The Rebooting Show

Mike White, the founder of Greater Long Island, has transformed a one-man blog into a vital regional news platform. He discusses the significance of community engagement in local journalism, emphasizing a scrappy, service-oriented approach while navigating industry challenges. They explore innovative funding strategies, such as avoiding paywalls to keep news accessible, and the unique advantages smaller media companies have in advertising. Additionally, Mike shares how organized events can boost local engagement and the potential role of AI in enhancing community news coverage.

David Bank, founder of Impact Alpha and a former Wall Street Journal journalist, discusses his journey into the world of impact investing. He shares insights on building a media company from scratch, highlighting the shift from sponsorships to a subscription model. David emphasizes the importance of identifying niche audiences and why persistence is key in this space. The conversation also touches on the complexities of ESG criteria in investing and balancing journalistic integrity with advocacy for social good.

Louise Story, CEO of Atlas Obscura and a seasoned journalist from The Wall Street Journal and The New York Times, shares her vision for the beloved travel brand. She discusses winding down their in-house experiences to focus on brand partnerships with tourism bureaus, which are now crucial for revenue. Louise also reveals plans for a travel-planning app rooted in community engagement, emphasizing the importance of audience relationships amid the rise of AI and changing media landscapes.

Adi Ignatius, editor-in-chief of Harvard Business Review, dives into the publication's latest venture, HBR Executive, tailored for senior leaders. He discusses the media industry's shift from volume to value, emphasizing the importance of average revenue per user (ARPU). The conversation touches on brand evolution amidst digital transitions, innovative pricing strategies, and the challenges of capturing busy CEOs' attention. Ignatius also explores the implications of AI in creative fields and the need for publishers to provide genuine, differentiated content to thrive.

Cynthia Littleton and Ramin Setoodeh, co-editors-in-chief of Variety, dive into the unique balance of B2B and B2C in entertainment journalism. They discuss the enduring importance of print media amidst a digital shift, the evolving nature of celebrity in the creator era, and how influencers are reshaping Hollywood. The duo also examines the role of AI in journalism and entertainment, emphasizing creativity and integrity. Their insights on collaboration and newsroom success shed light on maintaining relevance in a rapidly changing industry.

Substack's recent funding got a lot of attention for the headline valuation number, as all fundings do, but it's more interesting to examine what its new investment and investors say about the direction of the company. In this episode, I'm joined by Anonymous Banker to break down where Substack goes next and why OnlyFans is a better comp for its aspirations than YouTube.

In this discussion, an Anonymous Brand Marketer from a Fortune 500 company dives into the shifting landscape of marketing in the age of AI. They dissect how AI is reshaping traditional marketing methods while sparking a revival of brand marketing that resonates with consumers. The conversation emphasizes the irreplaceable value of in-person brand experiences and the need for companies to focus on meaningful connections rather than just data. They also touch on the cultural backlash against AI in advertising and the evolving role of individual creators in engaging audiences.

Steve Grove, CEO of the Minnesota Star Tribune and former tech executive at Google News Lab, discusses revitalizing local journalism amid modern challenges. He shares insights on why he left Big Tech, focusing on local relevance over scale. Grove details innovative strategies for restructuring the newsroom, enhancing community engagement, and launching new revenue streams. Additionally, he emphasizes the importance of rebuilding trust and genuine relationships between reporters and their communities, pivoting towards a sustainable future for legacy news.

Annelies Jansen, Chief Business Officer at ProRata and former Facebook executive, discusses how generative AI is reshaping the publishing industry. She emphasizes the urgent need for new economic models to ensure fair compensation for creators facing dwindling traffic. The conversation covers attribution systems, risks of a bifurcated media ecosystem, and the importance of collaboration among publishers. Jansen also highlights the emotional and ethical challenges of treating content as a mere commodity in an AI-driven landscape.

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.