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
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...
How Variety straddles B2B and B2C
Variety co-editors-in-chief Cynthia Littleton and Ramin Setoodeh joined me to discuss how they strike this balance. We talk about how you treat publications as bigger brands, why print still matters in these models, the changing nature of celebrity in ...
Substack's OnlyFans opportunity
Substack's recent funding got a lot of attention for the headline valuation number, as all fundings do, but it's more interesting to examine what its new investment and investors say about the direction of the company. In this episode, I'm joined by An...
The return of brand marketing
Of all the areas AI is poised to overturn, marketing is at the top of the list. In truth, Silicon Valley has long held marketing is low esteem. Google CEO Eric Schmidt once sniffed that brand marketing is "the last bastion of unaccountable corporate sp...
Inside the Minnesota Star Tribune’s Revival
Steve Grove spent over a decade inside Big Tech before returning home to Minnesota to run the Star Tribune. In this episode, we talk about what it takes to rebuild a local newspaper into a modern civic institution. Grove discusses why he left Google, h...
An AI grand bargain for publishers
Generative AI is upending the long-standing relationship between publishers and the platforms that distribute their content. As tools like ChatGPT and Google’s AI Overviews deliver direct answers, the incentive to click through to publisher sites is di...
Inside Vox Media's podcast strategy
On this week’s episode of The Rebooting Show, I spoke with Vox Media president of revenue and growth Ryan Pauley about how the publisher has become a podcasting juggernaut, with Pivot, Decoder and Today Explained franchises. Ryan discusses the “Lego ap...
The modernization of Cosmo
We held a live recording of The Rebooting Show from the Hearst House in Cannes. I spoke to Cosmopolitan editor-in-chief Willa Bennett and Hearst global CRO Lisa Howard about how Cosmo is evolving from a magazine and website into a multiplatform brand t...
The blurring of institutional and independent media
On this crossover episode, Semafor’s Ben Smith and Vox Media’s and Business Insider’s Peter Kafka join me to discuss the quickly vanishing divide between institutional media brands and independent upstarts. This is the second part of three part convers...
Inside Time's practical AI playbook
Jessica Sibley, CEO of Time, joins to talk about how the 101-year-old media brand is approaching AI with a clear-eyed strategy rooted in business fundamentals. We discuss Time’s shift toward B2B, why it phased out speculative bets like NFTs and no-code...
How the WSJ goes beyond ads and subscriptions
The Wall Street Journal has many advantages at a perilous time for news publishers. It has a massive paid subscriber base (4.3 million across print and digital). It caters to an affluent audience. It has a storied brand. While AI is threatening to over...
Google Zero
The landscape for digital publishing is shifting. At the center of this is Google search, the backbone of the open web. Google's embrace of "AI mode" last week was a sign that it will overhaul its approach to search with vast implications for publisher...
Henry Blodget on the media business in 2025
Henry Blodget built Business Insider into one of the few breakout successes of the traffic era. Now, with his new project Regenerator, he’s taking a different path—one that reflects the broader shifts in digital media. We talk about the collapse of pla...
Dynamo's Nicholas Carlson's pivot to video
Nicholas Carlson spent nearly a decade building Business Insider into a video powerhouse to complement its webpage model. Now, with his new venture Dynamo, he’s making a clean break from the old model. No articles. No CMS. No pageviews. Dynamo is a vid...
Anonymous Banker's bleak view of the media M&A market
I spoke with Anonymous Banker, an M&A advisor with a front-row view into the market for buying and selling digital media companies. Needless to say, it’s a buyer’s market. AB breaks down the market for digital publishing assets – broadly those with pag...
Inside HubSpot's go-direct media playbook
Kyle Denhoff, head of audience development for HubSpot Media, joined me to talk about how HubSpot has built one of the most effective media operations inside a tech company. We discuss how HubSpot’s practical, non-ideological approach to inbound market...
The Ankler's Janice Min embraces more with less
Janice Min joins to talk about building The Ankler into a focused, profitable media brand—and why she believes the future belongs to lean operators, not her past life helming glossy franchises. We talk about her transition from the high-gloss days of T...
Spin's IP strategy
Once a music magazine that competed with Rolling Stone to define cool in the pre-internet era, Spin is no longer really a magazine. Yes, it has brought the magazine (and Bob Guccione Jr) back, but Spin is an IP company now. It puts on Spin Sessions eve...
The Daily Upside's niche strategy
Inn this episode, The Daily Upside's Patrick Trousdale explains how niche products like Advisor Upside and ETF Upside are helping the company move up the value chain. We also talk about paid growth, building a newsroom, and why journalism—not just dist...
Semafor's Rachel Oppenheim on stakeholder media
Stakeholder media is how a media company can stay influential and build a real business—especially now, when scaled ad models are in a full race to the bottom. Everyone wants to move from passive audiences to active communities. Stakeholder media is a ...
Inside Dude Perfect’s highly profitable business model
An enduring challenge of the media business is finding leverage in models. This used to be fairly straightforward. Newspapers had leverage as quasi-local monopolies, Magazines had leverage that allowed Vanity Fair to pay a writer nearly $500k for three...
Morning Brew's Robert Dippell on moving into B2B
Morning Brew CEO Robert Dippell joins me to break down the fundamental differences between consumer and B2B media, why so many publishers underestimate the challenge, and how Morning Brew has built a thriving B2B business alongside its flagship newslet...
Adam Ryan on why newsletters are a channel, not a business model
Adam Ryan, CEO of Workweek, joined me this week to discuss his recent warning that the newsletter sector is overheated. Some points from the conversation: Newsletters are a commodity. The number of newsletters is growing faster than the number of reade...
B2B lessons for B2C
Sean Griffey, until recently the CEO of Industry Dive, joined me on The Rebooting Show to discuss the big things Industry Dive, and by extension a lot of B2B, got right. Sean was rarely mentioned in the collection of digital media CEOs of the recent de...
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