The Rebooting Show

Andrew Perlman, CEO of Recurrent — a publisher of niche brands across auto, military, home, and science. He talks about shifting revenue from affiliate search to events and experiential offerings. He explains scaling niche conferences, tying events to editorial, expanding into video and creator-led formats, and growing licensing, merch, and AI-driven operations.

Doug Leeds, digital media executive and CEO of RSL, explains why the traffic-for-content bargain is breaking as AI delivers answers without clicks. He discusses RSL’s open standard plus collective licensing, why pay-per-crawl fails, how licensing can scale like music royalties, and how collective leverage could help publishers and creators get paid.

Tom Packus, CEO of EX.CO, shares insights on the chaotic streaming landscape, highlighting challenges like app fragmentation and trust issues in 'agentic' advertising. Manas Mittal, from Uber Ads, discusses the booming $1.5B mobility advertising sector and its unique context-driven placements. Andrea Sullivan of VaynerMedia talks about VYVE, a community for leaders focusing on personal growth, and the importance of trust-based, intimate groups for fostering meaningful change. Join these industry experts as they navigate the future of digital advertising!

Geoff Schiller, Chief Revenue Officer at Vox Media, discusses the innovative talent-led franchise strategy shaping the company, including the rise of podcasts as key platforms for creators. He emphasizes flexible partnerships with talent, expanding their reach through multimedia channels. Mark Floriani, Co-founder of FloSports, dives into the booming world of niche sports, highlighting the importance of owning IP to enhance fan experience. He forecasts significant growth in middle and long-tail sports while steering clear of hype trends like pickleball.

CJ Gustafson, founder of Mostly Metrics and a former finance executive, shares his unique journey of transforming a newsletter into a thriving, $3 million B2B media business. He discusses the shift from subscriptions to sponsorships, revealing why CFOs are a lucrative audience for advertisers. CJ also dives into the intricacies of long sales cycles, the importance of product quality, and how intimate events can foster connections without becoming a full-fledged events company. His insights emphasize balancing growth with personal values in the media landscape.

Justin Smith, CEO and co-founder of Semafor, shares insights on their innovative events-first media model that propelled the company to $40 million in revenue in just 3.5 years. He explains how integrating events with journalism has made Semafor's approach uniquely profitable in a challenging media landscape. The conversation highlights the growing importance of corporate affairs budgets, global expansion strategies, and the deliberate choice to launch in less competitive markets like Africa and the Gulf.

In this engaging discussion, Sarah Personette, CEO of Puck and former Facebook executive, shares her vision for media without becoming an events-heavy brand. She emphasizes maintaining identity by strategically using convening power while keeping content at the forefront. Sarah also explores the importance of building subscriber relationships over chasing podcast revenue and how Puck has expanded into various channels, reaching over 100,000 subscribers. Her insights on balancing individual voices with a supportive framework paint a compelling picture of modern media dynamics.

Sara Fischer, Axios media correspondent, and Lachlan Cartwright, founder of Breaker, delve into the shifting landscape of media in 2025. They discuss the rise of personality-driven journalism and the pressures facing legacy newsrooms amid political and AI challenges. Lachlan shares insights from Breaker's launch and monetization strategies, while Sara emphasizes the importance of team building for sustainable newsletters. They also analyze significant industry deals, workforce unrest, and the evolving role of journalists in today's creator economy.

In this discussion, Vineet Khosla, CTO at The Washington Post with an impressive tech background from Apple and Uber, shares insights on transforming journalism. He explores shifting from traditional perfection to an iterative approach, emphasizing the need for personalized and conversational formats. Vineet argues for media outlets to become platforms rather than mere content suppliers to tech giants. He also highlights the potential of AI in journalism, predicting it will handle summarization while human journalists retain their critical roles.

Jason Wagenheim, North American CEO of Football Co. and a seasoned media executive, shares his insights on the evolving media landscape. He discusses the decline of traditional publishers and the urgent need for a shift toward creator-led video and social media. Jason highlights how the World Cup serves as a significant commercial opportunity for soccer in the U.S., and he explains strategies for engaging audiences through experiential content. The conversation reveals how soccer’s cultural rise is shaping modern storytelling and media business models.