Former National Security Advisor Jake Sullivan and Deputy National Security Advisor Jon Finer join Mixed Signals to talk about their leap from the Situation Room to the podcast studio. They explain why they started The Long Game, what they learned about media while running US foreign policy, and how the war in Ukraine became as much an information battle as a military one. The conversation ranges from Gaza and Al Jazeera to AI-generated propaganda, reactions to the Munich Security Conference, and whether Democrats ever figured out how to explain foreign policy to the American middle class.

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Gus Wenner, chairman of Rolling Stone and son of the magazine’s legendary founder, has spent years balancing the brand’s print heritage with its digital transformation. On this week’s Mixed Signals, Ben and Max talk with Wenner about his new holding company, Wenner Media Ventures, and why he thinks algorithms  disrespect audiences. They also discuss the venture’s investment in the hit video series Track Star, his defense of Rolling Stone’s most provocative journalism, and his potential future media investments.

When now-President Donald Trump decided to put on an apron and serve customers at a McDonald’s drive-thru on the 2024 campaign trail, it put Tariq Hassan, then McDonald’s chief marketer, in a tight spot. On this week’s Mixed Signals, Ben and Max sit down with the former Golden Arches CMO to discuss the Trump episode, why he thinks ad makers should engage with journalists, and what goes into a good celebrity Super Bowl ad.

A year into Hollywood’s heralded vibe shift, as major production companies in the US have increasingly catered to broader or more conservative tastes, a gay Canadian hockey romance was not an obvious choice to become a hit. On this week’s Mixed Signals, Ben and Max bring on Bell Media CEO Sean Cohan to unpack the success of Heated Rivalry and explain how it became an overnight cultural sensation. Cohan also talks about Bell’s strategy of using licensing deals to reach new audiences, the enduring power of a well-told romance, and why Canadian storytelling is only getting started on the global stage.

Stephen Dubner has spent 20 years proving that things aren't what they seem—and now he's not so sure that's always true. The co-creator of Freakonomics and host of one of podcasting's most enduring shows joins Ben and Max to talk about why he never sold to Spotify, how The New York Times shifted from telling readers things to telling them what to think, and his new self-funded TV experiment that's "like laundering podcast money." Along the way, Dubner explains how he accidentally got sucked into the Blake Lively-Justin Baldoni gossip vortex (Candace Owens was involved), makes the case for prediction markets over pundits, and reveals why he's now considering buying a pizza place with a Michelin-starred chef who hated his soup. Plus: the real reason insider trading bans are absurd, and why Mario Cuomo was wrong about vowels.

Sarah Rogers, the State Department’s undersecretary for public diplomacy, joins Mixed Signals for a wide-ranging conversation about free speech, tech regulation, and why she’s been rattling the patience of some European governments. Max and Ben press her on confronting Europe over X, the Digital Services Act, and online speech — including accusations that she’s carrying water for Elon Musk and the far right. Rogers traces her worldview back to the early internet, Gawker comment sections, and First Amendment litigation, and explains why she sees today’s speech rules as potentially dangerous.And, don’t miss this week’s bonus episode of Mixed Signals: Max turns the tables on Ben and brings on Semafor CEO Justin Smith to ask the two about their big media news.

Semafor CEO Justin Smith joins Mixed Signals for a candid discussion about why the digital media company raised $30 million late last year, and how it reached profitability in just three years.

Max asks Justin and Semafor editor-in-chief Ben Smith about the company’s $330 valuation, the company’s planned investment in the Gulf and East Asia, and what it takes to build a modern media company in 2026.

Justin and Ben reflect on lessons from earlier eras of digital media, and the triumphs and mistakes Semafor made in its first three years.

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Media veteran Ryan Lizza joins Mixed Signals for a raw, sprawling conversation about why he chose to publish an eight-part (and counting) Substack series responding to the most personal and public crisis of his career. Max and Ben press him on whether this was ever just a breakup story, why he believes the real scandal involves RFK Jr. and journalistic failures, and how Substack gave him the only viable way to tell the story in the first place. Lizza reflects on leaving Politico, burning bridges with legacy outlets, the cost of going public, and what this episode taught him about our changing media landscape.

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Shark Tank’s Kevin O’Leary joins Mixed Signals to talk about his buzzy turn as a ruthless tycoon in Marty Supreme — and how it felt playing a fictionalized version of himself. Max and Ben dig into what lessons he took from working with Josh Safdie and Timothee Chalamet, why Mark Cuban isn’t on Shark Tank anymore, and why he believes movie theaters aren’t going anywhere. They also talk about O’Leary’s media omnipresence, how his defense of Trump helped him influence the Republican tax bill, what he told  Zohran Mamdani when they met in New York, and why he thinks respect is more valuable than being liked.

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What happens when TikTokers replace TV hosts and interviewers, and presidential candidates start begging to be on their shows?

Brian Reed sits down in a Brooklyn wine shop with four of the internet’s biggest creators: Caleb Simpson, who gets people on the street to take him up to their apartments; Julian Shapiro-Barnum who interviews kids on Recess Therapy; Anania Williams of the LGBTQ quiz show Gaydar; and Jack Coyne, host of the music game show Track Star. Their videos reach more people than many major news outlets. But who gets control over what they run? When is money changing hands? What do they do when politicians like Kamala Harris and RFK Jr. come calling?

A frank conversation about the blurry grey area between this new form of entertainment and journalism.

Check out Question Everything's Substack, with more reporting on the war over truth, free speech, and tech’s role in it all. 

“Question Everything” is a production of KCRW and Placement Theory.

The Ankler’s Janice Min and FeedMe founder Emily Sundberg join Mixed Signals for a candid roundtable lookback at a disorienting year in media. They sound off on everything from YouTube’s domination, to the Charlie Kirk saga, and the increasingly niche areas of coverage for newsletters. Max and Ben also ask about Substack’s evolution, creator economics, and what media moments might be top of mind for 2026.

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