Ali Howell was a brother of the leaf long before he co-owned Brothers Smokin’ Stogies with his wife, Heather. From his first smoke in the late 80s when he served in the Army, to his career in psychology, and now as a boutique cigar brand owner, cigars have been central to Howell’s life for over thirty years. He talked with Cigar Life Guy about sharing meaningful moments, how he can’t help analyzing everything, and why even the most stubborn aficionado should add boutique cigars to their humidor.
First Premium Cigar
Cigar Life Guy: Tell me about your first premium cigar experience.
Ali Howell: I was 18, late 1989 or early 1990, stationed at Fort Leonard Wood, Missouri. Or as we called it, “Fort Lost in the Woods.” I smoked my first cigar with members of my squad. It wasn’t just about the cigar itself. It was a way to celebrate what we’d been through together, the hardships, the training, the bond we’d built. Sitting in that circle, passing around stogies, created a tradition that connected us as brothers-in-arms. There was something about that shared moment, that ritual, that went beyond just smoking. It was about respect, camaraderie, and acknowledging what we meant to each other. That day hooked me. From then on, whenever I got the chance to smoke a cigar, I took it. It became more than just smoking. It became a way to mark important moments and connect with the people who mattered.
Psychology and the Cigar Industry
Cigar Life Guy: How did you get into the cigar industry?
Ali Howell: My brother introduced me to Ismael Rodriguez Olivan, who’s a mad scientist when it comes to blending cigars. We clicked immediately. Eventually, I began discussing with him the idea of creating my own blend. At first, I just thought it would be cool to have a personal blend for myself. But the more I thought about it, the more I realized cigars had always meant something deeper to me. Since that first cigar with my squad, cigars represented brotherhood, connection, those moments where you put everything else aside and just exist with the people around you. When I mentioned creating a blend to my wife, she asked, “Why don’t you share it with the world instead?” That question hit me. If cigars had given me so much over the years, if they’d been part of some of my most meaningful moments, why would I keep that to myself? That’s how we jumped into the cigar industry. It wasn’t just about making another cigar brand. It was about sharing what cigars have meant to me and creating that same sense of brotherhood and connection for others.
Cigar Life Guy: What did you do before, and how does it help with Brothers Smokin’ Stogies?
Ali Howell: After I left the Army, I needed to understand what I’d been through. That led me to psychology. I spent almost two decades in clinical psychology before moving into Industrial-Organizational (I/O) Psychology. I/O focuses on improving organizations, making things better for employees while helping stakeholders save money. We have a motto: “We solve problems you didn’t know you had, in ways you can’t understand.” I’m also a professor of psychology. I love teaching people how psychology actually applies to their lives, not just textbook theory.
This background prepared me to run our business effectively. Every business has the same core structure. What I needed to learn was the culture of the cigar world. I talked to anyone willing to share their knowledge. Most people in the industry are reluctant to share their experiences, but we made it through with the help of a few who were generous enough to guide us.
Co-ownership and the Brothers Smokin’ Stogies Brand
Cigar Life Guy: What’s it like co-owning Brothers Smokin’ Stogies with your wife, Heather?
Ali Howell: Heather is the best business partner I could ask for. I’ve owned businesses before and achieved success, but I’ve also had negative experiences with past partners. Running BSS with Heather has been awesome. She has decades of experience in leadership and development, and she’s a master researcher. Where I lack certain skills, she shines, and vice versa. As an I/O psychologist, I can sometimes be too calculating. She brings me back down to see things from a different perspective, and I do the same for her.
Cigar Life Guy: What’s the most important thing to convey about a brand? How do you want the cigar world to see Brothers Smokin’ Stogies?
Ali Howell: I’m logical and straightforward. For me, the most important thing is explaining why a brand should be in someone’s humidor. We have seven different sticks, and each one takes you on a complete journey from the moment you light up to the final draw. Heather and I don’t see our cigars as just “a smoke”. They’re an experience. From that first puff, you’re stepping away from whatever stress or chaos is happening around you. As you move through the cigar, the flavors evolve, the moment deepens, and by the time you reach the end, you’ve had a chance to reset. Our customers tell us that smoking a Brothers Smokin’ Stogies cigar provides them with the journey of relaxation they need, that moment of chill, or creates togetherness when shared with others. We’re not trying to replace what’s already in a smoker’s humidor. We want to add to it, give them something they reach for when they need to get away from it all, even if it’s just for that hour or so.
Cigar Life Guy: Your website says, “cigars are always better shared with others.” What does this mean to you?
Ali Howell: We have a motto: “Want for your brother what you want for yourself.” It’s about genuine empathy and connection. It’s not just saying you care about someone; it’s actively wanting their experience to be as good as yours. When you find something that brings you joy or peace, that natural human impulse should be to share it, not hoard it. How good is something if you’re the only one experiencing it?
We design our cigars to create memorable moments, and we want smokers to share those moments with others. When I left the Army, I smoked at least once a day, sometimes twice. When cigar lounges started booming in the 1990s, my experiences were always positive. In 30+ years of smoking cigars, I’ve noticed that people put aside their personal views on religion, politics, gender, and race. They come together as brothers and sisters of the leaf. Our logo was inspired by this. When I was serving, we always sat in a circle and connected, despite coming from different backgrounds. That’s what “want for your brother what you want for yourself” really means. You’re not just tolerating someone else’s presence. You’re genuinely hoping they get the same peace, the same reset, the same connection that you’re getting. That’s brotherhood. That’s what the cigar culture does at its best. Why wouldn’t you want to share a great experience with others? We all know that good experiences are better when shared. Cigars are always better shared with others.
Challenges in the Cigar Industry and Passions Beyond It
Cigar Life Guy: What’s the biggest challenge you’ve faced in the cigar industry?
Ali Howell: Getting people out of their comfort zone. People hesitate to try boutique brands. They stick with the big names, the old heads of the industry. But those big brands started small, too (unless they came from money). The challenge isn’t just about brand recognition; it’s about breaking through decades of consumer habits and loyalty. People have their go-to cigars, and asking them to step outside is asking them to take a risk on something unknown. I get it. But here’s the thing: you can’t call yourself a connoisseur if you only smoke one brand and know nothing else. A true connoisseur explores, experiments, and appreciates the craft across the board. Once someone tries a BSS cigar, they make it part of their rotation. The trick is getting them to pick one up in the first place. But when they do, they’re not disappointed. That first experience usually opens the door. I want people reading this to know that boutique cigars bring something special to the culture. We’re not just copying what the big names do. We’re bringing our own perspective, our own passion, our own story. Don’t be afraid to give us little guys a chance. You’ll be surprised at what we bring.
Cigar Life Guy: What’s one of your passions outside of cigars?
Ali Howell: My biggest passion is psychology. It saved me by helping me understand not just how but why people do what they do. It’s given me the knowledge to help others, and now I get to teach. It’s such a part of my life that I have to remember to turn it off sometimes. My wife will tell you I can’t help but analyze everything, even when we’re just watching TV. My second passion, which many people in the cigar world may not know, is that I’m a huge Star Wars fan. The original trilogy, before Disney acquired it. I’ve been a fan since I saw the first film at the age of six. There’s nothing more fun than being a Star Wars nerd. Smoking a cigar while watching Star Wars, that’s the best.
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Photo credit: Ali Howell