The Rebooting Show

TechCrunch’s new owner faced a familiar challenge: modernizing an old tech stack built for a different era. Matt Gross, vp of digital initiatives at TechCrunch owner Regent, joins Beehiiv CEO Tyler Denk to discuss how they untangled years of tech debt, rebuilt email from the ground up, and reframed newsletters as core editorial products rather than traffic drivers.Note: This episode is part of a commercial partnership between The Rebooting and Beehiiv. Learn more about how Beehiiv works with enterprise publishers.

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.

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.

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.