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  • Last night, I swung by a burrito place in the West Village for a party to celebrate Breaker, the reliably excellent media newsletter written by Lachlan Cartwright. One media CEO remarked to me that it’s a good sign for the media business that it has several independent media-on-media outlets. Check out Breaker if you haven’t already.

  • Listen to my conversation with Beehiiv CEO Tyler Denk about the evolving world of newsletters, and why the lines are blurring between tools used by independent creators and enterprise publishers.

  • Thanks for the notes on The Rebooting’s fifth anniversary and feedback on formats. Send me feedback by hitting reply. Today’s is a postcard essay from Milan.

Tecnologica abusiva

Milan’s Duomo is a testament to a time when the powerful engaged in massive civic projects that outlived them and took hundreds of years to complete. These multigenerational humanistic projects projected power and instilled civic pride. They were the ultimate flex when oligarchs didn’t compete on megayachts and compute. 

Milan’s a tram city, a very human transportation that’s fallen out of favor on efficiency grounds globally. Classic yellow trams from the 1920s are reminders of a more aesthetic era, are interspersed throughout the city. They now serve as tasteful ad canvases for luxury brands like Fendi that follow the mandated strict aesthetic guidelines honoring the trams’ cultural legacy.

Milan insists on humanistic aesthetics over technological efficiency. You notice how lovely the coffee spoon is and wonder why we don’t have them in The Richest Country on Earth™.

Form often trumps function. I saw many remarkable Fiat Topolino, a remake of a 1930s car line. These miniature cars have two tiny air conditioning fans and can park almost anywhere. One option has ropes instead of doors. Not practical in the US. Still, the world is better off with the Topolino.

I found a promotional poster for an upcoming exhibition near the Duomo. Authorities covered it with a sticker reading pubblicità abusiva, indicating the unauthorized ad violated regulations and social norms. Imagine if the internet had publiccità abusiva slapped on SEO pages, floating videos, and intrusive webpage ads.

The Duomo is remarkable because it took generations of human toil. AI video outputs are uncanny but hollow: I’m promised this is the worst it will ever be. I’m not sure. It might get worse. Nick Cave had it right:

“Data doesn’t suffer. ChatGPT has no inner being, it has been nowhere, it has endured nothing, it has not had the audacity to reach beyond its limitations, and hence it doesn’t have the capacity for a shared transcendent experience, as it has no limitations from which to transcend.”

The buzziest AI marketing effort was a “brand residency” at the Air Mail shop in the West Village. Anthropic’s “Thinking” caps became a hot item. The X crowd lapped it up as the height of cool; it used “aesthetics” as a growth hack. There was irony in marketing AI through the scarcity of analog marketing.

Anthropic is positioning itself as the pro-human AI company. Yet its Claude chatbot is built off a moral obscenity: the purloining of humanity’s creative output. That inconvenient fact cannot be marketed away. Anthropic paid book authors a $1.5 billion settlement for training its models on pirated copies. When anything is data, you take shortcuts.

Silicon Valley longs for the nostalgia when it sided with the rebels and the creatives, not as the extractive Death Star upstreaming humanity by controlling the interface layer to set up toll booths. Cory Doctorow’s new book, Enshittification, details the path to tecnologica abusiva:

“All our tech businesses are turning awful. And they’re not dying. We remain trapped in their carcasses, unable to escape.”

In Milan, I found an Air Mail edicola collaborating with Manolo Blahnik for another fashion week. It carried a newspaper hagiography of Blahnik with his view of Milan. This marketing will remain protected from AI-created synthetic ads and Delta’s new ad network.

I’m obsessed with “proximity media” as an exit strategy. I define it as media experienced through physical context and at human scale designed to narrow the gap between synthetic, algorithmic realities and lived experience. It’s the antithesis of micro-targeting, infinite scale, and scrolling choose-your-own-reality feeds.

Across the West, there’s a sense of loss as people lose faith in progress. The Richest Country on Earth™ barely ranks in the top 25 for happiness. This isn’t surprising: China built the world’s tallest bridge; we got Meta’s Vibes AI slop app. Francis Fukuyama argues that “the screens”and social media are the main culprits for the rise of populism.

“​​The large tech platforms pursuing their own commercial self-interest created an ecosystem that rewarded sensationalism and disruptive content, and their recommendation algorithms, again acting in the interest of profit-maximization, guided people to sources that never would have been taken seriously in earlier times.”

Young people are turning to analog tech like CDs and flip phones, created before Big Tech’s technological abuses. The FT’s John Burn Murdoch posits we’ve passed “peak social media.” Being extremely online is extremely uncool. AI’s greatest promise — and Anthropic’s — is replacing humans with software, starting with entry-level jobs.

Silicon Valley has become attuned to vibes, so they might notice the direction the vibes are heading. A counterreaction to a world of synthetic slop and AI intermediation is coming. It will be more human and handcrafted, unoptimized and sincere.

I walked around the Duomo early one morning, before most tourists arrived for the requisite selfie, and peered at the thousands of statues on its facade. They portray the full pastiche of human existence, from kings to philosophers to biblical personalities, each sculpted through human craftsmanship.

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