In the Family: Maryland’s Tobacco Leaf

Rahul Gupta didn’t intend to join the family business, one which his father began four decades earlier. His father never pushed him, emphasizing education and encouraging him to pursue his own career path. He graduated from college in 2007 and settled in Philadelphia, working in finance until the recession. In 2010, he moved back home to help his father get their new cigar lounge, Tobacco Leaf, off the ground with the intent of going back to school for his master’s degree. But like many who enter the premium cigar world, he soon realized he didn’t want to leave. “I ended up falling love with the business,” he says.

Tobacco Leaf of Maryland

In the ’80s, as Gupta was growing up, his father owned a tobacco shop and a leather goods store in a Maryland mall. Gupta grew up a self-described “mall kid,” hanging out during weekends and summer vacations, running between stores and helping out when told.

It wasn’t an easy business to sustain at the time, before the cigar boom of the ’90s. Gupta’s father focused on mall locations, attracted by the security and built-in foot traffic a mall format offered. For the next two decades, the Gupta family businesses opened and closed in several locations, trying to find the right niche, the right space.

“We just bounced around from here to there for many years,” says Gupta. “I was in high school, so I helped out a little bit after school and on weekends. It was where I learned the basic concepts of retail and running a business.”

Tobacco Leaf of Maryland

By the early aughts, the Guptas had two locations, and business was “OK,” but they recognized the industry was changing and the cachet of a mall location had lost its sheen.

“We noticed being in the mall was good, but we weren’t dealing with the type of customers that we wanted to be working with,” Gupta said. “Each one of our stores that we had during the mall days, we were slowly growing. So, initially, we had a really small cabinet, basically like 100 facings. Then the next location we had probably 300 or 400 facings. And then from there, it kept growing. But there are limitations to mall locations and we recognized cigar lounges popping up everywhere. We felt like, OK, this is really the future of the industry.”

In 2010, the Guptas made the dive into a location with a lounge in Jessup, Maryland. They were still in a mall, per se, but this was a strip mall with a Starbucks and liquor store adjacent. It transformed their business.

“It was the perfect combination of neighbors and tenants. We had a very synergistic relationship with those businesses,” he says. “And being in Jessup, we were just south of Baltimore. There’s a military base that’s very close by, the NSA, and a lot of government agencies are very close. So it was the perfect location for a cigar lounge, because there’s really nothing there. Things really took off right away.”

Tobacco Leaf of Maryland

At 1,200 square feet, the lounge was like having an entirely new business for the family, and there were significant adjustments from a cash-and-carry location to a lounge. But Gupta believed they had found their niche, and he had found his calling.

He says: “It was so different than the mall operations. People would come in and we would get to talk to them. At the mall, it was strictly transactional. They buy something, and then you may never see them again. But with the lounge, customers hang out, and for an hour or two we’re just hanging out watching sports together or talking. And I’m getting to know them and their family. And my family too, obviously, with my dad and me working together. It was really cool. I ended up really falling in love with the business. So that’s what led me to get into it fulltime. And then slowly the business started to grow.”

Fast forward seven years and they started to think about the next step. It was 2017 and their lease was going to expire in a year. They felt ready to expand, to find a place with outdoor seating and more inventory space. It just so happened that down the road the owners of a classic diner were looking to sell the business and the property. It was a risk, both logistically and financially. Do they tear the building down and rebuild? Do they renew the lease at their current location? Do they have the money to invest in this? But the potential was evident.

“My father and I were really undecided, torn on what to do,” Gupta recalls. “And there was a point where we were going to walk away. But then we somehow just came up with the idea of, you know what, there’s a story here. The diner car was actually brought down from New Jersey back in the ’70s or ’80s and then they attached it to a new portion that they ended up constructing. It’s like two buildings in one with the diner car that you see from the front. So we’re thinking about this really cool diner and maybe we can make it work and it’s going to look really nice, and just trying to figure out how.”

The how was a big investment, contracting an architectural firm to create a unique customer experience involving multiple lounge areas, including an outdoor patio, a top-of-the-line ventilation system and a state-of-the-art Spanish cedar walk-in humidor across a 2,800 square foot floorplan. It took two years, but the father-and-son dream was realized.

Gupta says: “I give my dad a lot of credit, because I said, look, if we’re going to do this, we’ve got to do it all-out. I don’t want to do it half-ass. I’m 38 and my dad is going on 80, he’s ready for retirement, but he believed in it. He signed for every loan. It was a big risk, but he was fully committed.

“I’ve learned a lot from my dad, just by growing up at the stores and watching him … how he dealt with customers, the value and importance of relationships, making sure his employees were taken care of. He was always the last to get paid and he was always investing in the business. So, coming in to work with him, and being from the younger generation, I was able to add my ideas and energy to the business—expanding our selection, using social media, just taking his foundation to the next level.”

Tobacco Leaf of Maryland

Today, Tobacco Leaf in Jessup, Maryland, is about providing the best customer experience. Events are a big part of the business, Gupta says, and a driving factor for sales, used to attract and then retain customers.

“After moving into our new location, our focus has shifted to making events more experience-based,” he says. “What good is it having such a unique, destination-style cigar shop if we are going to feature a certain brand or product line and run the stale, typical, buy four, get one free event? Instead, we focus on harnessing what makes us stand out and what we feel are our strengths, such as our unique facility, our unmatched selection, and customer-first driven service model to offer experience-based events that will be remembered by those who attend and can’t be replicated.”

There are no plans for additional expansion, but Gupta is launching an e-commerce site soon to create additional revenue. He has a young family of his own now, too, so life/work balance has become a higher priority. After all, it’s the family, both at and away from work, that truly matters.

This story first appeared in PCA The Magazine, Volume 2, 2023. To receive a copy of this magazine you must be a current member of PCA. Join or renew today at

– Photos courtesy of Tobacco Leaf. Story by Greg Girard, managing editor of PCA: The Magazine. You can reach him at