diller’s fingerprints are all over pop culture. From inventing the Movie of the Week and pioneering the television mini-series to launching the FOX broadcast network, redefining home shopping channels, and popularizing dating apps — Diller has had a hand in shaping the American experience for decades.  His memoir, Who Knew, takes readers from his difficult childhood through his meteoric rise in Hollywood and finally, his reinvention as a groundbreaking internet entrepreneur.  And although much of the press around the book has focused on Diller’s sexuality and his relationship to his wife, Diane von Furstenburg, nothing in his personal life is anywhere near as fascinating as his singular career. Kara and Barry discuss his life, his family, his approach to business, and his take on Trump and how to beat him. Questions? Comments? Email us at [e-mail] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

How long does this go? An hour. One solid hour? That's correct, Barry. This is substantive. It's substantive. Hi, everyone from New York Magazine and the Vox Media Podcast Network. This is On with Kara Swisher and I'm Kara Swisher.

Today I'm talking to honestly one of my favorite people, Barry Diller, a media mogul, entertainment powerhouse and digital innovator whose fingerprints are all over American culture. If you ever watched a TV miniseries, sang along to the movie Grease, watched The Simpsons, Booktrip Online or found love on an app, you owe Barry a little bit of gratitude. His memoir, Who Knew, has been making headlines in part because he writes about his sexuality. Barry's attraction to men was the worst kept secret in Hollywood, mostly because he didn't really try to fool anyone. Barry simply didn't say much about his love life one way or the other.

And because he's been in a loving and romantic relationship with a woman for decades, Barry is married to fashion icon Dion von Furstenberg. People like to gossip about what they assume their relationship is like. But the truth is, Barry's private life is nowhere near as interesting as his career in business. Despite never going to college and showing next to no ambition in his late teens and early twenties, Barry went from the mailroom at William Morris to an executive office at ABC. Then he became CEO of Paramount Pictures, CEO of 20th Century Fox, and eventually he became his own boss and launched IAC. The media and internet conglomerate has had a

hand in Expedia, Match Group, Vimeo, Ticketmaster, HSN, Care.com,.dash, Meredith, and The Daily Beast, just to name a few. I think it's pretty astounding that this run is still going. I'm excited to talk to him because I'm always excited to talk to him. He's a very prescient person. He has lots of contrarian attitudes that are actually contrarian and not contrarian for the sake of being contrarian. He always challenges me and I challenge him back.

And it's always an honest conversation, even when we don't agree. It's been a real pleasure to know him in many decades and as you'll find, this book, you really do get to know him in a way that I hadn't before and we're going to talk about that and more. And our expert question for Barry comes from Sam Altman, the CEO of OpenAI, who Barry has gotten to know as a friend too. So stick around. show Small Ball, I'll be breaking down the series matchups, major performances, in-game coaching decisions and game strategy and so much more for the most exciting time of the NBA calendar. New episodes through the playoffs available on YouTube and wherever you get

your podcasts. Subscribe to Small Ball with Kenny Beacham so you don't miss a thing. It is on. Barry, thank you for coming on On. I'm happy to be on On. How long? I don't know how on I'll be, but I'm happy to be on how long I don't know how long I'll be How have we known each other I Should know I was wondering that it's certainly it's got to be decades. I was really decades. Yeah, but is it really 30?

Do you remember that old you remember you reaching out to me? No, tell me okay. I will tell you I was covering the internet for the Wall Street Journal I was the first person really covering it as a big thing. Well, that I know. And I got a phone call from two people. One was from Bob Iger, who's like, can I meet you and talk to you about this internet thing? And the other was from you. And you had me come to Los Angeles.

You had just bought City Search, it must have been? Ticketmaster, one of them. I think it was Ticketmaster. And I walked into your office and right on Sunset, right? It was just off Sunset and that weird chrome building that, what's his name, build? Fred. Fred Rosen. Fred Rosen.

Yes. And I walked in and I said, and you wanted to talk about the internet. You were the first person utterly curious about what was happening. No one else in Hollywood was. No other media person was. And we sat down and I said, this is a lot of chrome. He goes, you go, this is not my office. It's Fred fucking Rosen.

And that's how it started. Yeah, well that's a good beginning. Yeah, it was. And you were curious from the get-go, whether, and you had questions about all the internet people, you were meeting them and other people weren't doing it. That's true, yes, it was. And I was very- I was lucky.

I mean, how lucky do you get when you get to be at kind of the beginning of a revolution? And you're there and you're curious. Yeah, and you got it and other people were either scared of it or ignorant. And those were the two reactions I would get. Yeah, I was going to say, I think I was really lucky, lucky to be two things there at that time, which was total luck, and lucky that I'm curious. Right.

So the reason I'm saying we've known each other for a long time, we've talked over the years about the various things you've done, all the various companies you've had, including in media and stuff like that. I have to tell you I love this book. You sent it to me early and you were worried about what people would think of it, right? Of course. For lots of reasons. How could I not be? Right, exactly. Anything you do.

Let's just read. It was right in the beginning. I'm just gonna, well, maybe I should have you read it. No, you do it. Okay, I'll do it. It was about your mom, she sent you, you're tough from the minute on your parents, which I thought was really interesting. In a fair way, I don't think it was unfair. She sent me to sleep away camp for the first time when I was four, yes, four.

