Legendary media mogul and IAC chairman Barry Diller joins Dylan for a lively discussion on the shifting landscape of the media industry: Will Comcast’s spun-off cable assets thrive as a reimagined bundle or end up being sold to private equity? Do Hollywood heavyweights need greater scale to remain competitive? Can The Daily Beast transform into a powerhouse business? Then they dig into the future of the Democratic Party and Barry’s reasons for optimism in the new era of Trump and Elon.

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Former Hearst Magazines president Troy Young connects with Dylan to probe what went wrong at The Washington Post and CNN, and whether Will Lewis and Mark Thompson can fix their respective companies before the media business changes again.

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Former top CNN executive Andrew Morse joins Dylan to discuss his new career as C.E.O. of The Atlanta Journal-Constitution, where he’s applying the old NYT digital innovation playbook at the local level. Then they dig into his clashes with David Zaslav and Chris Licht, the unceremonious cancellation of CNN+, and the troubles afflicting the media landscape writ large.

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Jeremy Boreing, co-founder of the conservative media network The Daily Wire, joins Dylan to explore the surging impact of alternative media on modern politics and deliver his candid critique of legacy media's failures. Then he shares insights into the strategies driving his company’s accelerated growth and discusses what lies ahead as The Daily Wire closes in on surpassing $200 million in revenue.

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Punchbowl co-founders Jake Sherman and Anna Palmer join Dylan to discuss their vertiginous ascent from Politico all-stars to building a veritable Playbook rival. They dive into Punchbowl’s origin story, their tunnel-vision focus on Capitol Hill, the untapped potential of niche subscription markets, experimenting with A.I., and much more. 

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Jon Kelly joins Dylan to discuss the cascading effects of Brian Roberts’ monumental decision to spin off NBCUniversal’s declining cable assets. Then they get into Rachel Maddow’s $125 million contract renegotiation and how MSNBC survives without the NBC mothership.

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It’s a food media-themed doubleheader in The Grill Room! First, Dylan convenes with The Infatuation C.E.O. Paul Needham, who discusses the economics of his restaurant recommendation empire. Then acclaimed food writer and entrepreneur Alison Roman stops by to discuss her journey from legacy media to entrepreneurship and why her defenestration from The New York Times turned out to be a blessing in disguise.

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CNBC's Alex Sherman joins Dylan for the ultimate dish-fest across a series of juicy and mission-critical topics--Disney succession tea leaves, Dana Walden versus the outsiders, John Malone's Maffei moves, NBC's "Roundball Rock" deal blockers, Comcast's cable trial balloon, and much more.

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Dylan is joined by Axios co-founder Jim VandeHei for a wide-ranging discussion about the most pressing media storylines following Trump’s victory: Musk’s ascension and the future of X, the balkanized media landscape, the Dems’ Joe Rogan problem, the existential challenges facing The Washington Post and CNN, and much, much more.

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Dylan is joined by veteran Republican strategist and never-Trump media darling Tim Miller for an incisive post-election postmortem. Together, they dissect how the election unfolded, examine the failures of Democrats and the media to anticipate this new reality, and discuss what lies ahead for the political-media landscape.

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