The Rebooting Show

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 monetizes) beyond its pages.

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.

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 vs transactions Rachel Openheim, CRO of Semafor, discussed with me how Semafor is centering its business on stakeholder media, and why that moves events to the center from the periphery.

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 property that can be monetized in various ways. Dude Perfect is a great example of this. The four dudes from Texas A&M went from viral trick-shot videos on YouTube to building a very profitable media franchise with diverse revenue streams Beyond YouTube ads, Dude Perfect developed business lines in merchandise, licensing and live events.  It is a testament to the benefits of bootstrapping. According to an investor deck I saw, Dude Perfect grew to $35 million in revenue with over 50% EBITDA margins. That attracted a $200 million valuation in a funding led by Highmount Capital to expand the business. Andrew Yaffe, the Dude Perfect CEO who joined in October 2024 from the NBA, spoke to me on The Rebooting Show about how to build enduring franchise value in this kind of creator-led media business.

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, 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 Protection has broken open rates, AI tools like Superhuman summarize newsletters without opening them, and inboxes are being segmented, reducing visibility. Paid growth is a weak foundation. Many newsletters rely on paid acquisition and cross-promotion. The moment that engine turns off, engagement often collapses because there’s no real audience connection. Winners are thinking beyond email. The most successful publishers are building businesses around community, events, and services. Morning Brew, Workweek, and Lenny’s Newsletter all extend beyond just newsletters. Newsletters are a starting point, not a business. They are an MVP—a way to build an audience—but real success comes from expanding into new distribution and monetization channels.

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. 

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 of social media, as platforms have turned to adversarial algorithms that addict users and prey on human weaknesses. It's a different social media than the heady days of 2012-2015, when BuzzFeed mastered the art and science of creating shareable content. Jonah and I discuss the media landscape and why it's not too late to come up with an alternative social network built around joy.

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 world. That’s led to a stampede of the Lumascape to TV, which has always had better ad options than what was on offer on webpages. The promise of streaming with programmatic ad mechanisms is to marry the sight, sound and motion of TV commercials with the targeting and efficiency of programmatic. In this spotlight episode of The Rebooting Show, EX.CO CEO Tom Pachys discusses the transition of the TV ad model that is underway in streaming, the similarities and differences between TV and digital advertising, and why out-of-home is now a fast-growing ad category.  Learn more about EX.CO's new CTV product.

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.