I was a few years below the minimum age requirement, but she brought people who owned the camp and I stayed not with the campers, but with the camp owners in their house. For six wonderful weeks, I cozied up to the structure of a real family unit. Three years later, I went back to the same camp, but I was old enough to be in the general population. I was miserable.

I felt isolated and alone. In my desperation, I called my mother and begged her to come and pick me up. I remember waiting at the camp's entrance, sitting on a tree stump alone for hours. She assured me she would come straight away. As each car approached, I peered up expectantly, then resumed my vigil when it wasn't her inside. I stayed there all day. The head of the camp suggested several times I should come back inside, but I refused. Then it got dark and I knew she wasn't going to come. I gave up on my mother that night. There would be no rescue. There was no one to protect me. I knew then I was on my own."

That killed me. Kills me too. Here's why. I had the same experience. I had a very similar narcissistic mom and left me at school alone. And I remember thinking she's not picking me up. And it was, and I, when I read this book, I said, I thought to myself, it's nice to finally meet you, Barry Diller. Which was interesting. There's these things, and I'm sure we have all, there's these snapshots that are somewhere in there, in that brain, that are absolute perfect replicas of a moment.

And I have that snapshot of probably 12 total snapshots. Right, right. And I thought that was effective. And I want to start talking about this, because you've been a creative producer for decades. You write in this book. This is the first time I've been the product itself. It's an unnerving experience. We obviously ran an excerpt in New York Magazine and the book's about to get published.

Yes, which I didn't know I was doing. How is that for being stupid? Your publisher didn't tell you? Truly. Well, first of all, I thought an excerpt was they go in and they take a piece and they pull it out. Excerpt, right? What I didn't know, and I'm very, I mean, who gives a damn that? Yes, naive is the word when I think of when I think of Barry Doerr. No, no, believe me, I hold on to it. But this was really stupid because what I did not know and I never would have agreed

to if I had known is they take little pieces from here, here, here and here and that's an excerpt. I didn't know they had the right to do that. Yes, they do. They did that with my book too. They took pieces of it from all of them. You didn't like that. I know that.

You said I'm not, you told Maureen Dow that you've shortened your book tour because quote, I'm not. You're one of the few I haven't to cancel. I know. I would have been very angry. I would have found you and rounded you down. But you said, I'm not up for interrogation on aspects of my personal life. We'll get to that in a second because I am the least interested in that part of the story.

Maybe as a gay person. I will thank you for that. Only because, I'm going to ask you about it because about the family part because that's what was really important to me. Okay, good. You you for that. I'm going to ask you about it, because about the family part, because that's what was really important to me. Okay, good. You can do that. Probably because, one, I'm gay. I already knew you were gay, by the way, or bisexual, or whatever you want to say it.

I don't really care. And the other one, who cares? That's the other part. It's like, I don't really care. Yes, I know. And it wasn't a big secret. Why would you? Exactly.

It's none of my business. That said, obviously, it's entrancing media people for some reason. We're not going to go into that. I want to start. Isn't it interesting though, that in the, all, people haven't read this book, the people who are, who read the excerpt of it, but nobody's read the damn thing. And the amazing thing is the only thing that has been written is my relationship with a woman from which somehow they extract he's come out of the closet. And to me, I think if I've come out of the closet, it's the most brightly lit room with

a glass door. I mean, who, who, who, it's absurd. Well, nobody talks that way anymore. I mean, I think back in the day when there was— Oh, no, no. Right? I'm not talking about 40, no, 60 years ago. Jesus, I'm old.

But I'm talking about today. Why? It's amazing to me, and that's really old media folk. Right, that's correct. Anybody young or anyone who lives in the contemporary world would say, what are you talking about? Out of the closet at 83 years old? From what? When everyone has known about my life for a long time.

Well what I think it is, is that it's, I used to have people ask me, you know, Barry Diller's gay, I'm like, yeah, no shit, Sherlock. And then they go, well, he's with that woman. I'm like, he loves her. Like, he has a better relationship than you do with your husband, like, for sure. And they're closer and they're in love with each other. And they're like, how could that be? I'm like...

That's so quite amazing. I was like, what do you mean, how could it be? It's a love story. Isn't it amazing? Well, it's sort of like people ask me how I had a baby. Like, how did you do that? It's a love story. Isn't it amazing? Well, it's sort of like people ask me how I had a baby. Like how did you do that? I'm like, easily.

And actually much better so I don't have to look at your husband or something like that. And my children are gorgeous and tall because, you know, we get to pick. I want to go into the family part of it in just a minute. But I want to start with the book in your difficult childhood. You talk about your brother who is a violent abuse, is a drug addict, who died of... You talk about the lack of sense of self-import, and you do talk about your parents, sort of the lack of love in some ways and the surprises you had. Well, the lack of being a parent.

Being a parent, yes. They just didn't have a clue. So why... You end the book by saying, quote, being lucky enough to let a family build me into something resembling a person has been better than your success in business. I thought that was a pretty wonderful part and something I'd never, that I hadn't talked to you about. The idea of the family you've built with, it's Dionne Von Perch.

