
The Rebooting Show
246 episodes — Page 1 of 5
Inside Spotify's bet on agentic advertising
How Famous Birthdays managed ‘Google Zero’
The portal's comeback
WSJ's Josh Stinchcomb on why events are key
NBCU product chief: Big Tech is 'cherry-picking'
Subsidizing investigative journalism
Agentic advertising isn't ready for primetime
Workweek's Adam Ryan is betting on practitioner media
Affiliate in an AI world
Inside Hearst's GEO strategy
Why USA Today Co might quit Google
What publishers get wrong about community
Why AI could speed micropayments
Agents won’t replace human trust
TRB Live in Cannes: Publishers' Google problem
Esses' Ojus Jain on building an F1 culture brand
KRCW's Jennifer Ferro on building a community model
News as a feature
Dynamo's Nicholas Carlson on finding content-market fit
The new social with Rachel Karten
The Dow Jones recipe for growth
The revenge of brand
Inside Politico’s franchise playbook for Playbook
TV advertising has decentralized
Inside The Guardian's U.S. expansion
Journalism vs capitalism
Morning Brew’s direct thesis

Ep 219Axios bring 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...

Ep 218Dealmaking 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...

Ep 217The Puck model comes to food
EFormer 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 ...

Ep 216Reinvigorating the Philadelphia Inquirer
EThe 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...

Ep 215Inside Outside's media-as-flywheel strategy
ERobin 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.

Ep 214Journalism's product problem
EDmitry 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...

Ep 213Google wants search to die
ETaboola 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...

Ep 212The platform logic of entertainment
EThe 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,...

Ep 211Food Fix's Helena Bottemiller Evich on optionality
EFood 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...

Ep 210Yahoo's Kat Downs Mulder on the portal's comeback
EEverything 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 ...

Ep 209The connection economy
EIn 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...

Ep 208Content and community
ERecurrent 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...

Ep 207The open web needs a new economic model
EFor 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...

Ep 206The messiness of streaming advertising
EIn 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...

Ep 205Inside Vox’s talent-led franchise strategy
EThis 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...

Ep 203The B2B indie opportunity
EIn 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...

Ep 204Semafor's big bets
ESemafor'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...

Ep 202Why Puck isn't all-in on events
ECEO 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...

Ep 201What we learned about media in 2025
EAxios 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 ...

Ep 200Inside The Washington Post's product strategy
EThis 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...

Ep 199The post-pageview media model
EJason 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...

Ep 198The AP's pivot to tech
EThe 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...

Ep 197Building a post-scale media company
EDefector 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...