From Hollywood to High Tech: Barry Diller’s Remarkable Path

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From Hollywood to High Tech: Barry Diller’s Remarkable Path

Welcome to Remarkable People. We’re on a mission to make you remarkable. Helping me in this episode is Barry Diller.

Barry is no ordinary executive; he’s a force who’s reshaped industries from the silver screen to the search bar. As the former chairman of Paramount Pictures and Fox, and now the leader of IAC and Expedia, his influence has touched millions of lives—often without them realizing it.

In this episode, we explore the bold decisions, strategic risks, and creative instincts that have defined his career. Barry shares how growing up in a dysfunctional family taught him resilience, why hiring unproven talent pays off, and how to spot a truly great idea.

We also dive into his new memoir, Who Knew, which offers an unvarnished look at his journey—complete with moments of triumph, missteps, and plenty of surprises. It’s a testament to the power of curiosity, adaptability, and trusting your instincts in a rapidly changing world.

Whether you’re an aspiring entrepreneur, a creative professional, or simply someone who loves a good story, Barry’s insights will leave you thinking differently about success.

LISTEN TO THE EPISODE HERE

Please enjoy this remarkable episode, From Hollywood to High Tech: Barry Diller’s Remarkable Path.

If you enjoyed this episode of the Remarkable People podcast, please leave a rating, write a review, and subscribe. Thank you!

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Guy Kawasaki:
Hello. My name is Guy Kawasaki, as you all know, and I'm the host of the Remarkable People podcast. We go all over the world looking for remarkable people to capture their wisdom and their innovation and inspiration. And today we have someone, I think it's fair to say, of the legendary status. His name is Barry Diller, and he is legendary in the television and movie business.
He really shaped and reshaped those businesses. I also would say that he had a tremendous impact on online commerce and e-commerce. And he's the chairman, or he was the chairman of Paramount Pictures and later Fox, and he oversaw some of the most popular and successful movies like Raiders of the Lost Ark, Grease, Die Hard, which is my Christmas movie and Saturday Night Fever when everybody said John Travolta couldn't go from TV to movies.
Today he chairs IAC and Expedia, and he remains one of the most influential people and unpredictable people in media and tech. Is that a fair introduction for you, Barry?

Barry Diller:
It is a little overwrought, but it's okay. I can live with it.

Guy Kawasaki:
And he's the author of this book. This book is called Who Knew. We'll get into that. I love the title, Barry. That was a very clever title.

Barry Diller:
Thank you.

Guy Kawasaki:
So Barry, I wanna start, believe it or not, with Danny Thomas. And as I read your book, it seems to me that Danny Thomas got you that first job at William Morris, and then at William Morris you were in the basement or someplace and reading all the deals, and that gave you a foundation for your career. Is that an accurate retelling of that story?

Barry Diller:
Oh, completely. I was very lucky that I grew up, one of my closest friend's father was Danny Thomas, and so I grew up as much in their houses as in mine. And when I got to be nineteen and I had no clue what to do other than I was interested in the entertainment business, I thought, I wanna learn about it least.
I didn't want to be an agent. But the William Morris Agency, which was the largest and longest established, I think at that time, probably seventy years or so. And this is in 1960 something, and I got this job because of Mr. Thomas.
At that time, there were, obviously, this is way pre-digital, there were file rooms and this huge file room which had hundreds of file cabinets and in those file cabinets was the entire history of the entertainment business.
For the next three years, I ignored my little mail room job and I basically, I read the file room and that gave me this extraordinary foundation for understanding the very basics of the world that I was interested in.

Guy Kawasaki:
I could make the case that quote, “Who knew that reading all those files in William Morris' basement would lead to this foundation,” which would lead to your career. There are many instances of the concept of ‘who knew’ in your book. I have to say I love that concept. I interview fifty-two people a year.
That means I read fifty-two books a year usually, and honestly, don't tell the other fifty-one people usually I skim those books. Your book really sucked me in, and I swear I read every word of that book, Barry.

Barry Diller:
Oh, thank you.

Guy Kawasaki:
And bear it. After I finished the book, I said “Is there anybody who's a mensch in your life other than Danny Thomas? Because it sure looks like there was Danny Thomas and the rest of the industry is a bunch of gonifs.”