Dionne, yes it is. And your stepkids, Alexandre and Tatiana, and how they transfer you. I want you to talk a little bit about family so you can explain to people when they have to fixate on... Fixate on what? on the coming out part. Because you were building a family, that's what you were looking to do. Well, I don't know that I was looking to do it. For sure there was a year.

If you don't have family, how could there not be a year for a family? I mean, I went down the street to find family, you know, in my friend's parents. But that was, of course, not my family, and it was faux family, and while they may have been very nice to me in all different ways, I always had, which I didn't really realize, a yearn for a family. And it took me probably longer than many, but I was lucky enough that I met Dion and that family over decades formed around me. But anyway, it's that I didn't have an active verb here, basically. It happened to me and I wanted it. But I didn't know how to do it or take any, I don't like goals anyway, but I didn't have any practical process. It just happened

and it was kind of just natural dominoes. The book has a lot of insight and because you revolutionized multiple industries, but you say you're not a visionary, you can't see around corners, you keep saying this, your process is one dumb step forward, two bad course correcting as I went. I think you're giving yourself, you're sort of downplaying what you've done, but explain your process. I don't downplay it. It is true.

Explain that process. It's because the thing is that for me, and I love process. It's the only thing I actually really know is getting into a situation you get into out of curiosity and when you're in it, you at best, if it's a new idea, you don't know anything, nothing knows anything, and therefore you have to go truly one step after the other. That discovery, I love that. And I think through that, so I say, I don't think it's vision, I think it is bouncing off the wall this way and that way until you find a vein.

And the sweetest moment is when you find a vein that you actually understand and know that no one else does. And so you get to then make these steps and learn as you go. I've thought that the best way to be a manager is never to come in on top of an organization, but to start building an organization from yourself, meaning you are the first employee and you then in the early days you are hiring every task around you. So you learn those tasks and as you do that and build from the bottom up, you actually learn how

to manage. Whereas if you come in, as most people do, at middle levels or upper levels – And top down. And do it that way, top down, I think it's – Because it's already baked. Which is why most of those kinds of situations fail. But you don't consider that a visionary and being prescient or, you know, you write about your internal motivation.

You wrote, I wanted to count, which is all that's ever really driven me. I wanted to do something that mattered. Completely true. Why do you, when did it start to feel like you counted, did it, and why was that your motivation? Because I did not count. I mean, so obvious. All my psych stuff is just, it's almost so common that all my stuff is so obvious.

It's every iteration of classic. I mean, who else would have a nervous breakdown because they thought they were paralyzed? Right, which is such a symbolic thing to sexual whateverness. Yeah, so the counting Was because I didn't count and I and I felt that and I definitely felt that I had no self and so What did I want? I wanted that's, I would say, the biggest imagery I ever had was counting. In any way you want to slice that one. And it comes from such an obvious place.

So where was the first thing you did you felt like you did something that mattered that counted? Well, I think one of the things about that, which is different than status, by the way. Yes, completely. As well as like living in the moment, which I don't do, is that I don't even to this, look, obviously I do count. But in my little whatever, you know, that primitive brain, I probably still don't think I do. Right. So you're still barely sitting on the stump? In some ways, I think you never, I don't know, some people can leave it.

I don't think I can leave any of that. So is there a project you remember thinking, yes, this is what? There's many times that I have been realistic enough to say, aha, look, I did that. As soon as I say it, I wash it. I can't help it. Oh, wow. So give me... Well, the first big time I did it was when this movie, The Weekend,

was a complete anomaly to television at that time, so it was very discounted. And the morning, that was when you used to television at that time, so it was very discounted. And the morning, that was when you used to get ratings at 6 or 7 a.m. in the West Coast in the morning of the first movie of the week that went on the air. And it got this huge rating. Yeah. Was it Sunday, Monday, Tuesday? What was it? Tuesday. Tuesday movie of the week.

730. Yeah, that's right. ABC. And I I had of course this Wow, I Mean, I've had a lot of those wows. They don't last very long. Right, but that one. Do you remember the movie? Seven and darkness Wow about who's a horrible movie. Yeah, they're all I mean Think of more bromidic. This is the story, Seven in Darkness is its title.

It is the story of seven blind people who crash in a plane. So good. Crash in a plane on a mountain and they have to get down the mountain blind. Oh, fantastic. Seven in darkness. You need to do that again. Oh, it's a sort of missed. Who was the star?

Cloris Leachman? Oh, no. Milton Berle, of all people, who was a comedian, who none of your audience will ever know who that is, plus a bunch of B, C, and D. Well, those are the best kind. Yes. Yeah. Ex-mo. Yes. Yeah. Ex-movie people.

Yeah. So in 1986, you created Fox, a new broadcast channel with Rupert Murdoch, who has loomed large in your life. Yes. Talk about breaking through the big three that dominated for decades, because you were sort of the maverick. Look, I talked about earlier finding a vein. It took us a while.

