Business got really serious last year for Brian Desind, founder of Privada Cigar Club. With the world on lockdown and the demand for handmade cigars increasing dramatically, what began as a side hustle to sell off a collection of limited edition cigars eventually turned into an exclusive club of cigar enthusiasts—with Desind serving as its fearless, unapologetic leader. Much like some of the great entrepreneurs of our time, Desind moves at a rapid pace. If he has an idea or if there’s something he wants to do, he doesn’t spend much time talking about it or thinking about it—he does it. As a musician, he learned the power that comes from taking an idea and making it become reality sooner rather than later.
Those that have watched Privada Cigar Club’s growth over the past four years and witnessed the unique connection Desind has with its members and other cigar enthusiasts should not be surprised by Desind’s recent accomplishment: being voted as this year’s Tobacco Businessman of the Year at the Tobacco Business Awards. Like most successful businessmen, Desind is less about overanalyzing the cigar market and more about making things happen. Privada Cigar Club has reached its limit of members and become exclusive, leaving many waiting for their chance to get in on the action.
Desind has also created other businesses within the world of Privada Cigar Club for the benefit of retailers and consumers. He launched Farm Rolled, another subscription-based club within Privada that delivers cigar smokers cigars directly from the factories where they are rolled. To drive demand into traditional brick-and-mortar retailers that were negatively impacted by the COVID-19 pandemic, Desind created the Limited Cigar Association, a program that drives his audience and followers into smaller mom-and-pop stores as they seek out rare and limited editions cigar releases they won’t find anywhere else. If it seems like a good idea, Desind will pursue it and see it through, no matter how challenging or daunting it appears.
“I constantly have to remind myself [that] fear is the biggest killer of everything: of dreams, of hopes, of business and of money,” he says. “No matter what level you get to and how fearless you think you’ve become, a new fear arises and you just have to break through that shit.”
As a businessman, Desind knows that many entrepreneurs become fixated on details. There’s some value in that, but Desind lives by the mantra of “work close to the money,” which, for him, means that it’s more important to focus on the details that will yield results—everything else can be revisited later. Desind’s business and the success he’s experienced so far shows that, for entrepreneurs, there’s often no better teacher than life itself.
Desind was born in Manhattan, New York. His family moved after his father, a hat manufacturer and one of the biggest mentors of Desind’s life, moved his factory to Allentown, Pennsylvania. His family spent the next few years going back and forth between New York and Pennsylvania. This “double life“ led to what Desind views as one of his special abilities.
“We were always going back and forth, not during school and stuff, but [during] any holiday, we were back in New York,” he says. “That created a bit of a superpower that is something of a superpower for me. I feel like everyone has a superpower or a strength. That strength for me is seeing things from different perspectives.”
Desind developed his superpower even further following the divorce of his parents. While his father remained on what Desind considered to be the better part of town, his mother moved to a poorer area. Just as Desind had grown up seeing the different lifestyles of those who lived in New York versus Pennsylvania, he suddenly began to see how socially and economically diverse the world was as well. This allowed Desind to pick up on trends early on and to make friends with people from all walks of life—two abilities that he’d use later on in life—once he got involved in the cigar industry.
Desind’s childhood was far from ideal. Following his parents’ divorce, he spent much of his teen years in the streets of Allentown and getting into trouble, which contributed to his already different perspective on life and community. One thing remained constant in his life through his early 30s—his love of music. Desind was a singer and songwriter and started out as a rapper, long before Eminem made it big. Music producer Scott Storch helped Desind with his demo tape, and in turn Desind served as an unofficial assistant to Storch while they were in the studio.
“Music was my entire life,” Desind says. “I dedicated absolutely everything—every ounce of my passion and being—to music. As I got older, after Eminem came out, I realized [that] being a white rapper wasn’t going to be so easy. I started to learn how to sing, and so over time, I actually became quite a good singer. The biggest problem was that I was really more of a writer, even though I was trying to build myself as an artist. One song to the next would sound totally different. Just like how a cigar brand should have some consistency, so should an artist. An artist needs to have their sound, a brand needs to have its flavor, and I developed that sound a bit too late. It just turned into an unhealthy lifestyle that I eventually had to get out of.”
As Desind worked on his music career, he also worked in sales. Desind worked for many different companies—high-end Wall Street businesses, New York City financial firms, mortgage banks, commercial mortgage banks and retail. If it was a sales-related job, Desind probably worked it at some point but only for an average of two weeks to six months, at most. Even though he was, in his words, not the greatest employee, he learned a lot about sales with the help of his uncle, who worked for a large financial firm and encouraged Desind to take a sales course that all of his firm’s employees went through. The course helped give Desind’s approach to sales more structure, so instead of losing deals, he suddenly started to close them.
