The Grill Room

Latest Episodes:

Ben & Justin on Semafor’s $330M Valuation Jan 20, 2026

Show notes

Semafor co-founders Justin Smith and Ben Smith join Dylan to discuss their recent $30 million financing at a staggering $330 million post-money valuation—and to address some industry player-hating. They justify the math behind the valuation, break down the economics of a media company with a significant events business (while rejecting the idea that Semafor is events-first), and walk through their broader ambition to build a global, intelligent, independent news brand in the mold of The Economist and the Financial Times.

CBS News on the Rocks Jan 16, 2026

Show notes

Dylan and Julia dig into the mess surrounding a potential corporate sponsorship of CBS News’ “Whiskey Fridays” with Tony Dokoupil, after an Evening News set featuring a Jack Daniel’s logo leaked online. The controversy also sparked a bigger debate about whether corporate sponsorships lack journalistic integrity—or actually offer a viable lifeline to a news industry in perpetual decline.

The Gospel According to VandeHei Jan 13, 2026

Show notes

Jim VandeHei, the co-founder and C.E.O. of Axios, is back with hot takes on the industry’s biggest challenges: the media’s trust deficit, the imperative to serve hyper-targeted audiences, and how A.I. is writing journalism’s next chapter. Jim predicts a potential golden age for quality reporting—provided publishers actually embrace A.I.—and delivers a characteristically blunt assessment of The Washington Post and CBS News.

The Dokoupil Debacle & Semafor’s $330M Question Jan 09, 2026

Show notes

Julia and Dylan survey a volatile week in media: Tony Dokoupil’s rocky debut at CBS Evening News and the broader questions it raises about Bari Weiss’s leadership, Semafor’s eyebrow-raising $330 million valuation, the flood of A.I.-generated content overtaking Instagram and X, and plenty more.

Hollywood’s Future ’26 War Stories Jan 06, 2026

Show notes

Matt Belloni joins Dylan and Julia to chart the latest updates surrounding the Warner Bros. Discovery bidding war between Netflix and Paramount—and what each side stands to gain or lose. Then they dive into Hollywood’s accelerating A.I. anxiety in light of Disney’s pact with Sora 2, the upcoming film slate for 2026, YouTube's rights deal with the Oscars, and more. Plus: Matt explains his choices for Hollywood’s heroes and villain of the year.

CNN Sale Chatter, Meta TV & Other 2026 Predictions Jan 02, 2026

Show notes

Dylan and Julia forecast the media chaos to come, mapping out the storylines likely to dominate the year ahead—from the ongoing Warner Bros. Discovery drama to Disney’s Sora experiment, Instagram Reels invading connected TV, and the likely disruption of the ad market. They also predict CNN’s uncertain future, the waning influencer economy, the A.I. forces quietly rearranging everything, and much more.

Are the Kids… All Right? Dec 30, 2025

Show notes

Jim Steyer, the founder and C.E.O. of Common Sense Media, joins Dylan for a fascinating end-of-year conversation about which tech companies and social media platforms are getting it right (and wrong) when it comes to child safety. They also chat about his legendary class at Stanford and forthcoming podcast, his brother Tom’s gubernatorial bid in California, and much more.

Learn more about Starbucks industry-leading benefits at ⁠starbucks.com/partners⁠⁠.⁠

Media’s ’25 Crisis of Nerve Dec 26, 2025

Show notes

Julia and Dylan reunite to survey the stories that defined media in 2025, starting with the recent uproar over Bari Weiss pulling a ’60 Minutes’ segment critical of the Trump administration. Then they dig into the impact of David Ellison’s bid for Warner Bros., Trump’s omnipresent influence on the media ecosystem, the mounting pressures on legacy outlets, and much more.

Learn more about Starbucks industry-leading benefits at ⁠starbucks.com/partners⁠⁠.⁠

Katie Couric Goes Direct Dec 23, 2025

Show notes

The one and only Katie Couric joins Dylan for a wide-ranging look back—and forward—at her career, from her stints at the Today show, CBS, and Yahoo to building her own media empire. She digs into the collapse of monoculture, the rise of a creator-driven media landscape, why authenticity matters now more than ever, maintaining journalistic integrity in an era of relentless political pressure—and much, much more.Learn more about Starbucks industry-leading benefits at ⁠starbucks.com/partners⁠⁠.⁠

Media’s Anxiety Index Dec 19, 2025

Show notes

Orchestra C.E.O. Jonathan Rosen and Jon Kelly join Dylan live from New York to walk through new survey data capturing the media industry’s state of mind. They dig into the rise of subscription-based models, the FAST explosion, the creeping influence of A.I., and much more. Plus, cameo insights from Semafor’s Ben Smith and Feed Me’s Emily Sundberg who offer their own read on where the business is bending—and breaking.

Learn more about Starbucks industry-leading benefits at ⁠starbucks.com/partners⁠⁠.⁠