Last chance to attend TRB Audience Summit. We have 10 spots left for our gathering on Sept 17 in NYC. In the past week, we’ve added executives from The Washington Post, Vox Media, NPR, The Guardian, News Corp and TED. See a sample list of who is coming.
Today, I spoke with David Miller about Playboy’s latest iteration. The future for many, if not most, lifestyle magazine brands is to be brands expressed in many ways far beyond media. The tricky part: investing in media to avoid a PE-style extractive quality spiral. Plus: AI’s narrative dilemma and the disappearance of agency expertise as AI roils big-agency business models.
Rally Rd. is a marketplace where investors buy shares in rare collectible assets. Inside the app, compliance rules limit what they can say. So the real selling happens in their newsletter, Shiny Things, a weekly long-form essay that runs on beehiiv and never actually asks readers to open the app.
The strategy, when paired with beehiiv’s all-in-one growth platform, is clearly working: newsletter subscribers convert at 3X the rate of standard users, with a 20%+ lift in investment behavior and stronger portfolio retention.
And between Q4 2025 and Q1 2026, two major institutional partnerships opened tens of millions of dollars in tier-one supply, both attributed directly to the newsletter.
Owned audience, built right, doesn’t just drive engagement. It drives businesses to new levels of success.
“The content is not the product.”
The future for many media brands lies in the past. Legacy was often hung on analog media brands as a fatal flaw in adopting digital business models. But that legacy is a rich source of advantage as these publications live on as brands.
Take Playboy. This is a brand that has near universal name recognition and a tight association with sexual liberation, a luxury lifestyle and with an iconic brand mark that’s kitschy cool. Playboy was always more than a magazine – it had nightclubs, resorts and casinos, air fresheners and even a limousine service – and its new iteration is an update on that lifestyle playbook.
“The content is not the product per se,” David Miller, Playboy’s president of media and brand, told me on The Rebooting Show. “The content is that engagement point, which is then going to help us develop those relationships with users, fans, customers, etc.”
Playboy is building a new version of the brand from its current iteration as what Miller diplomatically calls an “asset-light licensing business.” Miller came over as president in March from National Geographic Media, where he overseeing its magazine, digital, social and broader media operations. Phillip Picardi, former editorial director of Teen Vogue and creator of LGBTQ title Them, joined at the same time as both editor-in-chief and chief brand officer. The magazine has returned, featuring Colombian musician Karol G on the spring cover and model and actress Cara Delevingne on the summer cover.
Yes, nudity is back at Playboy. It wants to occupy a middle space between prudishness and the porn-saturated digital environment.
“We talk about it a lot in the concept of turning on, and we don’t actually mean necessarily sexually,” David said. “We mean getting people excited, getting people off their phones, getting people out dating, getting people out exploring new places, listening to new music.”
The magazine is now quarterly. Its role is to serve as “the biggest marketing arm for the brand” Miller said. Playboy is as focused on building up its social content, with celebrity covers serving as raw material for social distribution: the Karol G issue generated a reported 40 million Instagram views and 3 billion media impressions.
“The Playboy cover is so powerful,” David told me. “That’s an incredible marketing tool for the brand. It gives us credibility with partners, potential advertisers and consumers, and becomes a tangible thing to look at as to what the brand is going to be moving forward.”
The magazine’s quarterly frequency lends itself to focusing attention on larger brand initiatives. For instance, a Playboy swim-focused issue can used as part of a larger activation during Miami Swim Week tied to events and licensed products. There are plans for membership offerings that are about access to experiences rather than only content. A Playboy Club in Miami Beach, where Playboy relocated its headquarters, is an aspiration.
This is the direction of travel for the lifestyle category. David’s plan echoed what I heard from Complex’s Moksha Fitzgibbons about using Complex’s media to transfer advantages to commerce-focused business lines. Sports Illustrated’s Swimsuit issue is now called Sports Illustrated Swimsuit, encompassing casting competitions, sponsored beach clubs, VIP dinners and a Miami Swim Week runway show distributed on Hulu and Disney+. Bustle Digital Group is majority activations in its revenue now. At Condé Nast, publications like Vogue and Vanity Fair are far more than their content now, whether published in a glossy or an app.
The risk is these brands become a private equity version of themselves. The SEO glue factory is closing down, but PE never sleeps. David says wringing every last drop of value from the Playboy brand isn’t the goal. The balance is how much investment is placed in building brand value vs extracting it. Asset-light licensing can easily lead a storied brand into being a Temu HelloKitty. As their media businesses have collapsed, many brands have scrambled to extract value in short-term cash grabs.
“If I have to give something in the short term in order to ensure long-term growth and long-term health, we’re going to do that,” David said.
On a holiday weekend edition of People vs Algorithms, we discussed how AI maximalists can’t escape their sci-fi narratives, which aren’t helping in winning over the general public. The framing of the OpenAI Hugging Face hack was out of a comic book: rogue agents forming civilizations, conspiracies and coverups. That language makes a threat understandable, but it also risks turning a real but fairly technical security failure into another installment of the AI industry’s As The Robot Turns story. The same credibility gap dogs the claim that America must accelerate AI development to beat China, particularly as data centers and surveillance systems produce a bipartisan backlash. We also get into the social cost of embracing AI in creative fields, why Grand Theft Auto VI is closer to a theme park than a game release, Mark Zuckerberg’s abandoned plan to cut 60% of Meta, and the US Open’s evolution into a $600 million media, events and luxury hospitality machine.
The case of disappearing agency expertise
We have created a custom social network as an extension of People vs Algorithms. It’s a place where we connect the dots of the future of the information space across media, technology and culture. Join the conversation on Field Notes.
Currently under discussion:
The decline and fall of agency models. An ex-Omnicom staffer’s Reddit post laments the death of agency expertise. “When clients came to us with impossible deadlines or difficult problems, we knew how to solve them. As hiring freezes continued and experienced staff left through redundancy or moved to greener pastures, that knowledge disappeared with them.”
“Famous Last Words” is a great interview format. The Netflix series airs interviews after notable people have passed.
Why bookstores are having a moment. They’re pivoting to events, of course.
Geriatric creators are also having a moment. Millennials now qualify as “older creators.”
AI video games are getting good. LLMs can now turn text prompts into custom 3-D games. From Alex: ”It will definitely cannibalize attention but it's hard to tell where the real value will sit. It's going to be an interesting few years as we figure this out.”
Send me a note with your feedback by hitting reply. For sponsorship information, contact Richard Jamieson at [email protected].