Cigar World WCW: Desiree Sylver, PhD Founder and CEO of Drunk Chicken Cigars

Welcome back to Cigar World for our next iteration of Women Crush Wednesday. In this exclusive interview, we sit down with Desiree Sylver, the trailblazing CEO and Founder of Drunk Chicken Cigars. Desiree shares her journey from hand-rolling cigars at home to building a nationally recognized company, all while breaking barriers in a traditionally male-dominated industry. With authenticity at the core of her mission, Desiree opens up about the inspiration behind the brand, her leadership philosophy, and the exciting future of Drunk Chicken Cigars.

Cigar World's Interview with Desiree Sylver, PhD Founder and CEO of Drunk Chicken Cigars

Jean: Desiree, thank you so much for taking the time today to chat with us. 

Desiree: Thank you so much for the thoughtful question—I appreciate the opportunity to share more about my journey and the heart behind Drunk Chicken Cigars. Your questions were insightful and made the experience feel like I am among friends, which I really appreciated.

I’m excited about what’s ahead and grateful to be included in your piece. Can’t wait to see the final article!

Jean: What motivated you to get into the cigar business, and how long have you been in it thus far?

Desiree: My journey into the cigar business started as a personal passion. I used to relax in my backyard with friends, enjoying cigars late into the night. Over time, I became more curious about the craftsmanship behind them. That curiosity led me to start rolling my own cigars, blending different tobaccos to create something unique.

What began as a hobby turned into something bigger when my friends kept asking for more of my cigars. Eventually, I realized I had something special. That’s when Drunk Chicken Cigars was born—right in my backyard, with a group of friends, a few cigars, and some chickens wandering around. The name came naturally from those moments, and it embodies the fun, unpretentious vibe I want people to feel when they smoke our cigars.

Now, more than five years later, Drunk Chicken Cigars has grown into a recognized boutique brand. We focus on high-quality, hand-rolled cigars that anyone can enjoy—whether you're a seasoned aficionado or just getting into cigars. Our motto, “Anytime if the Day Cigars,” reflects our belief that a great cigar experience doesn’t have to be reserved for special occasions—it should be enjoyed whenever you want.

Jean: I have to ask, why Drunk Chicken? I love it, but I feel like there is a story behind the name.

Desiree: This is a long story,…The birth of Drunk Chicken Cigars, LLC was a result of our friends and family gathering in our backyard, living the dream of good company, great food, and, of course, enjoying cigars together. Our backyard oasis was home to over a dozen chickens, our loyal dogs, and the occasional wildlife visitor. It was a place of tranquility and joy.  One fateful evening, during our typical Saturday festivities, something truly amusing unfolded. As we watched our chickens returning to roost, they seemed to stumble around in a manner that could only be described as drunk. We couldn't help but burst into laughter, witnessing their hilarious antics. It was at that moment that the name "Drunk Chicken" was born, capturing the essence of those lighthearted and unforgettable times.

Our backyard gatherings soon became known as Drunk Chicken events, and they grew in popularity. It became the go-to place for our friends and family to come together, a safe and welcoming environment where we could simply be ourselves. We established a simple yet meaningful entry fee for our guests: bring a cigar to smoke and another to share. This gesture sparked a quest among us to discover unique and intriguing cigars that none of us had tried before.

We embraced the spirit of adventure, always on the lookout for those hidden gems that would surprise and delight our palates. With every new cigar we discovered, the Drunk Chicken experience grew richer and more fulfilling. We knew we had stumbled upon something truly special. Driven by our shared passion for cigars and the desire to share our findings with others, we embarked on a new journey - the creation of Drunk Chicken Cigars, LLC. In October 2019, we officially launched our brand, eager to bring the essence of those magical backyard gatherings to a wider audience.

Our mission is clear: to create a selection of exceptional, one-of-a-kind cigars that ignite the same sense of wonder and joy we experienced in our early days. Drunk Chicken Cigars is more than just a brand; it's a celebration of friendship, laughter, and the pure pleasure of enjoying a fine cigar. We invite you to join us on this remarkable journey as we explore the world of cigars, one unforgettable blend at a time.  Welcome to Drunk Chicken Cigars, where the spirit of camaraderie and the pursuit of remarkable smokes converge. Let's raise our glasses and light up our cigars, for the adventure has just begun. Cheers!

Jean: What are some of the main objectives you have as the CEO/Founder of Drunk Chicken Cigars?

Desiree: As the CEO and Founder of Drunk Chicken Cigars, my main objectives revolve around growth, brand authenticity, and community engagement. First and foremost, I want to continue expanding our brand while staying true to what makes us unique—crafting premium, handcrafted cigars that offer an enjoyable experience for both seasoned smokers and newcomers alike.

A big part of my leadership philosophy is fostering a strong company culture. I strive to ensure my team feels empowered, valued, and passionate about our brand. As a leader, I believe in leading by example, maintaining a hands-on approach to everything from product development to customer engagement.

Another key goal is customer connection. Drunk Chicken Cigars started in a backyard with friends, and I want to keep that personal, approachable feel even as we grow. That means engaging directly with our customers, listening to feedback, and ensuring our cigars remain an ‘Anytime of the Day Cigar’—something people can enjoy without intimidation.

Finally, I’m focused on expanding our presence in the cigar industry by forging strong partnerships, increasing visibility in retail spaces, and continuing to innovate with new blends and experiences. I want Drunk Chicken Cigars to be known for its quality, authenticity, and inclusivity in an industry that’s constantly evolving.