Barry Diller:
I have only worked for really very few people. All of them could be described as mensches. All, well, maybe one exception.

Guy Kawasaki:
I mean you, are you trying to tell me that Martin and Marvin Davis are mensches?

Barry Diller:
First of all, the only one that I worked for was Martin Davis, who was a rat of the kind. Marvin Davis I didn't really work for because, I guess technically my agreement with him, he was the person who, quote “owned,” he didn't really own it, but promoted himself as owning Twentieth Century Fox which I left Paramount to join in 1984.
But my agreement with him was, I only had to speak to him once a year and he couldn't talk to anybody in the company, so I never quite thought I worked for him, but he was also a rat. The two Davises. Two bad Davises.

Guy Kawasaki:
Is this something I cannot ask about because much of the book has to do with your sexuality. Is it okay for us to go there in this interview? Yeah.

Barry Diller:
Do whatever you want.

Guy Kawasaki:
So yeah. Is this book the first time you really confirmed your sexuality and, has there been any positive or negative at this stage?

Barry Diller:
I don’t know about confirming it. As they say, you might notice that there's no question mark in the title Who Knew. It's not a question. It's actually Who Knew. And everybody knew about my life. I never hid my life. I never made any declarative statements because I thought I was too confusing.
It'd be a very long paragraph. I wanted to write the book because I just thought it was good story. So in telling that story, of course I had to talk about my life, and I did so directly and I’m kind of amused that a lot of the early reportage about it, a lot of the early coverage of it was about my sexuality, which I think for someone who's at my age is a rather curiously interesting thing for anyone to care about.
There it is, but I'm not sensitive about it.

Guy Kawasaki:
As I was reading the book. Okay, so have you been on an NPR interview for this book?

Barry Diller:
I think so.

Guy Kawasaki:
I guess it made a big impression on you. I hope when people ask you if you were on Guy Kawasaki's podcast, you'll remember. But

Barry Diller:
Okay, I’ll try. For sure I will. Your name is more memorable to me than NPR.

Guy Kawasaki:
When you listen to many NPR interviews, it's always these kind of softball questions, and I'm gonna hit you with a softball question, but I really want a hard ball answer. Okay. So one of the typical NPR or softball questions is: why did you write this book?
Now I'm asking you this question but understand that I'm coming at that question from the direction of Barry, you don't need the money. You don't need the credibility. You don't need the exposure. Why would you bother writing this book? Is it catharsis? Is it revenge? Is it boredom?

Barry Diller:
No, no, no.

Guy Kawasaki:
What is it?

Barry Diller:
It's quite a simple answer. I know a lot about storytelling. My life has been involved with telling stories and I don't know, maybe fifteen years or so ago, ten years ago, something like that I thought, the arc of my life is just a good story.
It's a good narrative. And then I thought, can I tell it? And the first thing is I thought, if I'm gonna do it, of course I have to tell it true. I'm not doing it for any other reason. And as I started to do it, I didn't think I'd ever really publish it. I just thought, I want to see if I can get the story down.

And after putting it away and bringing it back after a year or two or months putting it aside, the last couple of years, I thought, you know what? I think I will publish this. And the reason for doing it was purely, it's a good story. It's a good cracking drama, and I like drama and it's mine.
And I thought, if I wait too long, I'll never tell it, so why not tell it? That's the full and complete answer.

Guy Kawasaki:
Tell me somebody bought the movie rights.

Barry Diller:
No, there are no movie rights for sale. I'm not doing that.

Guy Kawasaki:
I'm seventy-one and I have this attitude that I picked up in your book, which is, I just don't give a shit anymore. I don't give a shit what people think. What are they gonna do to me? So tell me, Barry, that just oozes out of that book. I've read many memoirs and it's always about, yeah, I knew exactly what I was gonna do.
I was a visionary. I picked this; I did this. I'm a perfect person. That's not at all your memoir. I've never read a memoir like this.

