Forget traditional tech perks today’s elite AI enthusiasts are chasing something far more tangible: merchandise. Baseball caps embroidered with the word “thinking” are popping up all over New York’s West Village, but they’re not a philosophical statement or ironic accessory. They’re a status symbol proof that the wearer belongs to the inner circle of one of AI’s buzziest startups, Anthropic. The company, riding the momentum of its Claude model, recently teamed up with Air Mail’s newsstand for a pop-up event offering free Claude-branded tote bags, hats, and even a book penned by cofounder Dario Amodei. But supplies ran out quickly, fueling a mini frenzy. Among those lucky enough to snag the cap was Sunita Mohanty, cofounder of the healthcare AI startup Vibrant Practice. Visiting New York from San Francisco, she happened upon the post about the event and found herself amid a crowd of engineers, founders, and builders all donning the same cap like it was a badge of honor. Wearing hers on an early flight home, at least two fellow travelers complimented her. It was more than a cap it was a signal.
Of course, branded swag is nothing new in tech. From IBM’s classic “think” slogan to Mira Murati’s “Thinky” hats, the aesthetic has evolved alongside the culture. But this new wave of AI merch has transformed the category. It’s no longer about marketing it’s about belonging. “It’s a signal that you’re in the know,” Mohanty explained. “You feel like you’re part of this movement.” That sentiment is driving a merch arms race. Founders and fans alike are leaning into exclusive drops to build cultural cachet. Tech founder Andrew Pignanelli couldn’t get the hat, but his girlfriend secured a tote bag. He’s no stranger to the power of branding his own startup, the General Intelligence Company of New York, created rainbow sweaters that exploded online. The design drew backlash for resembling another brand’s clothing, but the exposure only fueled more demand. “It goes totally viral, and everyone thinks the sweater is super cool,” he said. The first batch of 40 sold out quickly, and another 150 are already gone before arrival.
Merchandise, in this sense, is more than wearable branding it’s proof of membership in a fast-evolving tribe. Apple laid the groundwork years ago with its “Think Different” campaign. Now AI is the new frontier of cool. The exclusivity of this gear adds to the allure. At OpenAI’s recent Dev Day, select developers received sleek, glowing token plaques but only if their companies had processed at least 10 billion tokens through OpenAI’s APIs. Recipients’ names flashed onscreen behind CEO Sam Altman, creating a moment of prestige more akin to an award show than a dev conference. Jeff Barg, AI engineering lead at startup Clay, was one of the honorees. Clay had processed 100 billion tokens. “They said it would be heavy,” Barg said of the email he received ahead of the event. It turned out to be a luminescent plaque reminiscent of YouTube’s creator awards sleek, shiny, and unmistakably cool. He also spotted friends’ names on the list, some of whom had passed the one trillion token threshold. “There was some friendly competition,” he admitted.
Cursor, another AI company, opted for a different prize. It created a standalone, functional “Tab” key a nod to its software, where pressing tab autocompletes code. Only a select few received the device, including Tel Aviv-based Cursor ambassador Elie Steinbock, who had organized multiple local meetups for the brand. “It’s not that useful,” Steinbock joked. “But it’s cool.” That kind of scarcity only amplified demand. Friends asked if he could get them one, but no luck. “It was in limited supply. I guess that makes it cool,” he said. “It’s a cool thing to have on the shelf.”
AI fandom is entering its merch era, and it’s only getting more intense. Developer Dan Shipper, cofounder of Every, also received OpenAI’s token plaque and was thrilled. “It’s beautifully made and I’m proud we hit that milestone,” he wrote in an email. But his post on X, where he also showed off his “thinking” cap, offered a more playful summary of what this all means in today’s tech culture: “Thinking cap in the streets,” he wrote. “Token plaque in the sheets.”
