ADI IGNATIUS: I am Adi Ignatius.
ALISON BEARD: I’m Alison Beard, and this is the HBR IdeaCast.
ADI IGNATIUS: All right, Alison. So today we’re going to be talking about taking risks. We’re going to be talking about looking around corners, and we’re going to be talking about whether good leadership is ultimately more about instincts or about processes. This all comes from an interview I did with longtime Hollywood and Media entertainment industry executive Barry Diller.
ALISON BEARD: I’m really looking forward to listening to this conversation because I covered IAC Barry Diller’s company when I was a junior media reporter at the Financial Times in New York. Diller was always the person that people in the industry looked to because he seemed to be able to predict what was happen next before anyone else.
ADI IGNATIUS: So yeah, controversial guy, but long record of success. Quick resume on Barry Diller. He became CEO of Paramount Pictures in his thirties. He launched the Fox TV Network with Rupert Murdoch in his forties. After that, he went on to oversee iconic productions like Raiders of the Lost Ark, like Home Alone, like The Simpsons. And nowadays, he stands at the top of a media empire that includes Dotdash Meredith, Care.com, the Daily Beast and more.
ALISON BEARD: Yeah, we know Hollywood films, TV, news, internet its a fickle and challenging world – media – and so it’s pretty impressive that he’s a guy who’s managed to stay on top of all of it for decades.
ADI IGNATIUS: And what’s interesting, he’s kind of an anti-HBR person in the sense that he’s not against us, but he’s not about processes, he’s very much about instinct, but I don’t think his track record is merely about luck. I think there’s a method to what he does, and that’s what I tried to uncover. So we talked about how he knows when he wants to work with somebody. We talked about when he decides a project is worth pursuing, and we talked about how he handles some of the big egos in the business.
ALISON BEARD: I can’t wait.
ADI IGNATIUS: All right, so here’s my interview with Barry Diller, founder and chairman of IAC, as well as the chairman of Expedia. He’s also the author of a new book, Who Knew. Here’s our conversation. Honestly, to start, you have proven uncommonly good at identifying trends before others do, and that’s TV serialization, it’s reality shows, it’s internet interactivity, dating apps, you name it. When you look back on that, is that just innate, or do you think there are ways to hone one’s ability to see around corners?
BARRY DILLER: I’ve always mistrusted this vision thing about seeing around corners. I don’t think I ever really did that. I think I have, maybe, I don’t know if honed is the word, and I do think it is important to emphasize instinct over almost everything else. And I have an ability, sometimes, and sometimes of course not, to recognize what is a good idea. If you prize that, if you pride instinct, then the most important thing you can do in the honing category is to keep those instincts clean.
How do you keep instincts clean? Mostly you guard against cynicism, and you keep a kind of naiveté, you hold naiveté as something important to keep as a cleansing agent to cynicism. Cynicism can kill any good idea. So I don’t think this stuff is learned. I think the only thing is to unlearn the history that you go through so that your instincts remain as pure as possible. Now, of course, over time they’re going to get corroded to a certain degree here or there, but if you try and keep wiping it clean and again prize naiveté and beware of certain kinds of sophistication and cynicism, then instinct can kind of reign.
ADI IGNATIUS: I mean, there’s a touch of Steve Jobs in your approach to all of this, prizing instinct over research or data. I think you’ve said it’s a fool’s game to try to predict audience appetites, but I guess I’m interested. What are the uses and the limits to data? I mean, I can’t imagine it’s a hundred percent no data. So what are the uses and limits to data to figuring out, let’s say, business strategy?
BARRY DILLER: The limits to data are projecting forward. I do not think you can ask people what they think of something and get a response if that something is new. I don’t think the responses are indicators of much of anything. I think most of research is wasted when you’re trying to make decisions as to what to do for the future. Absolutely, of course, factual data of all sorts of things, size of market, competitors, whatever the data tells you in real time about facts is fine to use. Of course, that’s useful, but anything that is, so to speak, predictive, I think, is mostly useless.
