Learning From Failure and Avoiding Cynicism

My guest this week is Barry Diller, one of America's most successful businessmen. At 83, he chose to publish a deeply personal book and open up about his successes and failures.

With surprising candor he details the rules he's lived by: trust first, confront directly, and make the call when the clock starts. In our conversation, he shares why success teaches you nothing, why failure is essential, and why instinct still beats algorithms in a data-obsessed world.

This episode is filled with Hollywood lore and business acumen.

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About Barry: He is the Chairman and Senior Executive of IAC, and is best known for founding the Fox Broadcasting Company with Rupert Murdoch and leading Paramount Pictures. Over his career, he has reshaped television, film, and online media.

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Approximate Timestamps:

(00:00) Intro

(01:48) Vulnerability and Writing 'Who Knew'

(05:20) Lack Of Confidence & Fake It Until You Make It

(17:58) Changes In The Entertainment Industry

(22:35) Instinct Vs Data

(27:17) AI's Impact on the Entertainment and Travel Industry

(42:35) One Dumb Step At A Time

(52:39) Accountability During Conflict

(55:06) Public Broadcasting Regulation And Fair Reporting

(58:04) What Is Success For You

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