The Rebooting Show
The Rebooting Show interviews those building and operating media businesses, offering an open view into how the smartest people in the media industry are creating sustainable media companies. The podcast delves into the strategies and challenges of modern media entrepreneurship.
Episodes
Inside the knowledge creator business
Josh Kaplan is co-founder and CEO of Smooth Media, a talent management company for knowledge creators: people like Joanna Stern, Matt Wolf, Cat GPT and the Breaking and Entering guys. Smooth started out selling newsletter and consulting services to cre...
The Lever's David Sirota on challenging 'corporate media'
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 ...
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 th...
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 majorit...
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...
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 hosp...
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 Com...
EX.CO's Paul Jelinek on TV Advertising's 'Major Transformation'
Paul Jelinek, chief business officer at EX.CO ( https://EX.CO ), joined me in Cannes for TRB Conversations, powered by EX.CO ( https://EX.CO ), to lay out why CTV programmatic advertising is still in its early days — and why that's about to change fast...
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 ...
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 ( https://EX.CO ), to break down how AI agents are already changing the way Spotify builds and sells advertising.Sendall explains why "the v...
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 t...
The portal's comeback
Rob Wilk, CRO of Yahoo, joined me in Cannes for TRB Conversations, powered by EX.CO ( https://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 ...
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 vol...
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 ( https://EX.CO ), to make the case that premium video has been underappreciated as the origin point of culture. That ends up leaving it ...
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 Th...
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...
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 adv...
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...
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 adve...
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 th...
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 ...
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 ( https://EX.CO ), recorded at Cannes, Brian Morrissey talks with Cosmin Ene,...
Agents won’t replace human trust
At the Bloomberg Studios in Cannes, Bloomberg Media chief commercial officer Christine Cook and HSBC CMO for corporate and institutional banking Nicole German joined me to discuss the current and future shifts as media moves into an agentic era. The co...
TRB Live in Cannes: Publishers' Google problem
People Inc CEO Neil Vogel explains his beef with Google and how publishing now requires running multiple playbooks customized for each brand. Axios chief media correspondent Sara Fischer says an AI marketplace can only emerge if Google participates. Ch...
Esses' Ojus Jain on building an F1 culture brand
Esses is betting a high-end print magazine will help establish brand credibility an email list alone cannot. Founder Ojus Jain is building a model that uses that credibility and editorial distribution to power brand activations around the crowded F1 ra...
KRCW's Jennifer Ferro on building a community model
KCRW is a local institution in Los Angeles, home to Morning Becomes Eclectic, the long-running music-discovery program. The public radio station is using its standing to lean into a community model that includes 100 events per year, such as a pie bakin...
News as a feature
The Reuters Institute's new digital news report lays bare the challenges facing journalism as people increasingly stop seeking out news products. Instead, news is a feature of other products. Jim Egan, one of the report's authors, joins me to discuss t...
Dynamo's Nicholas Carlson on finding content-market fit
A year after its launch, Dynamo’s Nich Carlson joined me to discuss what he’s learned in starting a YouTube-first video programmer. Dynamo is home to “Business Explains the World ( https://www.youtube.com/@BusinessExplainsTheWorld ),” a documentary-sty...
The new social with Rachel Karten
TikTok broke social media's original contract — grow followers, followers see content — and replaced it with algorithmic sorting that rewards entertaining strangers over satisfying your loyal audience. Link in Bio's Rachel Karten joins The Rebooting Sh...
The Dow Jones recipe for growth
In the wreckage of the scale era, The Wall Street Journal is one of the winners. It has 4.5 million paid subscriptions and the broader Dow Jones portfolio has 6.3 million with a foothold in B2B data assets like OPIS and Risk & Compliance. The Journal h...
The revenge of brand
Markets in the midst of technological change tend to have two camps. One is the legacy incumbents that have strengths in their brands and the other in upstarts that are nimbler. In digital media, it turned out brand won. At Possible, The Rebooting held...
Inside Politico’s franchise playbook for Playbook
At nearly two decades old, Politico's Playbook was an innovator in the now-familiar daily agenda-setting newsletter. Playbook is now more than a DC staple. It has editions in five countries with two more on the way. And it is looking to adopt a franchi...
