I was standing outside the AIR MAIL store on a Friday afternoon, squinting at my phone to text my friend, "THERE ARE NO MORE HATS." There were at least 30 people in line ahead of me. For Claude merch. But because I am a Claude and Anthropic stan, I came back the following Tuesday, the last day of the pop-up, got back in a very familiar line of maybe forty people waiting to get into a newsstand in the West Village for AI company swag. Still no hat. I did leave with a tote bag, a copy of Dario Amodei’s essay, Machines of Loving Grace, and, most importantly, a number of cool new connections.

The AIR MAIL newsstand is tucked into this early-20th-century row home that screams taste. Graydon Carter's place, the former Vanity Fair editor, brass fixtures, mid-century furniture, the kind of space where you half-expect someone dressed super well to be reading a physical newspaper with reading glasses perched on their nose. Anthropic picked it for their "Keep Thinking" campaign, and I have to admit: They understood the assignment.

Two Instagram posts on the @claudeai account. That's it. No responses to comments. Adweek reported over 5,000 people showed up anyway. I'd heard about it from two different people before I saw anything official: my book club friend posted it on his Instagram story, then I overheard a conversation at a coffee shop in Williamsburg. Word-of-mouth marketing that actually worked because they didn't try to force it.

Parker Ortolani called it "a magnet for New York's hippest nerds," and honestly? Yeah. But also, someone drove all the way from Columbus to check out the event. Poorva, who drove 8 hours from Ohio the day before but who did not seem even a bit tired, took notice of my crazy hat that my friends at Structify gave me. She's about to apply to Anthropic's Research Safety team and spent the last few months building a platform for teachers and students, AI-powered personalized learning with safety guardrails baked in, with the support of Claude Code.

We ended up in the backyard courtyard (because of course AIR MAIL has a scene-y courtyard), and she walked me through a demo on her laptop. The product she built, which she's planning on including as a portfolio item in her application, was impressive. There's something there, even beyond her candidacy for the role. The safety-first approach, the teacher perspective, the willingness to learn an entirely new skill set to build the thing she thinks should exist.

If Anthropic doesn't hire her, I told her she needs to keep going.

Alexis was behind Poorva in line. We started talking because we were all just... standing there. He took a career break earlier this year to surf in Europe. Just said "I need time" and went. Now he's back in New York continuing to kill it in his product design career, and I have his contact saved under "UX guy from Claude line" because I absolutely will need design feedback at some point for some future things I will build.

His college roommate Adam happened to be with him at the popup as well. Adam saw my hat (yes, I'm wearing it now as I type this), recognized it immediately because he went to high school with one of the Structify founders. Six degrees collapsed into about six seconds.

Alex was also in our casual conversation when someone came up to us and said, "Do you all know each other or something? You guys all seem like long time friends!" Alex has a background in computational math and history from college but now does product design and creative strategy. He moved to New York a month ago after living in Europe for a year. We talked about that weird liminal space of "figuring out what's next" while standing in line for free stuff we didn't need but somehow wanted.

Right before the coffee station, I talked to a woman (didn't catch her name, regret that now) who built her career in global communications in the advertising world. I asked her what she thought of Claude's strategy—this whole minimal-posting, let-the-brand-breathe approach. She said something I keep thinking about: "They're playing a different game. Not better or worse. Just different."

Here's the thing I couldn't stop noticing: there was no one from Anthropic there. Not on Friday. Not when I went back on Tuesday. No rep with a clipboard. No employees chatting up attendees. No booth or presentation or anything that screamed "we are here to tell you about our product."

Why?

I've thought about this a lot. Maybe they wanted us to talk to each other instead of surrounding some poor Claude employee with the same questions on repeat. Maybe they trusted that the people who'd show up, the ones willing to wait in line, the ones who already knew what a "zero slop zone" meant, didn't need the pitch. Maybe the absence was the strategy. B2B experiential marketing is shifting away from traditional trade show floors, and this felt like the logical endpoint of that shift. Create a space. Let the right people find it. Get out of the way.

But here's where I get stuck. I'm their ideal customer. My entire professional life is AI and LLMs. I'm literally using Claude, ChatGPT, Gemini, whatever else daily for work (but only for work). I live in the New York tech, AI, startup scene. I can articulate exactly why Claude feels different: the tone, the reasoning, the way it says "I can’t provide X output" if it rings a moral or ethical alarm.

But can someone outside my world see that difference?

My mom uses Claude now. She asks it questions about hot biotech companies or new chicken recipes. But before I downloaded it onto her phone, she had no idea what Claude is. Most people, consumers, probably don't. I genuinely wonder what Anthropic's play is for driving adoption beyond people like me. People who already care about AI safety and read Dario Amodei's blog posts and know what "alignment" means in this context.

Will taste-first marketing scale? Will quiet brand-building beat OpenAI's "we're everywhere all at once" approach? I have no idea, and we likely won't know until they continue their campaign. I'll be keeping track.

Oh, and after the event, I read Dario's Machines of Loving Grace essay that was printed and bounded in a classy, little, dark blue book that I took. Part 5 stayed with me, the section on work and meaning. Dario writes about how humans will probably maintain advantages in the physical world for a while, not because we're computationally superior, but because we still want to be together.

That's what clicked about the popup. Anthropic wasn't betting on their product features or their technical superiority. They were betting that even as AI gets better at everything we ask it to do, we still want to stand in line with strangers, talk about what we're building, exchange contact info in a courtyard, at least from my point of view. I didn't get the hat. But I left with Poorva's demo still open on my mental desktop, with Alexis saved in my phone for future UX questions, with Alex's career pivot story rattling around next to my own questions about what's next. I left with that communications exec's line about playing a different game.

And I left wondering what other spaces like this will emerge, not for products, but for the people using them to build things that matter. The ones willing to drive from Columbus or quit to surf in Europe or move to New York without a plan. The ones who show up when you create a space and then get out of the way.

I'll be keeping track of who builds those spaces next. And yeah, I'm still trying to score that hat.

Anthropic, can you create a swag shop as part of your campaign?