The Rebooting Show

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.

Steve Grove spent over a decade inside Big Tech before returning home to Minnesota to run the Star Tribune. In this episode, we talk about what it takes to rebuild a local newspaper into a modern civic institution. Grove discusses why he left Google, how he’s restructured the Star Tribune’s newsroom and business model, and why local relevance—not scale—is the bet. From rebranding the paper and redesigning its digital products to narrowing its editorial focus and launching new revenue streams, Grove is trying to prove there’s a path forward for legacy news.

Generative AI is upending the long-standing relationship between publishers and the platforms that distribute their content. As tools like ChatGPT and Google’s AI Overviews deliver direct answers, the incentive to click through to publisher sites is disappearing. In this episode, I talk with Annelies Jansen, chief business officer at ProRata, about the need for a new economic model—one that accounts for how publisher content is used and ensures creators get paid. We discuss the risks of a bifurcated media ecosystem, how attribution can serve as the basis for compensation, and what a fair trade in the AI era might actually look like.

On this week’s episode of The Rebooting Show, I spoke with Vox Media president of revenue and growth Ryan Pauley about how the publisher has become a podcasting juggernaut, with Pivot, Decoder and Today Explained franchises. Ryan discusses the “Lego approach” that snaps together different business models, with some podcasts as owned and operated and others as partnerships. We also get into the rebundling and how media companies like Vox can link with creators to provide the sales and distribution infrastructure most independent media operators will not build.

We held a live recording of The Rebooting Show from the Hearst House in Cannes. I spoke to Cosmopolitan editor-in-chief Willa Bennett and Hearst global CRO Lisa Howard about how Cosmo is evolving from a magazine and website into a multiplatform brand that aims to establish itself with a new generation as its guide to love and relationships. In this phase, a brand like Cosmo’s social handles on Instagram (4 million followers) and TikTok (890k followers) are just as important as the print magazine, which is now published quarterly.The days of “50 Ways to Drive him WILD in Bed” are long gone. It’s taking a more nuanced view of love and relationships with projects like the video series Blind Date and Cosmo Sports, a new franchise spotlighting women athletes. We also discussed doing more with less, how Cosmo’s next phase is more about creating IP, custom projects like the resale collab with DePop and events like its partnership with Bumble for the Valentine’s Day Love Ball. 

On this crossover episode, Semafor’s Ben Smith and Vox Media’s and Business Insider’s Peter Kafka join me to discuss the quickly vanishing divide between institutional media brands and independent upstarts. This is the second part of three part conversation. To listen to part one, visit Semafor’s Mixed Signals. Part 3 is available on Vox’s Channels. Mixed Signals with Ben Smith and Max Tani - https://link.chtbl.com/SemaforMixedSignalsChannels with Peter Kafka - https://pod.link/recodemedia

Jessica Sibley, CEO of Time, joins to talk about how the 101-year-old media brand is approaching AI with a clear-eyed strategy rooted in business fundamentals. We discuss Time’s shift toward B2B, why it phased out speculative bets like NFTs and no-code platforms, and how it’s building AI features that serve users without compromising editorial integrity. Jess shares how Time is keeping close to AI power players like Scale and OpenAI, while remaining disciplined about where it integrates AI into its products.

The Wall Street Journal has many advantages at a perilous time for news publishers. It has a massive paid subscriber base (4.3 million across print and digital). It caters to an affluent audience. It has a storied brand. While AI is threatening to overwhelm swathes of the industry, the Journal has benefited from advertising from flush AI companies. Yet it isn’t immune to the pressures facing publishing overall and news in particular.WSJ CRO Josh Stinchcomb joined the show to discuss how the Journal is using the trust its journalism engenders to make money in new ways that aren't related to either ads or subscriptions, including events, executive communities and as a brand halo for Dow Jones information products.

The landscape for digital publishing is shifting. At the center of this is Google search, the backbone of the open web. Google's embrace of "AI mode" last week was a sign that it will overhaul its approach to search with vast implications for publishers. Earlier this month, I spoke with Dotdash Meredith CEO Neil Vogel for the keynote session at the Media Product Forum, an event put on in NYC by The Rebooting and WordPress VIP. Neil laid out the pragmatic playbook Dotdash Meredith is using to thrive in a shifting landscape.

