If 2025 had a theme, it was the AI revolution. Artificial intelligence, machine learning, and large language models dominated the cultural conversation this year, and Westport’s Jay Norris was as plugged into the conversation as anyone. That’s partially because his company, Guesst, is at the forefront of using predictive analytics to help retailers and restaurants. Guesst’s AI, he explains, helps small businesses get new customers and increase revenue by suggesting merchandise that would perform well with their customers based on what’s already selling well in a specific neighborhood or geographic area. Guesst also launched Guesst Funding this holiday season, its revenue-based lending platform for more than a thousand merchants looking for cash advances this holiday season. Guesst represents and works with the owners/operators of Bryant Park Holiday Market, Columbus Circle, Union Square, Macy’s Herald Square, Rockefeller Center, and Grand Central Terminal's Holiday Market.
But Jay is also at the forefront of this conversation because that’s who he is: he’s always plugged in. “I would like to be remembered as a one-of-a-kind, trusted advisor for SMBs [small/medium businesses] who partners with and builds innovative software and AI solutions," he tells Westport Lifestyle. “That lets me be Jay Norris, without being a machine learning expert.” While he may not be a machine learning expert, he is an expert on the intersection of technology and commerce for small/medium businesses: he is the chairman of the Innovation and Technology Council of the Manhattan Chamber of Commerce, one of the founders and board members of StartUp Westport, founder of Westport10, a mentor with A Better Chance, and a proud board member of the Downtown Merchants Association and the Westport/Weston YMCA.
Jay is helping business owners envision how AI can be a tool rather than a threat, setting up SMB town halls, right rooms, and working as a 1:1 coach to make sure the human element doesn’t get lost in the shuffle. He’s the “SMB AI Catalyst.” “Think of AI as a thought partner,” he says. It’s us who are the thought leaders, he explains. In other words, whatever your “zone of genius” is, don’t use AI for that. It’s a support tool, but not a replacement for people, connection, or expertise. Jay is helping entrepreneurs find that balance. Last month, he launched the aptly named ThoughtPartnr.com, “an AI platform for our SMB organizations where we will inspire, educate, train, and connect business members with tangible AI solutions that will help them minimize cost and maximize returns.”
Through ThoughtPartnr.com, he’s connecting with chambers of commerce, including here in Westport, and local organizations like StartUp Westport (see page XX). “We’re connecting communities with solutions,” he says. You can learn more by listening his podcast, Visionary’s Podcast, following Jay @jaynorrisvisionary, or visiting thoughtpartnr.com
“Think of AI as a thought partner,” he says. We are the thought leaders.