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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Ex-CNN host Don Lemon joins Dylan in The Grill Room to reveal what he’s learned about the electorate from his tour of America’s battleground states. Then they trade war stories about Don’s meteoric rise during the Trump years, his dramatic defenestration from CNN, and his second-act hustle in the post-cable era.

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Media reporter Charlotte Klein joins Dylan for a candid conversation about her recently published Power Issue, New York's annual edition highlighting the under-the-radar people shaping the media capital of the world. Then they trade notes on the recurring themes underlying the industry: CNN’s subscription-based business model, CBS News’ D.E.I. shortcomings, WaPo’s reneged Kamala endorsement, whether local news can survive, and much more.

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Legendary newsman Brian Williams and his longtime executive producer Jonathan Wald join Dylan to dish about their new election night special for Amazon, the glory days of TV news, its current belt-tightened economics, his own time in the wilderness, why he didn’t take the CBS job, and why he decided to get the band back together for one evening—and what it might portend.

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