ADI IGNATIUS: So there’s a lot about how you led your career that’s almost a counter model for let’s say, what one might read in HBR, I mean, as you said, you weren’t particularly introspective, you didn’t set goals per se.
BARRY DILLER: No, I don’t like goals. If you want to be a doctor, that is a goal with a specific path to getting there, which isn’t going to happen unless it’s your goal. But specific business goals, my ringer here is those people who come into your office, that you see about their futures, and they say, “I want to run a studio or be head of a studio.” To me I throw them out. I mean, what an idiotic “goal” to have. I mean, if you’re interested, genuinely interested, for instance, in the entertainment business, all you need to do is start. It’ll take you where it ought to go, and you ought to go. You do not need to lead it.
ADI IGNATIUS: So it sounds like with new ventures, you have a similar approach. If you like the idea, do it. Don’t overanalyze.
BARRY DILLER: I have seen so many good ideas trashed by endless power pointing, endless examples of business plans. I was just looking at a business model the other day that went out to ‘29 or ‘30, and it had on this one page, it had probably a hundred figures. Every item getting down to net earnings, with absolute precision. And as I say to everyone in those things, I said, “Here’s the one thing I can guarantee you, this won’t be true. It may be lower or higher, but this other than an accident of monkeys typing; this won’t be true. So why bother with it?” But you do the amount of this that passes as kind of business intelligence, and that people actually stare at this stuff and say, “Well, it shows your margins are growing from 18 to 20 to 22 to 24% in the years ’27, ’28.” I mean I look at, I said, “What are you doing with this stuff?”
ADI IGNATIUS: So what’s left then is what is your instinct, this is-
BARRY DILLER: It is passion and arguing, and you listen kind of to the what is the truth of things? I love debate. I think debate is where most, at least good decisions, are the result of really fierce debate. And if you have a listening ear, and I don’t know how you train for that one, I think either got it or not, but if you have a listening ear in that cacophony of discussion, things ring true. You can hear something that indicates to you something that says, “I’m going to base my belief on that.”
We made a deal to acquire Expedia at just the exact moment when 9/11 happened. We did it a month before and we had a material out provision that if God knows things change, travel stopped a hundred percent and we spent hours and hours back and forth, should we do, can we do, how could we spend a billion dollars at the time, real money, buying a company that essentially has no business and who knows?
And also, shouldn’t we renegotiate? Shouldn’t we do this? This went on for hours as the day kind of approached where we ran out of the exclusion date for opting out. And I remember crystally clear in this meeting where this is all going on and on. Somebody said, “If there’s life, there’s travel.” And I said, “Done close.” Good or evil, certainly not evil, but that rang for me. That process, I love process, and that process, I think it’s a better one for me at least.
ADI IGNATIUS: Most people shy from confrontation. You seem to love it, and I guess to what extent do you think raw conflict can actually help create good business decisions?
BARRY DILLER: Well, conflict raw or others, I do absolutely believe in creating conflict. I have my own experience, I haven’t got much else. And the clashing of ideas, hearing people argue out of passion rather than PowerPoint. I think it’s just far more productive. And yeah, I do enjoy it. I mean, I think the clang of ideas, and it does get sometimes loud and it can be abrasive and some people don’t like it. And my feeling about that has always been, hey, if people are uncomfortable, I’m uncomfortable. So if you’re uncomfortable about this process, opt out, don’t do it. I’m not talking about this being abusive, but no holds barred argument is the way, at least teasing out from there comes the ability to take action or not.
ADI IGNATIUS: So through that process, I mean you’re going to probably fall in love with more projects than you can actually go forward with, so how do you decide when a new project or investment-
BARRY DILLER: That’s not really true. The sieve is very small. I mean, if you’re really honing for, is it a good idea? This may be my experience, but I think this is generally shared. Of course, there are good ideas, there aren’t a plethora of them.