Henry Blodget built Business Insider into one of the few breakout successes of the traffic era. Now, with his new project Regenerator, he’s taking a different path—one that reflects the broader shifts in digital media. We talk about the collapse of platform-driven distribution, why subscriptions are a more durable model, how venture capital never quite fit the media business, and what it takes to build in the current environment of fragmented attention and AI disruption.Check out The Rebooting's recent research report about AI and personalizationAttend The Rebooting's Online Forum with Recurrent and WordPress VIP on how Recurrent migrated its tech stack

Nicholas Carlson spent nearly a decade building Business Insider into a video powerhouse to complement its webpage model. Now, with his new venture Dynamo, he’s making a clean break from the old model. No articles. No CMS. No pageviews. Dynamo is a video-first media company focused on YouTube and LinkedIn, with a flagship show called Business Explains the World. In this episode, Nich explains why he’s betting on evergreen content, what he learned from Insider’s rise, and how Dynamo is approaching storytelling, distribution, and unit economics from day one. We talk about what it takes to start fresh in a mature platform ecosystem — and why the future of media might look more like TV than a homepage.

I spoke with Anonymous Banker, an M&A advisor with a front-row view into the market for buying and selling digital media companies. Needless to say, it’s a buyer’s market.AB breaks down the market for digital publishing assets – broadly those with page-based models – into three types of buyers:HarvestersCAC jockeysVanity projects/rich person playthings“If you're a publisher with a mostly ad-supported site, odds are your business will be worth less next year than it is now,” he said. Deals are still getting done, but the buyers are different. These are no-name PE firms above ice cream shops in the outskirts of Miami. We go through the list, which ranges from Valnet to Static Media to Savage Ventures to Regent. The playbook is to buy undervalued media properties, slash costs, and milk the programmatic revenue with hyper-lean models that rudely dispense with the nostalgia of “when the going was good.”“Any content they invest in has to be ROI positive within 30 days,” AB said. “You’ll never see them spend $20 million hoping advertisers show up. Those days are done.”Other topics we covered:How AI uncertainty is creating overhang that depresses valuations and makes long-term modeling nearly impossibleWhy the most resilient media businesses are lead-generation machines or conversion front-endsWe debate whether the Chernin Group content-to-commerce thesis was wrongHow Substack’s recommendation engine is the most efficient user acquisition channel in mediaWhat kinds of content investors still believe in (hint: high-intent verticals, not general news)Check out The Rebooting's new media product research reportSign up for The Rebooting's Online Forum on May 21 at 1pmET featuring a case study on how Recurrent migrated its CMS across a portfolio of sites without disruption

Kyle Denhoff, head of audience development for HubSpot Media, joined me to talk about how HubSpot has built one of the most effective media operations inside a tech company. We discuss how HubSpot’s practical, non-ideological approach to inbound marketing evolved into a full-fledged media business spanning newsletters, podcasts, and creator partnerships. Kyle shares how HubSpot balances editorial independence with business goals, the economics of building durable audience relationships, and why companies are better off thinking long-term rather than treating marketing like a vending machine. HubSpot's go-direct playbook offers a glimpse into how companies are rethinking owned media as a strategic asset, not just a marketing channel.Thanks to Marigold for sponsoring this episode. See how Hearst UK uses Sailthru by Marigold and Marigold Liveclicker to connect with millions of readers daily using personalization that feels one-to-one. From onboarding to retention, read to learn their winning strategy.

Janice Min joins to talk about building The Ankler into a focused, profitable media brand—and why she believes the future belongs to lean operators, not her past life helming glossy franchises. We talk about her transition from the high-gloss days of The Hollywood Reporter to the scrappy Substack era, the limits of venture capital in media, and how The Ankler is growing through high-impact events and B2B subscriptions. Janice shares lessons from Y Combinator, explains why editorial quality still matters, and reflects on the changing power dynamics in Hollywood.