Barry Diller:
But it wouldn't be the truth otherwise. And as I say, a lot of people who do these books, successful businesspeople let's say, I think they do it for fine reasons, but often it's to say, “I did this and I did that, and because I'm telling it to you, I'm teaching you something and you can use it.”
They’re often self-help books or they can be in some cases just books of ego. Here, look at how successful my life has been, et cetera. And I think that's fine. I don't have anything against it. I find it boring, but it's not some bad thing. Particularly a few of them Bob Iger's books, I think, which have been instructive.
Certainly Jack Welch wrote a very instructive book that about his life but also Jack was really a teacher. I'm not a teacher, I'm just a not terrible storyteller. And so because of that, I didn't have anything promotional in my mind. I've had certainly a lot of success I don't write it immodestly, but the story of those successes, all of which were founded in some parts of failure, is just part of a good story.

Guy Kawasaki:
It is truly an excellent story. I have to ask you, because I just love the title, just the, double, triple, quadruple entendre of the title.

Barry Diller:
Yes.

Guy Kawasaki:
I know the way you introduced the title; the first way was, I think it was when Leonard Goldberg said it after watching you go toe to toe with Charles.
And okay, so I understand he could say that “Who knew little Barry would be this mocker someday?” But who was the person who said, “God, that's the title.” Who picked those two words?

Barry Diller:
I will tell you, certainly about a year ago, I think. Literally one day, and it wasn't when I was writing the first description and when I used the words, who knew. But one day it popped into my head, the two words popped.
That didn't come from any other place then they just appeared. And as soon as it did, I thought, oh, that's interesting. And then over the next months, the more it worked around my head, I thought, wow, it has so many meanings for me.

Guy Kawasaki:
Yes.

Barry Diller:
And I thought, I'm gonna do this. And one of my editors, was a good friend of mine and someone I do listen to a lot, was very smart, said, “You cannot use this title. It's frivolous. Your book is more important than that. This is like a catskill joke. Don't do it.” And harangued me for about a month about not doing it. And in the end I said, “You know what? Sorry. I like it.” That’s how it happened.

Guy Kawasaki:
Barry, that editor was wrong because as I said, I read every page of this and there's so many who knew-isms? Who knew that Barry would be Barry the mocker? Who knew that reading files in William Morris' basement was gonna be good?
Who knew that finding the right woman was gonna make you change your identification or at least, I don't know, straddle it more? And who knew that John Travolta could make the transition to movies? Who knew that Bruce Willis, there's so many who knew-isms in this book. I love that.

Barry Diller:
I am glad. I’m glad that I did right.

Guy Kawasaki:
Who knew if Guy Kawasaki's right?

Barry Diller:
But I’ll accept that you’re right.

Guy Kawasaki:
This is an aside, but when I first picked up the book, the picture of the inside cover there is of Little Island, and it's kind of a test. If you don't know what that picture is, it means you haven't read the book to the end. So clearly I passed that test but was it a conscious decision not to put a little caption that says, “This is Little Island in New York and Barry's?”

Barry Diller:
I never thought of it. What happened is that when they were designing the book, and this is I guess a year ago or so, I had, I don’t know, read some other book. I don't even know what the book was, but when I noticed they had something. I later heard the phrase endpaper, which is the inside cover. And the outside cover, you could actually make a picture. And I looked at it. So I called up and I said, “Can I make pictures of those?”
And they said, “Of course you can.” I said, “Oh, that's great because not many books do that.” And so I've sorted around pictures, and I thought, ah, I like that there's a picture of the island, which I like. I thought that was really pretty. And then there's a picture that Annie Leibovitz took of me that we didn't choose for the cover as the end cover. And I never thought about titling them.
I just thought they were nice pictures. They're art.

Guy Kawasaki:
I really thought, oh, Barry is so sly, he's putting that picture there and he is gonna figure out who read the end of the book, because that's the only way you can figure that out. Okay. I can't tell you that my podcasts are linear and go straight from a to b. So I'm gonna go down a few rabbit holes.

Barry Diller:
Go wherever you want. It's fine with me.

Guy Kawasaki:
Okay. So I am really curious, what is it like to be photographed by Annie Leibovitz, because there's several of them in that book. So what is that like?