We didn't start out, I wanted us to be an alternative network, but dumb at the moment, dumbstruck, not having a clue, other than I wanted to do this. I knew that the three networks were all alike. They'd lost their personalities. They lost. As they got more and more successful and more and more dominant, they cove to like the center. They'd lost their personalities or their distinct personalities, which they had really in the beginning of broadcasting and radio actually carried on to television.

Anyway, I thought there should be a fourth network because I thought they were all the same. I didn't actually connect the next thing, which was they had to be an alternative. We had to be an alternative to the three. We couldn't just be the four. It took us a year or so. No, a little, yeah, about a year. And putting on series like they put on series until, all of which, by the way, didn't succeed, until I read the script called

Married, which was called Not the Cosmies, which was Married with Children. If ever there was an alternative show to what was on television, then it was Married with Children. As soon as that happened, as soon as I saw it, I said, that's the vein. And then we started, and then The Simpsons came after that, and Copps and all these shows that were, and all these shows that were truly an alternative to the three networks, and that's what Birth Fox, if we hadn't have done that, we would have failed. Right. And you were looking for that, that idea, and what would you say the vein is called,

if you had to name it? But what would you, that vein you're pushing there, besides just different, what would you say it was? Edgy, contrarian, not anti-social, but not conformist social. So no one would put on a show called In Living Color. I mean, it was just not inconceivable that anybody, any of them, Which made them more creative, including the Simpsons. Well, of course, yeah, much more fertile ground.

Right, absolutely. Well, but once the book focuses on your career in film and television when you were one of the most important people in entertainment, which went after comma, Barry Diller, one of the most important people in entertainment, but you're still an employee. So when you left Fox, one of the things, I do think you are an entrepreneur,

even though sometimes you say you're not, you absolutely are, you bought a stake in a home shopping channel, QVC, and eventually became an internet entrepreneur. Along the way, you had this epiphany, and you said it to me early on in our relationship, screens don't have to be just for narrative, for telling stories, screens can interact with consumers. So why do you think so many people miss that? And where did this startling revelation come to you?

Besides that it's obvious, right? Oh no, it came to me, and there's a screen right over there, it came to me in, again, in the most serendipitous way, which is I went to QVC because Dion, my wife, was thinking about selling on QVC and she asked me, she said, you should go see this thing anyway. In Florida? No, no, no, no, in Westchester, Pennsylvania. Okay, right. And so I go to this place to just check out what is this QVC thing, and I saw this primitive convergence of telephones and television sets and computers

working together. And I saw a screen like that, a little smaller, a green screen. And on it were the visualization of the calls that were coming in as products were being put up offering products. And when a product was up, you'd see the phone lines go like this, and then they'll come down, and then they'll go up and come down. And it just struck me, huh? That's a screen. I only know screens for telling stories. So passive. Passive.

Screen, telling stories on a screen. Screens can be interactive. By the way, a new word, that wasn't an active word then. I don't even know if interactive is a word. This is 92, 93. And I was struck by that. Thank God it was then, by three years later, the internet comes along and I had this primitive understanding in my fingertips of what this was about.

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Donald Trump's been back in office long enough to shock or surprise just about anyone who voted for him at this point. Be it the signal scandal, or the tariff turnarounds, the Jeanine Pirro of it all, the way he talks about Ozempic. And he takes the fat shot drug. So rude! I'm in London, and I just paid for this damn fat drug I take I said it's not working On today explained we're asking if any of his voters are experiencing voters remorse Especially those ones who are newer to his winning coalition younger voters black voters Latin voters. We're heading to Philadelphia Pennsylvania to ask them if

regrets? Do they have a few? And just by way of spoiler to get this out of the way, the answer is yes, they do. And he takes the fat, the fat shot drug. So one of the things you said in the book, you also have a quote from Robert Woodruff, the former president of Coca-Cola, who said, the world belongs to the discontented. That really struck out. You write, the greatest single explanation of those who succeed greatly. I'm not particularly discontented, but I agree with you on this. How do you talk to young people when you ask for advice?

Because that's kind of a dire way to think about it. If you're unhappy, you'll be successful. I don't know that it's well, is it? I don't know that it's- Because I don't find you to be unhappy. I don't know that it's well, is it? I don't find you to be unhappy. No, I'm not unhappy, but I'm definitely discontented, and I think there's a big difference between the two. Okay, explain the difference. Discontented means that whatever is known, or, sorry, can I say it any better than what the word picture that forms for me into some form that

anyone can understand? Which is that if you go along with things and don't have willfulness, meaning you see something and you're willful about it because it needs to be corrected. That discontent and willfulness is the difference, I think, between mattering or not mattering. Are you discontented, would you say, constantly still? No. No? No, no. Bless so.

No, I think you are. In a good way, not in a bad way. No, definitely. Listen, I no longer, in my concept of a job, I haven't had a job in a long time. And I don't mean that as an employee. I mean, I've, to my misfortune, actually, and I look for things where I can actually go back to work as I understand it, which is very linear and very one dumb step, but mostly I've passed. You passed.

