Leaders Playbook: Billionaire Barry Diller 1/21/26

Summary

Squawk Pod – Leaders Playbook: Billionaire Barry Diller (Jan 21, 2026)

Episode Overview

In this episode of "Leaders Playbook," CNBC anchors interview Barry Diller, legendary media mogul and tech investor, to dissect his six-decade journey through Hollywood, digital media, and tech. Diller, chairman of IAC and Expedia, reveals the instincts, management philosophies, and risk-taking mindset that have helped him repeatedly build and scale billion-dollar brands—from revolutionizing TV and launching Fox Broadcasting to capturing internet gold with Expedia, Match Group, and more.

Theme: Decoding the leadership philosophy, talent management, and gut-driven betting that enable Diller to spot market-changing opportunities—and the thinking behind his boldest moves.

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Key Discussion Points and Insights

The Power of Instinct

Timestamps: 01:04, 02:34, 04:07, 09:41

• Diller credits instinct as the animating force behind his career decisions:

  “It comes down to instinct and the ability to recognize a good idea and exercising your instinct and for sure not being afraid of risk.”
  — Barry Diller (02:34)

• He believes most of his breakthroughs stem from trusting his gut—especially when calculating risk:

  “I just don’t see risk where others do. And where others don’t see it, I do. It’s just cocked up a bit or abnormal.”
  — Barry Diller (09:41)

• In identifying online dating before it was mainstream, Diller says:

  “It’s so, so obvious what a good idea that was… I’m glad no one else saw it or wanted to pounce on it, but we sure did.”
  — Barry Diller (04:07)

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The “Buy, Grow, Spin Off” Playbook

Timestamps: 02:43, 03:32, 04:40

• Diller narrates how IAC’s unusual model—acquiring, growing, and then spinning out companies—was “one dumb step in front of the other”:

  “This was not imagined whole cloth... I thought that once an entity got to be of sufficient size that it ought to be independent... So it’s a weird business model, but it has certainly worked well for us.”
  — Barry Diller (02:48)

• Notable spinoffs: Expedia, Angie, Match Group (maker of Tinder, Hinge, OkCupid)—the latter reaching a $26.5 billion market cap after separation from IAC (03:32).

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Creative Conflict: Sparring for Better Decisions

Timestamps: 04:59, 06:04, 06:44, 07:17

• Diller encourages robust internal debate:

  “The best way to vet an idea is when you’ve got a group of people around a room and passion argument from each of them... That cauldron—I’ve always thought you push it past exhaustion because that’s when the good stuff comes out. That brew makes the decision.”
  — Barry Diller (04:59)

• He warns against cynicism, which “kills everything,” and stresses that creative friction isn’t personal—“My God, yes. Absolutely” his employees can push back (07:17).

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Post-9/11: Betting Big When Others Balk

Timestamps: 07:35, 10:37, 10:49

• On acquiring Expedia just before 9/11:

  “Obviously travel stopped cold after 9/11. So Expedia went from X revenue to 0... several people said, ‘this is not the time to pay over $1 billion for something so unpredictable.’ Someone in the room said, ‘if there’s life, there’s travel.’ And as soon as I heard it I said, close. I’m betting on that.”
  — Barry Diller (10:49)

• He acted not from spreadsheet forecasts but raw conviction, completing the deal in 2003 after weathering the crisis (11:31).

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Directness, Listening, and Talent Development

Timestamps: 11:49, 13:33, 14:06, 14:27

• Dara Khosrowshahi (current Uber CEO, former Expedia CEO) on Diller’s transparency:

  “Barry goes straight to the source... Every level that information passes through, you lose some fidelity, you lose some edge. The opportunities and the dangers are in that edge.”
  — Dara Khosrowshahi (12:16)

• Diller prefers promoting from within:

  “If you have to bring in people at senior positions from outside the organization, it is a failure. The best organizations bring people in at an early age... they get forged by your process.”
  — Barry Diller (13:43)

• Qualities he seeks: “energy and spark and a brain that I can understand.” (14:06)

• He lists talent forged under him—Michael Eisner (Disney), Jeffrey Katzenberg (DreamWorks) (14:14).

