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

0:00From October 7th to 9th in San Francisco, the Masters of Scale Summit returns. It's where the boldest minds in business, tech, and beyond gather to build the future. And we want you to join us. Hear from the CEO of the New York Times, scientists using cutting-edge technology to find cures, the leader of crypto powerhouse Coinbase, a retired four-star general, and many, many more. They're all on the same stage, and it's not just another conference. It is the gathering for remarkable people. Apply to attend at mastersofscale.com slash remarkable. That's mastersofscale.com slash remarkable. 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.

0:56And 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 going to function in your organization. It's just an extraordinarily difficult thing to do. 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.

1:42His 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. 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.

2:32Is that a fair introduction for you, Barry? It's a little overwrought, but it's okay. I can live with you. And he's the author of this book. This book is called Who Knew? We'll get into that. I love the title, Barry. It's a very clever title. Thank you. Thank you. So, Barry, I want to 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?

3:15Oh, completely. I was very lucky that I grew up, one of my closest friends' father was Danny Thomas. And so I grew up as much in their house as in mine. And when I got to be 19 and I had no clue what to do other than I was interested in the entertainment business, I thought, well, I want to learn about it. At 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 70 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.

3:59And 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 may room job. And 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. I could make the case that, quote, who knew that reading all those files in William Morris's 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.

4:44I interview 52 people a year. That means I read 52 books a year, usually. And honestly, don't tell the other 51 people. usually I skim those books, but your book really sucked me in. I swear I read every word of that book, Barry. Oh, thank you. Thank you. Thank you. And Barry, after I finished the book, I said, is there anybody who is 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 gonads. I have only worked for really very few people, all of them could be described as Menches. Well, maybe one exception.

5:31I mean, are you trying to tell me that Martin and Marvin Davis are Menches? No, I said, 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 he promoted himself as owning 20th century fox which i left paramount to join in 1984 but my agreement was 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 i had i had two bad davises Is this something I cannot ask about because much of the book has to do with your sexuality?

6:27Is it okay for us to go there in this interview? Do whatever you want. Yeah. Is this book the first time you really confirmed your sexuality? Was there any positive or negative at this stage? 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 it was too confusing. It'd be a very long paragraph. I wanted to write the book because I just thought it was a good story. So in telling the story, Of course, I had to talk about my life and I did so directly.

7:15And 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. But there it is. But I'm not sensitive about it. As I was reading the book, okay, so have you been on a NPR interview for this book? I think so. 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. Okay, all right, I'll try. For sure I will. Your name is more memorable to me than NPR. But I think so.

7:59When you listen to many NPR interviews, it's always these kind of softball questions. And I'm going to hit you with a softball question, but I really want a hardball answer. Okay. So one of the typical NPR 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 a binge? Is it boredom? What is it? It's quite a simple answer. I know a lot about storytelling.

8:40My life has been involved with telling stories. And I don't know, maybe 15 years or so ago, 10 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 going to 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, in the last couple of years, I thought, you know what?

9:20I 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. Tell me somebody bought the movie rights. No, there are no movie rights for sale. I'm not doing that. I'm 71 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 going to do to me, right? So tell me, Barry, that just oozes out of that book.

10:03I've read many memoirs, and it's always about, yeah, I knew exactly what I was going to do. I was a visionary. I picked this. I did this right. I'm a perfect person. That's not at all your memoir. I've never read a memoir like this. But it wouldn't be the truth otherwise. And as I say, a lot of people who do these books, successful business people, let's say. 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.

10:47Here, look at how successful my life has been, et cetera. And I think that's fine. I have anything against it i find it boring but it's not some bad thing particularly a few of them bob igar's books i think which have been instructive certainly jack welcher 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 because of that i didn't have anything promotional in my mind i've had certainly a lot of success, and 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.

11:31It 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. Yes. 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 to toe to toe. 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? 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 of, And when I used the words, who knew?

12:18But one day it popped into my head. The two words popped. They didn't come from any other place than 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. Yes. And I thought, I'm going to do this. And one of my editors was a good friend of mine and someone I do listen to a lot. He's 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.

13:06Not, not, not doing it. And in the end, I said, you know what? Sorry, I like it. That's how it happened. 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 going to be good? Who knew that finding the right woman was going to 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.

