The Rebooting Show

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 for individuals over institutions. Vox has leaned into shows like Pivot with Kara Swisher and Scott Galloway and A Touch More with Sue Bird and Megan Rapinoe, treating talent development less like scale media and more like a studio model. Then, a conversation with Mark Floreani, CEO of FloSports, on the rise of niche sports and the power of owning IP end to end—from registration and ticketing to broadcast and fan experience.

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 into a $3 million business with no full-time employees, built around a narrow, high-value audience of CFOs.We talk about why subscriptions are a useful base but not where the money is in B2B, how sponsorships actually work when sales cycles are long and considered, and why CJ has deliberately avoided becoming an events company. Mostly Metrics is now largely sponsorship-driven, sold out well into the future, and optimized for cash flow and leverage.

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 Semafor to get to $40 million in revenue and profitability in 3.5 years, why corporate affairs is growing in importance and value, and using a global orientation to expand the addressable market.

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 Hollywood, and partner-driven dinners—but only when they reinforce franchises and margins. The goal is to use convening power strategically, not let it become the business. Sarah joined me to discuss this and other topics, including why podcasting is more about relationships than revenue, how Airmail now brings Puck to over 100,000 paying subscribers.

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.

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.

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.”

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, rebuilt email from the ground up, and reframed newsletters as core editorial products rather than traffic drivers.Note: This episode is part of a commercial partnership between The Rebooting and Beehiiv. Learn more about how Beehiiv works with enterprise publishers.

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-boat strategy” — building for resilience, not scale.

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, and building a loyal global community. I sat down with Tyler at Monocle’s Paris café to talk about how he’s kept the brand consistent, why proximity to readers matters more than dashboards, and what lessons Monocle’s model holds for publishers trying to build durable, multifaceted brands.

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 publishers reported less traffic to their sites and less human traffic. “Those numbers were 10 times worse than a decade ago.”This has broken the open web trade of the crawling right for traffic promise. Cohen said, “For some bots, the crawl-to-traffic ratio is tens of thousands of times worse than it used to be.”Five takeaways from our conversation:Scarcity is required. Cloudflare’s pay-per-crawl model aims to restore balance by creating enforceable scarcity. “If you don’t have scarcity, there’s no market. Changing the defaults was the only way for a market to develop.”AI engines need publishers. Models rely on fresh, high-quality publisher content to stay accurate. “If you got asked a question and didn’t know what happened over the last two weeks, your answer is going to be stupider.”Pay-per-crawl is a first step, not the finish line. Cloudflare’s system lets publishers decide whether to block, allow, or charge AI crawlers. It’s a way to test how a content economy might form. As Cohen put it, “It’s the simplest thing you can do because you can count a crawl.”The goal is the Spotify model. Cohen pointed to Spotify’s emergence after Napster as a precedent for compromise. “There’s lots of money going to creators in that model… it took a while for that market to develop.”The problem is Google. Publishers face a lose-lose choice: block Google entirely or allow AI Overviews to rewrite their work. “If they want search, they’re also in AI overviews… They can’t both crawl and pay nothing.”