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“Fake It Till You Make It”

Timestamps: 14:55, 20:06

• Diller candidly admits:

  “You do. Fake it as you go... making others think you know something when you know nothing. And then eventually you’re figuring it out... eventually, there it is, no more faking.”
  — Barry Diller (20:06)

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The Role of Willfulness Versus Stubbornness

Timestamps: 20:54, 21:16, 21:32

• Distinguishing execution from inflexibility:

  “However good the idea is, unless the person is willful, nothing happens... unless you are willful, which means you will impose your will on whatever it is, nothing is ever going to happen.”
  — Barry Diller (20:54)

  “If you’re willful and somebody comes to you and they say something that you hear that amends your will, and then you’re willful about that. Hallelujah.”
  — Barry Diller (21:16)

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The Balance of Data and Instinct

Timestamps: 17:18, 17:30

• On the limits of data-driven leadership:

  “Data is good for history, past and math... but you cannot use them for anything that hasn’t happened yet or for predicting the future.”
  — Barry Diller (17:30)

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Fear, Vulnerability, and Risk Perception

Timestamps: 17:53, 17:59, 18:14

• Diller opens up about personal fears and how owning his sexuality shifted perspective on risk:

  “I had one big fear, and that allowed me to take other fears less importantly. I mean, I think constitutionally, it’s biology. I mean, I don’t take any particular pride in it.”
  — Barry Diller (17:59)

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Hollywood vs. Tech: Transferable Lessons

Timestamps: 18:32, 18:36, 18:38, 19:43

• Asked what Hollywood taught him about tech, he playfully demurs:

  “Nothing... Oh, it’s an exaggeration... probably the only pure thing is how much I prize—tell me what the idea is, and can I crunch that down into something I thoroughly understand and then have an instinct about?... But the world of technology is completely at the other side of the planet from instinct and editorial... So they’re completely different worlds.”
  — Barry Diller (18:36-19:43)

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On Negotiation and Trust

Timestamps: 23:19, 23:53, 24:10, 24:15

• Diller says he's not a master negotiator:

  “I really don’t care about the best deal... If you grind someone into the dust... there’s something inherently rotten about that... If I want something very badly, I don’t really care about price.”
  — Barry Diller (23:19-23:53)

• His biggest professional regrets are not failed deals, but:

  “I’ve trusted people... the biggest disappointments I’ve had... where trust was broken... That’s like a breach.”
  — Barry Diller (24:15)

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The Central Role of Curiosity and Luck

Timestamps: 22:05, 22:45, 24:57-25:16

• On the secret to longevity:

  “Probably curiosity more than anything. I think without curiosity as a base, I wouldn’t have gone anywhere and done anything. And then there’s serendipity.”
  — Barry Diller (22:05)

• “Everybody gets their amount of luck and serendipity... another reasonable definition of success is what do you do with it?”
  — Barry Diller (23:09)

• Even at the close, he says:

  “That’s the one thing—I still am curious, you know, it’s an unquenchable reservoir.”
  — Barry Diller (24:59)

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Notable Quotes & Memorable Moments

• “Unless you are willful, nothing is ever going to happen.” (01:13 & 20:54)
• “You cannot be cynical. Cynicism kills everything.” (01:51 & 06:09)
• “If there’s life, there’s travel.” (10:49)
• “You do fake it as you go.” (20:06)
• “If you have to bring in people at senior positions from outside the organization, it is a failure.” (13:43)
• “I just want to get it done at what I consider a fair transaction... And if I want something very badly, I don’t really care about price.” (23:53)
• “Curiosity... it’s an unquenchable reservoir.” (24:59)

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Timestamps for Key Segments

• Instinct & Risk: 01:04, 02:34, 09:41, 17:18
• IAC's Model & Successes: 02:43, 03:32
• Creative Conflict: 04:59, 06:04, 07:17
• Expedia and 9/11: 10:37, 10:49
• Developing Talent: 11:49, 13:33, 14:06
• Fake It Till You Make It: 14:55, 20:06
• Willfulness vs. Stubbornness: 20:54, 21:16
• Curiosity and Luck: 22:05, 24:57

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Takeaways

• Diller’s leadership is a masterclass in instinct, relentless curiosity, and betting on talent—coupled with an openness to conflict and a willingness to embrace, even manufacture, risk.
• His humility around negotiation, honest admission of “faking it,” and heart for fostering young leaders provide a candid, nuanced picture of entrepreneurial success.
• For Diller, boldness must be coupled with adaptability, the impatience of willfulness, and a drive to learn from every new environment—even if it means starting over.

