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The Rebooting Show

Brian Morrissey

The Rebooting Show gets into the weeds with those building and operating media businesses, giving an open view into how the smartest people in the media business are building sustainable media businesses. https://www.therebooting.com/ (www.therebooting.com)

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  • 27 episodes
  • weekly
  • Avg 36 min
  • English
Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.
  • #253
    September 29 · 23 min

    The Atlantic’s Nick Thompson on preparing for a post-web world

    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. Chapters: 03:21 Atlantic in 2031 Scenarios 08:07 Print as Lifeboat 09:32 Video Strategy 12:43 AI Inside the Business 17:22 Open Web 20:02 Future Media

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  • #252
    September 22 · 30 min

    The Guardian's Anna Bateson on adapting to AI

    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. Chapters: 03:22 Traffic Drops and Direct Audiences 05:30 Beyond Text Going Multimodal 07:32 Building The Guardian US 14:03 US Growth and 2031 Vision 18:53 AI Adoption Without Losing Trust 27:29 What Stays the Same

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  • #251
    September 15 · 48 min

    The mushy middle of AI adoption

    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. Chapters: 01:33 AI Inside the Newsroom 07:43 Future News Products and Trust 24:58 Liquid Content 29:32 Participatory News Interfaces 40:53 Hint Community Model

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  • #250
    September 8 · 40 min

    Playboy's next act

    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. Chapters: 01:33 From Nat Geo to Playboy 02:49 Rebuilding Playboy as Brand 07:51 Audience and Cultural Moment 16:51 Magazine Return and Business Model 35:46 Membership Events and Future

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  • #249
    September 1 · 40 min

    Media's life after the pageview

    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. Chapters: 01:31 Complex Reboot 06:47 Staying Relevant in Youth Culture 12:11 Live Shopping Craze 20:27 Commerce Drops and Festivals 35:45 Life After Traffic

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  • #248
    August 27 · 12 min

    EX.CO's Paul Jelinek on TV Advertising's 'Major Transformation'

    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. Also covered: Why AI and agentic tools are currently more useful as tactical marketing and discovery tools than as full transaction engines The differences between managing yield in online video versus CTV, and what's transferable Why hiring more salespeople isn't a scalable growth strategy for CTV publishers EX.CO's evolution from an online publishing platform (formerly Playbuzz) to a cross-channel yield technology company. Chapters: 01:17 Agentic Ads Reality Check 04:59 Exco Origins 07:24 What Changes in CTV 11:28 CTV Programmatic Timeline 12:00 Cannes Memory Lane

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  • #247
    August 25 · 40 min

    The return of movie theaters

    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 Highlights: 01:33 Media Shakeout Era 05:40 Why Cinema Wins 10:33 Gen Z Theater Revival 15:55 Screenvision Model 27:08 Ads Attention Future 35:03 Future Of IRL Media

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  • #246
    August 20 · 17 min

    Inside Spotify's bet on agentic advertising

    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. Also covered: Spotify's rebuilt ad tech stack: its own ad server, ads manager, and programmatic exchange (SAX) Why audio advertising has 30-year staying power, and what that means for attribution windows Spotify's new generative AI creative tool, available in 12 languages with 100 voices The "sponsor playlist" product and how Spotify is rethinking ad load in exchange for brand takeovers 00:00 EX.CO Spot 00:38 Intro 01:10 Welcome 01:28 Rebuilding the Ads Stack 03:58 Programmatic Audio Push 07:23 Free vs Premium Ad Experience 10:44 Agentic Ads Reality Check 14:28 Ways Off From Agent Negotiation 15:21 Cannes Memory Lane

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  • #245
    August 18 · 46 min

    How Famous Birthdays managed ‘Google Zero’

