

The Rebooting Show
Brian Morrissey
The Rebooting Show gets into the weeds with those building and operating media businesses, giving an open view into how the smartest people in the media business are building sustainable media businesses. https://www.therebooting.com/ (www.therebooting.com)
Episodes
Mentioned books

13 snips
Oct 7, 2025 • 51min
Beehiiv's Tyler Denk on email's centrality
Tyler Denk, CEO of Beehive and former Morning Brew team member, dives into the evolving media landscape. He emphasizes the importance of audience ownership through email, arguing it fosters habitual engagement. Denk compares Beehive’s open platform to Substack’s walled garden, detailing the flexible monetization strategies for creators. He also discusses the resurgence of advertising in newsletters and highlights trends toward niche content for sustainable success. Lastly, he shares Beehive's innovative roadmap focused on enhancing email and analytics.

31 snips
Sep 30, 2025 • 50min
Publishers need to go back to basics
Trevor Kaufman, CEO of Piano and expert in audience and revenue platforms, discusses the urgent need for publishers to refocus on their core audience relationships. He highlights the pitfalls of giving away content to giant platforms and the complex nature of publishing today. Trevor advocates for stronger homepages, cohesive subscription strategies, and measuring success through ARPU. He also addresses subscription fatigue, the resilience of the open web, and the renewed interest in micropayments despite previous failures.

23 snips
Sep 23, 2025 • 50min
Rough Draft Atlanta’s ‘meaningful, not massive’ approach to local
Keith Pepper, the Publisher of Rough Draft Atlanta, shares insights from his journey of transforming local newspapers into a modern digital-first news platform. He emphasizes a 'meaningful, not massive' philosophy, highlighting the importance of balancing hard news with community service journalism. Keith explains how direct mail and print advertising still drive significant revenue, while discussing the challenges of transitioning staff to embrace digital growth. His optimism for sustainable local news shines through as he points to successful regional models and recommends key industry peers.

52 snips
Sep 16, 2025 • 52min
Inside Forbes’s total monetization approach
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.

10 snips
Sep 9, 2025 • 52min
How Essentially Sports navigates shifts
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.

Aug 31, 2025 • 53min
Monetizing cowboys
In this engaging discussion, Deirdre Lester, CEO of Teton Ridge and former CRO at Barstool, delves into the evolving world of Western sports. She outlines Teton Ridge's ambitious plans to modernize rodeo and enhance the Cowboy Channel. Deirdre reveals how they are creating content through innovative partnerships and tapping into diverse revenue streams like sponsorships and SVOD. With a focus on authenticity and cultural impact, she believes Western sports are transforming from niche interests into a significant movement.

14 snips
Aug 26, 2025 • 50min
Greater Long Island's scrappy approach to local
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.

23 snips
Aug 19, 2025 • 57min
ImpactAlpha's 'hometown paper' approach
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.

29 snips
Aug 11, 2025 • 58min
Atlas Obscura's next chapter
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.

13 snips
Aug 5, 2025 • 49min
Moving up the pricing curve
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.