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The Rebooting Show

Latest episodes

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10 snips
Jun 23, 2025 • 1h

Inside Vox Media's podcast strategy

Ryan Pauley, President of revenue and growth at Vox Media, shares insights on how Vox has risen to be a podcast powerhouse with shows like Pivot and Today Explained. He presents a ‘Lego approach’ to business models, integrating both owned content and partnerships. The conversation highlights the shift towards decentralized media, the evolving landscape of brand sponsorships, and innovative monetization strategies. Pauley also discusses the impact of AI on audience engagement and the need for meaningful connections in today’s media.
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12 snips
Jun 16, 2025 • 37min

The modernization of Cosmo

Willa Bennett, the Editor-in-Chief of Cosmopolitan, is leading the brand into a new multiplatform era, and Lisa Howard, Hearst's Global CRO, is all about strategic growth. They dive into how Cosmo is evolving from print to digital, particularly on platforms like Instagram and TikTok, engaging a fresh audience with modern takes on love. Projects like Blind Date and initiatives showcasing women athletes reveal a shift in content. They also share insights on innovative partnerships, like the Valentine's Day Love Ball with Bumble, showcasing how brands can create meaningful connections in today's media landscape.
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12 snips
Jun 12, 2025 • 22min

The blurring of institutional and independent media

Media professionals dive into the fading lines between institutional and independent media. They discuss how alternative media is becoming more professional, adopting traditional formats while maintaining authenticity. The conversation highlights the challenge of competition influenced by financial incentives. Politicians are also tapping into podcasting for engagement ahead of the 2024 elections, emphasizing humor and adaptability. The new media landscape showcases how creators are thriving against traditional outlets, making authenticity vital in an oversaturated market.
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11 snips
Jun 9, 2025 • 1h 2min

Inside Time's practical AI playbook

Jessica Sibley, CEO of Time, shares insights on how the iconic brand is adapting to AI with a focus on solid business strategies. She discusses the shift towards B2B models and the phasing out of speculative ventures like NFTs. Sibley emphasizes the development of AI features that prioritize user integrity and the importance of maintaining editorial standards. Additionally, she highlights Time's collaboration with AI leaders like Scale and OpenAI while navigating the complexities of integrating technology into a historic media landscape.
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15 snips
Jun 3, 2025 • 51min

How the WSJ goes beyond ads and subscriptions

Josh Stinchcomb, Chief Revenue Officer at The Wall Street Journal, shares insights on the publication's innovative strategies. Discover how the Journal is thriving by expanding into events and community engagement, moving beyond traditional ads and subscriptions. Stinchcomb highlights their focus on AI technology, video and audio content, and initiatives like the Leadership Institute to enhance audience and sponsorship value. Explore the evolution of the Journal House and its role in high-profile events, redefining business networking in today's media landscape.
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20 snips
May 26, 2025 • 33min

Google Zero

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.
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9 snips
May 20, 2025 • 1h 4min

Henry Blodget on the media business in 2025

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.
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May 13, 2025 • 1h 7min

Dynamo's Nicholas Carlson's pivot to video

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.
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4 snips
May 7, 2025 • 1h 6min

Anonymous Banker's bleak view of the media M&A market

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.
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6 snips
Apr 29, 2025 • 51min

Inside HubSpot's go-direct media playbook

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.

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