We're now in the AI pop-up era

Eight billion people in this world and you think your soulmate is in line to buy a Claude thinking cap.

Oct 18, 2025

The long lines had died down by the time I arrived.

The first week of October, it seemed everyone on my timeline was only talking about one thing: a baseball hat with the phrase “thinking cap” on it. In a partnership with Air Mail as a “brand in residence,” Claude invited people to stop by the West Village newsstand for the hats, as well as tote bags, coffee, and print copies of “Machines of Loving Grace,” an essay by Dario Amodei, the CEO of Anthropic.

“SAY NO TO SLOP,” Anthropic staff member Sam McAllister wrote in an X post. Other techies praised the pop-up’s elements of human connection and simplicity.

claudeai

A post shared by @claudeai

Even the Instagram announcement for the pop-up feels inviting, featuring the pouring of coffee, warm-lit snapshots, and the buzz of conversation, set to jazz music. It’s a stark contrast from the slop-y, scammy, sterile, icky feeling that much of the tech industry has delivered lately.

It’s also not the first time an AI company has enticed users with free coffee. In June, I stopped by Perplexity’s “Curiosity Café” coffee truck. I predicted we’d see more AI companies emphasizing storytelling and authenticity over efficiency. Perplexity even opened up a physical coffee shop location in Seoul called Cafe Curious. And if you haven’t gotten your coffee fix from Anthropic or Perplexity, you can stop by Café Cursor.

I stopped by the Perplexity coffee truck

Kristin Merrilees

Jun 7

Read full story

But while this type of marketing—which swears it’s about people, not machines—might help scrub away some of the bad vibes many of us, especially creatives, associate with AI, it’s not a sure thing. It only took a few minutes on my commute back from Air Mail to see a vandalized “Friend” ad on the subway.

I did appreciate get-your-thinking-cap.com, which lets you experience waiting in line for one virtually. Bill Dybas, who I’ve previously interviewed about his project photographing San Francisco’s tech ads and billboards, made the game using Claude Code. He told me it took about four hours to create.