ADI IGNATIUS: So, do you have kind of a formula or a rough formula?
BARRY DILLER: No. No, I mean, listen, you’re always assessing risk. My ultimate risk test has always been, and I got this very early, very luckily, is don’t bet the farm. Do not bet your enterprise on anything. And so long as you’re not doing that, it allows you, of course, to make mistakes, which if you’re not doing something is celestially wrong.
That is your big guidepost, and then of course, you do assess if you’re making investments or buying companies or building businesses: A, what’s the risk? Is it tolerable? Are you thinking it through enough? Which is very, very hard to do, to project all the things that are going to happen in year two, three, four, five, and at least assessing them correctly, which usually you don’t do, but trying to do that is a good gauge of risk.
Somebody was saying to me yesterday, we were looking at one business, and they said, “Well, yeah, this idea is a good one. These people they’re really talented and they probably will create value, but I can’t see them creating a lot of value like multiple billions of value.” And I said, “So you’re willing to say that you’re going to bet that they are going to create value, but for some reason that I’d like to tease out more, you’re saying there’s a ceiling on it.” It’s silly to do that.” Risk as reward. It’s silly to cap the reward in your mind. Who knows what’s going to happen. So long as you think it’s going to succeed and determining whether it’s “worth your while”. Worth your while, meaning how successful is it going to become, I think it’s a fool’s game.
ADI IGNATIUS: So there’s the exciting part of this process, which is launching an idea you’re excited about, and then there’s the sort of more drudge-like managing a project to hopefully a successful outcome. Were you any good at that part of it, or did you sort of lose interest after the idea was hatched?
BARRY DILLER: Oh no, no, no, no. As I said, I love process. So for me, getting it executed, that’s the best part. The best part is one dumb step in front of the other, making your mistakes or you make less of them as you go in any venture, I enjoy that process. A lot of my friends say, “Oh no, no, I just want to get to the end of it. Just give me the success and I can go on.” For me, it’s the process that I like and enjoy. Once it’s actually a success, I’m not that interested. I’m not a great steward.
ADI IGNATIUS: So we’re HBR, so I’m interested, then are there takeaways from how do you make process work? We sort of talked about how do you decide on ideas? How do you make process work to get to that successful stage?
BARRY DILLER: For me, and again as I say, all I got is my own stuff. It’s learning every step of it. If it’s an original thing, learning it as you go, every step down to molecules, it is the depth of understanding every aspect of it. The great way to learn to be a manager is not through I think an educational process, but it’s starting a company with the first employee, you and each employee thereafter, scale it any way you like, up to a hundred, a thousand, whatever. Past a thousand, you’re not going to know anyone really, or you’re certainly not going to know the 14th hundredth.
But in that process of starting something and knowing every role in the company as you build the enterprise, because you are operating every role in the company, that’s how you learn to be a manager. That’s the great luck. The experience that I’ve had again, I was able to do that early, and then I got dropped in at age of 32 to being chairman of Paramount Pictures, which was vastly larger organization than I knew or understood. And to come in as chief executive of a company that has got a lot of people in it and its own processes, it’s doable, but it’s a nightmare because you have to reverse engineer it so you understand it down to its lowest core, and that drives everybody crazy.
ADI IGNATIUS: Talk about the politics of dealing with big, unpleasant egos in the business world of trying to get things done, because I think there are a lot of them in the entertainment industry. Maybe they’re everywhere, but-
BARRY DILLER: Well, of course, they are. I mean, the entertainment industry is people and personalities, and so excesses are going to abound. But look lucky or unlucky, I have dealt with every grade of personality from A to Z, and I’ve dealt with many outsized personalities. I love outsized personalities. I wish there were more of them around rather than button-blue-suited folk. I think the entertainment business, particularly, is one that thrives on excessive personality, and there’s no rulebook here in dealing with people of big personality.
I think in a way it’s probably easier the bigger the outsizedness, because it gives you the entrance in a way to argue it down when it’s on the table rather than hidden. I’d rather that than passive-aggressive, I’d rather that than small devious folk. I find it easier.
