Morning Brew CEO Robert Dippell joins me to break down the fundamental differences between consumer and B2B media, why so many publishers underestimate the challenge, and how Morning Brew has built a thriving B2B business alongside its flagship newsletter. We also discuss the role of events, the shift to creator-led media, and why some of Morning Brew’s early growth strategies wouldn’t work today.Check out The Rebooting's new audience development research report, in collaboration with Omeda.

Adam Ryan, CEO of Workweek, critiques the overheated newsletter market. He argues newsletters are becoming commoditized as their numbers outpace readers. Ryan cautions that reliance on paid growth leads to fleeting engagement without real audience connection. He emphasizes the importance of expanding beyond email, highlighting successful businesses that integrate community and events. The conversation reveals newsletters as a starting point for building connections, not a sustainable standalone business model.

Sean Griffey, until recently the CEO of Industry Dive, joined me on The Rebooting Show to discuss the big things Industry Dive, and by extension a lot of B2B, got right. Sean was rarely mentioned in the collection of digital media CEOs of the recent decade. Yet Industry Dive achieved one of the standout exits of the category. He led the B2B publishing company to a $525 million exit to Informa. At the end of 2024, Sean left his role at Informa TechTarget to enjoy “semi-retirement.” I’ve found over the recent years that the worlds of consumer and business publishing are coming together. It used to be they spoke differently and had different priorities. Now, you have publishers like Punchbowl and Puck executing B2B strategies. Semafor relies on events as the bulwark of its revenue model. Publishers are more likely to talk up their newsletters than ComScore numbers.Some of the lesions we discussed:Focus on a specific audience. Industry Dive would turn off ads if it had a story picked up by Reddit that led to a flood of viral traffic. That’s because the people arriving weren’t the “right people.” B2B isn’t about reaching everyone. Know who you’re writing for. A trick of B2B that narrows the focus: Write for a specific job title. Media properties nowadays can be messy, but they need to have a person in mind (and know enough similar people exist).Get receipts. Industry Dive focused its business model on marketing services and lead generation. In B2B, budgets are far greater for demand generation than branding or thought leadership. Do more with less. Industry Dive operated dozens of publications in verticals like wast management, retail, marketing and Tk. But it operated a single platform. That allowed it to quickly move to create new brands, even if it sacrificed unique branding elements.Go direct. Media companies have three core areas: creation, distribution and monetization. Sean criticizes consumer publishers for relinquishing control over distribution by chasing search and social traffic and monetization by relying on programmatic advertising middlemen. B2B media markets have developed differently, allowing companies to avoid those kinds of dependencies. 

In this engaging conversation, Jonah Peretti, CEO of BuzzFeed and herald of the 'Anti-Snarf' manifesto, dives deep into the evolution of social media. He shares insights on the shift from genuine connection to algorithm-driven manipulation, highlighting the addictive nature of platforms today. Jonah discusses BuzzFeed's ambitious pivot toward becoming a social network focused on positivity and user-generated content, while reflecting on the challenges of sustaining meaningful engagement in the current digital landscape.

Tom Pachys, CEO of EX.CO, is at the forefront of programmatic advertising solutions for Connected TV (CTV). He delves into the transformative shift from traditional TV advertising to digital models, emphasizing the merging of sight, sound, and motion with precise targeting. Pachys elaborates on the complexities of measuring ad effectiveness and the rise of dynamic out-of-home advertising. He discusses the necessity for sophisticated tools and strategic data use in navigating this evolving landscape, paving the way for more efficient ad practices.

Pete Pachal, a seasoned news editor and author of The Media Copilot newsletter, dives into the compelling dynamics between AI and the publishing industry. He discusses the groundbreaking Deepseek model from China and its implications for the global media landscape. The conversation also highlights the challenges publishers face in adapting to basic AI applications, the evolving role of AI in journalism, and how user experiences in search are shifting. Pachal warns of potential misjudgments in the emerging AI market and emphasizes the need for balance between human authenticity and technological advancement.

This is set up to be a banner year for alternative media. Axios senior media reporter Sara Fischer joined me on The Rebooting Show to discuss why institutional media has lost power and influence to an assortment of podcasters, YouTubers and independent creators — and steps it will take to adapt. Three key ones:Embrace curiosity. Much of institutional media feels like a set piece. Cable news shoutfests are obviously performative. Fact checks often come off as assembling facts to back up a preordained conclusion. Some of the most popular and influential independent creators present as curious. Speaking truth to power is not enough.Build around trusted voices. Later this month, Axios will roll out a membership program built around Sara’s Media Trends newsletter. Axios CEO Jim VandeHei has spoken of the need to elevate “stars,” particularly as AI does Smart Brevity by default. The market will drive this as unique talent has more options than ever — and the risk:reward ratio is often scrambled in the Information Space as the solo path is less risky and offers greater potential rewards. Pick a lane. The current news market is geared to ideological publications The Free Press, The Daily Wire, etc – leaving an opening for nonpartisan news, as hard as that is to pull off. Thanks to EX.CO for sponsoring this series.

On this week’s episode of The Rebooting Show, I was joined by Alex Kantrowitz, who writes the Big Technology newsletter and hosts a podcast of the same name, in order to discuss the year ahead in tech platforms. We covered a lot of ground, including:The slightly unseemly kowtowing to the incoming Trump administrationOpenAI’s wonky economicsAlex’s bet on AI “companions”Why X has proved doomsayers wrongThe bright spot of individual creators amid a lot of media industry gloomCheck out the Big Technology newsletter and podcast. Learn more about TRB partner EX.CO's expansion of its award-winning ad server to upgrade programmatic auctions in CTV and digital-out-of-home environments.

Mike Mallazzo, writer of the reliably excellent Zero Clicks newsletter from Martech Record and a veteran of digital publishing and marketing, joined me on The Rebooting Show to discuss the state of affiliate and what to expect in the category in 2025. The hopeful view: The efforts to stamp out affiliate arbitrage  will ultimately reward those who put in the work to create high-quality content that’s actually useful, as opposed to churning out affiliate content to arbitrage their brand’s high ranking in the search results pages. As Mike points out, "Without huge arbitrage opportunities, affiliate is a bad business model... We had a 10-year golden era of arbitrage that made affiliate a great business model.” 

Join Kristin Roberts, Chief Content Officer at Gannett, Imtiaz Patel, Chief Consumer Officer, and Renn Turiano, Chief Product Officer, as they explore the transformative impact of AI on media. They explain how Gannett is reinventing article formats to boost local engagement and enhance user experience. The trio discusses the delicate balance between traditional practices and AI innovations, grapples with subscription fatigue, and shares strategies for constructing effective performance-driven advertising in an increasingly digital landscape.