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 bifurc...
Jul 01, 2025•57 min•Ep. 171
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 distributio...
Jun 23, 2025•1 hr•Ep. 170
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...
Jun 16, 2025•37 min•Ep. 169
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/SemaforMixedSignals Channels with Peter Kafka - https://pod.link/recodemedia...
Jun 12, 2025•22 min•Ep. 168
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 ...
Jun 09, 2025•1 hr 2 min•Ep. 167
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 Jou...
Jun 03, 2025•51 min•Ep. 166
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 thr...
May 26, 2025•33 min•Ep. 165
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'...
May 20, 2025•1 hr 4 min•Ep. 164
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 approachin...
May 13, 2025•1 hr 7 min•Ep. 163
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: Harvesters CAC jockeys Vanity 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. Dea...
May 07, 2025•1 hr 6 min•Ep. 162
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 ...
Apr 29, 2025•51 min•Ep. 161
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...
Apr 22, 2025•1 hr 4 min•Ep. 160
Once a music magazine that competed with Rolling Stone to define cool in the pre-internet era, Spin is no longer really a magazine. Yes, it has brought the magazine (and Bob Guccione Jr) back, but Spin is an IP company now. It puts on Spin Sessions events, sells t-shirts at Urban Outfitters, licenses its archive for streaming projects, and runs a record label with Randy Jackson. CEO Jimmy Hutcheson explains how a magazine brand has moved on to become a cultural brand that exerts influence (and m...
Apr 14, 2025•56 min•Ep. 159
Inn this episode, The Daily Upside's Patrick Trousdale explains how niche products like Advisor Upside and ETF Upside are helping the company move up the value chain. We also talk about paid growth, building a newsroom, and why journalism—not just distribution—is the long-term differentiator.
Apr 08, 2025•46 min•Ep. 158
Stakeholder media is how a media company can stay influential and build a real business—especially now, when scaled ad models are in a full race to the bottom. Everyone wants to move from passive audiences to active communities. Stakeholder media is a variant. It’s defining features: Elite audiences operating in interconnected, complex ecosystems Focused media, intentionally not for everyone Ability to convene stakeholders with the brand as glue Business model geared to long term relationships v...
Apr 01, 2025•56 min•Ep. 157
An enduring challenge of the media business is finding leverage in models. This used to be fairly straightforward. Newspapers had leverage as quasi-local monopolies, Magazines had leverage that allowed Vanity Fair to pay a writer nearly $500k for three articles a year – and still be nicely profitable. And so on. It’s increasingly hard to find that kind of leverage beyond a few exceptions to the rule. The closest is likely in lean creator businesses that have created valuable intellectual propert...
Mar 25, 2025•45 min•Ep. 156
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....
Mar 17, 2025•50 min•Ep. 155
Adam Ryan, CEO of Workweek, joined me this week to discuss his recent warning that the newsletter sector is overheated. Some points from the conversation: Newsletters are a commodity. The number of newsletters is growing faster than the number of readers. AI tools and cheap platforms like Beehiv have made launching one easy, but most newsletters lack true audience affinity. The inbox is not really a direct connection . It’s a platform like any other, subject to change. Apple’s Mail Privacy Prote...
Mar 10, 2025•54 min•Ep. 154
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 ove...
Feb 25, 2025•53 min•Ep. 153
BuzzFeed has always been a company that plays with the boundaries of media, technology, and internet culture. From its early days mastering viral content to its ill-fated attempt to build a sustainable news division, the company has been in a constant state of reinvention. Now, CEO Jonah Peretti is making perhaps his boldest move yet: transforming BuzzFeed into something more than just a publisher—into a social network. In Jonah's telling, this move springs from a frustration with the direction ...
Feb 17, 2025•55 min•Ep. 152
The worlds of TV and internet publishing operated separately. The platforms, the dynamics and even the language used was completely different. Linear TV was brand focused and driven by scarcity dynamics while the internet quickly became a direct marketing machine. Those divisions have nearly erased, thanks in large part to the rise of streaming. Once TV began to be delivered across IP it was inevitable that the digital ad system would be ported over to be married with what was formerly a stodgy ...
Feb 03, 2025•45 min•Ep. 151
This week, I'm joined by Pete Pachal, a publishing veteran who writes The Media Copilot newsletter that focuses on the intersection of the news business and AI. Pete and I discuss the recent breakthrough with Deepseek, and what it means beyond Silicon Valley and the stock market. We also get into how publishers are adapting to AI, why many of the product use cases are fairly basic to date, and how news consumption is likely to change as agentic AI takes off....
Jan 28, 2025•1 hr•Ep. 150
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 preor...
Jan 20, 2025•54 min•Ep. 149
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 administration OpenAI’s wonky economics Alex’s bet on AI “companions” Why X has proved doomsayers wrong The bright spot of individual creators amid a lot of media industry gloom Check out the Big...
Jan 13, 2025•50 min•Ep. 148
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 rank...
Jan 06, 2025•56 min•Ep. 147
In this live podcast, I spoke to Imtiaz Patel, chief consumer officer; Kristin Roberts, chief content officer; Jason Taylor, chief sales officer; and Renn Turiano, chief product officer. We discussed rethinking the article page, the imperative to provide a better user experience, why Google is so frustrating, using AI to drive subscriptions, and how AI answer engines are like Uber.
Dec 12, 2024•47 min•Ep. 146
At Metro, the free London newspaper, the comedown from the traffic era was jarring. At the end of 2022, with Facebook turning off the traffic taps to news and a Google update hitting, overall traffic dropped in half, Metro’s director of audience Sofia Delgado told me in a conversation at WordPress VIP Innovation Showcase in London. “We had a newsroom that came of age in the era of Facebook,” she said. “We had a lot of bad habits and we were used to doing things quickly. Suddenly that wasn't work...
Dec 02, 2024•14 min•Ep. 145
Stagwell CEO Mark Penn is a veteran of politics. In this discussion, he examines how shifting audience behaviors and trust patterns are reshaping where Americans get their news. The conversation delves into the thorny challenges of advertising on news content and why brand safety concerns are usually overblown. Penn outlines how news organizations can build sustainable businesses by adopting lessons from political campaigns, while warning that chasing ideological audiences risks further eroding ...
Nov 19, 2024•34 min•Ep. 144
AI-powered search engines have clawed a foothold in the critical search market that controls distribution on the open web. Media management consuling firm Activate estimates 15 million people are using these answer engines rather than Google, which is adding AI summarization to its results. By 2028, Activate expects that to rise to 36 million. The open question is whether publishers can stem this tide. Michael Wolf, the CEO of Activate, sees a fundamental shift in the search market, as generativ...
Nov 05, 2024•41 min•Ep. 143
Blockworks CEO Jason Yanowitz discusses how Blockworks has evolved the company from an events business to podcast network to news provider to becoming a data and information play with media, events and franchises feeding the core data and research business. This kind of shift is hard to pull off. Among the issues we discuss: Using podcasts for broad reach and affinity News as a credibility driver Pulling back on B2C events to focus on B2B Using media to drive “negative CAC” for information servi...
Oct 28, 2024•44 min•Ep. 142
