Author’s Note: See a brief video interview with Adam DeSiena of Doc James Cigars on Facebook page Bruce The Blog.

When Adam DeSiena graduated Pace University with a degree in psychology 25 years ago, he was uncertain about how to turn his education into a vocation. As he says, “You can’t do much with a B.A. in liberal arts.”

Then, in 1993, his dad, who was in the printing business, came home with an idea for Adam. One of his accounts was a tiny tobacco shop in Yorktown. It was operated by a man named Don Jorgensen, who a dozen years before had purchased the store from its founder, Harold James.

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Mr. James had been a pharmacist in Croton-on-Hudson. He liked to custom-blend his own tobacco, a sideline that led customers to start calling him “Doc.” When he retired as a pharmacist, “Doc” James opened a cigar shop, naming it after himself.

Originally situated virtually out of sight, behind Lakeland Deli on East Main Street in the hamlet of Shrub Oak, Doc James Cigars later moved down the road a stretch to occupy a more visible, and visually unique, location—an old caboose structure, on Barger Street, between routes 132 and 6.

Adam’s dad told him that Don Jorgensen was ready to retire, and his cigar shop was for sale. Adam jumped at the chance. The price was right, with the bonus of being his own boss.

A quarter-century later, as Adam DeSiena and his core clientele celebrate his silver anniversary in business, Doc James has evolved into a frolicsome fraternity house for responsible adults who just want to kick back and socialize after a hard day’s work. Having moved two more times since its caboose days, its current, spacious home is across the road from that legacy location. A blow-out party recently was held at the club to mark the auspicious milestone.

The social-club setup is like a duplex arrangement, turned on its side. There’s a 900-square-foot retail shop that welcomes all walk-in customers. On the other side of the wall, viewable through a window in the shop, but with a separate entrance, is the Doc James members-only club. It’s $48 a month, and Adam is offering a first-time winter membership plan for $35 a month, good for December-April. (For more information: 914-962-9388; docjames.com.)

The club’s 1,300-square feet include cigar lockers, three large-screen TVs, a wet bar, refrigerator, plenty of leather lounge chairs and, of course, a card table. Lining a “wall of fame” are framed caricatures of Doc James’s most prominent patrons through the years.

What’s particularly impressive about Mr. DeSiena’s longevity and success with Doc James, which currently counts 80 members in its club, is that he started with no experience whatsoever in running a business. He’s the classic example of a self-made entrepreneur. “I learn on the go,” as he puts it. So far, so very good.

One of Mr. DeSiena’s strengths is his ability to adapt to market dynamics. When New York State in 2004 outlawed smoking in public places, he saw that severe limitation as an opportunity to provide a safe haven for cigar mavens. That’s when Doc James added a members-only club option for its retail customers, giving them a welcoming home away from home to enjoy a leisurely smoke with like-minded cigar aficionados. “The irony,” Adam says, “is that the state legislation helped increase my business.”

Depending on the mood of the assembled, there are times when the joint is jumpin’ late into the night. As the sole proprietor, with a young family, Adam figured out how to let the members enjoy the full benefit of the club without his having to be on premises all the time. Each member gets a key fob for 24/7 access, and everyone cleans up afterwards. “It works out well for me,” Adam says. “We never have any issues.”

Typical of the Doc James crowd—who are visibly proud of their camaraderie—is Jimmy Zaccagnino. A dozen years ago, when he worked at Mohansic Golf Course, the assistant pro was Adam’s brother, Josh, who recommended Doc James to Jimmy for cigars. (Josh operates the only other Doc James Cigars store, in Mamaroneck.)

When Jimmy walked in to buy cigars (at the previous Doc James store), he didn’t know a soul. Yet, the regulars immediately made him feel like one of their own, affectionately addressing him as “Jimmy Boy.” He was sold on the spot.

“Everybody here is a good guy,” says Jimmy. “It’s a great place to go, relax, have a lot of laughs, a lot of arguments. We talk about politics, sports, guys’ businesses. For the first time in my life, this became a place where I feel I really belong. We are involved with the Yorktown Feast of San Gennaro and Toys for Tots. Adam does a lot for the community. You do some good and have a good time.”

The most poignant display of how deep the Doc James brotherhood ethos runs was in full view earlier this year when one of the group’s most beloved members, Matt Bloom, passed away suddenly. There, at the funeral service, I watched in admiration as his comrades clustered, consoling each other, paying respects to one of their own.

As Adam DeSiena commemorates his silver anniversary in business, there’s no denying that Doc James has provided nicely for him, his wife, Heidi, who works at Salem Golf Club, and their kids, Aidan (13) and Kaitlyn (10). Much like a wine sommelier, in order to purchase new cigar blends, he needs to try each. I asked him about the health implications.

Estimating that most members average a cigar smoke a day, Adam says, “It’s a big misconception that cigars can kill people, especially second-hand smoke. I’ve always maintained what kills people is the chemicals in cigarettes, not tobacco. There’s not a cigar customer that I know of, in 25 years, who died because of lung cancer.”

In fact, one of Doc James’s newest products it sells is reputed to alleviate a variety of ailments: CBD oil. It is made from the cannabis plant, but, unlike marijuana, does not contain the psychoactive ingredient of THC that causes the marijuana high. One concentrated form of CBD has been certified by the Food and Drug Administration as a prescription treatment for epilepsy.

Even at the currently high retail price range of $50 to $200 (for a 1500mg bottle), he says CBD is selling very well at Doc James.

Adam DeSiena swears by CBD oil as an effective form of self-medication for sleep disorders, anxiety, and as an anti-inflammatory remedy, among other uses. “It’s helped my digestive system,” he says. “If I didn’t believe in it, I wouldn’t sell it. Rather than taking pill after pill, it’s a holistic approach.”

Besides, what could be more natural than to carry a health product in a store that’s named Doc James?