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For listeners: This episode offers a rare, practical look at the mindset and mechanics behind one of business and media’s enduring trailblazers. Diller’s candor, quotable insights, and clear-eyed view of talent and risk are instantly applicable for any entrepreneur or leader.

Transcript

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[Narrator]

On this episode of Leaders Playbook, It.

[Barry Diller]

Comes down to Instinct Billionaire business mogul.

[Narrator]

Barry Diller reveals the key leadership strategies behind six decades of success.

[Barry Diller]

Unless you are willful, nothing is ever going to happen.

[Narrator]

How the media legend turned tech titan, reinvented the movie industry, launched the Fox Broadcasting Network and built Internet brands embraced by millions his approach to negotiation if.

[Barry Diller]

I want something very badly, I don't really care about price.

[Narrator]

His appetite for ambitious bets.

[Barry Diller]

I just don't see risk where others do.

[Narrator]

And leading through crisis Travel stopped cold.

[Barry Diller]

After 9 11, so Expedia went from X revenue to 0 revenue plus the.

[Narrator]

Core principles that help him make bold decisions and win big.

[Barry Diller]

You cannot be cynical. Cynicism kills everything.

[Narrator]

Leader's Playbook Barry Diller starts now. I'm meeting Barry Diller at his company's headquarters in Manhattan. Diller is chairman and senior executive of iac, a holding company he started to buy and grow tech and media businesses. He's also chairman and senior executive of Expedia Group, overseeing a portfolio of travel brands. I'm here to talk leadership and learn how he's consistently innovated and scaled multibillion dollar companies.

[Interviewer]

You've incubated and spun off some of the most recognizable companies of the Internet age. What is it about your approach that's enabled you to consistently identify winners?

[Barry Diller]

It comes down to instinct and the ability to recognize a good idea and exercising your instinct and for sure not being afraid of risk.

[Interviewer]

What made you decide to create this kind of holding company? It wasn't something that other people were doing in the Internet space.

[Barry Diller]

Like anything it was kind of one dumb step in front of the other until we figured it out. This was not imagined whole cloth, but after a while we really did have this very unique business model of being a conglomerate that is also an anti conglomerate. I thought that once an entity got to be of sufficient size that it ought to be independent, that it ought to be spun out away from this corporate headquarters conglomerate into being on its own, it would then live in a much more transparent environment. So it's a weird business model, but it has certainly worked well for us.

[Narrator]

One of IAC's biggest success stories from Diller's buy, grow and spin off strategy is Match group. Back in 2003, Diller acquired the dating website match.com and then over almost two decades, it developed and acquired more dating platforms including Tinder, Hinge and OkCupid. Create a robust dating portfolio called Match Group. When Match Group fully separated from IAC in July of 2020, the dating company's market cap was over $26.5 billion.

[Interviewer]

What did you see in online dating before it was a mainstream thing?

[Barry Diller]

It's so, so obvious what a good idea that was. I certainly was alive and awake to the idea that if you could replace this process of being fixed up by other people or going to bars, if you could supplement that with an online interactive service where you could kind of flip through people who interested you and they could do the same and then you could match what a better mousetrap that would be. I'm glad no one else saw it or wanted to pounce on it, but we sure did.

[Narrator]

Dillard's buy, grow and spin off playbook worked over and over. IAC created nine publicly traded companies from travel site Expedia to Angie, the platform that connects homeowners with home improvement pros. One of Diller's key management strategies is what he calls creative conflict.

[Barry Diller]

To me, the best way to vet an idea is when you've got a group of people around a room and passion argument from each of them, which usually is in conflict with somebody else's thought. That kind of creative conflict of pushing that idea or that discussion about whatever it is and hearing as many disparate voices hopefully all argued passionately that cauldron if you make it last long enough, I've always thought you push it past exhaustion because that's when the good stuff comes out. That brew makes the decision. If you have an ear and I'm very lucky because I know how to listen, that you hear something in that and it's a truth for you, you Say, wow, that I can pull on it can be loud and argumentative and somewhat brutal, but I love it.

