The Grill Room

Latest Episodes:

The Information Age Sep 04, 2026

Show notes

Jessica Lessin, the founder, editor in chief, and C.E.O. of The Information, joins Dylan and Julia to unpack the record growth behind her 13-year-old subscription business. She explains her bet on China coverage as rivals shutter Asia bureaus, the push into finance reporting to track AI’s reshaping of Wall Street, and her expansion into video with TITV and a new AI Deep Dive show. Lessin also weighs in on the “information mafia” of alumni going independent and tech’s cratering public image.

The Next Weather Media Supercycle Sep 01, 2026

Show notes

Julia and Dylan make the case that climate and weather coverage—supercharged by an incoming Super El Niño—could become news media’s next dominant storyline. They discuss why outlets like CNN and the New York Times are investing early, how AI skepticism is boosting trust in authoritative reporting, and why reframing weather through food, sports, and daily life could turn it into a real subscription business.

Media’s Great A.I. Shrug Aug 28, 2026

Show notes

Julia and Dylan spar over Stan Druckenmiller’s A.I.-assisted Wall Street Journal op-ed and what it signals for trust in media. Julia argues transparency is essential as A.I. creeps into newsrooms and op-eds alike, while Dylan makes the case that the line between “using A.I.” and “writing” is blurrier than purists admit...

Do Democrats Need a Rebrand? Aug 25, 2026

Show notes

Peter Hamby joins Dylan to decipher new polling on the Democratic Party’s perception problem—to wit, Trump may be historically unpopular, but voters still don’t love Democrats, either. Then they dig into the A.O.C.-Mamdani favorability gap, why Bernie’s brand of populism ages better than the “intersectional” variety, and the Gavin Newsom content-studio model for winning back young men and Latino voters ahead of 2028.

The Times–Pablo Torre Loophole Aug 21, 2026

Show notes

Julia and Dylan trade notes on the dueling NBA and ESPN investigations into the Clippers and the odd dynamics of the Times’ licensing deal with Pablo Torre, using it to explore how legacy outlets increasingly outsource journalism—and risk—to independent creators. They also dig into CNN and MS Now’s new “all-access” membership services, and whether cable news can reinvent themselves for a D.T.C. world.

The Smart Brevity Manifesto! Aug 18, 2026

Show notes

Axios’s Jim VandeHei joins Dylan to make the case for radical simplification in the age of A.I., drawing on his new book, Simplify, as well as Axios’s own moves to kill off sports and Policy Pro while doubling down on politics, tech, events, and local news.

YouTube’s New Velvet Rope Aug 14, 2026

Show notes

Dylan and Julia break down YouTube's new monetization rules—an A.I. slop-proof 8,000 view threshold designed to crown a class of “premium” creators and pull news brands deeper into its orbit. Plus: What Bob Iger and Josh Kushner’s $12.5 billion Lakers bid reveals about the state of sports and Bob’s post-Disney life.

Politico's Power Play Aug 11, 2026

Show notes

Jonathan Greenberger, the unconventional editor in chief of Politico, joins Dylan to explain how a business-side executive ended up running the newsroom—and what it means for Politico's future. They discuss the relaunch of Playbook and its early scoop streak, the push to make every franchise multi-platform (podcasts, video, events), and Politico's bet that its global footprint can turn political disruption into a worldwide story. Greenberger also opens up about newsroom AI hackathons, the competitive threat from Punchbowl and Notus, and his pitch to TV talent thinking about jumping ship.

The Business Insider Rescue Plan Aug 07, 2026

Show notes

Christian Baesler, the new C.E.O. of Business Insider, joins Dylan to lay out his strategy for revitalizing the media company. He makes the case for monetizing scale beyond the website, doubling down on pro-consumer niches like AI Insider and CMO Insider, and using A.I. to sharpen the publication’s journalism. Baesler also shares his vision for Business Insider to become a platform for independent creators—like a music label for journalists or… Substack.

The Times’ Talent Trap Aug 04, 2026

Show notes

Julia and Dylan discuss Ross Douthat’s move from The New York Times to CBS’s 60 Minutes—and what it signals about the Times’ pivot to video, which may have inadvertently created a star system with real talent-retention consequences. They also dig into the broader challenge of holding onto talent inside legacy organizations, the growing pull of going independent, and why video has become so central to driving engagement and keeping audiences.

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