Our Tech-Artist Future May Look Like Justin Stewart

At 28, art remains his backbone. Or is it tech? Or is it art? Or is it tech?

Conceptual artist and tech startup founder Justin Stewart wears many hats. Photo: Franel Morris.

Tech startup founder, fashion model and conceptual artist Justin Stewart has lived a lot of lives, and he’s only 28. His story fascinates me because I think it’s the future of the artist-as-technologist.

Stewart has walked the runway in Paris and studied game theory at the University of Pittsburgh. A conceptual artist, he once supported the work of other artist friends by floating on a flight of stairs on the Charles River in Boston — towed to safety by people on shore yanking on a 1,000-foot rope. His Instagram bio reads “entrepreneur, data scientist, conceptual art, model.”

Stewart’s current job? Co-founder of a startup, CherryPickAI, that offers beauty product companies vital customer insights from social media comments using artificial intelligence and natural language processing. The Instagram bio of his co-founder, Melissa Munnerlyn, reads: “We’re reinventing the business of beauty in a social-first world.”

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“Getting gangsta with a whiteboard.” Photo: Justin Stewart.

Stewart’s mother, who is white, is an artist from Arkansas. It was she who took him, his musician-DJ brother, Madison, and his dancer-performance artist sister, Jo, around LA for modeling and commercial gigs because she thought her kids were handsome.

Stewart’s father, who is Black, is a math teacher from Jamaica who was pleased when his son turned to study math and economics at Reed College in Portland, OR. His senior thesis was on “Randomness as Fairness”: “Understanding the difference between economic theory and economic reality.”

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Attending a doctoral program in micro-economic theory at the University of Pittsburgh led to working for a few Silicon Valley startups, and he continued to model. However, what he really wanted to do was move to NYC and, in Stewart parlance, “make dope shit.” By which he means emulate his heroes, including painters Mark Rothko and Wassily Kandinsky, architect and design theorist Christopher Alexander, and musician and producer Dev Hynes, also known as Blood Orange, whom the New York Times described as a “nerd polymath.”

Justin Stewart resting on his favorite game theory books back in his Reed College days. Photo: Matthew DAnnunzio

So Stewart moved to NYC to make dope shit. In substantive terms, this meant co-founding a “conceptual art collective” called Prime Set, which organized and curated events involving music, visual art and tech aimed at highlighting people’s relationship with their basic senses. He collaborated with a visual artist and sculptor who is fascinated by tape players and tapes as a medium to consume music; with his brother Madison, they produced The Talulah Blooms Tape, which is dedicated to their sister Jo and was sold at MOMA PS1.

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Art is great, Stewart told me, but NYC is expensive. He therefore did what you might call the Stewart shimmy, toggling back again to numbers and business and eventually joining a “data bootcamp,” which moved him back to technology. That’s how CherrypickAI was born. Stewart and co-founder Munnerlyn are close friends from high school. Rather than build their company in Silicon Valley, they’re working in an NYU-sponsored artificial intelligence incubator in Soho. The company’s M.O. makes sense: In a world where model, Kardashian family member, and social media influencer Kylie Jenner can sell her makeup directly to a huge Instagram following and have a company worth hundreds of millions, companies need meaningful, actionable insights into what their customers want to buy right now and why.

Stewart’s familiarity with celebrity and its uses, along with his quantitative skills, make this a good fit, and investors are taking notice. By the end of the year, CherryPick will close its $1M seed round. Stewart hopes to diversify the investor pool.

Yet art remains his backbone, the place he returns to — and will, he assures me, return to again. In an email, Stewart told me: “Most people I talk to who ask me if I am an artist or used to make me kind of anxious or self-conscious because I don’t fit squarely in a certain mold… But at the end of the day, the way that I have been raised to think about art is as a form of human expression, almost even as way of living.”