[Interviewer]

How can others develop that ability to identify the signal through the noise?

[Barry Diller]

Let's say after you through this cauldron, you're in a resting position. And what you will hear is what that resting position gives you for your own instinct. And once you've reached that level, it's solid and you can act on it. At least I can act on it. I don't know that there's a teaching process for that. You cannot be cynical. Cynicism kills everything. If you want to use your instincts, you have to brush that clean every day, practically.

[Interviewer]

Can you give us an example of when creative conflict revealed a new truth to you?

[Barry Diller]

Every example of anything I've ever done. And it's not a single truth. It's not like you listen and you wait for that one thing to clang into your head. You hear things that if you're listening, they either convince you this way or that way. And at some point, through this process, you are convinced. I just think it's a good process.

[Interviewer]

So are your employees and all the people who report up to you, are they able to have a creative conflict with you?

[Barry Diller]

With me? My God, yes. Absolutely.

[Narrator]

For Diller, creative conflict helps him understand complex situations and figure out how and when to take big swings. Coming up. Just as Diller plans an ambitious bet on travel, tragedy strikes.

[Barry Diller]

Several people said this is not the time to pay over a billion dollars for something so completely unpredictable.

[Interviewer]

And later, what made you such a good negotiator?

[Narrator]

The surprising way a billionaire tech titan makes deals.

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[Barry Diller]

Yeah, I do.

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[Dara Khosrowshahi]

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[Narrator]

IAC Chairman Barry Diller has developed trusted strategies over his decades long career that help him innovate and grow multi billion dollar companies. Diller's creative conflict identifies ideas and his instinct and willingness to take risks helps bring them to fruition.

[Barry Diller]

I just don't see risk where others do. And where others don't see it, I do. It's just cocked up a bit or abnormal.

[Interviewer]

Some of the risks you took professionally.

[Narrator]

Seem courageous to me, to an outsider.

[Barry Diller]

But not to me. Most of the things I'm interested in are things that haven't existed before. And that's by definition risk. God knows not all of them work, but that either daunts you or it doesn't.

[Narrator]

In July 2001, while Diller was the CEO of a cable channel, USA Network, he saw opportunity in the Internet and announced plans to acquire a controlling interest in Expedia, an online travel agency, buying a 75% stake for about $1 billion. And that's when Diller started to really focus on tech. But before the Expedia deal was completed, a devastating terror attack shook the nation.

[Interviewer]

You invested in Expedia and made this big deal right before 9 11. You could have pulled out of the deal, but instead you decided to double down. What was it that you saw in that moment that other people didn't see?

[Barry Diller]

Obviously travel stopped cold after 9 11. So Expedia went from X revenue to 0. Revenue came back relatively quickly. But at that critical moment, which is when we had to make the decision, there was no business. And yes, several people said this is not the time to pay over $1 billion for something that right now is so completely unpredictable. Someone in the room, when we were talking about this at the height of the argument, said, if there's life, there's travel. And as soon as I heard it I said, close. I'm betting on that. And if there isn't life, then who cares Anyway?

[Narrator]

Diller completed Expedia's acquisition in August of 2003 as he established IAC as a holding company for startups. A key player in the deal, a young IAC executive, Dara Khosrowshahi, who later became Expedia CEO and now runs Uber.

[Interviewer]

You kicked off your career Working for Barry Diller at iac. What did you learn working with him?

