Jay Norris
Jay Norris

Jay Norris has always been on the move. It's not just a personality trait; it's a philosophy, a way of living, and a responsibility he carries. As the founder and CEO of GUESST, a software and AI-powered platform designed to empower small to medium-sized businesses (1-500 employees), Norris is more than a tech entrepreneur. He's a champion for the people who bring vibrancy and authenticity to our neighborhoods, restaurateurs, boutique owners, and local service providers, the backbone of American life.

"I want to be a momentum for people," he says. "Positive momentum."

That momentum began in Lafayette Park, a mixed-use neighborhood in downtown Detroit, where Norris grew up. His childhood was surrounded by small businesses: delis, art galleries, nightclubs, and family-run restaurants that pulsed with creativity and independence. He didn't recognize it then, but he was witnessing something profound. "I saw freedom in their eyes," he recalls. "They woke up every day, providing for their families on their own terms. That nourished me."

That early exposure to entrepreneurship planted a seed that would grow through decades of experience across marketing, entertainment, and real estate. In the music industry, Norris helped legends bring their artistic visions into the world. Later, he transitioned into commercial real estate, where he represented tenants, a less common path in a field largely dominated by landlord advocates. Yet even there, he felt pulled toward helping people realize their dreams.

"There is a common thread," he explains. "I have always found myself alongside people birthing ideas into the world. Whether it was an artist, a restaurant owner, or a tech founder, I want to help give structure to that dream, to help them bring it to life."

That mission is deeply personal. Norris' father, who worked in banking and provided small business loans, laid another layer of foundation. "I didn't think much about it until later in life," he says, "but now I realize that I'm following in his footsteps, just with software instead of signatures."

This ethos led to the creation of GUESST, an AI platform that tracks retail and restaurant leases and performance data in real time. By identifying key business metrics and making them actionable, GUESST helps entrepreneurs stay in business longer and make smarter decisions. "I couldn't keep consulting one client at a time," Norris says. "Technology was the only way to scale my impact."

But he's clear: GUESST is just one tool in a much larger toolkit.

"GUESST is one cylinder in a hundred-cylinder engine," he says. "It's a great entry point, but I want to surround myself with other AI and software solutions that address different pain points small and medium businesses face."

The road has not always been smooth. As a tenant rep in Manhattan, Norris saw firsthand how quickly businesses could disappear. He says. "That broke me. These people had mortgaged their homes, put everything into their dreams. And the system didn't care."

He pitched the idea of tenant support services to his former brokerage firm and was told to "Just sell." That was not enough. He left and began building an advisory group focused on long-term sustainability for small and medium businesses, now a fully fledged strategic advisory firm, Lifestyle Equities. GUESST emerged from that desire to not just place businesses in spaces, but help them stay there.

The deeper driver behind all this is community. "I walk down streets and see my friends, dry cleaners, tailors, cooks gone. That's not just a business loss. That's a loss of culture," Norris says. "They are what I call neighborhood amenities. They bring the spirit to a place."

That spirit is what he wants to protect. Through his podcast "Visionary's" where he interviews high-impact entrepreneurs, to inspire up-and-coming entrepreneurs. In his leadership roles as Co-Chairman of the Manhattan Chamber of Commerce and board member of Startup Westport, Norris is constantly connecting dots between people, resources, capital, and opportunity.

"I'm a connector," he says. "That's my gift. Whether it's bringing a merchant and a banker together or tracking KPIs to measure impact, I'm using software to scale what I have been doing my whole life: helping people build their dreams."

He sees every introduction as a potential bridge, and every bridge as something that should be measured. "We connect people, but do we ever track if it worked? That's what we are building now: the systems that let us improve every time we help someone," Norris says.

At the heart of it all is belief. Belief in small business as the American dream. Belief in technology as a tool, not a replacement. And belief in community as the foundation of a healthy economy.

"Who wants to live in homogeneous communities? I know I don't," he says. "I don't think we are meant to. Small businesses are the beating heart of our communities."

For Jay Norris, moving forward is about lifting others as he goes, one entrepreneur, one idea, one connection, one community, at a time.