    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.” Chapters: 00:00 Beehiiv Spot 01:29 Welcome 01:56 Famous Birthdays Story 05:27 Staying Flexible in Media 07:43 Google Zero Reality Check 11:29 Retention Over Scale 14:09 Monetization Without Direct Ads 22:52 Open Web and AI Future 24:56 Creator Data Strategy 29:45 Open Web Future 35:48 Shorts Versus Longform 38:51 Search First UX 42:27 Copyright And AI Deals

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  • #244
    August 13 · 17 min

    The portal's comeback

    Rob Wilk, CRO of Yahoo, joined me in Cannes for TRB Conversations, powered by EX.CO, to make the case that 30-year-old Yahoo is in the middle of a genuine business turnaround, not a nostalgia play. Rob breaks down Yahoo's first-party data advantage across search, email, and content (with 75% of users logged in), why he calls competitors' data "a fish stew" of third-party signals, and how that data now powers Yahoo Scout — the company's first new search product in 17 years, built using a rented LLM alongside Bing's grounding API and Yahoo's own first-party data. Chapters: 00:00 EX.CO Spot 00:34 Intro 01:11 Welcome 02:55 First Party Data Edge 06:12 Portal to AI Era 08:46 Yahoo Scout Search Return 11:44 Creators and Brand Deals 14:27 Cannes Memory Lane

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  • #243
    August 11 · 12 min

    WSJ's Josh Stinchcomb on why events are key

    Events have moved from a side business to a core commercial product at The Wall Street Journal. CRO Josh Stinchcomb says the long lead times and scarcity let publishers lock in sponsor commitments earlier, which matters when advertising budgets are volatile. The event is increasingly the beginning of a larger marketing program rather than an add-on at the end. It creates the executives, conversations, video and podcast material that can then become a broader branded-content campaign. The value is less about filling a big room than convening the right 100 or 200 people, facilitating introductions and making the event accountable to actual business outcomes. Chapters: 00:00 EX.CO Spot 00:36 Intro 01:24 Welcome 01:45 Inside Journal House 03:17 Convening as Strategy 04:25 Events as Main Dish 08:46 Stitching Dow Jones Assets 10:38 Cannes Memory Lane

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  • #242
    August 6 · 21 min

    NBCU product chief: Big Tech is 'cherry-picking'

    Ryan McConville, chief product officer at NBCUniversal, joins me in Cannes for TRB Conversations, powered by EX.CO, to make the case that premium video has been underappreciated as the origin point of culture. That ends up leaving it shortchanged by the platforms that built their businesses on top of it as advertising was subsumed by performance marketing. “If you only feed the bottom of the funnel, you eventually run out of new customers. Brand and performance are intimately linked. If you take your foot off the gas on brand, it’s just going to raise the cost in your other channels. It’s all performance—it’s simply different parts of performance.” Chapters: 00:09 EX.CO Spot 00:36 Intro 01:40 Welcome 02:28 Rebooting TV for Streaming 05:11 Comcast Tech Stack Advantage 06:26 Attribution and Culture Credit 08:08 Proving TV Performance Lift 11:25 Democratizing CTV Buying 14:04 Agentic AI Hype Check 19:08 Buyer Agents and Whats Next

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  • #241
    August 4 · 39 min

    Subsidizing investigative journalism

    Funding investigative journalism is a unique challenge. On The Rebooting Show, I spoke to Scott Stedman, an independent investigative journalist who is using a coffee subscription service as a business model to fund his open-source investigations at The Newsground. He’s attempting to recreate the news subsidy that was lost with the unbundling of media. Scott and I discuss his career, why he doesn’t believe in the business model of journalism companies and why accountability journalism will find innovative models. Chapters: 00:00 Beehiiv Spot 01:29 Welcome 02:07 Why Investigative Journalism 04:28 Making It Sustainable 06:43 Freedom Over Newsrooms 13:05 Creators And Video Shift 19:03 Newsground Coffee Model 27:48 Behind The Scenes Journalism 32:45 Crowdfunding And Growth 35:31 Inspirations And Future

