The Grill Room

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The YouTube Half Nelson Mar 25, 2025

Show notes

Puck’s streaming guru Julia Alexander joins Dylan for a high-level conversation about YouTube’s stranglehold on the news industry—and the seismic shift it’s triggering. Julia explains how digital creators, news influencers, and opinion leaders across YouTube, TikTok, and Instagram are rewriting the playbook, forcing legacy media giants to either adapt or risk irrelevance in a world where independent voices are driving the narrative.

Making a Racquet Mar 21, 2025

Show notes

Caitlin Thompson, founder of ‘Racquet,’ joins Dylan for a deep dive into her mission to make tennis more vibrant and accessible through her quarterly magazine, blending top-tier journalism, tennis fashion, travel, and escapism—and offering a refreshing contrast to the sport’s corporatized past. Caitlin also weighs into the evolving media landscape, underscoring the need of mission-driven storytelling to elevate the sport.

A Lessin in Media Mar 18, 2025

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Jessica Lessin, founder and C.E.O. of The Information, joins Dylan for a candid conversation about how The Information has thrived and remained profitable after 11 years, why deep expertise and loyal audiences are more important than chasing scale, and her approach to backing sharp-minded entrepreneurs through recent investments in Semafor, The Ankler, and others. Jessica also weighs in on how Silicon Valley’s power players are recalibrating in the era of Trump 2.0.

Emma Mar 14, 2025

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Beloved yet controversial Wall Street Journal top editor Emma Tucker joins Dylan for a candid discussion about evolving the historic business, change management, tough choices, and the future of the news media business.

It’s The Economist, Stupid Mar 11, 2025

Show notes

Zanny Minton Beddoes, the editor-in-chief of The Economist, joins Dylan for an inside look at the publication’s unusual position within the media firmament, and how the ultimate business traveler rag is refreshing itself for the digital first era: still all-in on the virtues of classical liberalism, but with a dose of A.I. powering its expanding global footprint. Plus, Beddoes and Dylan dig into the magazine’s unwavering editorial independence at a time when independent media is under attack.

White House Press Pool Kremlinology Mar 07, 2025

Show notes

‘The New York Times’ Peter Baker joins Dylan to dissect the fraught relationship between the Trump White House and the press, from expelling the Associated Press to handpicking the press pool—tactics he likens to historical press suppression in Russia. They also weigh in on the changes at ‘The Washington Post’ under Jeff Bezos, and the fight to maintain journalistic integrity in an increasingly politically charged environment.

Zaz's Cablenomics Mar 04, 2025

Show notes

Bill Cohan joins Dylan to dissect the three-year evolution of Warner Bros. Discovery since David Zaslav’s bold 2022 merger of WarnerMedia and Discovery. He breaks down W.B.D.’s rising streaming profits, declining linear TV business, and its $19 billion debt reduction—bringing the company closer to a credit upgrade. With speculation swirling about a potential merger with NBCUniversal or Comcast’s SpinCo, Bill examines what’s next for W.B.D., the strategic loss of NBA rights, and the broader ripple effects on networks like CNN and the media landscape writ large.

Oppenheim’s Opus Feb 28, 2025

Show notes

Former NBC News president Noah Oppenheim sits down with Dylan for a candid, no-holds-barred conversation on the media industry’s uncertain future. He dives into the chaos engulfing MSNBC, shares his unfiltered take on SpinCo, and offers his outlook on the fate of NBC News. Finally, he reveals how he helped bring Netflix’s hit-series ‘Zero Day’ to life.

30 Rock’s Kutler Era Feb 25, 2025

Show notes

Axios’s Sara Fischer joins Dylan to scrutinize the dawn of MSNBC’s Rebecca Kutler era, where a wave of personnel and talent changes at 30 Rock aims to steady the embattled legacy mediaco. Sara also offers her assessment of the state of the broadcast news industry and considers whether it has any future in the streaming age.

A White House Media War Feb 21, 2025

Show notes

Eriq Gardner joins Dylan to dissect the wave of MAGA-driven lawsuits targeting Trump’s media adversaries. Eriq highlights casino magnate Steve Wynn’s efforts to revive his 2018 defamation suit against the Associated Press, which he hopes is elevated to the Supreme Court, potentially setting the stage for a SCOTUS showdown that could challenge the landmark ‘Times v. Sullivan’ ruling. The duo debate whether a better legal framework exists and suggest how media organizations can navigate these shifting legal battlegrounds.

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