Reflecting on 40 Years in the Cigar Business – A David Garofalo Editorial
40 years in the cigar business—what an extraordinary journey it’s been! As I sit back and reflect, I’m filled with gratitude, amazement, and pride at how far we’ve come. Ten years ago, I wrote about celebrating 30 years in this industry, and now, here we are, marking an incredible milestone I could have only dreamed of.
Back in 1985, Two Guys Smoke Shop was born in Somerville, Massachusetts. My lifelong friend, Paul Antonelli, and I opened a tiny 200-square-foot store. Paul eventually decided the cigar business wasn’t his calling, so I turned to my actual brother, John, to keep the dream alive—because Two Guys needed two guys. John joined me, and the rest, as they say, is history.
We outgrew that small shop in no time, moving to a 500-square-foot space just down the street. By 1987, we added a second store in East Boston and launched a mail-order and catalog division. A year later, we opened another shop in Everett, Massachusetts—our hometown. Then came the Cigar Boom of the 1990s, and we were perfectly positioned to ride the wave. The timing couldn’t have been better.
The Bold Move to New Hampshire
In July 1996, Massachusetts imposed its first cigar tax—a 12% levy that threatened to crush our business. Despite my efforts to fight it, the tax went into effect. The final straw was the “floor tax,” which required immediate payment on all unsold inventory. It was a devastating blow, but I wasn’t ready to give up. Instead, we made a daring decision: pack up everything and move 30 miles north to tax-free Salem, New Hampshire.
Starting over in a state where we had no track record was risky, but it turned out to be the best move we ever made. Our new 2,500-square-foot store—larger than all three of our Massachusetts locations combined—opened its doors, and business took off like wildfire. Customers followed us across the border, some traveling over 30 miles to keep supporting Two Guys Smoke Shop. Their loyalty was incredible, and it wasn’t long before we became New England’s highest-volume cigar retailer.
When Massachusetts raised its cigar tax to 30% in 2001, even more customers made the trip to Salem NH. By then, we’d outgrown our space again. Directly across the street, we purchased an 8,000-square-foot building—formerly an Apple Computer Town store—and transformed it into a cigar mecca. On the opening day in January 2002, despite 18 inches of snow, hundreds of cigar enthusiasts came out to see what was then the world’s largest cigar store. It was a moment I’ll never forget.
Expanding the Empire
The momentum didn’t stop there. In 2006, we opened a second New Hampshire location off Exit 1 on Route 95 in Seabrook and we added a third store at Exit 1 on Route 3 in Nashua. That location, a former Hooters restaurant, underwent a complete renovation and opened in 2007 as a 6,000-square-foot cigar haven.
Looking back, it’s hard to believe how much we’ve grown. I often drive by that tiny Somerville shop and remember the dreams I had back then. Even in my wildest imagination, I never envisioned Two Guys Smoke Shop becoming a household name among cigar enthusiasts nationwide—and even internationally. It’s been an incredible ride, and I’m endlessly grateful.
Heartfelt Gratitude
Success like this doesn’t happen alone. It takes a team of dedicated, passionate individuals, and I’ve been fortunate to work with some of the best. To all the staff, past and present, who’ve been part of this journey: thank you. Your hard work, loyalty, and belief in Two Guys have been the backbone of our success.
I’m also deeply thankful to the manufacturers, brand owners, and sales reps who’ve supported us over the years. From creating exclusive blends to participating in our legendary events, your partnership has been invaluable. Together, we’ve built something extraordinary.
On a personal note, I want to thank my family. My late father, John, and my brother John—both gone too soon—remain a source of inspiration. My wife, Lori, and my daughter, Gianna, have been incredibly supportive, allowing me to dedicate so much of my time to this business. And to my mother, Angela, who’s been my biggest cheerleader: thank you for always believing in me.
Looking to the Future
None of this would have been possible without you, our loyal customers. Your unwavering support has been the foundation of our success. Whether you’ve visited once, bought online or made Two Guys your regular destination, you’ve played a vital role in our story. Thank you for choosing us and for spreading the word to friends and fellow cigar lovers. Your loyalty and enthusiasm have taken us further than I ever imagined.
As we look ahead, I’m more excited than ever for what’s to come. With 40 years behind us, I can promise you this: the best is yet to come. Here’s to the next chapter of Two Guys and to many more years of serving you, our cherished customers.
Sincerely,
David Garofalo
Owner and Founder
Two Guys Smoke Shop