ADI IGNATIUS: So let’s build on that. So let’s talk about deal-making. I mean, you’ve definitely learned deal-making from some of the best minds in the entertainment business. What’s your best advice on how to make a good deal?
BARRY DILLER: Oh, I have a simple advice. You can say leave something on the table. The best negotiations make each side equally dissatisfied and therefore equally satisfied, and I understand leverage. Of course, you can’t be in business and not understand leverage. And when you’ve got it, it’s applicable only to an appropriate degree. If you overuse it and 50% of situations are where the leverage is very one-sided. Wisdom says you don’t push it to the wall, and that’s always been my attitude about negotiating. And I’ve been an observer in other situations where people have squeezed and have used their leverage and hammered it home to the true disadvantage of the other side, and one way or the other, I think it leads to tears.
ADI IGNATIUS: So I also want to ask about your early career, and you accomplished a lot, an impressive amount of success at a young age. A lot of it was sort of fake it till you make it, and I wonder is that… Do you think that’s sort of a secret to getting ahead in the early stages of your career?
BARRY DILLER: Oh my God, yes. I mean, unless you have some ability to do that, they will pull the rug from you and probably should. I mean, if you can’t, at critical moments, and I’ve been in those critical moments where I have to fail before I can succeed. I need to make things worse before I can make things better. Because, in the making things worse, so to speak, I’m learning about what the situation is. So at those moments when you’re close to people, saying, “Well, we’re going to take this away from you, or throw this idea out, or cancel this.” You better be able to, in the clutch of that moment, sell it through before it’s actually there.
Paramount’s the best example. I came into Paramount at the age of 32, and by the age of 34, everyone said they were going to throw me out because in order to retool this business, which I thought was necessary, we went through a very, very competitively tough couple of years and good work was being done under the hood, but the car was not driving very well. So I came very close to them saying, “It’s two years you haven’t done it, go away.”
Same was true of when we founded Fox Broadcasting. The early shows we put on failed. We hadn’t yet figured out how to be an alternative network. We hadn’t found our voice, and the industry and my colleagues, many of them said, “You’re never going to do it.” Now I being enmeshed in the work of the day knew I was making progress, but there was nothing to show for it until there was. So you better be able – fake it is a whatever word, but you better be able to either get lucky timing or be able to promote beyond reality what’s going to be a success as against what everybody is sure is going to be a failure.
ADI IGNATIUS: So yeah, I think you say in the book that one of your mantras for business is it’s the timing, stupid. How do people make timing work for them? Is it just a matter of… How do you create good luck?
BARRY DILLER: Oh, no, no, no, no, no, no, no, no. There’s no such thing. I mean, my life is one of serendipity. You can’t array the constellations to be “in your favor”. You’re just lucky enough that what you do at a moment, the constellations are aligned for you. There’s so many endless, boring examples of this. Bill Gates at 12, 13, 15, 17 is interested in primitive computing and decides to write code for computing for what was, at most, a hobbyist’s form.
He decides to do this at a moment. He didn’t create the fact that, at just that moment, it was becoming computationally possible to do at scale. So he couldn’t have arranged the timing, but he was interested in an area, and I doubt that he was predictive of what was going to happen. He had a hope of what might happen, and so he was interested in doing it. You can’t arrange that. You just get lucky enough.
ADI IGNATIUS: I’m enjoying compiling the business philosophy of Barry Diller because a lot of it is unconventional, and I’d love what is your philosophy then for hiring good people, which I suspect is also unconventional?
BARRY DILLER: Well, hiring off of big resumes is unproductive, I think. I mean, I look for energy, edge, smarts. I’m so impressed with some of these people who do these very long interviews with people on hiring process, asking them abstruse questions about this or try and indicate this or that. It may be helpful to go through such elaborate, long processes. But every hire you make, I don’t care if you spend 4,000 hours with that person, when that person goes into a position in your company, everything flips around because the job does not have absolute predictors inside of it, nor the environment with other people, nor that person in such an environment. You can’t replicate that by an interview process that I know of. You can’t replicate what life is going to be like when that person is inside your company in a particular position, other than certain base qualifications for very technical work, which you’ve either got or you don’t got.
