

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

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.

10 snips
Jul 28, 2025 • 49min
How Variety straddles B2B and B2C
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.

Jul 18, 2025 • 50min
Substack's OnlyFans opportunity
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.

9 snips
Jul 15, 2025 • 48min
The return of brand marketing
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.

11 snips
Jul 8, 2025 • 52min
Inside the Minnesota Star Tribune’s Revival
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.

6 snips
Jul 1, 2025 • 57min
An AI grand bargain for publishers
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.

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.

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.

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.

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.