The Rebooting Show

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.

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 personalization

Attend 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:

“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:

Check out The Rebooting's new media product research report

Sign 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.