The Rebooting Show

Sherry Phillips, the CEO of Forbes and a veteran in media leadership, shares insights on transforming the iconic brand for today’s chaotic media landscape. She reveals how Forbes is evolving beyond just a magazine, embracing diverse revenue streams like events, e-commerce, and branded content. The discussion highlights the challenges of digital traffic decline, the impact of Google on publishing, and Forbes’ new strategies to engage younger audiences. Phillips also touches on the intersection of celebrity culture and the creator economy, emphasizing brand adaptation in a rapidly changing world.

Suryansh Tibarewal, cofounder of Essentially Sports, dives into the transformative journey of his platform from a college passion project to a significant player in sports media. He shares insights on adapting to traffic changes and shifting business models, particularly moving towards direct ad revenue. The conversation also touches on harnessing Google Discover and the importance of engaging niche sports audiences. Suryansh emphasizes the role of community and innovative marketing strategies in helping them navigate the competitive landscape of sports coverage.

This episode is sponsored by Piano. Check out the new report from The Rebooting and Piano that examines how revenue leaders at publishers are taking a "total monetization" approach.Deirdre Lester is no stranger to how sports brands can influence culture. She served for four years as the CRO at Barstool as it grew well beyond its roots in sports banter to develop several revenue streams. At Teton Ridge, Deirdre sees a similar opportunity in the niche of Western sports like rodeo. Teton Ridge is betting big on Western sports and lifestyle — acquiring The Cowboy Channel, building original programming around rodeo, and elevating events like the American Rodeo into marquee sports properties. It’s part media company, part sports IP owner, and part entertainment studio, with the aim of modernizing a tradition-rich category while keeping its authenticity.Deirdre and I talk about what it takes to grow in a time of constant industry change, and why she believes Western sports are not just having a cultural moment, but building into a lasting movement.

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.