Confessions of a Mogul (with Barry Diller) episode artwork

EPISODE · Jul 24, 2025 · 1H

Confessions of a Mogul (with Barry Diller)

from Stay Tuned with Preet · host Preet Bharara

Media executive Barry Diller, one of the industry's most successful moguls, is behind some of America’s most popular films and TV shows, from Home Alone to The Simpsons to Roots. He’s now the chairman and senior executive of IAC and Expedia Group. Diller’s new memoir, Who Knew, is a candid account of his family, his career, and his sexuality – long a source of public speculation and debate. He joins Preet to talk about what it was like to bare his soul, how Hollywood died when the “tech overlords” took over, and why he thinks conflict is essential.  In the bonus for Insiders, Diller gives his take on the current political moment, and whether AI can replace the artist’s process.  Then, Preet answers questions about President Trump’s attempts to shut down the Department of Education and the difference between justice and revenge. Join the CAFE Insider community to stay informed without hysteria, fear-mongering, or rage-baiting. Head to cafe.com/insider to sign up. Thank you for supporting our work. Show notes and a transcript of the episode are available on our website.  You can now watch this episode! Head to CAFE’s Youtube channel and subscribe. Have a question for Preet? Ask @PreetBharara on BlueSky, or Twitter with the hashtag #AskPreet. Email us at [email protected], or call 833-997-7338 to leave a voicemail. Stay Tuned with Preet is brought to you by CAFE and the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Media executive Barry Diller, one of the industry's most successful moguls, is behind some of America’s most popular films and TV shows, from Home Alone to The Simpsons to Roots. He’s now the chairman and senior executive of IAC and Expedia Group. Diller’s new memoir, Who Knew, is a candid account of his family, his career, and his sexuality – long a source of public speculation and debate. He joins Preet to talk about what it was like to bare his soul, how Hollywood died when the “tech overlords” took over, and why he thinks conflict is essential.  In the bonus for Insiders, Diller gives his take on the current political moment, and whether AI can replace the artist’s process.  Then, Preet answers questions about President Trump’s attempts to shut down the Department of Education and the difference between justice and revenge. Join the CAFE Insider community to stay informed without hysteria, fear-mongering, or rage-baiting. Head to cafe.com/insider to sign up. Thank you for supporting our work. Show notes and a transcript of the episode are available on our website.  You can now watch this episode! Head to CAFE’s Youtube channel and subscribe. Have a question for Preet? Ask @PreetBharara on BlueSky, or Twitter with the hashtag #AskPreet. Email us at [email protected], or call 833-997-7338 to leave a voicemail. Stay Tuned with Preet is brought to you by CAFE and the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Confessions of a Mogul (with Barry Diller)

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This episode was published on July 24, 2025.

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Media executive Barry Diller, one of the industry's most successful moguls, is behind some of America’s most popular films and TV shows, from Home Alone to The Simpsons to Roots. He’s now the chairman and senior executive of IAC and Expedia Group....

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