They call him the Cigar Authority, and not only because that is the title of his famous podcast. David Garofalo finds himself among the day’s quintessential cigar men by fairly popular acclaim. He’s built a large retail business, Two Guys Cigars, with three successful brick-and-mortar locations in Salem, Nashua and Seabrook, New Hampshire, moving millions of cigars every year—more cigars, he tells us, than any other B&M outfit. His sales amount to about $15 million per annum in cigars alone.
Beyond that, he has branched out into book-authoring and paid public speaking. His Cigar Authority podcast recently transmitted its 1,000th episode, and Garofalo made at least an appearance in every one of them. His United Cigars Group now markets 18 active lines.
Mainly, though, the man just enjoys retailing. As busy as his ventures keep him (Garofalo works just about every waking hour), you’re more likely to find him working the floor in one of his shops than spending time in any office. Garofalo wants to meet his customers and vendors, and people in general. He enjoys time spent talking with his employees. In short, he wants relationships. His easy knack for good chemistry with the widest variety of people has made David Garofalo a millionaire and a genuine guru in the ways of retail. Nor does it matter if he cannot accommodate any hobbies or recreational travel or distractions from business affairs. At age 64, Garofalo is loving the busy life.
Hard work is the most conventional advice endorsed by any successful retailer. Garofalo worked a steady seven days a week until five years ago, when he decided to start taking Sundays off…sort of. “Everything is in my briefcase, and I take it home,” he says. “Business never stops, so even on Sundays, if I don’t have a honey do list, I can grab the briefcase and get some things done—not because I have to, but because I like it. I want to stay engaged with promotions and ideas and numbers. I don’t follow sports. I don’t golf. I don’t take vacation trips. This is it. Thirty-nine years ago I found the occupation that I love: the cigar industry.”
There were early signs that Garofalo might have the makings of a business dynamo. His parents John and Angela Garofalo taught him the value of a dollar from his earliest formative years. Instead of playing with toys when he was little, Garofalo burned through pads of paper creating imaginary businesses—such as a “cartoon college” by which he sought to instruct how to tell stories through creative images; and, he adds, “When I was 7 or 8 I formed a wrestling fan club, and it became the No. 1 wrestling fan club in the world. By age 12 I had won worldwide fan club of the year at one of the wrestling conventions. I always wanted to make a success of anything I set out to do.”
Soon after graduating from Everett High School in Everett, Massachusetts, Garofalo bought his first enterprise, a diner. He then sold that business for a modest profit and undertook a vocation managing nightclubs. “I’d turn barrooms into discotheques,” he says. “I brought in DJs, lighting, sound, and I had as many as seven nightclubs running at a time. This kept me going until I was 30.”
It was during his nightclub years that Garofalo first learned to love premium cigars—in his case, Macanudos and Royal Jamaicas. It was also during his nightclub period, specifically in 1985, that he ventured to open a cigar store—“my first Two Guys store,” he says. “But it lost money for a while, so nightclub DJing kept me afloat until the cigar boom hit and Two Guys really took off.”
Garofalo’s first partner in the cigar business was a close friend named Paul Antonelli (the original, first “other guy” in Two Guys), but Antonelli had other business interests that were doing well, so after a year, he sold his half to Garofalo. Next, Garofalo’s brother John joined the business and became the second “other guy” in the Two Guys story, but after 18 years of partnership he passed away suddenly, leaving Garofalo to buy out his brother’s widow and make it a one-owner operation.
It was Garofalo’s daughter Gianna who first suggested to him, in 2010, that he begin exploiting the business potential of social media. Today she handles accounts payable and marketing for the family business, and she takes some pride that her suggestion took flight in her father’s podcast, Cigar Authority—“the longest-lasting cigar podcast ever,” says Garofalo.
A typical day in the Garofalo home starts early with a cup of coffee and a business meeting with Garofalo’s wife Lori, who serves as the company bookkeeper. Once the day’s priorities have been established, Garofalo is off on his rounds for the day. “I have three retail stores and a warehouse as well as a distribution center which handles United Cigars, all within an easy drive of home,” he says. Then, when he heads back to the house in the evening, he goes over paperwork with the missus, and the cycle repeats. “Life is rinse and repeat for me,” he says, “very regimented, that’s how I like to live my life, without a lot of surprises. I get enough surprises in business, so I try to minimize them in my normal routine.”