Barry Diller:
First of all, she has been in me and my wife's life for decades and decades, and she's a good friend of ours. And over the years, for, I don't know, Vanity Fair pieces or other pieces. I think she exclusively worked for Vanity Fair for a while, and she would do these pieces Vanity Fair and I would somehow be in them.
Having your picture taken by Annie is just to obey what she tells you to do because she's very clear and very strong. Best example of that is what she did with Queen Elizabeth, who I think in the only probably of a very long and glorious life, only time Queen Elizabeth was ever seen to be angry and unpleasant was towards Annie Leibovitz, who made her change her costume few too many times.
Anyway, so. You get used to being photographed by Annie and doing what you're told. And when Diane and I got married, Annie said, “I'm gonna come and take your wedding pictures.” She took a whole series of pictures because we did not get married in the big production.
We just down to city hall and got married. But she took the pictures and, she's done that several times for us.

Guy Kawasaki:
I wonder if she ever took a picture of Steve Jobs, because that would be two monumental eagles going at it.

Barry Diller:
I don’t know. She's taken pictures of almost everybody of any note.

Guy Kawasaki:
Because Steve Jobs is a controls freak’s controls freak. So that would've been very interesting.

Barry Diller:
She would've won.

Guy Kawasaki:
I don't know, Barry. I might debate you on that one.

Barry Diller:
I knew both. Yes.

Guy Kawasaki:
Okay. You trumped me there, no pun intended. Listen, part of the pain, you discussed that you really had no brothering from your brother. You had no fathering from your father. No mothering from your mother, and yet you say that these negatives, it helped prepare you for your career.
So walk me through that. How did that sort of dysfunction in your early family help you in your career?

Barry Diller:
I think two things can happen. I think everybody gets some dysfunction or some certainly pass through some difficulties growing up. I had a dysfunctional family and in kind of I think somewhat an extreme, not that they weren't nice people, they were, but they had no parenting. And their parents had no parenting, and they had no clue what to do as a parent.
But I think two things can happen. One is you've totally fall apart and almost never recover. And the other is it forces you not only to be independent, but it also, for me, the things that were difficulties in my childhood were things that gave me enormous advantage all throughout, but certainly when I started my little career. They gave me superpowers.
And so as painful as a lot of it was, the tools that I gathered from the dysfunction were really the tools to success.
One is that, in my little body, I needed to please my mother. So I learned how to do that. I learned how to seduce her, and please her. As I started in my twenties, of course nobody wanted to pay attention to me, I used that. I didn't use it.
I just had this ability to please people and be particularly, in acuity, know what paths there were towards pleasing them and getting them to pay attention to me. So that was one and another was that because I had one big fear growing up, a fear, this is in the sixties and seventies, the fear of the reveal of homosexuality. If you have a big fear, it allows you that all business risks and issues of failure.
I wasn't afraid of that at all. I had a bigger fear than that. And so that was probably more than anything what gave me real propulsion is that I was able to take risks. It wasn't courage, it was biology and that I didn't think of these things as risky, and they're endless pieces of all.
I mean, that's a couple of examples. I could go on and riff more.

Guy Kawasaki:
As I read your book, I am a business book writer, and everything for me comes down to pulling out little recommendations and tactics and you didn't do that per se in the sense of a business writer would say lesson one, lesson two, lesson three.
But I have compiled for you, Barry, the gospel according to Barry. And I'm gonna ask you about some of these main gospel points so that you can riff on them and explain them. Okay. Because I think there's a lot to learn from your book. So let us begin the gospel according to Barry. So number one is that the idea is the key.
It trumps the actors; it trumps everything else. It's the idea. And I would say in the tech business, I think it's the same thing. So talk about how the idea is reign supreme.

