The Atlantic’s C.E.O. Nick Thompson joins Dylan for a candid conversation about the existential challenges of leading a media company, centered around the looming threats and opportunities of A.I. Nick envisions a media ecosystem where their web presence goes away, and lays out his growth strategy to mitigate the concerns: building the strongest possible direct relationships with readers while cutting out reliance on tech platforms altogether.

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NBC News vet and former Meet the Press anchor Chuck Todd joins Dylan for a candid conversation about his departure from the network after nearly two decades. He reflects on the decline of media trust, the urgent need to revitalize local journalism, and how the internet has reshaped news consumption. Chuck also scrutinizes the nationalization of politics before the duo switch gears to explore the potential for podcasts to evolve into dynamic, multi-hour programming, à la ESPN’s signature daytime shows.

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MSNBC’s Chris Hayes joins Dylan for a thrilling and sobering deep dive into how social media and smartphones hijacked our brains; how attention became the single most powerful currency in the political economy; and why Donald Trump is singularly effective at commanding it.

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John Ourand joins Dylan for an insider’s look at how the NFL is preparing for the upcoming Super Bowl in New Orleans—and whether the league is feeling the effects of small-market Chiefs fatigue. The duo also delve into the crucial role of live sports rights in keeping media businesses afloat, and explore how streaming giants like Amazon and Netflix are reshaping the future of sports broadcasting.

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The New York Times’ Ben Mullin joins Dylan for a deep dive into Mark Thompson’s attempt to transform CNN from a cable television network into a digital and streaming juggernaut. After a round of mass layoffs, the duo contemplate whether CNN as a digital-first enterprise can maintain the network’s influence in a post-linear landscape, and whether Thompson actually has a plan to get there.

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NBC News correspondent Jacob Soboroff joins Dylan to share his unique experience covering the devastating Los Angeles fires, which destroyed his childhood home in Pacific Palisades. Then, as Trump’s inauguration looms with ambitious deportation plans, Jacob provides an inside look at his extensive reporting on immigration at the border.

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Ashlee Vance, the former Bloomberg tech reporter and Musk confidant, joins Dylan to discuss his high-risk, high-reward leap into launching his new company, Core Memory, a sci-tech media startup. After a decade-plus entrenched in the world of legacy media, Ashlee offers a glimpse into how he’s approaching his new business venture and leveraging his unique access to cutting-edge technology. Then he and Dylan delve into the transformative potential of A.I. and the interplay between Silicon Valley and Donald Trump.

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Jon Kelly joins Dylan to ruminate on a handful of developments across the media landscape: Will Lewis’s fantasy subscriber number for The Washington Post; Emma Tucker’s stalwart leadership at The Wall Street Journal; the latest on Mark Thompson’s CNN digital transformation strategy; and the impending A.I. newsroom revolution.

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Ian Orefice, founder of EverWonder Studio and former TIME Studios president, joins Dylan to dig into how live sports has become the next front in the streaming wars. Then they kibitz about EverWonder’s role in producing the record-breaking Netflix Christmas NFL games and whether the Tyson vs. Paul fight represents the future of sports media rights battles to come.

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Semafor co-founder and former BuzzFeed E.I.C. Ben Smith joins Dylan to survey the media landscape heading into 2025. They discuss how news organizations are bracing for the impact of Trump’s return to the Oval, delve into the recent wave of departures at The Washington Post, unpack a few of Semafor’s strategic initiatives, and explore the rising influence of newsletters in shaping media distribution.

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