The Rebooting Show

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.

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.

Patrick Trousdale, CEO of The Daily Upside, shares insights from his transition from investment banking to media entrepreneurship. He discusses how niche products like Advisor Upside and ETF Upside are enhancing their value chain. The conversation covers the pivotal role of original journalism in differentiating their brand and navigating the evolving newsletter landscape. Trousdale emphasizes sustainable growth through meaningful B2B relationships and addresses challenges posed by AI tools on content creation, advocating for detailed insights over summarization.

Rachel Oppenheim, CRO of Semafor, a media company specializing in stakeholder media, dives into innovative approaches to journalism and audience engagement. She discusses the shift from passive viewership to active community-building and the importance of meaningful events. Oppenheim emphasizes the need for authenticity in communications and shares insights about forging long-term relationships over transactional ones. She also reflects on how Semafor adapts to the evolving media landscape by centering on stakeholder engagement and niche market focus.

Andrew Yaffe, CEO of Dude Perfect, shares insights into the transition from viral YouTube stars to a thriving media franchise. He discusses how they effectively diversified revenue streams, from merchandise to live events. Yaffe emphasizes the importance of creating durable intellectual property and strategic growth in content creation. He also explores the delicate balance between capital raises and maintaining brand integrity, showcasing Dude Perfect's journey as a testament to the power of innovation and family-friendly entertainment.

In this conversation, Robert Dippell, CEO of Morning Brew, shares insights into the unique challenges of B2B media compared to consumer models. He discusses Morning Brew's successful transition into the B2B space and the importance of innovative audience engagement strategies. The talk covers the shift towards creator-led media, the necessity of diversifying revenue streams, and how early growth tactics have evolved. Dippell emphasizes adapting to audience feedback and building strong brand identities, making this a must-listen for media enthusiasts.

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.