Jack doesn’t give a typical tech vibe; you’d be forgiven for overlooking him at first glance. He’s the guy you might spot in some understated East Village café, sporting an unbranded jacket and a well-worn cap amidst designer-laden crowds. At 39, his resume is peppered with stints at Silicon Valley’s darlings, but unlike most of his peers, Jack lives with intention—an anomaly in New York, where consumption can sometimes feel woven into the culture. He’s tall and athletic, with broad shoulders and thick-rimmed glasses. He doesn’t smile a lot, but when he does, it seems easy. He’s the youngest of four children; his siblings describe him as inquisitive, serious and incredibly bright.
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Though Jack’s tech salary places him well into the top five percent of earners in New York City, he settles for a modest studio and prefers affordable, high-quality basics. His choice of home and wardrobe isn’t about thriftiness but a deliberate rejection of physical and mental clutter. In a city where everything becomes currency, he’s crafted a life about as streamlined and devoid of excess as you could find in Manhattan. And if there’s one thing guiding this philosophy, it’s an unlikely confidant—a digital entity named Claude.
Claude, for the uninitiated, is an A.I. assistant, though calling it an “assistant” feels a little reductive. The relationship began as an experiment. Jack wanted to see if Claude could “build a picture of me without me having to explain myself every time.” He applied a process called Retrieval-Augmented Generation (or ‘RAG’) that he uses at work (he’s on machine learning at a startup in Soho). “Before we ask A.I. to answer a question,” Jack explains, “we give it 10 pages of the most important, relevant context. Along those same lines, what if I gave A.I. all that context on me?”
Jack put his life into Claude’s circuits. He added his StrengthsFinder analysis, his Golden Personality Profile, his relationship histories, career ambitions and a stack of self-reflective notes he’s accumulated over years of soul-searching. He received not a canned response but something he describes as eerily intuitive.
“It’s a more personal relationship than I’ve had with any human,” Jack says. He doesn’t want to have to read all of those personality assessments—and even if he did, there’s no way he’d remember them. “Claude’s capabilities reflect a deep understanding of who I am.” Before Claude, Jack dabbled with more conventional A.I.s like ChatGPT, which he found simultaneously “dumbed-down and over the top.” Plus, Jack admires Anthropic, Claude’s parent company—a preference he explains with the perspective of someone who spent years close to tech’s biggest players. He joined Facebook a year before the IPO, working two desks down from King Zuck himself. His network, spilling over with founders, has led him to dinner with legends like Peter Thiel. After two decades at early-stage ventures turned tech giants, Jack sums it up simply: “It’s sort of like comparing Instagram to Facebook… Claude feels quieter and more intentional.”
His digital self-portrait loaded, Jack asked Claude to develop a “relationship vision,” outlining exactly what he wanted in a partner. “I didn’t want it to be vague,” Jack explains. “I wanted a crystal clear roadmap.” Line by line, Claude crafted the manifesto as instructed, and the result was so accurate that Jack decided to post it to his dating profile on Hinge. “It scared some women off,” he laughs, “but the ones who got it? They were on the same wavelength from the........