Why? Why? Yeah. I can tell from this book. Why? Because I, no, because I have other interests and I'm still interested in, I'm not interested in everyday business. It really does bore me. I mean, if you just give me an ordinary

shepherding of a successful business, please, I'll go Venezuela. But if you give me something that's got a challenge in it, then kind of I'm up for it. Okay. Let's talk about your business. You've been running IAC since your former CEO left earlier this year to run a home services company, Angie, which you spun off from IC. You recently added a board member after facing pressure. You've got an activist investor, as many people do, and board changes. The stock is down. What is your plan right now for IC? Because you are running it.

You do have a job. La, la, la. Yeah, I guess I do. But I'm not, I have very good people that have good responsibilities in the company, and so I think there's enough creative process that doesn't absolutely need me. I can stir it somewhat at the top and challenge what they come up with. But I have such a long, I've never sold any stock, so I have an endless long-term point of view with it. I'd rather the stock not be down, except that it being down from a high is healthy.

Right, was it 140? Because, because, what is it? I don't even know what it is. 40. Well, 140 at some point. It was during the pandemic. Yeah, okay. Well, silly days. But I think that if properly managed, so to speak,

that's a healthy environment. That's good. This company of ours, now 25 years or somewhat more than that, has gone through several revolutions and we spun off 11 public companies. So we are at a period now, and we've been in it for probably two years, where the two companies that we had left, both post-COVID, some self-inflicted, some conditional, have had huge problems they had to get through. And that took like two years. And we're, Angie, we spun off. That was one of them. The one that's still there, the biggest enterprise, is DDM, which is

the world's largest print and digital publisher, is doing really well now. But it had a real, listen, we bought Meredith, Joan People Magazine, and all these other magazines, and we had to bring them over to a digital model because they hadn't been digitized, and that took us about two years. But now we're outperforming every other publisher. So that's good. So we have a really good going business, and we have capital. And now, because the larder is bearer, now we've got to get new stuff.

So when I last interviewed you for the Bajas in 2023, you praised, for example, Netflix business model and said they had an evil genius for luring their competitors into overspending our streaming. Many years ago, you gave me the single best quote I've ever gotten from someone, which you said, Hollywood is so inbred. It's a miracle their children have teeth. I don't know if you remember. Did I say that? You did say that.

Oh, God. So good. It was so good. Talk a little bit about where Hollywood is because Netflix certainly shaken them up. Disney is gaining momentum and Warner Brothers Discovery's streaming efforts were profitable last year, not hugely profitable. Fox is going to launch a new streaming service. How do you look at that now?

Well, it's kind of, listen, I did say, okay, you can give me not visionary, but some prescience, which is I think more than five years ago or seven years ago, I said Netflix won. You did. And they did. It was prescient. They won. And after they won, along came two other tech overlords, Amazon and Apple, and they, with unlimited resources and a different business model, are in streaming in a parallel technology-led manner.

That has left, quote, Hollywood hegemony gone forever. It is not that any of these companies that over invest in streaming, which many did, thinking they could compete with Netflix's The Great Fools game. I'm not saying they won't build over time profitable businesses. They probably will, but they will never dominate ever again. The game is gone. Right. Gone.

And it doesn't mean they won't exist, but they will not only be smaller businesses, but the more important thing is for that word, hedge money, is that in the history of entertainment, up until this period happened with Netflix, anything that came along in media, Hollywood bought and submerged into its core. So they held this for 75 years. Right. And any VCRs came, a cable came, all of these things were sucked up through this power of these...

Sure. Just the way tech companies are doing it. Big media companies. Until Netflix. It's gone now. What it means is they'll no longer dominate media ever again. They can't. Will they still have businesses that do well? But will they have great growth? I think it's impossible.

It's impossible. So one of the things we also talked about at the time, and I think because there's another thing coming, you were working putting together a coalition of publishers to sue AI companies. Yes. And also working on an effort to get Congress to narrow copyright laws so that AI companies couldn't scrape kind of. Although you can't put your, you know, putting your hand up on the train track in front of tech is like a, you know, this is like a, it's going to get run over. Yes, but you said it was a delusion they'd make their own economic relationship with

these big entities. But in May, you did sign a partnership agreement with Microsoft and OpenAI. Vox also has a deal with OpenAI. Talk about why, when you're saying that, you can't put your hand up in front of them. What does that mean? And how do you look at AI now? Well, what you can do is, of course, you can,

it is possible, you know, my brain out loud is, it might have been possible a year or two ago to have gotten a law narrowly passed that redefined fair use, in which case the economic, the tracks that the economics went on, train tracks they went on, would have gone more to publishers. But that did not happen. Once that did not happen, then unless you define fair use narrowly, all content is going to be sucked up in the maw of AI. It's reality. Will you get paid for it as we started to get paid and you say Vox is starting and other publishers will begin to get paid?

Yes they will. Will they take anything but the tiniest sliver share of whatever is to be actually gained? I doubt it. But they will, I don't say they won't survive, but they won't giantly prosper because that's almost impossible. So AI, and I'm not going to do the bimbo of change everything we know here, but if you have, and I think more and more, personal brands will be able to survive because their brand speaks clearly and loudly.