TV advertising has decentralized
The decentralization of digital media has arrived for TV. The TV advertising system is being remade in the image of the data-focused, automated ad systems that came to dominate the internet. TV was always the holdout, thanks to scarcity. That’s changed...
Inside The Guardian's U.S. expansion
Much of the U.S. news landscape is doom and gloom, but The Guardian is a quiet success story. Powered by reader contributions, The Guardian now has a 150-person newsroom and draws more web traffic than The Washington Post. Guardian U.S. managing direct...
Journalism vs capitalism
In this live recording from the International Journalism Festival in Perugia, Italy, I debated Peter Erdelyi, director of the Center for Sustainable Media, about the role of state subsidies in building sustainable media businesses. Chapters: 00:00 Beeh...
Morning Brew’s direct thesis
Morning Brew CEO Robert Dippell discusses why there are two types of publishers: those with a passive connection to their audience and those with a strong connection. Sponsored by Beehiiv, the modern email system used by leading publishers like Time, T...
Axios COO Allison Murphy on bringing the franchise model to local
Allison Murphy, COO of Axios, joined me to discuss the evolution of Axios Local five years in. Axios plans to be in 43 cities by the end of the year. It is adapting its franchise model to build around individual reporters. In this model, the journalist...
Dealmaking atmospheres
Christian Muche built Dmexco into Europe's biggest digital marketing event, walked away, and then launched Possible in Miami Beach — after Martin Sorrell told him the world didn't need another marketing event. We talk about what it took to launch a new...
The Puck model comes to food
Former Athletic and Puck exec Max Tcheyan is launching Caper, a media brand covering the power dynamics behind the restaurant world. Max explains why he thinks food media is where sports media was in 2016, how dining culture has become a status marker ...
Reinvigorating the Philadelphia Inquirer
The Philadelphia Inquirer is a typical big city newspaper that's been in retreat for a generation. Now under a unique nonprofit ownership structure, the Inquirer grew revenue last year and turned an operating profit. CEO Lisa Hughes, the former New Yor...
Inside Outside's media-as-flywheel strategy
Robin Thurston raised $150 million to turn Outside into more than a magazine. He explains how the company married media brands with mapping apps, SaaS platforms, and a festival to reach profitability at $125 million in revenue.
Journalism's product problem
Dmitry Shishkin, a veteran of the BBC and former CEO of Ringier International, has a back-to-basics suggestion: Journalism needs to adapt more of a product mindset. Too much of what newsrooms produce is basic news updates rather than acting as a utilit...
Google wants search to die
Taboola CEO Adam Singolda has built his company on open web publishing. He sees the dynamics of the open web changing, as the battle for AI surpremacy acclerates the shift from traditional web search, putting in motion a cascading series of second-orde...
The platform logic of entertainment
The industrial logic of media, premised on scarcity, has been replaced by a platform logic that is no less centralizing. Meet the new boss. Entertainment industry veteran Darren Cross breaks down what platform logic is, and how it dictates what's made,...
Food Fix's Helena Bottemiller Evich on optionality
Food Fix's Helena Bottemiller Evich has achieved sustainability. She has a recurring revenue business that exceeds her salary at Politico, with a 10% free-to-paid conversion rate. This gives her the option to continue as is as a solo operation or expan...
Yahoo's Kat Downs Mulder on the portal's comeback
Everything comes back in fashion. Why not the portal? Yahoo is a true legacy brand of the internet. An OG portal that failed to stem the rise of Google, missed on buying Facebook and for the last four-plus years has been a ward of private equity under ...
The connection economy
In this episode, I talk with James Capo, CEO of audience data platform Omeda, about why the traffic-driven media model has finally run out of road and what replaces it. We dig into the idea of a “connection economy,” where audience relationships—not pa...
Content and community
Recurrent CEO Andrew Perlman discusses how the publishing company is focusing its niche brands increasingly on events as it retools its model from the traffic era. Affiliate revenue is now a third of what it was at its peak, while experiential has rise...