You don’t need to interview anyone for five minutes. You just need to see what their technical abilities are or they’ve shown to be. And the failure rate is so high. Hiring people for senior positions is madness. Unfortunately, it has to be done. So it is a madness we all participate in because if somebody doesn’t work out at a high position, and you are unlucky and frankly guilty of not having somebody in the company that you know to promote into that position, and have to look outside, which means you failed. But if you do hire somebody for a senior position, it’s dice loaded against you more than 50%, I think.
So the best path for hiring is to hire people at the earliest stage in the most junior part of an organization where they can learn from you, you can learn from them, they can grow up in your environment and you get an assessment obviously sometimes with people you hire at the junior most position, you say, “Well, that didn’t work out, and you’re gone. No harm, no foul in six months or three years. But if those people grow up in your organization, they become the body of the future, and that’s healthy. The opposite of that is – up to the CEO level. CEO doesn’t work out, you hire a firm to find candidates, and you interview them. What a horrible process.
ADI IGNATIUS: So you didn’t attend business school, and when you’re writing, to be honest, you seem dismissive of MBAs and the skill sets that they bring. Is that fair?
BARRY DILLER: I think you end up with too much rigidity. There are a lot of aspects of education that I wish that I’d had. But for general business experience, I think other than again, a general knowledge, I can only do my own stuff. I was lucky enough and truly lucky enough that I was really interested in the world of entertainment and certainly every aspect of its business. At the age of 19, I got to go to the best school, which was I read the file room of the William Morris Agency, which was the largest entertainment agency, which had the history at that time going back 70 years of about every major figure in the entertainment business and their entire career, every transaction that was made, every formation of every development, if you read it. So I had the greatest history lesson, and where could you ever be so lucky to be so grounded in the business that you read its history? I wasn’t reading. It’s present as much as I was reading its history, and that’s what grounded me. So I think that anytime you can get a hold of that, great.
ADI IGNATIUS: So you kept your sexuality closeted for years, and for people who are listening to this who are unsure whether they can come out at work, I’d be interested in the toll it took on your life, and really, what your advice is 2025, how to truly be yourself in a work environment.
BARRY DILLER: I got no advice. Well, advice. First of all, mine was a different time. Mine was the sixties and seventies. By the time I was 32, I was at a very senior position. And I presume that everyone knew I didn’t make declarations for a number of reasons. As I wrote, I was chicken. But also, the times were not conducive to it. And in reality, I don’t think it really would’ve made much difference. My own history, I did not make declarations, but I did not hide anything. I was not in… If I was in a closet, it was a closet with a door open and a light shining. I wasn’t changing the way I lived my life, I just didn’t make declarations. And look, the healthiest thing, of course, hard though it may be and still is to a degree, although sexual fluidity is much more understood today, of course, than it was then.
The best thing, of course, is – look I like privacy for a lot of reasons. And one of them clearly is that I was afraid of it otherwise. But another part of it is I like privacy in a world today where there is very little of it. And so, notwithstanding that saying that I think if you’re living your life being in a situation where you actually have to lead a fraudulent life, which I never did. I had very strong rules about not doing that.” That’s an additional burden. And I think today, notwithstanding what any administration wants to do, the march of progress here is going to continue. This is going to get easier for people, not harder for people. Nobody’s going to be able to put a hand up and stop that, I believe, notwithstanding autocratic, socially conservative societies.
ADI IGNATIUS: That was a big notwithstanding. I’m interested in your thoughts on the entertainment industry now. I mean, you’ve been through waves.
BARRY DILLER: Yes.
