The Rebooting Show

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.

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.

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.

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.

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.

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.

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 Economist won’t limit the amount of people who can subscribe, it follows the less-is-more strategy in sticking to its legacy values and hand-crafted journalism while modernizing its distribution and presentation.

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 thriving ad business. She also discusses how the Times’ bundle — from Games to The Athletic to Cooking — opened new surface areas for news-averse marketers, and why video is the big test for the NYT as it strives to become the Netflix of news.

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, low-trust world—and that audiences now crave conviction over detachment. She explains how The Bulwark grew out of the ashes of The Weekly Standard to become a mission-driven newsroom defending liberal democracy, why she sees “no conflict, no interest” as the new media ethos, and how transparency about values builds more trust than feigned objectivity. The conversation covers the transformation from Never Trump to pro-democracy brand, Tim Miller’s breakout as the face of its YouTube expansion, and why The Bulwark doesn't consider itself "a Substack."

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, dealmakers and investors, communicators, and smart local professionals — and how each connects to a product, event, or revenue line. We get into how “no opinion” coverage is a competitive advantage in Washington, how local works when it’s “localized national” rather than pizza-parlor advertising, and how Axios uses AI to turn audience insight into business intelligence.

We also talk about the new entanglement between business and government, why Axios treats live events as “the physical manifestation of the newsroom,” and how its custom GPT gives the sales team daily prospecting hit lists. As Jacquelyn put it, “I want every human to become superhuman.”