The Grill Room

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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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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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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