The open web needs a new economic model
For two decades, the economics of the open web rested on a simple bargain: platforms indexed content, publishers got traffic, and monetization happened downstream. AI breaks that loop by delivering answers without the click. This week, I’m joined by Do...
The messiness of streaming advertising
In the second round of our TRB Conversations powered by EX.CO, I spoke to EX.CO CEO Tom Pachys about why the streaming landscape is even more chaotic than online advertising; Manas Mittal from Uber discussed why mobility advertising has become a new ca...
Inside Vox’s talent-led franchise strategy
This episode features two conversations I had at CES as part of TRB Conversations, powered by EX.CO. First, a discussion with Vox Media CRO Geoff Schiller on the company’s bet on talent-led franchises, and why podcasts have become the proving ground fo...
The B2B indie opportunity
In this episode, I talk with CJ Gustafson, the former CFO behind Mostly Metrics. CJ didn’t come from journalism or media. He came from operating. He started writing to document the playbooks he’d built as a finance executive. That side project turned i...
Semafor's big bets
Semafor's recent $30 million funding round at a $330 million valuation is a needed jolt of confidence in the media sector -- and an endorsement of its events-led media model. CEO Justin Smith joined me to discuss why putting events first allowed Semafo...
Why Puck isn't all-in on events
CEO Sarah Personette is blunt that she has no interest in becoming an events company, warning that "over-rotating" to events is how media brands lose their identity. Puck runs a limited slate—two premium ticketed summits, insider breakfasts in DC and H...
What we learned about media in 2025
Axios media correspondent Sara Fischer and Breaker founder Lachlan Cartwright are two of the best reporters who are attuned to the daily changes to the media business. They joined me for a year-end episode that covers key themes of the year, including ...
Inside The Washington Post's product strategy
This week I spoke with Washington Post CTO Vineet Khosla about the collision between a legacy shaped by perfection and a future shaped by iteration. We get into why the Post is pushing beyond the one-size-fits-all article, how conversational and person...
The post-pageview media model
Jason Wagenheim has lived the full arc of media’s transformation, from the late-stage magazine era to the current scramble to build durable franchises in a post-pageview world. We talk about how the shift to mobile foreshadowed the AI disruption now hi...
The AP's pivot to tech
The AP is quietly becoming a core supplier to the AI economy. I talk with Kristin Heitman, the Associated Press CRO, about how a 178-year-old cooperative built on serving newspapers is shifting to a business where newspapers now account for under 10 pe...
Building a post-scale media company
Defector is one of the clearest test cases of what comes after the scale era. Born out of the Deadspin walkout and structured as a worker cooperative, it has achieved something most digital media operations haven’t: five years of stability with zero st...
Caliber's Ramin Beheshti on Gen Z news
Caliber CEO Ramin Beheshti says younger audiences who aren’t typing URLs into browsers and aren’t interested in being talked down to. We get into why the traditional news product is mismatched with how people actually consume information, why platform-...
How Tangle became a $4m+ revenue, profitable news business
Isaac Saul started Tangle in 2019 without a platform job, a big name, or the institutional head start many Substack-era independents enjoyed. He describes himself bluntly: “When I started Tangle, I was a nobody.” In this episode, we talk about how he h...
The Schneps Media local news playbook
The Schneps Media story is a blueprint for how local publishing can still work when it’s treated like a real business, not a civic charity. Josh Schneps explains how he and his mother built a diversified local empire by combining print, digital, and ev...
Inside The Economist’s Ferrari strategy
The Economist’s president Luke Bradley-Jones looks to Ferrari as an example of a brand that’s been able to use scarcity to drive value. Ferrari has avoided the trap of many luxury brands in chasing scale and in the process diluting their brands. While ...
How the NYT makes subs and ads work together
The New York Times has become the rare publisher proving that subscriptions and advertising can strengthen each other. Chief Advertising Officer Joy Robins explains how a subscriber-first model creates the engagement, trust, and data that fuel a thrivi...
