New York Magazine Is Bringing Back Classifieds
And more retro moves from an algo-fatigued media world.
POD 167: Retro Digital
After two decades of scale chasing, feed optimization, and platform dependence, the industry is rediscovering older mechanics that actually work: events, newsletters, sponsorships, classifieds, and direct audience relationships. Plus: The difficulty of changing legacy media organizations; micro-dramas as modern media format; and field notes from CES, the Affiliate Summit and an Ojai turtle sanctuary.
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Troy: The turtles don’t care.
They are uncomplicated. They move slow, mate late, live long. They take long naps. They read books. I know this because I hung out at a turtle sanctuary this week.
Media could use a turtle break.
A break from the algorithm hustle. Which is why these “retro” moves are welcome as far as I am concerned. Retro isn’t blind nostalgia. It’s how media survives without becoming completely flattened. The algorithm wants sameness. Retro reintroduces shape.
The algorithm has one job: maximize engagement. To do that, it flattens everything into the same form. Same feed. Same incentives. Same emotional gradients. Everything competes with everything, all the time.
Retro formats reintroduce boundaries the algorithm doesn’t handle well. Newsletters that end. Human prerogative. Trusted connection. Folksy ad reads. Real life engagement!
Retro media works because it slows things down just enough to stay legible. It re-introduces friction. Not as a moral stance, but as a practical one. Friction creates shape. Shape creates identity. Identity is the one thing the feed can’t fully absorb.
Platforms are unbeatable at machine scale. What they struggle with isn’t meaning itself, but meaning that doesn’t convert cleanly into signal.
Platforms aren’t neutral infrastructure. They’re economic systems whose incentives shape what gets made long before anything hits a feed.
So media is adapting the only way it can: by selectively importing mechanics that still function under platform rule.
That’s why this moment feels contradictory. Hyper-modern distribution paired with retro mechanics. AI agents next to coupon communities. Micro-dramas next to newsletters. FAST TV next to YouTube.
The real divide now isn’t old vs. new or legacy vs. digital. It’s media that fully submits to machine optimization versus media that reintroduces constraints that make it fit us humans better, alongside the inevitable algorithmic hum.
Both live on platforms. One optimizes for velocity. The other optimizes for meaning.
Brian: Turtles are survivors.
We’ve discussed my fascination with sea turtles. They find their way back to where they were born, sometimes the exact beach, after spending decades floating on sargassum mats miles out in the ocean during their “lost years.” A lady sea turtle might lay 80 eggs for only a few to survive the perilous sprint (relatively speaking) to the ocean. The upside is if the turtle does make it to the sea, it gets to live as long as 100 years, much of the time spent hanging out in the middle of the ocean with easy access to a crustacean buffet.
You bring up a good point about the divide in publishing being between those who make the dash for the freedom of the seas. Most will not make it, realistically speaking. Jim VandeHei talks a lot of sense with Dylan Byers on the latest Grill Room podcast. Jim is clear-eyed and candid about the challenge of the moment. It starts with an identity crisis: Publishers need to know who they are.
Sounds simple, but that’s a pre-requisite to make it across this chasm. Algorithms tend to destroy brand coherence because they treat each piece of content as a SKU independent of the brand bundle. That means you give over much of the edit function to the algorithm. I don’t know if many will be able to find an identity after so many years of trying to be for everyone. As my fellow CES attendee Chuck D said, if you don’t stand for something, you’ll fall for anything.
Retro is part of a back-to-basics ethos. The most interesting digital media properties are not breakthrough formats. TBPN is SportsCenter for tech. Newsletters are throwbacks to pamphleteering. Podcasts are talk radio. Events were probably the original media format. Jim put it best: You just have to be essential.
Alex: Turtles all the way down.
When we started listing all the ways media was going “retro” I asked myself whether this was just nostalgia. Another bundle of wishful thinking the industry is telling itself.
It’s not. These formats never stopped working. They just got replaced by technologists like me convinced that strangers in feeds should replace social chatter, binge drops should replace weekly episodes, and email was dead. When you’re dealing in technology and innovation the urge to make new stuff is really strong.
Silicon Valley loves repackaging the old as breakthrough innovation. 90s Internet Relay Chat became Slack and Discord. ICQ and AIM became WhatsApp and Signal. Substack made newsletters work by simply sucking less than everything that came before it.
So New York Magazine launching classifieds acknowledges a need that never disappeared, just got underserved by Facebook Marketplace. This isn’t cozy nostalgia. It’s the industry realizing we might as well give people what they want. The turtles were right all along.
Turtle power.