No treatment of Garofalo’s business life would be complete without mention of his two books. One, The Cigar Authority Cookbook, was assembled from recipes submitted by podcast guests. But Garofalo’s other book arguably brought him magnified renown as a business leader. David vs. Goliath: How to Compete, and Beat, the On-Line Giant, published in 2019, describes more than 100 examples of promotional techniques that can be applied to most B&M retail settings, not just tobacco shops. We asked if sales of that book were still strong, and Garofalo replied, “Enough to have made it worthwhile. I am still receiving a check from the publisher every month. It’s enough for me to take my wife out for a nice dinner, at least.”
Garofalo also generates income from public speaking. His first speaking gig was at Harvard University. Other engagements have been for national sales meetings at J.C. Newman and Perdomo, as well as various cigar trade shows and local businesses.
Garofalo’s positive influence of course extends to elevating the tastes of customers who seek to learn more about cigars. In that vein, Garofalo was a cigar “influencer” long before the term came to be applied to social-media personalities. He recalls one particular customer who came into his shop: “This was way back, before Cigar Aficionado,” he says. “This customer was looking for Rigoletto Black Jacks for his father-in-law.” After Garofalo supplied him with five boxes, the man next asked for recommendations of some premium smokes for himself. Later, the customer wrote a letter of appreciation to Garofalo, in which he included an actual review of the premium smokes he had purchased at Garofalo’s suggestion. “I thought that was very interesting,” says Garofalo. “In fact, it was so striking that I’ve kept the letter all these years, because cigar reviews weren’t really a thing back then. And I told the fellow he should consider getting into the cigar business since he took such a keen interest. Well, eventually he did get into the business.” That man was Steve Saka of Dunbarton Tobacco & Trust. Other early Two Guys customers who would go on to make their marks in the industry included Mike Cusano of Cusano Cigars and Pete Johnson of Tatuaje.
Garofalo keeps 30 full-timers in his employ, and a few part-timers as well. Some employees have been with him for as long as 30 years. Ed Santamaria, vice president of operations and buyer for Two Guys says, “Dave is passionate, constantly on the go, and always thinking about the business and the industry. He is also a true gentleman, known for his kindness and generosity to his employees and customers, and to our vendors and the world at large. I can tell you that in my 30 years with the company I have always been treated like family. At Two Guys we feel like we’re all succeeding together.” Santamaria’s son Nicholas is now the 3rd generation of Santamarias working for Two Guys.
Jonathan Barbeau, known as “Mister Jonathan,” serves as manager at the Two Guys anchor shop in Salem, and he is a fixture on the Cigar Authority podcast. Mister Jonathan says, “David Garofalo is the greatest boss I ever had in my life. He is easy to work for, and there is no pressure, although Dave has high standards. But we at Two Guys have lots of meetings where we get our direction. Dave has spent decades working out a blueprint for doing business. We call it the Two Guys way. Improvement is what makes Dave tick—improvement in business, in personal life, in everything.”
Garofalo’s favorite cigar these days is the ultra-premium Atabey line. “I put United Cigars together around that brand,” he says. And he loves his own Garofalo line, which is made at the Perdomo factory in Estelí, Nicaragua. But he also keeps a stash of Toscanos around for more casual moments. Garofalo said in a recent Cigar Authority podcast episode that he figures he has smoked 2,000 boxes of cigars in his lifetime, so far.
Garofalo has been with PCA from its early days as RTDA, and he has served two three-year terms on the board. (He noted, “I am grateful to the board of directors that they pivoted away from customers on the trade show floor.”) His current interests include promoting a New England Cigar Expo, to be held in September. “This will be the second year of the Expo. We’re staging it in a big field in New Hampshire, at Dreamer’s Ranch in Windham. At the first Expo, we launched the Cigar Hall of Fame, where we inducted three cigar brands, and we’ll be inducting three more brands this year,” he says.
So, on the whole…yes, David Garofalo leads a busy life, to put it mildly. But it is a life that he built very deliberately around an industry and business that he passionately loves. Having secured the life he wanted makes him more than just your average business guru, for he has actually achieved unmitigated happiness, making him indisputably a winner at life’s game. In this capacity, he offers something important to teach any of us who wish to learn. You can find David Garofalo at 2guyscigars.com.
– Photography by Jared Burnett. Story by William C. Nelson.
This story first appeared in PCA The Magazine, Volume 3, 2024. To receive a copy of this magazine, you must be a current PCA member. Join or renew today at premiumcigars.org/membership.