I think Substack, for instance, or forms of Substack, or your podcast or others podcasts where there there is no possible Disintermediation for you. Yeah, there just isn't a nice little business now Now it doesn't mean that you're gonna build some giant enterprise, but can you earn? Severely large amounts of money. Yes, of course you can and severely large amounts of money? Yes. Of course you can. And brands at a higher scale than an individual, for instance, I think our People magazine brand,

so long as we invest in it and build that brand, that is our best defense against AI. But that means people will come to us directly, rather than indirectly, through search mechanisms. And that's the only salvation. Because you're making something someone wants, right? And they can only get it from you. That's what I would say.

Yeah. So long as you keep to that rather than anything generic, anything generic, anything without brand potential, individual or corporate brand potential, is going to be valueless. Valueless and therefore not. So one of the things that we have every episode as an expert send us a question sort of in that genre, let's hear yours. Hi, I'm Sam Mullen. I'm the CEO of OpenAI and a huge fanboy of Barry Diller.

Very few people manage to succeed to such an extent in one industry and it's almost unheard of to succeed so much in two industries. And so my question is, what have you learned and how have you done it? I'll add to that. It was a very nice question. In the book you write instinct and grit were all we had. I think what he was asking for is how do you shift between industries? He's probably looking for his next gig, I guess.

It's relatively rare. I did it by creating a vacuum and getting lucky enough, as I said, to land at this place where I had this epiphany about something earlier than other people got it or that it developed. So that was my experience. I think it's, I think people shifting, I think it's relatively rare. I shifted because I did not want to work for anyone anymore. I wanted something of my own.

I didn't want to continue this delusion that I'd always had that this company was mine. And that's how I acted. And when I realized that was a delusion, I wanted to see, can I do anything on my own? That was like a forcing mechanism and then once I forced myself out onto my own I Also thought I don't really want to repeat myself. Those were two things one I wanted out and one I didn't want to dancing monkey. I call it. I did. Yeah, I didn't want to just run another movie company I'd already run

Three by that time. No, two, and then I had a third with Universal for a year and a half after that. But I didn't want to do that, and I didn't want to become a producer or something like that. Right. You didn't want a big deal? No. So I created this vacuum into which something came.

So it was more negatives than it was positives. It was two negatives. I wanted out and I didn't want to repeat myself. Right. I was always saying I was a bad employee and I don't want to talk to you anymore. That's what I would say. I can't talk to you anymore. I'm tired of it.

That's good. Do you think a future Barry Diller would be able to succeed when they strike out on their own? A lot of corporations and creative decisions will be made using algorithms and AI and the things Sam is doing. Do I think it's still possible? Yeah, but I don't have a clue how. I think, I do think, as I said earlier, bimbo talk, everybody about AI.

But the implications for it are so conceptually enormous that I think, and it's all going to happen really soon, it's like that's the thing Sam says, which is when he used to say to me, when I first started knowing Sam, eight, ten years ago, and before I think he was still at Y or something. Y Combinator, yeah. And he said 30 to 50 years, and then it was 20 to 30 years. And then about two or three years ago, we said five years. Right. Which you yourself took in because you told me you were shifting your employee base and

trying to figure that out. But so it's coming really fast now. And so its consequences are going to be in the next five to ten years, I mean its revolutionary consequences are going to be in that convulsiveness in the next. I can't predict that, what that is, but I can make, can I make the analogy that is this the same as agrarian going to industrialized? I don't know, I mean, you know, this was a nation of farmers. I don't think it's as neat, but test it. So around the later part, mid-later

part, railroads came and stuff, and so there's this enormous change of rural agrarian to industrial. And it was a huge disruption. Is it an analogy to today where, by the way, many things changed, but many things opened up that compensated for that change? Are we at a period now where the kind of changes that are going to happen actually do not have positive pockets of opportunity? What do you think? And I don't have a friggin clue except that I have so much native optimism that I doubt it. Oh, wow.

That I doubt it. You doubt. My native optimism is right now, is burden cover, sat on top of because I think the consequences of this are like nothing we've seen before. We'll be back in a minute. Support for On with Kara Swisher comes from Fresh Air on NPR. Fresh Air is an award-winning podcast with host

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podcasts. How much money does it actually cost to do a home renovation? This week on Net Worth and Chill, I'm joined by Bachelorette contestant turned home renovation expert, Tyler Cameron. From having just $200 in his bank account to getting a TV show on Amazon Prime, this episode is packed with practical advice whether you're a homeowner or just hoping to be one someday. Two ways to take this.

First one is, you're going to renovate your home while you're doing it. Are you doing it to make money? If so, then I'd focus on your kitchen. I'd focus on your bathrooms Plus get the inside scoop on which projects are worth DIYing and which are better left to the pros Listen wherever you get your podcasts or watch on youtube.com slash your rich BFF I'm gonna talk about politics and I would end up talking about the book at the end the one more question about the book You were a prominent Democratic donor. We talked about a lot you said before the election President Trump was a rotten person You've always been very clear you gates learned from you

I guess when he was just talking about Elon recently saying that he's killing children across the globe You said you hoped that he would be pushed into this is that amazing? No, I love that he did it. No, but isn't it amazing Elon Musk who? I love that he did it. No, but isn't it amazing? Elon Musk, who did this flash thing, because I think it's really accurate. So US Open, and I'm in one of those boxes things. And Elon is with our little group of eight people or whatever. And there are 20,000 people in that stadium.