13:48I love that. I'm glad. I'm glad that I did right. Who knew if Guy Kawasaki is right? I'll accept it. You were right.

14:11This is an aside, but when I first picked up the book, the picture on the inside cover there is of Little Island. Yes. 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. 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 that it had something I later heard the phrase end paper, which is the inside cover and the outside cover, you could actually make a picture.

15:04And 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're nice pictures. They're art. They're art. I really thought, oh, Barry is so sly. He's putting that picture there and he's going to figure out who read the end of the book because that's the only way you can figure that out.

15:48Okay. I can't tell you that my podcasts are linear and go straight from A to B. So I'm going to go down a few radios. Go wherever you want. Fine with me. 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? First of all, she has been 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 for Vanity Fair, and I would somehow be in them.

16:30Having 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. I think in the only, probably of a very long and glorious life, the only time Queen Elizabeth was ever seen to be angry and unpleasant was towards Annie Leibovitz, who made her change her costume a few too many times. Anyway, so you get used to being photographed by Annie and doing what you're told. And when Dionne and I got married, Annie said, I'm going to come and take your wedding pictures. And she took a whole series of pictures because we did not get married in the big production.

17:17We just went down to City Hall and got married. But she took the pictures and she's done that several times for us. Wow. I think she's the best photographer alive. I wonder if she ever took a picture of Steve Jobs because that would be two monumental eagles going in. That would be... I don't know. She's taken pictures of almost everybody of any note. Because Steve Jobs is a controls freak, controls freak. So that would have been very interesting. She would have won.

17:50I don't know, Barry. I might debate you on that. I knew both. Yes. Okay. 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 mothering, 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? I think two things can happen. I think everybody gets some dysfunction or some certainly pass through some difficulties growing up. And I had a dysfunctional family.

18:36And in kind of, I think, somewhat in 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 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.

19:29One 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 20s, 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. And so that was one. And another was that because I had one big fear growing up, a fear, this is in the 60s and 70s, the fear of the reveal of homosexuality. If you have a big fear, it kind of allows you that business risks and issues of failure.

20:24I 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 there are endless pieces of all. I mean, that's a couple of examples I could go on and riff more. 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.

21:09But I have compiled for you, Barry, the gospel according to Barry. And I'm going to 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. I think that the discipline, it sounds like a bit of a romantic thing. the idea. Of course, the idea is important.

21:54But 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 you 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 a good idea? Is it a 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.

22:52And 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's 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 too, 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.

23:47But all of those processes, over-educated 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 determining 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. Also, that's a great segue to the second gospel of Barry Diller, which is the utility of creative conflict.

24:44So you're saying there should be conflict, right? Absolutely. I love conflict. Again, for whatever reasons in my youth, I was somewhat, I guess, inured to it. And I found very early, certainly in my 20s, the more I could get not 100 people, but 2, 4, 6, 8, 10 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.

25:36Again, 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. The next gospel is be fully prepared to call the whole deal off. So what is that about, Barry? Well, 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.

26:30Now, maybe you can trick yourself later to try and recover, but you have to have 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 and walk out of the room. Now, there's a chance that you're going to 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, no, wait a minute. But I think you've got to be prepared for the ultimate, for the loss. Now, Barry, I'm going to push back a little bit on you.

27:17You say fake it until you make it. But then later in the book, you also say you are or you aren't. Oh, no. Those are two totally different concepts. That's what I want. 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 got to 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 got to 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.

28:09And I, therefore, when later things became successful, I would look back and 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 or not is completely different. That came about, at least for me, that phrase which I soldered deep into my brain is because after being a corporatist for 30 years, when I was 49, 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. But in the end, it was binary. You either are or not capable of being independent.

28:58And that rolled around in my head for six months or so that more than anything forced me to take action and become independent. You also state that you should be able to pitch a movie in 60 seconds. So what makes a great pitch? Because the same thing applies to pitching a business, a book. Yeah. Well, again, this goes to the 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 got to work on it some more in order to be able to crunch it down. Some ideas are difficult than other ideas.

29:42And yeah, I very much believe that you got to 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 got to 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. 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 10 scripts and you read two. And you made the point, like, how can you read 10 scripts in such a short time?

30:28But isn't that kind of contradictory to you should be able to pick up the idea in 60 seconds? I mean, 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.