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:

1. 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.”
2. 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.”
3. 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.”
4. 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.”
5. 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.”

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 differences in their approaches to monetization and audience engagement. We also zero in on trends in the newsletter space, including the shift towards niche content and sustainable business models. Finally, Tyler outlines Beehive's future roadmap, including enhancements to their platform and services for both small and large publishers.

This episode is sponsored by Piano

The essential challenge for publishers is similar to most businesses: find a way to control their relationship with the customer. 

That means going back to basics, argues Trevor Kaufman, CEO of Piano, and giving people reasons to come directly to publishers. Too often published have chosen audience development tactic — fish where the fish are, etc — over sound business strategies, Trevor told me on the Rebooting Show ahead of this week’s Piano Academy in Paris.

“Fundamentally, creating a loyal audience that shows up at your front door; that’s the business of publishing. And we get too distracted with a pivot to video, or apps, or Facebook, or AI, instead of asking what it means to be a subscriber, a member of this brand.” 

Other issues we discussed:

• The “original sins” of publishing: giving away content to Google for free and letting intermediaries seize the advertiser relationship
• Why publishing is near the top of industries ranked by “complexity per dollar” of revenue
• How Piano has evolved into managing the entire subscriber journey, from ad-block prompts to newsletters to bundles.

See The Rebooting's recent "total monetization" research report done in collaboration with Piano.

Keith Pepper has a handy reminder of his goal with Rough Draft Atlanta: a Post-It note on his computer that reads simply “meaningful, not massive.”

That’s the approach Keith has taken with Rough Draft Atlanta, a local news business focused on well-heeled areas of the Atlanta area that Keith has built after buying a clutch of community newspapers in 2020. Keith has mostly worked on the tech side of media his entire career, but he felt the pull to local news for the next phase of his career. We discuss how Rough Draft relies on direct mail of all things as a critical and reliable distribution channel, why print still far outpaces digital in monetization of local, and making tough choices in the balance of hard news and service journalism that often gets a bad wrap but is critical utility for local news. 

This episode is sponsored by Piano. Piano’s Digital Revenue Optimization solution helps digital services grow revenue by better understanding and influencing their customers’ behavior. Piano unifies analytics, segmentation, and commercial personalization in one AI-driven application, enabling sites and apps to efficiently maximize the value of every user visit. For more information, visit piano.io.

On Oct 2, I'll be speaking at the Piano Academy in Paris. My talk will focus on "things that won't change" in the AI era. Find out more about the Piano Academy.