Barry Diller:
I think that the discipline, it sounds like a bit of a bromidic thing. The idea, of course, the idea is important, but to me, a crunching down on the purity of an idea is absolutely the process. The only process I know. And that means that, you don't listen to research, or data.
You listen to your instincts. And your instincts are, if you're lucky and you're not cynical because cynicism destroys instinct I think, if keep a kind of naivete and you're open and then you create a situation where you get a lot of people clanging around about a particular idea, is it good idea?
Is bad idea? Will it work? Will it not work? What are the problems with it? Et cetera, et cetera, et cetera. And in the cacophony of that, if you're listening and you keep your instincts kind of fresh, you can recognize better what is a good idea and what isn't.
And since no one can tell the future, I believe about much of anything where there's editorial matters at hand, where there's not a factual absolute certainty of the future then all you got is your instinct and all you got is your ability to separate, make the determination of a good idea or one that isn't. And I think that's true in creative affairs, and it's been true for me very much in business affairs.
I think two, if you're analyzing a business or an idea for a business or buying a business, I found, at least for me, that too much of a factual base or projections that are no projections are worth the paper they're not written on, anymore. But all of those processes, overeducated people picking apart a business and in the negative as reasons not to do something, analysts, et cetera.
The longer they go at you, the more destructive it is to actually determine whether something is any good to pursue or not. And what I do is I listen for someone's passion. If I hear passion about something, I really do pay attention to it, and it does help guide me. And so this concept of the idea is everything.
I think it is bromidic. For me, the process of determining it is the gold.

Guy Kawasaki:
Also, that's a great segue to the second gospel of Barry Diller, which is the utility of creative conflict. So you are saying there should be conflict, right?

Barry Diller:
Absolutely. I love conflict. Again for whatever reasons my youth, I was somewhat, I guess near to it, and I found, I very early, certainly in my twenties, the more I could get not a hundred people, but two, four, six, eight, 10ten in an environment, in a room, let's call it, to talk about something.
And the more I could sometimes by turning them into encounter sessions that just lasted long enough that people's inhibitions broke down, the more I could get conflicting argument just pure argument, the more I could hear a truth in there.
And so I think that creative conflict is just a great tool. Again, all this comes down to whether or not you have the ability to listen, even if you're making a loud argument that you can actually hear, listen and hear a truth or a passion. And for me, those are divining rods.

Guy Kawasaki:
The next gospel is: Be fully prepared to call the whole deal off. So what is that about Barry?

Barry Diller:
If you're in a negotiation. And this is guaranteed to happen in a great percentage of negotiating, which is if you feel strongly about an issue, a point, and you take the position of I want to do it this way as against that way, or whatever the issue is.
You have to be prepared in your mind. Now maybe you can trick yourself later to try and recover, but you have to the ability, and I guess it does take courage of some kind, or at least it's a mind trick of courage. Not necessarily in reality, but you have to be prepared if the other person says no, to get up walk out of the room.
Now there's a chance that you are gonna get through the door to the other side, and you'll never hear from it again. But mostly before you get close to the door, you'll be called back and say, “Now, well, wait a minute.” But I think you gotta be prepared for the ultimate, for the loss.

Guy Kawasaki:
Now, Barry, I'm gonna push back a little bit on you. You say, “Fake it until you make it,” but then later in the book you also say, “You are, or you aren’t.”

Barry Diller:
Oh no, those are two totally different concepts.

Guy Kawasaki:
That's what I want, to learn. All right.

Barry Diller:
They are not in conflict. The fake it until you make it is that at least in my experience, when you start something new, you don't know anything. And what you gotta do is take a step forward and a couple of steps back, bounce off the walls, course correct as you go, make less mistakes as you go, and that in some way before you get there, you are faking it and you gotta be comfortable with that process.
And so it's just been my experience that a lot of times because I was so unprepared, and I had so much responsibility so early in my career, and I, therefore, when later things became successful, I would look back say, “How the hell did that happen?”
Because I was faking knowledge that I did not have just to get through the day. The other concept of ‘you are or you're not’ is completely different. That came about, at least for me, that phrase, which is soldered deep into my brain is because after being a corporatist for thirty years, when I was forty-nine, I wanted to be independent, or I was yearning to be independent.
And it struck me that was a binary thing, that you could argue your way, rationalize, do whatever. In the end, it was binary, it was you either are or not capable of being independent. And that rolled around in my head for six months or so. But more than anything forced me to take action and become independent.

Guy Kawasaki:
Okay. You also state that you should be able to pitch a movie in sixty seconds. So what makes a great pitch? Because the same thing applies to pitching a business or pitching a book.