Yeah, and these boxes are open for people who don't know. It's not like football box. Yeah, yeah. No, no, they're all exposed. And I was just amazed. I was hardly surprised, you know, Elon's celebrity. But I'm telling you, a third of the faces in that audience were looking at him and not at this champ game that was taking place.

And whenever there was a break, I'm telling you, hundreds of people came on the road, the walkway just below us, to snappies and to say, you know, will you please sign my thing? It's the most important thing to me. It was like, and I thought, wow, I've seen a ton of celebrity in my life. I ain't never seen that one. If today he was in that box, they'd throw tomatoes at him. They would. And it's only September to May.

I've never seen anything as swift as that. What do you explain it? Why do you? Well, look, I, you know, I personally like him, but I also think, I don't know if I said this, but he's like entitled to his megalomania. For his accomplishments. He is entitled to megalomania. Unfortunately, if you wear a megalomania act, your tuning fork ear is lost. And he lost it. And so that's why he did not need doing, saying,

I want to go and cut waste out of government, but do it with a thoughtful, kind hand to come in, they just didn't even thought of it. With a chainsaw as an imagery when you're actually firing people and you are someone of vast resources, is so, forget everything else, tuneless, that this is what, that's why people would throw tomatoes at him anyway. So, do you think that Trump was the reason for it? Because you have called Trump, you said he should be pushed in the dust of your history,

you said he's an evil character. He's still going to be one of the most consequential presidents. I think he's pulled down Elon Musk and used Elon as a heat shield. I think that may be true. But you know, I don't, I, when he got elected this time, you know, in the first four years, I said I'll either move to Canada or join the resistance. I joined the resistance, I was not the biggest cheerleader, but I certainly was in that. Yeah, you were.

This time, I thought, you know, all right, give it a try. See what happens. You know, I thought this about the tariff thing, which I think it's going to end in tears. But you know what? It's a big gamble. I like big gambles. Maybe you can pull it off. Maybe manufacturing can come back. Maybe it can end taxes for people where you just simply get money from others. Okay, give it to him. Let him … don't be in this derangement syndrome, and let's see giving it a little good spirit rather than violent negative spirit and that's my attitude right now and and

You know, unfortunately when I then You know, I it's hard to maintain that attitude When you read that we are against immigrants of all kind unless they're white South are against immigrants of all kind unless they're white South Africaners. So it's not working. When you hear it, it's like, oh Jesus. Right. Oh Jesus. See, I have the feeling that he could have been a very successful president if he just

didn't, you know, one of the things I'm hearing from people is, I'm for deporting illegal immigrants but not that way. I'm for reforming government but not that way. I'm for reforming government, but not that way. Like the way they're doing it is casually cruel, strange, weird characters. Yeah, it's... Were you surprised by the in... I would say an unhinged nature of this. He's just going for it with everything, whether it's immigrants, whether it's the plane, whether...

It's pushing everything imaginably. It's pushing... It's pushing so much on the table. It's either someone or he or somebody said, we're going to do everything, full force, all at once, which is scare them all into utter submission or be able to keep changing the day's news because we've got so much that we're throwing out. I actually think it's great that he's done that. I'd rather it...

You see it. Well, better than the boiling frog, you know? I don't want to be... I don't want to slow burn. So I'd rather get it all out there Okay, let's see if any good comes of these things or anything, you know solid comes and let's make a judgment when that happens rather than in the Process of it any prescience right now where you think it's going I think it's not gonna go I As I said, I doubt it,

but I don't know yet. So to be clear, instead of being horrified by Trump, you think pushback is Trump Derangement Syndrome, or not, I can't tell. No, sorry. Do you think Trump Derangement Syndrome does exist? Because I do think that people are getting out of the way. No, no, no. Yes, it does.

Of course it exists. So that's not the successful strategy right now. I think that's, I absolutely think it's a terrible strategy. I think the only strategy for, I think the only strategy is, there are three branches of government. Those three branches of government are not on the, forget progressive, which I hate the term progressive, although parts of it, of course, I like. Who wouldn't?

But the three branches of government are all on the Republican side, on the side, I want one of them back. So all work has to go in 26 to get Congress out of being what it is now, which is a, which is non-existent. And that's the goal. Don't do anything else, don't yell, don't complain, don't go off doing really scary things, which is start doing riots that then cause reaction to riots, which cause civil war or horrible worse things. Elect a Congress that can take power back from the presidency. Presidency has too much power. No one should have that kind of power.

No individual can have that kind of power. I don't care who that individual is, but no one can have that power. No one should have that kind of power. No individual can have that kind of power. I don't care who that individual is, but no one can have that power. And the only way to get it back is get Congress. Right. Or wait till 28 and elect someone else. One of the things though that's happening in media is this bending knee thing. You've defended, for example, Sherry Redstone as she tried to settle this lesson. You know, it's so amazing. Even this morning I had breakfast with whatever, an important person, who said to me, how could

you do that about Sherry Redstone? I've had a number of people, I only did it because when someone asked me the question I thought to myself, because I know that's her situation, which is she really was in technical bankruptcy. And if it costs you settling an insane suit, okay, settle it. But I have been more criticized for that than anything as like, how could you say that's a right thing to do? I don't think you said it's a right thing to do.

