Emerson’s Cigars | Tobacconist magazine

Emerson’s Cigars

A Second-generation Tobacconist Story

Story by Greg Girard
Photos by Jacob Krekura

There’s a third-generation chocolatier in Italy, Giovanni Ferrero, who said, “Tradition is like a bow. The more we stretch the bowstring, the farther we can throw the arrows of modernity and innovation.”

If Ferrero had been speaking directly to Scott Regina of Emerson’s Cigars, it’s not hard to imagine Regina nodding his head in agreement. Regina is the second generation behind Emerson’s Cigars, which has four retail locations throughout the Virginia Beach, Virginia, area. And he learned firsthand the benefits and the challenges of passing on a family business. 

For Regina, his first experience with the premium tobacco industry was in the early 2000s, helping his then future father-in-law and founder of Emerson’s Cigars, Dwight “Chad” Chadbourn (Emerson is his middle name), navigate the ever-increasing and still relatively new forms of technology that were challenging the best of the baby boomers with a whole new way of looking at business.


“He really didn’t understand computers or the internet at the time, or how to use it for marketing a business,” says Regina. “He didn’t know what email was, so I said, ‘Take a pad of paper and put it by the register, and start asking customers for their email addresses. He started collecting addresses, and then he’s faxing me notebook page after notebook page of these lists. I said, ‘OK, now let’s do an email campaign for an event.’ He sent me pictures later of the event. I think it was with Avo. It was crazy. There were like 300 people that showed up.”

At the time, Regina was in Vermont, working at a manufacturing company on the operations side while going to graduate school for an MBA. His future wife, Chadbourn’s daughter Tara, was going to law school. Regina wasn’t thinking too much about cigars, except for when he smoked one on occasion with friends or the one time he helped Chadbourn at the stores while transitioning from California to Vermont. He was just happy to help and get his hands into a bit of marketing. But it did get him thinking.

“It was fun, exciting,” he says. “[Chadbourn] had, I thought, a lot of cool things going on. He had the Opus X Harley Davidson on display in the store. He had a ’60s Chevy delivery truck that he modified. So he had the romance parts down when it comes to premium cigars, but he didn’t know how to tell the story. So it was cool to help him get that message out.”

And even though life was good in Vermont, Regina kept thinking about that month he’d spent on the front lines of the premium cigar industry. He says, “Looking back, that month definitely changed my life. Being able to sit on the porch with [my father-in-law] at night, smoke a cigar and learn about the industry. Working in the store and being a part of it. And I knew nothing about cigars. I was the guy who’d go into the humidor to try to help someone, [and] they would ask me a question and I’d go right back out of the humidor and ask, ‘Hey, what about this, that?’ It was just a cool environment. And after that month, when I left, he said, ‘Well, if it’s something you like ….’”

After the email blast and successful event, Regina continued to help when he could. He was soon tasked with building Emerson’s Cigars’ first website. Then he was helping take online orders for the business until, eventually, in 2006, the path to working full time for the business became a natural progression. He had no illusion about what he was getting into; Chadbourn made sure of that. “[My father-in-law] did the hard work. Opening a store and getting a business established is very hard. He would tell me stories, like one day when he didn’t have a single customer or the day he had one customer … who came in to return something. He said, ‘You have to go home and tell your wife, well, we had negative $200 in sales today.’ I don’t know if I would go back to work the next day.”


It was a clear and needed lesson about the realities of small-business ownership: Take nothing for granted and keep looking for ways to improve. Regina recognized that the best way to continue growing was to find a balance between fostering the personal relationships the premium cigar industry is built on and introducing some new business processes that could help attract more customers. 

Relationships count
On the personal side, it was simply maintaining the strong relationships Chadbourn had created over the years and establishing some of his own. “So 2006 was my first real taste of everything,” Regina says. “I visited Rocky [Patel] in Honduras. I went to my first trade show. And I was hooked. I was hooked because I was enjoying time with my father-in-law but also because of the family aspect of the industry. And now I look, and I’m doing business with the children of the people that my father-in-law was doing business with. Those relationships have had a lot to do with our success.”

Developing relationships also meant rolling up his sleeves and getting involved to protect the industry. Emerson’s Cigars was one of the founding members of the Cigar Association of Virginia. After learning the ropes of advocacy from the likes of Glynn Loope, executive director of Cigar Rights of America and another force behind helping to get the Virginia association off the ground, Regina joined the IPCPR board of directors, where he currently serves as secretary.

“What I love about the associations is the ability to share ideas,” Regina says. “It allows you to learn from other people in the industry. As an entrepreneur, sometimes [I] get really stuck on what I think is right or the way that I think it should be done. So to work with others on the same level as you is refreshing and helps me look at things a little bit differently.”

Along with the collaboration and sharing of ideas, Regina notes that the associations are also vitally important to protect the industry. “We’ve been in some battles, whether it’s smoking bans or taxes. But this industry, when it seems like we’re getting down and we’re getting kicked, we have the ability to rally and get stronger. I’ve seen it at every level of government. I don’t like politics getting involved in businesses, but since that’s the way it is, I think that there are a lot of great people in the industry that are coming together and fighting every day. The associations help us do that.”  

Business savvy
Focusing on business growth, Regina approached the challenge by asking a few key questions. What is our foundation? What defines us? What is our vision? What can we do new or better to be successful? His answer to them all: service.

“I can’t say it enough: We’re fortunate because we have a great team. Whether it’s the people at the office or the guys in the warehouse or the store managers. But most importantly, it’s the guys on the front lines creating that experience for our customers. They take a lot of pride in using their experience and expertise to guide each customer in the right direction.”DSC_9851.web

It’s not by some stroke of luck, however, that Regina has such a strong team in place. He notes it takes a consistent and ongoing effort to develop and maintain high-quality customer service. He recognized the business needed some structure to make it perform better. From brand training to incentive programs to creating an employee handbook, he found that each element he introduced to the company built a stronger foundation for the business. 

“Take our sales process that we train everyone on,” Regina says. “That was definitely a difference-maker for us. It’s not rigid where it says, ‘You have to do this.’ It’s more of, ‘These are some guidelines, and as a sales associate or store manager, you’re going to put your touch on it. Using this as a foundation, you’re going to figure out how to make it work.’ We found this gave them much more confidence to provide the best possible service.”

Regina will be the first to admit it hasn’t all been smooth sailing. There are always challenges, especially in a multigenerational business. Not every decision made on both sides of the generational gap is agreed upon. “There were some tough conversations,” he says. “When you’re sitting across the table from a family member, while you want it to work out absolutely perfect for them, you also need to make sure that it’s something that does not handicap business growth. But we always had a rule: that we’re going to have those conversations, but once the conversation is over, then that’s it. As bad as we argued, or maybe as upset as we were at the time, once we closed our notebooks, it was family time.”

In the end, it’s about stretching that bowstring of tradition with new ideas but never allowing it to snap. “I take a lot of pride in being able to say ‘second generation.’ That we’ve been here since 1975,” says Regina. “I feel like I’ve got just as much passion and energy about the business today than I did when I first got into it.”     



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