GUESST and the Greater Goal: Jay Norris Introduces Tech Solutions for SMBs in the AI Era

Jay Norris is a man on a mission. His goal is as bold as it is necessary: to help one million small to medium businesses adopt artificial intelligence and thrive in an economy that often overlooks them.

As the founder and CEO of GUESST, a software platform designed to help small and medium-sized businesses (SMBs) manage retail and restaurant leases, track performance data, and strengthen their financial sustainability, Norris is not simply building software. He's building lifelines.

"Small businesses are the soul of our communities," he says. "They represent the American dream, owning something of your own, building it from scratch, and leaving a legacy. That dream is under threat. And I want to change that."

In the U.S., small to medium-sized businesses make up to 44% of GDP. Yet despite their importance, they're among the most vulnerable. According to Norris, a significant number of restaurants in Manhattan go out of business within the first two years. "I have watched entrepreneurs pour everything into their dreams, only to lose it all because they lacked the tools or support," he says. "That's unacceptable."

GUESST was born out of that frustration. While working as a tenant rep in commercial real estate, unusual in an industry that typically favors landlord representation, Norris became disillusioned by how little the system cared about small business survival. When he proposed offering advisory support to tenants, he was told to "stick to selling." Instead, he left to build something better.

"I didn't want to be the person who placed someone in a retail space and walked away," Norris explains. "I wanted to be the person who made sure they could stay there."

GUESST bridges that gap. The platform uses AI and sales data to track merchant performance in real time, giving businesses and property owners who lease to them key insights that can lead to more equitable lease terms, improved financing opportunities, and smarter decision-making. "We have helped thousands of businesses so far," he says. "But we are just getting started."

The GUESST platform is designed to benefit both sides of the equation: tenants gain visibility and control over their financials, and landlords gain transparency and performance-based insights that foster trust and reduce turnover. "It's not about choosing one side over the other," Norris says. "It's about creating win-wins in the system."

That systems thinking is part of a broader vision. Norris knows that tech alone is not the answer. That's why he's building what he calls an "SMB ecosystem," a network of AI tools, advisors, and resources designed to meet business owners where they are, in their communities and on their terms.

He says, "Entrepreneurs are often isolated and burned out. They don't trust easily, and I get that. I want to earn that trust by showing up in person, asking the right questions, and delivering tools that actually help."

His plans are global. GUESST is planning to expand into Europe, the UK, and Australia by the end of the year. But Norris is quick to point out that this isn't just about scale, it's about impact.

"The dream is big, but it's rooted in something very human," he says. "These are people running dry cleaners, cafés, neighborhood bookstores. When they thrive, entire communities thrive."

In his role as Co-Chairman and board member of the Manhattan Chamber of Commerce and an active co-founder and board member of Startup Westport, Norris is also influencing policy and partnerships from the top down, pushing for better access to capital, increased transparency, and more robust support networks. But his heart is in the field.

"I call it building SMB cultural currency," he says. "I want to be out there, walking their streets, eating their food, wearing their designs, so I can understand how to serve them."

Part of that service involves building systems to track whether interventions actually work. "I'm a connector by nature," he says. "But I don't just want to introduce a business to a banker. I would like to track the KPIs of the relationship to measure something meaningful, did they get a loan? Did they grow? And if not, why not?"

It's a new model of entrepreneurship, one that combines technology, accountability, and a deep respect for human experience.

Beyond GUESST, Norris is bringing in other thought leaders to help shape the future of SMB support. He's hosting the Visionary's Podcast, where he interviews successful entrepreneurs to inspire the next generation, and he's organizing speaking engagements worldwide to share strategies and build bridges.

"Technology is a tool, not a savior," he says. "What really changes lives is connection, human connection. I'm just using tech to make those connections more powerful and more measurable."

To Norris, small businesses are not stepping stones; they are the foundation. He says, "Every great company starts small. If we don't support that beginning, we lose the future."

And Jay Norris is not about to let that happen. He's on the move, meeting, listening, building, and doing it all with a mission that's as urgent as it is timeless: keeping the dream alive for one million small businesses.