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, has spent 25 years steering a small, independent newsroom through every shift in digital media. He discusses how TPM survived the traffic era, why it avoided venture capital, and what he calls the “small-boat strategy” — building for resilience, not scale.

Tyler Brûlé has built Monocle into one of the most distinctive media brands of the past two decades. At a time when others chased clicks and platforms, Monocle went the other way. It invested in print, opening cafés and shops, launching a radio station, and building a loyal global community. I sat down with Tyler at Monocle’s Paris café to talk about how he’s kept the brand consistent, why proximity to readers matters more than dashboards, and what lessons Monocle’s model holds for publishers trying to build durable, multifaceted brands.

Bots are taking over the internet, previewing a new world where agents interact and humans consume bot-created content. Cloudflare, a leading content delivery network, saw this coming.

Cloudflare Chief Strategy Officer Stephanie Cohen told me that publishers reported less traffic to their sites and less human traffic. “Those numbers were 10 times worse than a decade ago.”

This has broken the open web trade of the crawling right for traffic promise. Cohen said, “For some bots, the crawl-to-traffic ratio is tens of thousands of times worse than it used to be.”

Five takeaways from our conversation:

In this conversation, Beehiv CEO Tyler Denk joins me to discuss the evolving landscape of media, focusing on the importance of audience ownership and the role of email as a primary distribution channel. We compare Beehive and Substack, highlighting the differences in their approaches to monetization and audience engagement. We also zero in on trends in the newsletter space, including the shift towards niche content and sustainable business models. Finally, Tyler outlines Beehive's future roadmap, including enhancements to their platform and services for both small and large publishers.

This episode is sponsored by Piano

The essential challenge for publishers is similar to most businesses: find a way to control their relationship with the customer. 

That means going back to basics, argues Trevor Kaufman, CEO of Piano, and giving people reasons to come directly to publishers. Too often published have chosen audience development tactic — fish where the fish are, etc — over sound business strategies, Trevor told me on the Rebooting Show ahead of this week’s Piano Academy in Paris.

“Fundamentally, creating a loyal audience that shows up at your front door; that’s the business of publishing. And we get too distracted with a pivot to video, or apps, or Facebook, or AI, instead of asking what it means to be a subscriber, a member of this brand.” 

Other issues we discussed:

See The Rebooting's recent "total monetization" research report done in collaboration with Piano.

Keith Pepper has a handy reminder of his goal with Rough Draft Atlanta: a Post-It note on his computer that reads simply “meaningful, not massive.”

That’s the approach Keith has taken with Rough Draft Atlanta, a local news business focused on well-heeled areas of the Atlanta area that Keith has built after buying a clutch of community newspapers in 2020. Keith has mostly worked on the tech side of media his entire career, but he felt the pull to local news for the next phase of his career. We discuss how Rough Draft relies on direct mail of all things as a critical and reliable distribution channel, why print still far outpaces digital in monetization of local, and making tough choices in the balance of hard news and service journalism that often gets a bad wrap but is critical utility for local news. 

This episode is sponsored by Piano. Piano’s Digital Revenue Optimization solution helps digital services grow revenue by better understanding and influencing their customers’ behavior. Piano unifies analytics, segmentation, and commercial personalization in one AI-driven application, enabling sites and apps to efficiently maximize the value of every user visit. For more information, visit piano.io.

On Oct 2, I'll be speaking at the Piano Academy in Paris. My talk will focus on "things that won't change" in the AI era. Find out more about the Piano Academy.

Forbes CEO Sherry Phillips discusses how the 107-year-old brand is retooling for a far messier media market. Forbes is less a magazine than a platform that turns brand equity into revenue across multiple surfaces: advertising, branded content, newsletters, a licensing network that spans 67 editions in 43 languages, an e-commerce arm, and a fast-growing slate of more than 100 events that now account for up to 30% of revenue.

This week, I spoke to Essentially Sports cofounder Suryansh Tibarewal about how it is adapting its strategies in a time of traffic flux. Essentially sports is a high volume web publisher, one i’d consider as a classic pageview publisher. Suryansh and I discuss how essentially has continued to benefit from Google Discover, shifting its business model to focus more on direct sold revenue rather than programmatic and how its fan perspective is a differentiator in a crowded category.

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.