The Rebooting Show

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...

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...

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...

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...

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...

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 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...

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...

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 ...

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...

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 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...

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 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-...

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 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...

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 ...

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...

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,...

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...

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,...

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...

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...

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...

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...