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  • #240
    July 30 · 15 min

    Agentic advertising isn't ready for primetime

    Agentic advertising was the buzzword of the year at Cannes this year. It stands to reason this hype is ahead of reality. Jon Roberts, chief innovation officer at People Inc, gives a reality check of where the hurdles to agentic advertising, which holds the promise -- yet again -- of establishing direct paths between advertisers and publishers. “Is this just AI jazz hands, or is there something actually there under the hood?’ Discovery and planning agents, packaging agents — those are pretty low risk, and they’re definitely possible. They make the planning process faster, while humans still set up the deals and line items. The highest-risk piece is negotiation. These models are hard-coded to be nice, and the worst thing you want to do is put a nice AI negotiator against a human on the other side. They’ll give that stuff to you for free. Humans should negotiate, but AI systems can do the heavy lifting, and we’ll crawl, walk and run into it.” Chapters: 00:09 EX.CO Spot 00:37 Intro 01:37 Welcome 01:57 Agentic Advertising Hype 05:56 Publishers and Ad Tech Tax 07:40 Agents and the Content Bargain 11:13 New Monetization Models 13:38 Best Cannes Memories

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  • #239
    July 28 · 49 min

    Workweek's Adam Ryan is betting on practitioner media

    One of the more promising areas of media is expert practitioners who are both good at their jobs and at explaining their fields. Workweek is a B2B media company built with this ethos at its core. Adam Ryan, CEO of Workweek, joined me to discuss the advantages of practitioner media and why Workweek is focused on proving to its advertisers that they're reaching their potential customers. Chapters: 00:00 Beehiiv Spot 01:29 Welcome 02:03 What Is Workweek 03:24 From Newsletters to Communities 06:39 Going Wide Then Narrow 08:47 Creator Model and Retention 12:27 Practitioners Keep Their Jobs 18:41 Advertising Not Lead Gen 23:32 Community Platform 27:01 Email Identity Graph 28:53 Events As Community Engine 30:58 Free Events Sponsor Model 33:51 AI Impact On B2B Media 38:05 Digital Versus In Person Mix 40:35 Stop Chasing Subscribers 44:53 Substack Recs And Fake Growth 47:54 Data Decay And Better Signals

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  • #238
    July 23 · 47 min

    Affiliate in an AI world

    The shift to performance marketing has increased thei importance of affiliate operations at publishers. AI is upending the old playbook. That’s because of AI agents. Agents will increasingly be on the loose to make buying decisions. The question is how publishers will influence those agents with their commerce content but also how they’ll get credit. The recent controversy over Phia’s cookie stuffing is testament to how affiliate is premised on getting credit for the sale. "If you have an AI agent, the cookie is injected into your browser,” said Madeline Sullivan, founder of shopping app Scout and affiliate publishing veteran who spent eight years at Forbes Vetted. “So if an agent is using a different browser — let's say you have a Mac Mini where your agents live — that agent is going to be on a completely different browser. How are we thinking about people's digital identity to provide credit to the publishers?" Chapters: 00:00 Beehiiv Spot 01:29 Welcome 02:17 Commerce Journey 05:08 SEO Era And Google Changes 09:38 Owning Audience For Commerce 13:51 AI Citations And Getting Paid 16:49 Scout App 21:48 Affiliate Scandals: Honey And Phia 28:38 AI Agents And Attribution Future 37:59 Distribution And Creator Partnerships 44:05 Trust And Content Evolution

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  • #237
    July 21 · 19 min

