The Rebooting Show

1d ago

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 the rise of personality-driven reporting, the pressure on legacy newsrooms, and the politicized dealmaking that’s reshaping Hollywood.

3d ago

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 personalized formats change the relationship between readers and reporting, and what it takes for a newsroom to think like a product organization without losing its editorial core. Vineet walks through the shift toward voice as an interface, the role AI will play in expanding how journalism is packaged, and why publishers need to stop viewing themselves as content suppliers to platforms.

Dec 11

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 hitting publishers, why Football Co is leaning hard into creator-led video and social distribution, and how the World Cup has created a rare commercial tailwind for a sport that has finally broken through in the US. Jason breaks down the decline of the website as a business model, the rise of branded content and experiential, and why soccer’s cultural moment offers a template for what modern storytelling businesses can still be.

Dec 9

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 percent of revenue and tech companies already make up 15–20 percent, with that share expected to double over the next few years. We get into how AP prices its data, why recency has become the new battleground, the long-tail demand from companies building their own models, and what this shift signals for the future of licensing across the media industry.

Dec 4

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 staff turnover. I talk with Defector COO Jasper Wang about the upside of that model, the limits it imposes, hitting a subs ceiling, and why Defector is comfortable with the tradeoffs.

Dec 2

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-native formats have beaten the homepage, and how Caliber is trying to build news that fits into people’s lives rather than demanding the reverse. Ramin explains the logic behind The News Movement, The Recount, Capsule, and the new SaySo app, and why he thinks the future is less about institutional brands and more about trusted individuals delivering information at the speed of culture.

Nov 25

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 hustled his way from zero readers to a 450,000-person list and 70,000 paying subscribers, and how he’s trying to make the shift from a creator-led project to a durable media company. We get into his decision to add new voices, the limits of solo output, the temptation to do more, and why he thinks the next phase of media is about building systems, not personalities.

Nov 20

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 events into a single ecosystem that feeds itself. He talks about why print still drives more than half of their revenue, how they use events to build relationships and coverage, and why proximity—not scale—is the true advantage in local media. We also get into the economics behind their acquisitions, the logic of staying focused on New York, and how they’re adapting to AI and shifting audience habits without losing touch with their roots.