Barry Diller:
Yeah. This, again, goes to idea. Just tell me the idea. If you can't tell the idea with clarity, if you can't do that, then it probably really isn't a good idea, or the idea is too ephemeral and you've gotta work on it some more in order to be able to crunch it down. Some ideas are difficult than other ideas. And yeah, I very much believe that you gotta understand what the thing is with clarity.
Particularly today, there's so many things that are confusing because there's so much information and data out there and all of that. You've really gotta try hard to separate it out and get the purity of the thing. And it does ring a bell once you get that done. And if you don't, I think it's tough to proceed.

Guy Kawasaki:
Okay. Now you also tell a great story about how you and David Picker were flying across the country and in that flight, David Picker read ten scripts and you read two and you made the point like, how can you read ten scripts in such a short time? But isn't that kind of contradictory to you should be able to pick up the idea in sixty seconds?

Barry Diller:
We're dealing now with editorial material, scripts that are designed to become movies, and you can pick up the idea really fairly quickly, but if you think them, again, you're dealing with written material. And that written material is only there to be visualized.
It's not a narrative process. It's for you to imagine what those stage directions and what the indicators are as well as the dialogue and descriptions are. And I believe, at least for me, first of all, I'm a slow reader, and for me, way past the idea is the actual quality of what you're trying to create, what content you're trying to make.
Idea is the first stage, it's not the last stage, it's the first stage, but the quality of it can't be determined by fast read. At least for me. I'm just too slow for it.

Guy Kawasaki:
My last gospel, although there are more, the last gospel, is you recommend that you hire unproven people and throw them in the deep end of the pool. And meanwhile, every venture capitalist in Silicon Valley is saying, “We wanna hire a proven world class team.”
And you're saying quite the opposite.

Barry Diller:
Some people do it and they do it well or whatever, but my process is that we’re talking about the people in an organization, not necessarily a founder, entrepreneur, who come in all colors and shapes and sizes, but I think it's probably true there too.
But anyway, in building an organization, it is best to hire people at an early stage of their career where they don't have experience and put them into situations for which they don't qualify. And the imagery of dropping them into the deep end of the pool and see who swims.
And I just think that's a much better process to determine who you want to keep and promote than hiring people who have experience and resumes and think that you can in an interview process or any kind of interview process, suss out how they're gonna function in your organization.
It's just an extraordinarily difficult thing to do. So I think it's a failure when a company has to reach out to hire a chief executive from a roster of other chief executives, I think you failed.

Guy Kawasaki:
You mean as opposed to internally promote.

Barry Diller:
Yes, you should only internally promote. That should be it. To me that is the definition. Now, right now we're dealing with compensation packages in the multiple billions of dollars going for hires, particularly in artificial intelligence. I am not saying they'll quote that certainly they won't all fail, but I think that's a dicey proposition. I would be very skeptical of that.

Guy Kawasaki:
So if Mark Zuckerberg calls you up and says, “Barry, I'm offering a hundred million dollars for these AI programmers and AI experts and I'm gonna build the dream team.” Is he basically building the New York Yankees of AI?

Barry Diller:
Good luck. If I owned them, I would sell them to him and pocket the money.

Guy Kawasaki:
Yeah, you would?

Barry Diller:
I would, yeah.
We're in such unknown territory with AI. And my expertise in this is, probably minimal. Although, no, I would say it's minimal. Whatever. I don't have any credibility, but yeah, I'm skeptical.

Guy Kawasaki:
Speaking of skepticism in AI, you tell a story about how you just took over Ticketmaster, Ticketmaster had sued Microsoft because Microsoft was getting Ticketmaster content and putting it on city search, and you draw the parallel between Ticketmaster and Microsoft and OpenAI and all these publishers.
So do you think it's crazy that these people who own content are trying to tell OpenAI and all the LLMs not to scrape us?