    Inside Hearst's GEO strategy

    Mike Nuzzo, svp of Hearst Data Solutions, explains how Hearst is measuring its visibility and favorability inside answer engines, restructuring editorial content into formats LLMs can more easily use, and exploring how GEO could become part of its advertising business. We also discuss the collapse of the traditional marketing funnel, the difference between machine knowledge and human wisdom, and the possibility that publishers will eventually operate separate layers of the internet for humans and robots. Chapters: 00:00 TRB 237 - Mike Nuzzo 00:09 Ex.co Spot 00:33 Intro 02:08 Why LLM Discoverability Matters 03:50 Measuring Citation and Favorability 05:50 Making Content Robot Friendly 08:06 Knowledge vs Wisdom 14:18 Monetizing LLM Influence 15:28 Robot Internet and Human Internet 17:46 LLM Referrals Rising

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  • #236
    July 16 · 16 min

    Why USA Today Co might quit Google

    USA Today Co CEO Mike Reed explains why he's willing to walk away from Google search traffic within the next 12 months, how the company is building direct-to-consumer relationships through newsletters and social to offset the loss, and why he thinks the "one crawler" problem — Google refusing to let publishers separate AI Overviews from search indexing — is forcing his hand. Chapters: 00:35 Intro 01:00 Gannet to USA Today Co. 02:18 Four Digital Revenue Streams 04:10 AI and the Broken Web Deal 08:51 Traffic Proof Points 11:50 Humans vs Agents Web 13:30 AI in the Newsroom Rules

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  • #235
    July 14 · 55 min

    What publishers get wrong about community

    Daniel Scharff isn't a media guy. He's a CPG operator who stumbled into community-building almost by accident, looking for people to talk to at trade shows. That accidental start turned into Startup CPG, a Slack-based community that's become a trusted gathering spot for direct-to-consumer operators in packaged goods. We talk through what it actually takes to build a community that people show up for: why "the things that don't scale" are the whole point, why Slack works better than purpose-built community platforms despite not being designed for the job, how to think about trade shows versus owned events, and why proximity to the industry — not content production — is the real unlock for publishers trying to build the same thing. Chapters: 01:29 Intro 08:23 Why CPG Is Exploding 10:39 Forces Driving New Brands 17:17 From Meetups to National Slack 24:13 Signature Series and Events 27:39 Monetization Free Community 32:09 Educational Partner Webinars 38:43 Measuring Reach And Engagement 42:52 Hiring And Team Growth 44:09 Partnerships And Success Ops 49:20 Scale Versus Depth 51:14 Trade Shows 52:35 Why Slack Works

  • #234
    July 9 · 42 min

    Why AI could speed micropayments

    AI agents are consuming content at a scale the web was never built for — and they don't watch ads, subscribe, or click. In this episode of TRB Conversations, powered by EX.CO, recorded at Cannes, Brian Morrissey talks with Cosmin Ene, CEO of Supertab, about why the old ads-vs-subscriptions dichotomy breaks down in an agentic world — and why micropayments, an idea publishers have circled for two decades, may finally have found its moment. Cosmin makes the case that grounding — not AI training — is the real emerging monetization opportunity, why bulk licensing deals actually hurt publishers by capping upside and hiding usage data, and why he believes the market for AI-agent content payments will regulate itself the way any two-sided market does. He also walks through how Supertab Connect works in practice: rights declaration, pricing, metering, and settlement — and makes the case that this is publishing's "YouTube moment," circa 2007, not a fast-money play. Topics covered: Why AI agents threaten the ad- and subscription-funded web What "grounding" means and why it's more valuable than training-data settlements Why publishers' old fear of subscription cannibalization doesn't apply to agents The problem with one-off bulk licensing deals (and the information asymmetry they create) How AI-agent price discovery will actually work Why publishers shouldn't expect meaningful revenue for 12–24 months — and what to do now 00:00 Intro — is AI scraping breaking the open web? 04:00 Why ads and subscriptions don't work on AI agents 12:00 What "grounding" means and why it's the real opportunity 16:00 The math problem with suing AI companies for content 25:00 Inside Supertab Connect: rights, pricing, metering, settlement 38:00 Why publishers shouldn't expect fast revenue

Showing 1–20 of 27 episodes