[Dara Khosrowshahi]

God, what did I not learn? I kind of feel like I owe my whole career to Barry, honestly, and I learned so much from him. But I will tell you one particular lesson that I got from Barry is Barry goes straight to the source. You know, you know how direct he is. And the way that I met him, actually, I was an investment banker at Allen and Company, and he was working on this deal, Takeover, Paramount Pictures. And as the price of this deal got higher and higher and higher, he wanted to understand exactly who was building the financial model, et cetera. And I was the lowly analyst there, and he spent two hours with me with my walking him through the financial model. So the first thing you take out is, here's Barry Diller listening to a little crap analyst in a bank. And two, he wants to hear it directly. He doesn't want to hear it through an associate or VP or managing director for him. He always told me, like, every level that information passes through, you lose some fidelity, you lose some edge. And the opportunities and the dangers are in that edge. So that has led me as a leader, like, I Talk to Executive 2, 3, 4 levels down from me. I want to hear the edge. I want to hear the good stuff and the bad stuff, because that helps me make a better decision. I've learned so much from him. But the skill of listening and going directly to the source versus getting a bunch of filtered information to you, I think has been one of the most valuable lessons from him.

[Narrator]

Diller made Khosrowshahi CEO of Expedia when he was 36 years old.

[Interviewer]

You have a track record for what you call throwing people into the deep end and promoting very young people into CEO positions. Why is that your approach?

[Barry Diller]

I think that as a company, it is a failure if you have to bring in people at senior positions from outside the organization. The best organizations bring people in at an early age where they don't have much experience, where they get forged by your process.

[Interviewer]

What are the qualities you look for?

[Barry Diller]

I look for energy and spark and a brain that I can understand. If those ingredients are there, it's worth a try.

[Narrator]

Diller's process for identifying and developing talent has forged a notable list of executives, including Michael eisner, who became CEO of Disney, and Jeffrey Katzenberg, who founded DreamWorks and DreamWorks Animation.

[Barry Diller]

I'm not much for the, quote, concept of teaching. I think you function. And if the people that primarily you interact with have kind of grown up with you or they've started with you what processes that they are around, they adopt by osmosis and they just go automatically.

[Narrator]

Coming up, the Titan makes a startling admission.

[Barry Diller]

You do fake it as you go.

[Narrator]

And later Diller's strategy for growth.

[Barry Diller]

Unless you are willful, nothing is ever going to happen.

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[Narrator]

Throughout his career, Barry Dillard, the billionaire chairman of IAC and Expedia, has had a track record of promoting young talent into high pressure roles, echoing his big responsibilities early in his career. By age 32, Diller was head of Paramount Pictures where he greenlit blockbuster films including Grease, Saturday Night Fever and the Indiana Jones franchise. By the time he was 44, Diller launched the Fox Network with Rupert Murdoch. He leaned on instinct, greenlighting edgy programming to attract younger audiences including Married with children, the Simpsons, 21 Jump street and Beverly Hills 90210. And those instincts were right.

[Interviewer]

You've talked so much about instinct, instinct, instinct, instinct at the core of your ability to identify new opportunities. How much do you weigh the importance of looking at data when making decisions?

[Barry Diller]

Well, data is good for history, past and math and things that are data focused and you can use them to some degree but you cannot Use them for anything that hasn't happened yet or for predicting the future.

[Interviewer]

Looking at all your bold decisions over the years in Hollywood, in tech, you.

[Narrator]

Seem fearless to me.

[Interviewer]

So I was surprised to read in your book that you struggled with fear and anxiety around things like flying or public speaking.

[Barry Diller]

Well, I did. I had one big fear, and that allowed me to take other fears less importantly. I mean, I think constitutionally, it's biology. I mean, I don't take any particular pride in it.

[Narrator]

The one big fear Diller's referring to here is a secret he kept about his sexuality for decades. He writes about it in his 2025 memoir, who Knew? For Diller, the one big risk of being outed made all other risks in his life seem smaller, and that emboldened him in the boardroom.

[Interviewer]

What was it that you learned in Hollywood that you've been able to bring to tech?

[Barry Diller]

Nothing.

[Interviewer]

Nothing?

[Barry Diller]

Oh, it's an exaggeration. My own sense of things, my own instincts are, of course, brought by the history of my life. And so, yes, to that extent. But really, probably the only pure thing is how much I prize. Tell me what the idea is, and can I crunch that down into something I thoroughly understand and then have an instinct about? That was taught to me by narrative forms, by essentially being an editor and using what is the idea as the center of galvanizing what to do. Yeah, I probably brought that forward. But the world of technology is completely at the other side of the planet from instinct and editorial. Because technology, of course, is. Physics is based upon math, ones and zeros. It's a mathematical process, a technical process. So they're completely different worlds.

