What Naples architecture lacks in history compared to Florida’s more storied cities, such as St. Augustine for instance, it certainly makes up in scope and scale. A leisurely cruise down Gordon Drive is all the proof one needs, as the facades of multimillion dollar estates gaze out to onlookers through verdant fronds and foliage. But what about the interiors of these homes? Who designs them? Who is entrusted with creating the elegant and often elaborate elements resting within the walls and windows?
In the case of fine millwork, cabinetry, and finishes, a conceivable answer is Thomas Riley Artisans’ Guild, a Naples-based woodworking company with a reputation of being one of the finest in the United States. Its roots are humble. Founded in 1991, the company was created by Thomas Riley (known as Tommy to most) with a mere four employees operating from a 3,000-square-foot building located off Taylor Road.
Originally from the Empire State, Tommy first experienced Southwest Florida in 1970 when—as a favor to a friend—he drove a car southward from New York to Naples. It was a paradise found.
“I loved it,” says Tommy. “It was a sleepy little town then. There was no I-75 here yet, The Ritz-Carlton didn’t exist, and Grey Oaks and the Vineyards neighborhoods were mostly tomato and strawberry fields.”
Tommy—who at the time aspired to be a police officer in New York—decided to pivot from law enforcement, instead making an interstate move to Naples in 1975, when he opened Say Cheese, a gourmet specialty shop. With its Park Shore Plaza location and fine cheeses, meats, wines, and chocolates, Say Cheese attracted the Naples elite and flourished for several years. By the early 1980s, however, big-box grocery stores had encroached on Naples, affecting small mom-and-pop shops, taking a bite of Say Cheese’s market share. “They used a note from the playbook and started selling high-end cheeses and wine,” he says.
Intrinsically entrepreneurial, Tommy rallied, shifting gears in 1984, collaborating with his good friend, Bill Herbst, a talented furniture refinishing and antique restoration artisan. Tommy joined Herbst, who had started a wood refinishing business. Working side by side, the pair formed a pragmatic partnership. As Tommy explains, “He handled more of the creative side, while I had a more managerial role.”
Because Herbst and Tommy were well-connected and focused on superior craftsmanship, they landed noteworthy jobs from affluent Southwest Floridians. “One of the first larger projects was refinishing a portion of the mahogany woodwork in a Collier family home in Port Royal,” recalls Tommy. “We stripped and refinished it all; it took months. That was an inspirational project.”
Chiseling a niche in the market, Tommy and Herbst continued with their refinishing business for several years. Around 1989, however, Tommy’s visionary mind started to think bigger. His plan was ambitious, if not idealistic. He would form a team of highly skilled craftspeople working to create exceptional custom woodworking products within a collaborative culture based on precepts of fairness, honesty, love, and kindness. And these specialized, luxurious products would be mostly targeted to a specific and limited clientele: those who could afford them.
Only a couple years later with guidance from some important mentors, including several prominent businesspeople in Naples, Tommy created Thomas Riley Artisans’ Guild with a mission it still abides by today: “serving a discerning clientele with monumental-quality products and white-glove service.”
Throughout his tenure with the company, Tommy, who is now retired, maintained his leadership position—estimating, coordinating sales, and organizing the team to get things done. “I learned that I have a skill for managing people,” he states. “I appreciate others’ talents, and my job revolved around motivating the artisans and showcasing and selling their work to high-end clients.”
“Tommy has an incredible sense of humor, authenticity, and charisma,” says Chad Jensen, CEO/creative director for Method & Concept, a Naples-based contemporary art gallery and design studio and a Thomas Riley Company. “He’s an easy person to follow because he demonstrates such a high level of care, honesty, and empathy; he is never above performing even the most menial task.”
As Naples grew in the 1990s, so too did its affluent demographic, providing more demand for the guild’s products and services. “In year one, we reported $300,000 in sales,” recounts Tommy. “Then, it doubled the next year. For five to six years, it doubled every year.”
Today, Thomas Riley Artisans’ Guild boasts approximately 80 employees, including two of Tommy’s sons, Matt and Ben, who currently own and operate the company from a large North Naples campus comprising multiple buildings. Matt serves as CEO, while Ben is president and chief operating officer. Their footprint has also expanded outside of Southwest Florida, with work being done in Palm Beach, as well as California, Connecticut, Illinois, Massachusetts, and New York.
Impressive yet not overwhelming, the campus houses design, manufacturing, and engineering departments, as well as administrative offices and showrooms. Within the walls, there are old-school tools of the trade to be found. However, the buildings are equipped with massive cutting-edge woodworking and finishing machinery, too, including high-dollar modern marvels that would intrigue the likes of Thomas Edison or Henry Ford.
“Since our inception, it’s been a priority to invest in state-of-the-art equipment, facilities, and software to assist our team in providing monumental- quality craftsmanship, while continuing to use and teach the ‘Old World’ craftsmanship methods,” says Ben, who holds a degree in manufacturing engineering from Boston University and is responsible for the company’s finances, administrative operations, and workflow processes.
Even with all the high-tech gadgets, the real wonders of the company are its employees, who design and create the most intricate, sophisticated of jobs. “There aren’t a lot of shops that can execute the type of work our team does; every job we do is like a prototype,” relays Matt. “We have a team of problem solvers, however, and they get excited about new challenges.”
At least some of these new challenges have involved reimaging, reinvigorating, or renovating the old. “As Florida ages, it gives us an avenue to maintain windows and doors but also to remodel,” says Matt. “We were there for the original Naples boom, but we’re still here more than 30 years later to redo much of the work we did. That’s a pretty cool thing.”
While Tommy retired from the business to enjoy life alongside his wife, Carol, on a North Carolina farm, he is more than confident in the leadership from Matt and Ben, who are expanding. Among other ventures, they have acquired a finishing company called Acanthus International. “The boys are diversifying,” Tommy explains.
For Matt, it’s an honor to help carry the torch. “What [Tommy] has done as an entrepreneur isn’t easy,” he says. “I’m proud of what we learned from someone who had people in mind, not profits. What differentiates us is our culture, and our core values will not change. We know our identity.”
Producing luxury artisanal millwork for the most discerning of clients requires planning and a process. Tastes are beyond discriminating, expectations are sky-high, and precision is paramount. Every order is a tall one. So, how has Thomas Riley Artisans’ Guild managed to deliver time and time again? According to Tommy, a shoulder-to-shoulder mentality has a lot to do with it. “The person driving the truck is just as vital as the artisan woodworking,” he says. “The opportunity for failure is great in this business. Everyone is important.”
Meet Tommy Riley: A Man with Much to Smile About
When Tommy Riley left New York for Naples in 1975, he wasted little time, quickly setting up shop—a gourmet specialty store to be exact—just off US 41 in Park Shore. Here at Say Cheese he sold everything from meats and cheeses to smoked fish and caviar to fine wines and chocolates, all the while building business relationships that would later serve him well. To commemorate Tommy’s first Naples-based venture, a break room paying homage to the Say Cheese store was constructed on the campus of Thomas Riley Artisans’ Guild. While Tommy has stepped away from this enterprise, he has a new agritourism project underway. He and his wife, Carol, acquired a 33-acre property in Western North Carolina, where Tommy has plans to create a farm that’s sustainable and regenerative and that will double as an event venue. It’s an ideal place to gather family together, too, including sons Matt, Ben, Andrew, and Adam.