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The Rebooting Show

The Rebooting Show

246 episodes — Page 1 of 5

Inside Spotify's bet on agentic advertising

Aug 20, 202617 min

How Famous Birthdays managed ‘Google Zero’

Aug 18, 202646 min

The portal's comeback

Aug 13, 202617 min

WSJ's Josh Stinchcomb on why events are key

Aug 11, 202612 min

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

Aug 6, 202621 min

Subsidizing investigative journalism

Aug 4, 202639 min

Agentic advertising isn't ready for primetime

Jul 30, 202615 min

Workweek's Adam Ryan is betting on practitioner media

Jul 28, 202649 min

Affiliate in an AI world

Jul 23, 202647 min

Inside Hearst's GEO strategy

Jul 21, 202619 min

Why USA Today Co might quit Google

Jul 16, 202616 min

What publishers get wrong about community

Jul 14, 202655 min

Why AI could speed micropayments

Jul 9, 202642 min

Agents won’t replace human trust

Jul 7, 202652 min

TRB Live in Cannes: Publishers' Google problem

Jun 30, 202638 min

Esses' Ojus Jain on building an F1 culture brand

Jun 23, 202655 min

KRCW's Jennifer Ferro on building a community model

Jun 19, 202649 min

News as a feature

Jun 16, 202641 min

Dynamo's Nicholas Carlson on finding content-market fit

Jun 9, 20261h 3m

The new social with Rachel Karten

Jun 2, 202642 min

The Dow Jones recipe for growth

May 26, 202653 min

The revenge of brand

May 19, 202647 min

Inside Politico’s franchise playbook for Playbook

May 12, 202656 min

TV advertising has decentralized

May 5, 202630 min

Inside The Guardian's U.S. expansion

Apr 28, 20261h 4m

Journalism vs capitalism

Apr 21, 202637 min

Morning Brew’s direct thesis

Apr 14, 202641 min

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...

Apr 7, 202645 min

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...

Apr 3, 202647 min

Ep 217The Puck model comes to food

E

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 ...

Mar 30, 202633 min

Ep 216Reinvigorating the Philadelphia Inquirer

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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...

Mar 24, 202651 min

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

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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.

Mar 17, 202651 min

Ep 214Journalism's product problem

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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...

Mar 10, 20261h 7m

Ep 213Google wants search to die

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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...

Mar 4, 202652 min

Ep 212The platform logic of entertainment

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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,...

Mar 2, 202649 min

Ep 211Food Fix's Helena Bottemiller Evich on optionality

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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...

Feb 24, 20261h 3m

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

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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 ...

Feb 16, 202640 min

Ep 209The connection economy

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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...

Feb 10, 202644 min

Ep 208Content and community

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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...

Feb 2, 202641 min

Ep 207The open web needs a new economic model

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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...

Jan 27, 202653 min

Ep 206The messiness of streaming advertising

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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...

Jan 22, 202627 min

Ep 205Inside Vox’s talent-led franchise strategy

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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...

Jan 20, 202620 min

Ep 203The B2B indie opportunity

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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...

Jan 16, 20261h 14m

Ep 204Semafor's big bets

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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...

Jan 13, 202652 min

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

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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...

Jan 6, 202655 min

Ep 201What we learned about media in 2025

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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 ...

Dec 18, 202544 min

Ep 200Inside The Washington Post's product strategy

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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...

Dec 16, 202551 min

Ep 199The post-pageview media model

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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...

Dec 11, 202543 min

Ep 198The AP's pivot to tech

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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...

Dec 9, 202541 min

Ep 197Building a post-scale media company

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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...

Dec 4, 202551 min