It's a thing you have to do. You said you bend the knee of the guillotine to the guillotine. Right, yes. You don't want you said it's a right thing to do. It's a thing you have to do. You said you bend the knee of their gilleteen to their head. Right, yes. You don't want to get your head cut off. Right. Right. Anyway. Yeah. Yeah. All right. So. You also defended Jeff Bezos, but I'm, we're not getting into that today. Oh yes, I will do that. Yes. But you don't, but you don't need me to do it. No, I don't need you to do that. So, but is there a downstream consequence to this? To what? To these attacks on the press and stuff. You yourself are facing. Attacks on the press? The media, these lawsuits, these things. Oh my God.

You guys are getting a defamation lawsuit at Daily Beast, which you own by Chris LaSavita for defamation. Is that a problem, do you think? Because they're using it, nuisance lawsuits. Of course it's a terrible problem. Again, first of all, one of the things I really do believe is that it's only three years and some months. I want it to be shorter by getting Congress to curtail the powers of the presidency and for all of those reasons. That's now a year and a half,

right? But in three and a half years, or three and whatever months, there will be a new election and Trump will not be the president no matter what, I believe. So I'm kind of have an equanimity about this period, except that I do think there are, there's another scenario, a very dark scenario. I don't think it's going to happen, but it could happen. That's why I want the, that's why I feel so strongly about 26. But I think that the things that are happening in the media and the things that are happening in the politicizing, in the politicization that's gone so edged. So I said, and I really do, I hate the woke left and I hate the woke right.

So when we have this application now that's having this downstream effect, this can be, this could be permanent, could be. Could be. So it does need to be fought. I love Harvard. And I would, if you asked me about Harvard a month ago, I would say I hate Harvard. But this new guy said, there are lots of things wrong with Harvard that I'm going to fix, but the government isn't going to order me to do it.

I love the law firms. My sympathy will go to Sherry for guillotinous, but to law firms who are going, no, law firms who will be maybe a tenth less successful, that they folded is heinous. Yes, I agree. I hold them totally to account. Yeah, okay, two more questions. It's still a little earlier, but the jockeying for the 2020

presidential Democratic nomination started. You're still presumably on the Democratic. Is there anybody who you think could win in 28? The names would be Gavin Newsom Alexander Ocasio-Cortez Gretchen Whitmer Andy Beshear who I just met by the way Pete Buttigieg Westmore who I just interviewed Why do you not say Ginny? I got him too Josh Shapiro. No, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no, no.B. Pritzker, Gina Raimondo. Yeah, what about it? Which one of these? What do you think about the Democratic field? Oh, many of them. I mean, I don't have anyone at this moment.

I don't want to have anyone. I want someone to resonate. What do you want from that candidate? Oh, I want, if we do not have a centrist, sensible, I mean, obviously centrist left, but centrist candidate who understands, I blame the, I don't blame Trump, I blame the Democrats, I blame Biden, I blame 30 years of elitist condescending progressive extreme politics for how we got into this position. So I want the antidote to that, loud and clear. All right.

Very last question. This is a bracingly honest memoir. I expected nothing less. I think you're tougher on yourself and more open-out your insecurities than anyone could have expected. Do you think it's worth it to have done it? Do you recommend other people examine their lives carefully and share this much about themselves?

Right now, right this minute, absolutely not. Why? A month or two from now, because it's, because the truth is it's so exposing. Proxology, exactly. And I didn't, you know, my ability to come out and come out and meddle, I didn't get it. I didn't think that was going to happen. All right, it's not that I didn't think anything was going to happen. It's not that I didn't think anything was going to happen.

I just, whatever. So when I saw, and it's not the biggest, hardly news day, but when I realize I go out into the street and people know me now in a totally different way. It's that, and I've always, forget my fears of exposure at that earlier time. I've always been private. I always, I like privacy. I like that for whatever reasons. It's very rare.

But I like that, okay? It's gone. And right now I feel it like I feel... I feel exposed and... And I don't... I like what I wrote. But I don't like that consequence. Something happened on the street where someone said something you did like. When they said it.

That I did like? That you like, that you heard from someone now that you're exposed. I've heard only great things. I've heard so many great things. Isn't that great? It bewilders me because I have a hard time with that. But of course I like it and people have been extraordinarily nice in the last 10 days since the New York thing came out.

Nevertheless, I also feel exposed. and in the last 10 days since the New York thing came out. Nevertheless, I also feel exposed. Yeah. And that. You know what the problem is, Barry, and we'll end on this. They like you, they really like you. No, no, no, no, no.

All right, thank you. You have to say bye. Oh, bye bye. Bye. Bye. Bye. Bye. Bye.

Bye. Bye. On with Kara Swisher is produced by Christian Castor-Bassell, Kateri Yocum, Dave Shaw, Megan Burney, Megan Cunane, and Kaylin Lynch. Nishat Kurwa is Vox Media's executive producer of podcasts. Special thanks to Eric Litke. Our engineers are Rick Kwan and Fernando Arruda, and our theme music is by Trackademics. If you're already following the show, you count.

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