While he continued to work on his sales career, Desind felt disillusioned with the music industry, leading him to make the decision to give up his dreams of being a music artist. He resented the time he felt he had wasted pursuing a music career and moved to Miami, where he knew that he wanted to eventually start a business of his own—but he had no idea what it would be. He began working for an auto transport company and was surprised by how the industry operated, with promises being made to customers that were often broken without any apology. Desind was inspired to get his own broker’s license, which allowed him to start his own auto transport operation, and he used the skills he had learned as a music artist, such as leveraging video and websites, to put his own stamp on the industry that he viewed as flawed and ready for something different.
“I made it very clear that we were not a trucking company but that we were a broker, and that every single [trucking] company that calls you is the same exact thing, so beware of people promising you things that they can’t keep and people telling you that they’re a transport company,” he says. “Over time, I kept drilling this into consumers’ heads. Eventually, other people started working it into their pitches—that we were all brokers—so I had an impact on that business. It’s a very, very, very stressful business, and no one leaves happy. Everyone is disappointed: The car never shows up on time, sometimes drivers disappear for weeks or don’t answer their phone, and they don’t tell you where the car is. It’s an absolute nightmare.”
As had occurred throughout his life, Desind used what he learned from his auto transport business to help launch another business. This time, however, it was one that focused on cigars. When Desind was about 35 years old, he decided that his love for sneakers felt a bit immature, but he wanted to transfer that sneakerhead-collecting energy into something new. Desind was living in Tampa at the time, a city known for its strong cigar culture. Because he owned his own business, Desind was able to work from wherever he wanted and chose Tampa Humidor as a workplace. While there, he was shown a series of limited edition cigars that included the 2014 Las Calaveras and Tatuaje Monster. Suddenly, he had a new obsession and began amassing a huge collection of limited cigars. It didn’t take long before his collection filled an entire room with rare cigars from floor to ceiling. When he and his wife decided to move to Los Angeles, Desind was suddenly faced with the realization that he wouldn’t be able to take his cigar collection with him.
“So I said, ’OK, I guess I gotta sell some of this stuff.’ I went to sell these cigars, and I realized that no one understood the collectible cigar game—it just hadn’t come to fruition yet. I went to try to sell these cigars, and people were lowballing me on things that I had aged for four or five years. It was disheartening, to say the least,” he explains. “The idea that I got was that cigars are not taken seriously, not as a craft, not as an artisan product, and so I said to myself, ‘If I’m going to sell these things at a discount, I’m going to make sure these people know what they’re getting.’ So I created a subscription business. I would put the cigars in a box, and I would write about each cigar. Each month, I sold three cigars with a writeup on each one: the story behind them, what made them rare, the tasting notes, the pairing notes—it really created an experience, but I didn’t realize that that’s what was happening.”
What started off as an effort to sell products ahead of a move in 2017 launched a brand-new business: Privada Cigar Club. Desind saw that his efforts were helping other cigar smokers better understand what made the cigars they were receiving so special and why they should take the cigar lifestyle itself more seriously. Desind and Privada Cigar Club were building an experience and putting the artisanal nature of cigars front and center. Eventually, Desind sold through his entire collection, but his business was far from over—Privada Cigar Club had just begun.
Building a Following
It’s not uncommon to see Desind in a new YouTube video or reaching out to Privada’s many followers on Instagram. He’s managed to build not only a loyal following but a community of cigar smokers that have a passion and love for the rarest of cigars. Desind confesses that it was never his intention to become the face of Privada Cigar Club. Following his experiences in the music industry, the last thing Desind wanted to do was be in front of a camera and put himself out in front of the public once again. He also knew that once he started making himself the face of the company, there would be no going back. It wasn’t until after he participated in an online live interview with Bryan Glynn of Cigar Obsession that things changed, and he began to rethink his stance on being a more public figure.
“I did this live with Cigar Obsession and had a great time. On the way home, my wife called me and said the club membership had doubled. We knew right away that we weren’t attracting the Cigars International crowd or the bundle-buying crowd. These weren’t older dudes. We knew we had a younger audience right from the beginning. My wife was like, ‘I’m telling you, they want someone that’s willing to commit to being the face of younger cigar smokers.’ And she was right. From that point on, I made it a point to get in front of the camera, give my opinions and share my knowledge.”