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.

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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.

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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.⁠

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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.

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Andrew Ross Sorkin, founder of The New York Times’ DealBook and co-host of CNBC’s Squawk Box, joins Dylan for a candid conversation about the ins and outs of his media business. He walks through a typical day in his life, explains why he’s prioritizing quality over quantity (and skipping the media-empire chase), and breaks down his approach to high-stakes interviews. They also dig into the DealBook Summit—his toughest interview yet, his white-whale guest—and the advice he’d give to anyone trying to break into media in 2026.

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Dylan and Julia reunite to chew over Disney’s new deal with OpenAI, which will pump more than 200 Disney characters into Sora so fans can generate their own content with the company’s most valuable I.P. They also check in on the WBD sweepstakes: how Paramount and Netflix stack up, what each company’s contingency plans looks like, the regulatory headaches ahead, and much more.

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Yahoo C.E.O. Jim Lanzone joins Dylan and Julia for a tour of the company’s Apollo era, four years after the private equity behemoth bought the business for just $5 billion—nearly $120 billion shy of its peak valuation. Lanzone breaks down Yahoo’s growth strategy: the metrics that actually matter, how the company monetizes at scale, and what the endgame looks like. They also dig into Yahoo’s A.I. ambitions, and what it takes to run a mass-market consumer business in a media landscape focused on niche and specialized content.

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It’s been 20 years since How I Met Your Mother premiered, and just over 10 years since the finale. Josh Radnor, who played “Ted” for nine seasons teams up with series co-creator Craig Thomas for this episode-by-episode rewatch podcast. For the superfans, HWMYM (listen to the trailer to learn how it’s pronounced) will get into all the secrets, theories, and pineapples, but we'll also use HIMYM – and our relationship to it two decades later – to talk about life and love and art and everything in between. How We Made Your Mother… a flashback podcast for a flashback show.  You can listen to all episodes of season 1 now, and join Josh and Craig as they dive into season 2! 

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Julia and Dylan revisit the endlessly looping Nuzzi-Lizza saga, questioning whether we’re still covering journalism or merely documenting a public breakup. They dissect the collateral damage of the drama: Substack’s structural vulnerabilities, Vanity Fair’s brand calculus, and the reputational fallout for both combatants. Plus, they swap their Spotify Wrapped revelations and discuss how Spotify turned an annual recap into a global marketing juggernaut.

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Makena Kelly, senior writer at Wired, joins Julia to wade into the Venn diagram of politics, internet culture, and technology. They discuss Elon Musk’s curious cameo in the Trump administration, the rise of influencer gatherings over traditional press, and how online fandoms can turbocharge campaigns like Zohran Mamdani’s. They also explore how creators are reshaping political media and the tightrope reporters walk to stay objective through it all.

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