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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Former Hearst Magazine president Troy Young reunites with Dylan to discuss what lies ahead for the media industry as we turn our calendars to 2025. In particular, they home in on the significant role that A.I. will play in transforming how news is consumed and distributed—and the need for media companies to adapt to new consumer behaviors in order to stay relevant.

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Green room machine John Heilemann joins Dylan to look back on this year in media: the procession of entertainment and tech C.E.O.s kissing Trump’s ring; the headwinds facing Jeff Bezos at The Washington Post; the rise of Elon and twisted power of X; the most significant media macro trends; the industry’s biggest winners and three sorriest losers; and why 2024 was the year of the podcast in politics.

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Famed Democratic strategist and CNN senior political commentator David Axelrod joins Dylan for a candid, wide-ranging conversation about podcasting. He reflects on being an early mover in the podcasting space, the art of podcasting, the influence that podcasting has had on our politics and culture, the future of the political-media landscape in the age of Elon, and much more.

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Jon Kelly joins Dylan to discuss Matt Murray’s surprising ascent to the WaPo executive editor job. And then Eriq Gardner swings by to weigh in on Bob Iger’s Trump settlement calculus.

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Legal analyst Jeffrey Toobin joins Dylan to scrutinize ABC News’ $15M settlement with Trump, which has everyone in the political-media industry abuzz about the signal this sends to MAGA and its adversaries. While many perceived this to be a very winnable case for ABC News, their striking decision to settle for such a high price tag has led to a myriad of questions surrounding the media climate as we head into Trump 2.0.

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Bill Cohan joins Dylan to dissect the stark financial calculus behind David Zaslav’s decision to separate Warner Bros. Discovery’s growth assets from its declining linear TV networks—a move that’s made Wall Street practically euphoric. Then they dive into Zaz’s ultimate endgame: to build, to sell, or to spin?

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