Barry Diller:
I said this from the very beginning. And there are now some, I think, new attempts to stop scraping without authorization. I absolutely believe that fair use, the fair use doctrine, which is you can use some material, without quote, violating copyright. I think that does not apply in LLM content acquisition because the result of it, if everything that is copyrightable is sucked up into LLMs, there will be no publishing.
I mean, there will be no foundation for publishing because it's literally a license to steal and you can't have any foundation of property ownership if there's a technological tech method for displacing you and disintermediating the content from the consumer. And so there's Cloudflare, which is a security system, that is starting to be applied. I hope we're doing it. I hope all publishers use it.
The leverage will only change this leverage, which does not exist i.e. getting paid for content will only change when they cannot appropriate your property. And have to come to you and say, “Alright, I want to buy it. What terms will you offer me? Or what terms will I offer you?”
That's when the leverage begins to change. And I'm hopeful through litigation, which, certainly you are aware New York Times is doing and we'll probably be doing, and others are doing certainly, and or transactions and or preventing scraping.
This leverage will return where it should be to the creator, to the publisher.

Guy Kawasaki:
So this idea that Cloudflare that the sites that they host can stop crawling unless the crawlers pay, I think is a brilliant idea.

Barry Diller:
No, no, no. I shout it to the skies. Every publisher should adopt it, have it as their practice. And if every publisher does it, I promise the leverage will change.
It will change the industry, and we will not have to go through essentially what the recorded music business went through, which was fifteen years of destruction because it took that long for the leverage to change when Spotify and Apple Music came along and properly guarded copyright, and then the leverage began to change. And listen, I think it's already happened to a degree, to publishing. I just hope it doesn't continue.

Guy Kawasaki:
Okay. You could make the case that with Ticketmaster, Ticketmaster was in the business of selling tickets, right? Not content.

Barry Diller:
No, no, no. But I'll tell you, and I've thought about this a lot, I've actually talked with Mr. Gates about this several times, since we had our altercation about it so long ago, which is what Microsoft was doing. And this is very early, this is 1994, 1995, 1996, something like that.
Just as the internet is starting to get used, what Microsoft was doing is taking Ticketmaster’s copyrighted content, the selling, the page, the web pages that were the transactional pages that they were offering to their consumers to buy tickets, and they were taking that without legal permission, and they were displaying it on their own systems.
And Ticketmaster said, “You can't do that.” And sued Microsoft. And I came in and not fully understanding the deep basis of this and not wanting a fight with Microsoft and thinking probably realistically that little Ticketmaster is not gonna stop the tide of free web taking of everything at the time that it just wouldn't work.
And I probably was right. But that was a principled stand. It's exactly analogous to scraping. And, who knows what would've happened in the world if Ticketmaster had continued its lawsuit and prevailed, it would've stymied the development of the web.

Guy Kawasaki:
I was at Apple during those days, and I'll say that the fact that Bill Gates, it's a little bit of hypocrisy because in my humble opinion, he ripped off the Macintosh interface for Windows. So, you know, it's dishonor among thieves if you ask me. But yeah.

Barry Diller:
You know more about the history of this, but Bill Gates is business genius. Truly rare, absolute genius, pure business understanding. And when you think that Microsoft was able to negotiate with IBM, the earliest stage, the ability to sell its software independently, and that IBM allowed them to do it, but Gates got away with it, is the birth of their personal computer business.

Guy Kawasaki:
One of the things as I was reading your book that just came back to me over and over again is I got to ask Barry, how can you tell if an asshole has talent? Because everybody can check the asshole box, but how do you know which asshole actually has something?

Barry Diller:
Oh, that's a lens. Well, you know, I've really been lucky. I've dealt with a lot of people. I've dealt mostly with in good relationships with people that I respect. And so as a class, I don't kind of say, that's the whole class. You have to determine whatever from that class. In the first decades of my career, I was working only with really creative people, and they run the rainbow, but since then, in the last twenty years, actually now thirty years, it's a long career.
I've been involved with a lot of internet, e-commerce, and tech and all of that. And on a moral spectrum, I actually think the people in the entertainment business, are higher on that than the people in tech.

Guy Kawasaki:
Really?

Barry Diller:
Yeah. Tech look, as you know, better than me, it's so pragmatic. It's so ruthlessly pragmatic. It's ruthless.

Guy Kawasaki:
I mean to name names. Are you saying that people like Thiel and Zuckerberg and Musk are worse than Marvin and Martin?

