TRB at 5

Today’s conversation: Tyler Denk, CEO of Beehiiv, speaks to me about how the next generation of media is built on direct connections to audiences.

Paramount’s $150 million purchase of The Free Press is a bet on Bari Weiss remaking CBS News. It is an off-the-spreadsheets exit — good luck getting 10x revenue for your newsletter — driven more by intangibles than banker math, although Anonymous Banker promises to walk me through the banker math on this week’s PvA.

It shows how media brands will be built: lean, individualistic, point of view-driven, with direct audience ties and a strong audience revenue base. At The Rebooting’s Media Product Forum earlier this year, Daniel Hallac, chief product officer at TFP, remarked how fortunate he was not to deal with the platform challenges legacy media companies face. Starting from scratch is a competitive advantage in a rapidly shifting environment.

Later, a reflection on five years of this newsletter and what’s next.

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Why Time’s email engagement is soaring

Time’s newsletters reach over 2 million readers every week. Until recently, they were stuck with clunky workflows, limited insights, and flat engagement. After migrating 13 newsletters and millions of subscribers to beehiiv—with zero downtime—things changed fast. Open rates on “Inside Time” jumped 63.8%. Click-through rates across their portfolio increased to 11.7%. Editors now publish faster, with better tools and real-time insights. Time proves that even the most established media brands can evolve—and thrive—when they own their email strategy.

See how beehiiv powers leading media brands.

Email as the center

The shift in media is from traffic-based to audience-focused models, evident in the prioritization of email. Email is a strange building block for publishers since it’s an old technology from the 1970s. For most consumer media companies, email was an afterthought, with automated emails that marketed the website.

That’s changed by necessity as publishing has shifted to focus on direct ties and becoming a habit with specific audiences.

In this week’s episode of The Rebooting Show, I spoke with Tyler Denk, CEO of Beehiiv, which powers this newsletter and partners with The Rebooting (and a company I invested in). Tyler knows the power of email from building Morning Brew when most consumer publishers weren’t email-centric.

“People are very quick to proclaim that email is dead and that a surplus of newsletters is bad or there’s some ceiling there,” he said. “You don’t have to log into Netflix and you don’t have to watch YouTube videos. For almost any working professional, you have to log into your email to communicate and do business in the world. That’s the centralizing force that brings people back to email.”

We also get into how Beehiiv’s building a modern email platform. I’ve been impressed by the level of control it’s given me that I felt was missing using other platforms.

Go deeper

Subscribe to Tyler’s Big Desk Energy for a build-in-public view of building Beehiiv.
Learn more about how modern brands build with Beehiiv.

TRB at 5

Exactly five years ago, I sent the first issue of The Rebooting. One of the biggest lessons I’ve learned is about the power of conversation..

Conversational formats will grow as ChatGPT becomes a larger platform and chat evolves from information retrieval to content consumption. The most valuable things I do now are around conversation. My best writing is done conversationally. (Thanks for the newsletter format notes from last week. More on that on Thursday.)

Podcasting develops a bond with listeners. I’m told what else they’re doing when they listen to The Rebooting Show or People vs Algorithms. In the engagement-driven attention era, that would be a negative. But that’s not the case anymore. Walking the dog is a pleasant routine, and being part of that is valuable.

In Paris, I visited the Monocle cafe and shop and spoke with Tyler Brûlé. We discussed “proximity” as a goal for Monocle’s brand. That comes through conversations, especially in person.

In my years in this business, I’ve seen conversation is a valuable part of the Information Space. I started selling newsletter ads, but when I began private dinners two years later, most of my ad demand shifted to the conversational product.

Our most effective partnerships revolve around fostering conversations. Our goal is to work with partners aligned on creating a sustainable media ecosystem. We help them start conversations with prospects.

The most powerful marketing is introductions. The more you can make products like conversations, the better, because that’s in service of a conversation.

I want to create a conversational events format. I found at the Media Product Forum event we did in collaboration with WordPress VIP the most valuable parts were when attendees became participants in the conversation. We have dinners and breakfast salons down. (We have breakfast salons with Beehiiv and Piano this month.) Next year, we will do an AI x Media Forum and a Direct Audience Strategies Forum that will take a conversational approach.

The key to conversations is the right people. That’s what the media business is about: getting the right people in the room. Media provides the leverage.

The other lesson of the last five years is that getting people to take actions is critical, especially in a niche. Audience activation rate is the North Star of this business.

One of the bad B2B terms is webinar. I call them online forums because the first rule of webinars is don’t call them webinars. But hear me out: webinars are conversational media. They’re interactive conversational programming, at least how I do them. Our Online Forums had 3,800 attendees the last two years.

We recently started a 15-participant roundtable where we invite media executives to discuss a specific topic.

The next step in my quest to reinvent the webinar is a regular conversational show called TRB Live featuring deep dives into specific topics and expert conversations.

I want to make this part of TRB Pro, our membership program. I want to redo it from access to paywalled posts and past newsletters to insights, with TRB Live, virtual and in-person gatherings, and research. Since 2024, over 2,500 people downloaded research.

I’m excited about the path ahead. We have had great partners who have been forgiving of my missteps and willing to try new approaches. I’ve found that meaningful rather than a purely transactional approach.

Thanks to collaborators over the past five years: Jay, Justin, Melissa, Michelle, Jenn, Elaine, Jesse, Tyler, Dayna, Mike, Vanja, Alex, Troy, Blake, Kerri, Kristine, Kate, Kelley, Robert and others. The independent path isn’t solo.

Thanks for reading, subscribing, and being part of the ongoing conversation about the evolution of media in the Information Space. Send me a note by hitting reply.

Go deeper

Year one: “I believe we’re seeing the start of a new wave of changes in digital publishing, reminiscent of the Web 2.0 growth of new digital brands out of the blogging movement.”
Year two: “ I see newsletters as less about email and more about independent publishers, often solo but not always, who are developing more human media products that are audience-focused and focused on primary engagement.”
Year three: “Sales is a lot like reporting: It rewards persistence.”
Year four: “It’s impossible to fully focus on content while operating what’s in essence a marketing services business.”

For sponsorship information, see how we work with partners like Beehiiv.

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