The Rebooting Show

The Lever founder David Sirota joins me to discuss why corporate media still sets the terms of the political conversation, even as its business model weakens. We get into the opening for independent investigative outlets, why reader funding brings its own pressures, and the challenge of serving an audience that sometimes wants its beliefs affirmed more than its assumptions challenged. We also discuss what Zohran Mamdani understands about media and why the left needs to do more than copy the right’s playbook.

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The Atlantic CEO Nick Thompson is preparing for a media business where the web plays a far smaller role. That could mean more print issues, stronger relationships between readers and individual writers, and new ways to get paid when AI agents become the audience. Recorded at TRB Audience Summit, this conversation starts with what the industry could look like in 2031 and explores how The Atlantic is positioning itself for that future, why Nick expects a new generation of media startups, and whether AI companies will build an economic system that sustains the journalism they depend on.

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The Guardian CEO Anna Bateson is a realist. She sees the need to prepare for when publishers are connecting information to AI pipes. “Our website may become something that is more of a service to agentic audiences rather than where you have the majority of human traffic,” she said. Recorded live at TRB Audience Summit on Sept 17, 2026.

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Publishers are adding AI tools, but the news product remains largely unchanged. Martin Schiori, former deputy publisher and AI lead at Sweden’s Aftonbladet and now co-founder of newsletter startup Hint Media, joins Brian Morrissey to discuss where that leaves news businesses. We explore the choice between becoming AI-powered information services and building around human relationships, why journalists’ identities as writers complicate adoption, and the risk of trying to do a little of everything without giving audiences a compelling reason to come back.

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Playboy is rebuilding itself as a lifestyle brand for a new era. President David Miller joins me to discuss why content is now the brand’s marketing engine, the return of the magazine, and Playboy’s expansion into licensing, events, membership and hospitality.

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Complex president Moksha Fitzgibbons joins Brian Morrissey to discuss the company’s evolution from an advertising-dependent publisher into a business spanning media, commerce and live events. They examine why content and commerce usually fails, how Complex rebuilt its audience around video, and what it takes for a media brand to turn cultural relevance into product sales and 100,000 event tickets. The conversation explores a larger shift in publishing: Media’s value increasingly lies in what it can make happen beyond the pageview.

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Paul Jelinek, chief business officer at EX.CO, joined me in Cannes for TRB Conversations, powered by EX.CO, to lay out why CTV programmatic advertising is still in its early days — and why that's about to change fast.

In this TRB partner episode, Jelinek explains why he thinks agentic advertising hasn't fundamentally transformed the industry yet, how EX.CO's "yield engine" technology — originally built for online publishers — is now being ported to CTV and digital out-of-home, and why he believes CTV programmatic today looks like online video did eight years ago.

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Never bet against the need of young people to get out of the home and socialize. Movie theaters are seeing a revival, driven by young audiences. Geoff Schiller, CEO of movie theater ad network Screenvision, joined me to discuss why this is a long term trend. A veteran of digital media, Geoff has a blunt assessment of "legacy" digital media: It's mostly zombies. Instead, the bigger media opportunities lie in the renewed appeal of shared experiences. We discuss cinema’s advantages as a high-attention advertising medium, and why AI could make physical media more valuable.

This episode is sponsored by beehiiv, which powers the email of the biggest brands like Time, TechCrunch and more. See how beehiiv powers leading brands

Check out TRB Audience Summit on Sept 17.. We have over 100 participants confirmed for the event on Sept 17 in NYC. They’re senior leaders from Bloomberg Media, The New York Times, BBC, Condé Nast, The Wall Street Journal, Hearst, The New York Post, Vox Media and the Associated Press. The day is built around the issues media operators are dealing with right now: life after Google Zero, consumer revenue, AI products and audience strategy. Join us

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Per Sendall, co-head of ads at Spotify, joins Brian Morrissey in Cannes for TRB Conversations, powered by EX.CO, to break down how AI agents are already changing the way Spotify builds and sells advertising.

Sendall explains why "the vast majority" of Spotify's code is now being written by software agents, how the company built and open-sourced a CLI plug-in that lets brands buy audio ads using natural language, and why he thinks agentic negotiation is still years away — because AI models are "hard coded to be nice," making them easy for human negotiators to exploit.

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Famous Birthdays is a classic open web publishing success story. Evan Britton bootstrapped the publisher to fill a simple need: People were seeking out information about the new crop of influencer and creator celebrities. Traffic peaked at 25 million three years ago. Evan wanted to sale it to 100 million and be a top ComScore site. Now, traffic is down to 20 million. Now, it’s focused more on “intentional” traffic and building community around that while building out a B2B information business. “A lot of those users are coming to our site because they know Famous Birthdays,” Evan told me. “They didn’t just randomly stumble onto it.”

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