The Rebooting Show

Neil Vogel, CEO of Dotdash Meredith, discusses the rapidly changing landscape of digital publishing driven by AI advancements in search technology. He shares strategies for publishers to thrive, emphasizing the power of first-party data and building direct audience engagement. The conversation covers innovative media strategies, the evolution of content consumption, and adapting to new formats. Vogel also tackles challenges posed by 'Google Zero' and the importance of diversifying content strategies to maintain brand trust in this dynamic environment.

Henry Blodget, the mastermind behind Business Insider and now leading a new venture called Regenerator, shares insights on the media landscape's evolution. He discusses the decline of platform-driven distribution and the rise of subscription models as a robust alternative. Blodget emphasizes how venture capital has struggled to fit within media and highlights the challenges of capturing fragmented audience attention in the age of AI. He also examines innovative media approaches that resonate with younger audiences, ensuring traditional journalism adapts to modern demands.

Nicholas Carlson, founder of Dynamo and former editor in chief at Business Insider, shares his video-first approach to media. He emphasizes the benefits of evergreen content and the emotional impact of video storytelling. Carlson discusses the challenges of breaking from traditional models while focusing on engagement and high-quality production. He also explores the financial complexities of video creation and the innovative strategies needed to thrive on platforms like YouTube and LinkedIn, highlighting the future of media as more television-like.

In a revealing conversation, Anonymous Banker, an M&A advisor with specialized knowledge in digital media, offers keen insights into the current landscape of media acquisition. He categorizes buyers into three groups and explains why ad-supported sites are facing valuation drops. The discussion also delves into how AI is negatively impacting forecasting and the need for ROI-positive content within tight timelines. Other highlights include the durability of lead-generation models and the implications of major tech platforms dominating advertising revenue.

Kyle Denhoff, Head of Audience Development for HubSpot Media, dives into HubSpot's innovative media operations. He discusses how inbound marketing has transformed into a full-fledged media business, emphasizing editorial independence and long-term audience relationships. The conversation highlights the shift from traditional marketing to sustainable, audience-first strategies. Denhoff also addresses the evolving media landscape, the growing importance of partnerships with creators, and the future of B2B events in fostering genuine connections.

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.