The Rebooting Show

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.”

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 PianoThe 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 relationshipWhy publishing is near the top of industries ranked by “complexity per dollar” of revenueHow 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.

Forbes CEO Sherry Phillips discusses how the 107-year-old brand is retooling for a far messier media market. Forbes is less a magazine than a platform that turns brand equity into revenue across multiple surfaces: advertising, branded content, newsletters, a licensing network that spans 67 editions in 43 languages, an e-commerce arm, and a fast-growing slate of more than 100 events that now account for up to 30% of revenue.

This week, I spoke to Essentially Sports cofounder Suryansh Tibarewal about how it is adapting its strategies in a time of traffic flux. Essentially sports is a high volume web publisher, one i’d consider as a classic pageview publisher. Suryansh and I discuss how essentially has continued to benefit from Google Discover, shifting its business model to focus more on direct sold revenue rather than programmatic and how its fan perspective is a differentiator in a crowded category.

This episode is sponsored by Piano. Check out the new report from The Rebooting and Piano that examines how revenue leaders at publishers are taking a "total monetization" approach.Deirdre Lester is no stranger to how sports brands can influence culture. She served for four years as the CRO at Barstool as it grew well beyond its roots in sports banter to develop several revenue streams. At Teton Ridge, Deirdre sees a similar opportunity in the niche of Western sports like rodeo. Teton Ridge is betting big on Western sports and lifestyle — acquiring The Cowboy Channel, building original programming around rodeo, and elevating events like the American Rodeo into marquee sports properties. It’s part media company, part sports IP owner, and part entertainment studio, with the aim of modernizing a tradition-rich category while keeping its authenticity.Deirdre and I talk about what it takes to grow in a time of constant industry change, and why she believes Western sports are not just having a cultural moment, but building into a lasting movement.

Mike White built Greater Long Island from a one-man blog in Patchogue into a regional news brand spanning Suffolk and Nassau counties. A veteran of the New York Post and Daily News, Mike took a scrappy, bootstrapped approach—publishing five stories a day, focusing on what neighbors actually care about, and treating advertisers like partners. We talk about how hustle, service journalism, and local roots can sustain media businesses when so many others are shrinking.

David Bank left the Wall Street Journal after a long run covering tech and philanthropy and assigned himself to a new beat in impact investing, a world of private capital being directed toward social good that legacy outlets largely ignored. That journalistic instinct grew into ImpactAlpha, which over the past decade has grown into what David calls the “hometown newspaper” for the “agents of impact”: investors, entrepreneurs, and institutions rethinking finance.In this conversation, we talk about the messy reality of building a media company from scratch — from early sponsorships to subscription revenue, near-acquisitions that never happened, and raising money from mission-aligned investors. David also reflects on why the best publications start in overlooked niches, and why persistence is the real moat.

Louise Story, CEO of Atlas Obscura and veteran of The Wall Street Journal and The New York Times, joins me to talk about steering a beloved travel brand into its next chapter. We discuss her decision to wind down the in-house experiences business, why brand partnerships — especially with tourism bureaus — are now the company’s core revenue stream, and how she plans to turn Atlas Obscura’s community into the foundation for a robust travel-planning app. Louise also shares how her product background shapes her approach and why building direct audience relationships is critical in an era of search decline and AI disruption.

Adi Ignatius, editor-at-large of Harvard Business Review, discusses how HBR is expanding beyond traditional subscriptions with the launch of HBR Executive, a $700 premium tier aimed at senior leaders. We talk about the shift from volume to value in media, the importance of ARPU, the tension between brand legacy and innovation, and how publishers can better monetize the most valuable parts of their audience.

Variety co-editors-in-chief Cynthia Littleton and Ramin Setoodeh joined me to discuss how they strike this balance. We talk about how you treat publications as bigger brands, why print still matters in these models, the changing nature of celebrity in a creator era, how Variety builds franchises like Actors on Actors and the challenges facing the entertainment industry.

Substack's recent funding got a lot of attention for the headline valuation number, as all fundings do, but it's more interesting to examine what its new investment and investors say about the direction of the company. In this episode, I'm joined by Anonymous Banker to break down where Substack goes next and why OnlyFans is a better comp for its aspirations than YouTube.

Of all the areas AI is poised to overturn, marketing is at the top of the list. In truth, Silicon Valley has long held marketing is low esteem. Google CEO Eric Schmidt once sniffed that brand marketing is "the last bastion of unaccountable corporate spending." The mathification of marketing will go into hyperdrive, as AI is used to create some kind of agentic ecosystem of bots persuading bots. All of this is great scifi to Anonymous Brand Marketer, a Fortune 500 marketer who sees as much BS as promise in AI's application to marketing. ABM sees it both rationalizing and driving efficiencies in performance marketing while leading to a mini-resurgence in the kinds of brand marketing that connects to humans in ways that a Salesforce agent cannot.