Barry Diller:
No, no, no, no, no, no, no, no. Wait a minute. No. The Davises are rats. They're the vast, vast minority of the people that I dealt with in the entertainment business.

Guy Kawasaki:
Okay.

Barry Diller:
And still deal with. And no, I am saying that I think, and it is true, it's a colder, more ruthless atmosphere.
It's a more pragmatic atmosphere. There's less emotion and empathy. I'm not saying the characters of these people that are at all quote lacking or not lacking. Some aren't, like most of humanity.

Guy Kawasaki:
Okay. I have two more questions for you. I wanna know, when you had 25,000 dollars’ worth of pennies dropped in Jeffrey Katzenberg’s lawn, was that an act of gratitude?

Barry Diller:
Yes.

Guy Kawasaki:
Was that an act of sarcasm that you're such a cheap bastard?

Barry Diller:
No, no, no.

Guy Kawasaki:
I’ll give you your bonus in pennies. So what was that?

Barry Diller:
It was fun. It was simply a fun idea. It was snarky and theatrical, and it was absolutely to show him how appreciative we were. That's what it was done for. And he knew it too, so, yes, that's for sure.

Guy Kawasaki:
So now let's just look back and say, Barry, if your grandchild or somebody came up to you and said, “Grandpa, tell me, how do I proceed in my career? How do I become a remarkable person?” What would Barry Diller say to a grandchild about becoming remarkable?

Barry Diller:
Follow your curiosity. That's all I know. I don't know a single thing other than that.

Guy Kawasaki:
Follow your curiosity.

Barry Diller:
Yep, yep.

Guy Kawasaki:
And what if your curiosity doesn't look like it's gonna be at all viable or lucrative or anything?

Barry Diller:
Tough luck. Go become a shoe clerk.

Guy Kawasaki:
Okay. Oh, okay. I lied. I gotta ask you one more question. You have been through transitions of television and movies. You had a really interesting experiment where you put out VCRs for the movies when the movies were in the theater, and you figured out that more people went to the box office even though you could buy the VCR.
So you did that and so now there's VCRs, there's DVDs, now there's streaming. So having seen all this barrier, what's the prediction for entertainment? Is it like all gonna be TikTok videos is like the creative genius is all that gone, what's happening now?
What's the next step?

Barry Diller:
No. The thing we have now, there's the good and the bad of it. We have so many options from one minute stuff to twelve minute, hour to multi-hour to miniseries, to movies. We just have so much optionality, so much is being made and produced. Now, the downside of that is that nothing lasts very long. Things come and go so quickly.
You do very good work. You make a good series or movie, and even if it's really successful, it's come and gone just because there's so much optionality. And so I think the only thing we know, and I do think we know this, is that there's going to be more optionality and there'll be more creators.
Whether those creators are AI bots and, machine learning, and true artificial intelligence. Or not, there's still gonna be humans creating things and I do not know if there's a contest between the two. I know in a contest between a robot and a human, the robot is gonna win, in terms of your physicality.
But I don't know much more than that. Anyway, nice talking to you.

Guy Kawasaki:
Wait, Barry, I just thought of one more question that only you can answer this question. Okay. I promise you.

Barry Diller:
Okay fine, fine, fine.

Guy Kawasaki:
All right. Trump versus Murdoch, who is your money on?

Barry Diller:
Murdoch.

Guy Kawasaki:
Really?

Barry Diller:
100 percent.

Guy Kawasaki:
Really?

Barry Diller:
I’ll take that bet. I’ll take the over/under.

Guy Kawasaki:
That says a lot.

Barry Diller:
Nice being with you.

Guy Kawasaki:
Thank you very much. Let me thank Madisun Nuismer, co-producer with Jeff Sieh. Tessa Nuismer, researcher, Shannon Hernandez, sound design engineer. And of course I have to thank Barry many times as I was preparing for this interview, I said, “Who knew that someday Guy Kawasaki could interview Barry Diller?” Wow.

Barry Diller:
Well you did and I enjoyed it. And I thank you.

Guy Kawasaki:
Thank you very much.

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