The Rebooting Show

Sarah Longwell, publisher of The Bulwark and founder of Republican Voters Against Trump, discusses the decline of neutrality in political journalism. She argues that transparency and conviction are essential for trust in today's polarized climate. Longwell highlights The Bulwark's evolution from a Never Trump site to a pro-democracy platform, emphasizing the importance of defending liberal democracy against anti-democratic forces. The conversation touches on the site's diverse audience and its strategic use of YouTube to engage and expand its reach.

Jacquelyn Cameron, the Chief Revenue Officer at Axios, shares her expertise on audience segmentation and B2I strategies. She delves into how Axios categorizes its audience into five core personas and explains how this drives product and event connections. Jacquelyn highlights the competitive edge of 'no opinion' coverage in D.C. and discusses the importance of localized national advertising. Additionally, she elaborates on the role of AI in enhancing audience insights and how Axios uses live events to create a tangible newsroom experience.

Matt Gross, VP of Digital Initiatives at Regent, and Tyler Denk, CEO of Beehiiv, discuss TechCrunch's major email strategy overhaul. They dive into the challenges of upgrading outdated tech infrastructure and how they reframed newsletters from mere traffic drivers to vital editorial assets. Topics include the importance of building an email-first CMS, practical tactics for audience growth, and balancing comprehensive reporting with personality-driven content. They also share insights on modern acquisition methods and the future of email in publishing.

Josh Marshall, founder of Talking Points Memo, shares insights from 25 years of navigating an independent political newsroom. He discusses the 'small-boat strategy' that prioritizes resilience over scale and the challenges of programmatic advertising. Marshall explains how TPM's early pivot to a membership model provided crucial stability during an advertising collapse. He reflects on the impact of Google’s dominance, the rise of independent journalism, and the ongoing significance of human perspective in media, posing questions about the future of journalism in an AI-driven world.

Tyler Brûlé, the founder of Monocle and a visionary in niche media, discusses the brand’s unique strategy that prioritizes print over digital trends. He shares insights on cultivating close relationships with readers, emphasizing that understanding audiences can't be reduced to data alone. Tyler reveals how Monocle navigated the challenges of the financial crisis while expanding its reach through cafés and shops. He also critiques the contemporary media landscape and highlights the importance of maintaining quality in both print and digital formats.

Stephanie Cohen, Chief Strategy Officer at Cloudflare, discusses the evolving role of AI and bots in the online ecosystem. She reveals startling trends: human traffic to publisher sites has plummeted, while bot crawls have surged. Cohen outlines Cloudflare's innovative pay-per-crawl model designed to restore balance and demand for high-quality content. She envisions a Spotify-like marketplace where publishers control access and monetize their content. The conversation highlights the urgent need for clarity and control in the age of AI.

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.

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.

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.

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.