ADI IGNATIUS: I’m assuming AI will dramatically remake everything. It’ll just change how we create content. It’ll change how we think about audiences. It’ll end up being hyper-personalized. What’s your sense about the future, and if you want to try to create good luck to succeed in this future, what are the weak signals to look at?
BARRY DILLER: I think the thing about AI is no matter what we say, we think, we do, we don’t learn. Whatever, we’re on the precipice of probably the most radical thing that maybe has ever happened to humanity with general artificial intelligence, which is coming much sooner than anyone had ever thought. I think that therefore, so many aspects of it, the deeper aspects of it, are so unpredictable. As for the superficial, so to speak, will it simplify basic task making, yes, it will. Will it enable you to write “copy” without a human touch? Yes. But that’s copy. Will it enable actual creation? I don’t know. I don’t think anyone really knows, and I’m pretty sure that that’s the last statement is true. I’ve not read anything, heard anything, or seen any example thereof. I’ve seen, yes, can it make you sound like Shakespeare? Sure. Can it make my voice sound like George Clooney’s? Sure. And will it simplify a lot of task-making in every area? Sure. Beyond that, who knows?
ADI IGNATIUS: Then the question is how do we position ourselves to not just sit back and say, “Hey man, as it’s going to turn out?” But to-
BARRY DILLER: You can’t position it’s day by day. You can’t. It’s unpositionable because it’s unknown. We don’t know the extent of this tool-making. We just don’t know other than have your hand standing on a train track trying to hold up the train from coming down the road to crush you, which is taking place. And in some cases, productively with litigation, saying that chatbots can’t take your copyrighted material and subsume it into oblivion. And that’s, I think, I’m totally in favor of some of that litigation. Do I think it’s going to be the end answer? No, I don’t. Because the train’s going to come across that track no matter what you do, but technology has no bar holds. It’s impossible. So anyway, unknown.
ADI IGNATIUS: So we always live through uncertainty and unknown. This feels like an era of hyper uncertainty.
BARRY DILLER: It’s beyond hyper. It will be the revolution. I mean that to me is guaranteed it will be a revolution.
ADI IGNATIUS: So given all this uncertainty, again, it’s political and geopolitical in addition to technological, what’s your advice for business leaders who are thinking, good lord, how do I survive and make it in this environment?
BARRY DILLER: Well, I can tell you, we own the world’s largest publishing entity, called DDM, which owns People Magazine and 63 other magazines. And of course, our big worry is because of artificial intelligence, we will lose direct traffic. It will be subsumed and searches, so to speak, which we depend upon, obviously, to discover our publishing material, are going to be radicalized in the future, and they will be. What are we doing? We’re saying one thing. All we’ve got is, for instance, let’s take People, we have our People brand. And when you say People, People understand it, and they know what it represents. And so long as we do everything we can to strengthen the brand characteristics of People is our only defense of our brand. So I say to everybody, you will not be dependent upon anything other than your own ability to differentiate and make whatever it is you do. Be clear to people so they can determine whether or not they want that thing, and that’s your defense. Defense is your offense on brand characteristics.
ADI IGNATIUS: It’s the people, stupid, but we’re out of time. I want to thank you for joining us. This is a great, great conversation.
BARRY DILLER: I hope so. All right, thank you.
ADI IGNATIUS: That was Barry Diller, chairman of IAC and Expedia and author of the new book Who Knew. Next week, Alison will speak with computer scientists and former tech executive Telle Whitney about why and how the tech industry needs a reboot.
For more leadership insights, we have more than 1000 episodes of IdeaCast plus more HBR podcasts to help you manage your team, your organization, and your career. Find them all at hbr.org/podcasts or search HBR in Apple Podcasts, Spotify, or wherever you listen.
Special thanks to our team, senior producer Mary Dooe, associate producer Hannah Bates, audio product manager Ian Fox, and senior production specialist Rob Eckhardt. And thank you for listening to the HBR IdeaCast. We will be back on Tuesday with a new episode. I’m Adi Ignatius.
