Sometimes the road to success can be circuitous. In 2002, Scott Regina was working in retail while living in Northern California with his future wife, Tara Chadbourn. She had been laid off from her job in San Francisco because of the “dotcom bust,” and after joining Scott in Lake Tahoe, she realized her career needed a new direction. She decided to pursue a law degree and was accepted to Vermont Law School. The couple then moved back east, but not initially together. While Tara settled in Vermont, Scott made a detour to Virginia to briefly live with his future in-laws. Dwight “Chad” Chadbourn, who had previously owned six Tinder Box franchises, was launching his own Emerson’s Tobacco (Emerson was his middle name), and Scott was eager to help.
“I didn’t know anything about cigars except from having smoked with my father-in-law,” says Regina. “But I worked for him for a month, and I basically did everything he didn’t want to do. I cleaned bathrooms, I painted the walls and helped as a sales associate. And before I moved to Vermont I said, ‘I want to do something to help. Do you mind if I start sending emails to customers about events?’”
While not really knowing much about email at the time, Chadbourn was intrigued at the prospect of attracting more business. Regina says he asked Chadbourn to put a few note pads next to the registers, collect email addresses and then every week or so tear off those pages and fax them over. Now in Vermont, Regina compiled an email list for Emerson’s, which he used in order to send out a blast about an event with Avo Uvezian.
“Chad called the next day and said ‘What did you do? There are 350 people in the store!’” When Regina explained he had sent an email to the customer list, Chadbourn asked him what else he could do. “I said, you should have a website. He said, ‘I don’t know what that is, but okay, let’s do it!” Regina had never designed a website before, but he brought his digital camera to Virginia, photographed the stores, the displays and the merchandise, and from there built a website. “We posted events on there and sent out emails. This was all while I was pursuing my MBA in Vermont.”
The launch of the website prompted Regina to speculate that maybe he should sell things on it. So, he built a store online and they started getting orders. “The order would come in online, I would fax it to the store, and they would pack it up and hand-write the shipping label,” he says. “They would fax me the tracking information and I would send the customer an email saying we shipped your order.” Emerson’s current expansive website grew from this humble beginning.
In 2005, Regina’s interest in the business took a quantum leap forward when Chadbourn asked him if he and Tara would be interested in moving back to Virginia, with the intent of joining him in the family business, and to eventually take over. Chadbourn said he had an offer but would turn it down if Scott and Tara moved back. Scott leapt at the idea. “One of the things that attracted me to the cigar business, to work with Chad in Emerson’s, was that I had worked in businesses where I had a little piece of what was going on,” he says. “I did mapping, I worked in GIF, I was in operations when I was in retail in California. While I was working on my MBA I was learning about operations—marketing, financial management and all aspects of running a business—and here was an opportunity for me where I could do a little bit of all of that, in an established business.”
The icing on the cake was the opportunity to work with his father-in-law. “He was so personable, but it was never about him, it was always about his employees, friends or family,” says Regina. “He was the guy who always made sure everyone had a good time. He had a way of lighting up a room. That’s how he approached business. He was a pleasure to be around. People would come to the store because they wanted to see him.
“I always tell people that he did the hard part, because it’s so hard to start a business. I was so fortunate to get to meet him, with him being so welcoming, and letting me join him in the fun,” says Regina. “He’d tell me how, in the early days, he’d have a day of good sales, then someone would make a return, and he would lose money that day. I don’t know if I could’ve handled that. But he just wasn’t a quitter; the word ‘no’ wasn’t in his vocabulary.” Emulating Chadbourn’s enthusiasm and work ethic is Regina’s enduring tribute to his father-in-law, friend and mentor, who passed away in July (see sidebar).
Today, Regina has grown Emerson’s to five locations in the Coastal Virginia area, with more than 30 employees. He has also expanded operations to include a partnership with a craft brewer, Makers Craft Brewery in nearby Norfolk, where Emerson’s has a 30 x 40-foot free-standing walk-in humidor and lounge. The partnership also gives Regina access to the extra space for events, including Emerson’s annual Coastal Virginia Cigar Festival that raises money for local charities. Last year’s festival raised funds for Frog Dogs, a veteran-run service that trains former military service dogs for adoption by veterans of the Navy SEALS Team. They will also be the beneficiary of this year’s Coastal Virginia Cigar Festival in September. All the event’s proceeds are donated to the charity.
In May of this year, Emerson’s held a cigar dinner to celebrate the store’s landmark 50th anniversary. The day’s activities began with a meet and greet with Rocky Patel at Emerson’s Greenbriar location, which is, as Regina says, “a store he’s done a ton of events at.”
“Rocky was one of the first people I met in the business, and I’ve always been close with him,” says Regina. “I appreciate how hard he works, and he’s been great to me.”
Reflecting on half a century of successful retailing, Regina is sanguine about Emerson’s staying power during the last 50 years and going forward. He is proud to have persevered through good times and bad, surviving a doubling of Virginia’s OTP tax, and thriving during the COVID-19 pandemic. In addition to his role as CEO of Emerson’s, Regina is also very active in organization and advocacy for the industry. It started with Virginia’s 2005 OTP tax on cigars. Chadbourn, together with several other prominent Virginia retailers, formed the Cigar Association of Virginia, with the mission of lobbying against the tax. Chadbourn informed Regina that the association had been formed, and that, as he remembers it, “‘You’re the secretary.’ I asked if they took a vote and he simply said, ‘I didn’t want to do it so you’re going to do it.’ That was the beginning of my advocacy.”
Since then, Regina has served on the boards of both the TAA and the PCA and has been elected president of each organization as well. “I think they looked at me as someone who embraced technology and could use some of those skills to help the association,” he says. It was during his presidency that the PCA trade show calendar was moved up to March, for both 2024 and 2025, and by all measures was a great success. “I’ve heard great feedback from people that attended,” he reports. “People really enjoyed it, and I feel like people really had a good show.”
Growing and nurturing his business, serving his community, advancing the cause of the industry through advocacy and leadership, keeping an eye toward the future while acknowledging the history that preceded him—these form the building blocks of Scott Regina’s formula for success in business, and in life.
With his five stores all running at a high level, Regina still holds out the possibility of further expansion. “I think we’ve got the coastal Virginia area pretty well covered, but I’m always willing to listen if an opportunity comes along,” he says, as if he needed to add another project to his already hectic schedule. But it seems that he thrives on taking on challenges and seeing them through to fruition. That should keep him busy for quite some time to come.
– Photography by Jacob Krekura. Story by Larry Wagner.
This story first appeared in PCA The Magazine, Volume 3, 2025. To receive a copy of this magazine, you must be a current PCA member. Join or renew today at premiumcigars.org/membership.