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.

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)

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).

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).

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).

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).

“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)

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)

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)

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)

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)

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)

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)

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)

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

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.

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.