The Rebooting Show

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...

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-heel...

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, newslett...

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...

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 cultu...

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 d...

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 journ...

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 ...

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 med...

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 ...

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 An...

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 sp...

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, h...

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 di...

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 ap...

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 t...

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 convers...

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...

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 over...

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 publisher...

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 pla...

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 vid...

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 pag...

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 market...

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 T...