The Bulwark's anti-neutrality approach
Sarah Longwell, publisher of The Bulwark and founder of Republican Voters Against Trump, discusses why neutrality no longer works in political journalism. Longwell argues that legacy media’s “studied impartiality” has become a liability in a polarized,...
How Axios segments its audience
Axios CRO Jacquelyn Cameron breaks down how Axios thinks about audience segmentation in an age when every publisher says they’re “audience-focused.” Jacquelyn explains why Axios organizes around five core personas — influencers, C-suite executives, dea...
How TechCrunch rebuilt its email strategy
TechCrunch’s new owner faced a familiar challenge: modernizing an old tech stack built for a different era. Matt Gross, vp of digital initiatives at TechCrunch owner Regent, joins Beehiiv CEO Tyler Denk to discuss how they untangled years of tech debt,...
Talking Points Memo's small-boat strategy
Josh Marshall, founder of Talking Points Memo, has spent 25 years steering a small, independent newsroom through every shift in digital media. He discusses how TPM survived the traffic era, why it avoided venture capital, and what he calls the “small-b...
The Monocle Playbook
Tyler Brûlé has built Monocle into one of the most distinctive media brands of the past two decades. At a time when others chased clicks and platforms, Monocle went the other way. It invested in print, opening cafés and shops, launching a radio station...
A Spotify model for AI
Bots are taking over the internet, previewing a new world where agents interact and humans consume bot-created content. Cloudflare, a leading content delivery network, saw this coming. Cloudflare Chief Strategy Officer Stephanie Cohen told me that publ...
Beehiiv's Tyler Denk on email's centrality
In this conversation, Beehiv CEO Tyler Denk joins me to discuss the evolving landscape of media, focusing on the importance of audience ownership and the role of email as a primary distribution channel. We compare Beehive and Substack, highlighting the...
Publishers need to go back to basics
This episode is sponsored by Piano The essential challenge for publishers is similar to most businesses: find a way to control their relationship with the customer. That means going back to basics, argues Trevor Kaufman, CEO of Piano, and giving people...
Rough Draft Atlanta’s ‘meaningful, not massive’ approach to local
Keith Pepper has a handy reminder of his goal with Rough Draft Atlanta: a Post-It note on his computer that reads simply “meaningful, not massive.” That’s the approach Keith has taken with Rough Draft Atlanta, a local news business focused on well-heel...
Inside Forbes’s total monetization approach
Forbes CEO Sherry Phillips discusses how the 107-year-old brand is retooling for a far messier media market. Forbes is less a magazine than a platform that turns brand equity into revenue across multiple surfaces: advertising, branded content, newslett...
How Essentially Sports navigates shifts
This week, I spoke to Essentially Sports cofounder Suryansh Tibarewal about how it is adapting its strategies in a time of traffic flux. Essentially sports is a high volume web publisher, one i’d consider as a classic pageview publisher. Suryansh and I...
Monetizing cowboys
This episode is sponsored by Piano. Check out the new report from The Rebooting and Piano that examines how revenue leaders at publishers are taking a "total monetization" approach. Deirdre Lester is no stranger to how sports brands can influence cultu...
Greater Long Island's scrappy approach to local
Mike White built Greater Long Island from a one-man blog in Patchogue into a regional news brand spanning Suffolk and Nassau counties. A veteran of the New York Post and Daily News, Mike took a scrappy, bootstrapped approach—publishing five stories a d...
ImpactAlpha's 'hometown paper' approach
David Bank left the Wall Street Journal after a long run covering tech and philanthropy and assigned himself to a new beat in impact investing, a world of private capital being directed toward social good that legacy outlets largely ignored. That journ...
Atlas Obscura's next chapter
Louise Story, CEO of Atlas Obscura and veteran of The Wall Street Journal and The New York Times, joins me to talk about steering a beloved travel brand into its next chapter. We discuss her decision to wind down the in-house experiences business, why ...
Moving up the pricing curve
Adi Ignatius, editor-at-large of Harvard Business Review, discusses how HBR is expanding beyond traditional subscriptions with the launch of HBR Executive, a $700 premium tier aimed at senior leaders. We talk about the shift from volume to value in med...
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