[Narrator]

Long before he was running Paramount, Diller got his start in the mailroom at William Morris Agency. From there, he scored a role as an executive at abc, where he created Movie of the Week and developed the TV miniseries format. One of his most successful was a broadcast watched by more than half the country. His surprising strategy for succeeding in those roles with little experience. Fake it till you make it.

[Barry Diller]

You do. Fake it as you go. You can't do it if you try and do it any other way. If you actually try and find some methodological way, you probably fail. So I think faking it until you get it, in other words, making others think you know something when you know nothing. And then eventually you're figuring it out as you go. And eventually, there it is, no more faking.

[Interviewer]

We've talked about how you come to your ideas, creative conflict, listening to your instinct, identifying those new truths. And when it comes to executing You've talked about using blind willfulness. Is it a strategy or is it just your passion and action?

[Barry Diller]

However good the idea is, unless the person is willful, nothing happens. I mean, certainly you need energy and edge and whatever, but unless you are willful, which means you will impose your will on whatever it is, nothing is ever going to happen.

[Interviewer]

So what's the line between willful and stubborn?

[Barry Diller]

Stubborn is, again, stupid. I mean, if you're willful and somebody comes to you and they say something that you hear that amends your will, and then you're willful about that. Hallelujah.

[Interviewer]

So willful is about executing once you have your strategy, of course, yes.

[Narrator]

Diller's leadership playbook. Following instinct, leaning into creative conflict to identify the right path, executing with blind willfulness, and sometimes just faking it. For six decades, Barry Diller's seen extraordinary success, first in media, then in tech. Here's what he says drives it.

[Interviewer]

What is it about Barry Diller that's enabled you to have so many decades of success across so many different industries?

[Barry Diller]

Probably curiosity more than anything. I think without curiosity is a base. I wouldn't have gone anywhere and done anything. And then there's serendipity. People take a lot of credit for their great success in different industries and things, but a lot of it is timing and circumstance. And I was just lucky that, for instance, in the kind of third act of my life, the interactive or e commerce part, I came along in 90 too, was starting to learn about interactivity. So by 95, when the Internet really got used by normal people, I was kind of there and ready.

[Interviewer]

You talk about luck, but what I see is a lot of hard work and taking advantage of the right opportunities.

[Barry Diller]

I think on average, everybody gets their amount of luck and serendipity. And of course, then it's, well, what the hell do they do with. And that is, of course, another reasonable definition of success is what do you do with it?

[Narrator]

Throughout Diller's career, he's overseen massive deals, acquiring Expedia, Match, and Angie before taking them public. But what he says about those deals is surprising.

[Barry Diller]

I don't know that I'm such a good negotiator. I really don't know that I am. I don't really think I am. I know people, and I been in too many situations where I have recognized a real talent for negotiating. My attitude is I really don't care about the best deal. If you grind someone into the dust or on this or that provision of a transaction, I think that there's something inherently rotten about that. I don't want to do anything dumb, but I also don't. I don't have any competitive thing with it. I just want to get it done at what I consider a fair transaction. That doesn't make me a great negotiator. And if I want something very badly, I don't really care about price.

[Interviewer]

What do you think your biggest professional failure has been? That was it? Negotiating a deal that didn't go your way?

[Barry Diller]

No. The real mistakes, the big mistakes have been, well, there's certain stuff that's just dumb and wrong, and you get a certain amount of that if you do multiple things. But the other part is I've held onto this naivete and I've trusted people and I would say the biggest disappointments I've had, and there have been very few but where trust was broken. And that to me is like. That's like a breach.

[Narrator]

After six decades in Hollywood and tech, how has his leadership style evolved?

[Barry Diller]

I don't think it's ever changed.

[Interviewer]

And you're still motivated by curiosity?

[Barry Diller]

I'm curious about different things than I was. And I will always be, because new stuff is what, when it comes into view, is what ignites my curiosity. That's the one thing I still am curious, you know, it's an unquenchable reservoir.

[Narrator]

For Barry Diller, curiosity is the engine. Creative conflict helps him find a path, and instinct is his compass. More valuable insights from some of the top business minds in the country. On the next episode of Leaders Playbook.

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