Jean: And what are some of the largest hurdles you have experienced so far?

Desiree: One of the biggest hurdles I’ve faced as the founder of Drunk Chicken Cigars is establishing a presence in an industry that is deeply rooted in tradition. The cigar world is often dominated by longstanding brands, so breaking in and earning credibility required persistence, high-quality products, and strategic networking. I overcame this by staying true to our unique identity, engaging directly with consumers, and building relationships with industry insiders who respected our commitment to craftsmanship.

Another challenge has been scaling the business while maintaining quality. As demand for Drunk Chicken Cigars grew, it became critical to ensure our production processes remained consistent without compromising the boutique quality that defines us. To address this, I focused on working with skilled rollers, maintaining strict quality control, and implementing efficient production strategies.

Additionally, navigating regulations and logistics in the cigar industry has been a learning curve. From taxes to compliance laws, ensuring we meet all legal requirements while running a successful business required a lot of research and expert guidance. I’ve tackled this by staying informed, seeking legal counsel when needed, and making compliance a priority in our operations.

On a personal level, balancing leadership, growth, and brand authenticity has also been a challenge. It’s important to scale while still keeping that personal, approachable feel that Drunk Chicken Cigars was founded on. I’ve addressed this by staying hands-on with my team and customers, ensuring that no matter how big we grow, our brand remains connected to its roots.

Each of these challenges has been a learning opportunity, reinforcing the importance of resilience, adaptability, and staying true to my vision.

Jean: What are some things you are most proud of in your career?

Desiree: One of the things I’m most proud of in my career is building Drunk Chicken Cigars from the ground up. What started as a backyard passion project has grown into a respected boutique cigar brand with a loyal following. Seeing our cigars enjoyed by people across the country—and even internationally—is an incredible accomplishment.

Another major milestone has been breaking barriers in the cigar industry. As a Black woman entrepreneur in a traditionally male-dominated space, I’ve had to work hard to establish credibility and carve out a place for Drunk Chicken Cigars. Being able to inspire others and show that this industry is open to anyone with passion and dedication is something I take great pride in.

Additionally, I’m proud of the impact we’ve made on the cigar community. We’ve fostered a welcoming and inclusive brand that makes cigars accessible to both longtime enthusiasts and newcomers. Our “Anytime Cigar” philosophy resonates with people, and that connection with our customers is one of the most rewarding aspects of this journey.

On a personal level, I’m proud of my growth as a leader. Navigating business challenges, expanding operations, and maintaining a hands-on approach while staying true to my vision has been a learning experience. Being able to create jobs, mentor others, and see my team thrive is incredibly fulfilling.

Overall, my career has been defined by perseverance, innovation, and a commitment to excellence, and I’m excited for what the future holds for Drunk Chicken Cigars.

Jean: So tell us a little bit more about you, not just CEO/Founder Desiree, but let us get to know you a bit more.

Desiree: Sure! Outside of being the CEO and Founder of Drunk Chicken Cigars, I’m just Desiree—someone who loves a good laugh, great company, and, of course, an excellent cigar. My journey into the cigar industry started as a passion, but before that, I had a completely different career path. I have a background in contracts, and finance several decades years working in the government sector, which surprises a lot of people when they first meet me. But at my core, I’ve always been someone who loves to create, build, and bring people together.

When I’m not running Drunk Chicken Cigars, you’ll probably find me relaxing with a good smoke, enjoying great food, or traveling to explore new cultures. I love meeting new people and learning about their stories—it’s one of the best things about being in the cigar industry. Cigars bring people together in a way that’s special, and I’ve been lucky to connect with so many incredible individuals along this journey.

Not to sound like a broken record, I also have a soft spot for animals, which is why Drunk Chicken Cigars has such a unique name! The brand was inspired by the free-roaming chickens in my backyard, and their carefree attitude perfectly embodies what I wanted for the company—something fun, unpretentious, and welcoming to everyone.

At the end of the day, I’m just someone who believes in working hard but also enjoying life. Whether that’s through a great cigar, an interesting conversation, or just taking a moment to appreciate the journey, I try to embrace every part of the experience. I hope that when people enjoy a Drunk Chicken Cigar, they feel that same sense of relaxation and connection that sparked this whole adventure for me.

Jean: What is your favorite cigar to smoke right now, and what do you like to pair with your smoke?

Desiree: Absolutely—I'm right there with you! Pairing is such a personal experience, and honestly, it changes with my mood, the time of day, or what kind of vibe I’m going for.

Right now, I’m really enjoying The Mother Clucker. It’s bold, flavorful, and has just the right amount of complexity to keep me coming back to it. It’s the kind of cigar that demands your attention in the best way possible. When I smoke it, I like to pair it with a good dry red wine or a great bourbon—something with a rich, oaky finish that complements the strength of the cigar without overpowering it.

But I’ll be honest—I love smoking the entire Drunk Chicken lineup. Each blend has its own personality, and I enjoy switching it up depending on my mood. Some days it’s the Original, smooth and mellow; other times it’s the Fat Hen for something more playful. I think that’s the beauty of our brand—we offer variety without sacrificing quality.

At the end of the day, my favorite pairing is all about balance and vibe. Whether it's coffee, wine, or whiskey, if it enhances the moment and the cigar, it's the perfect match.

Jean: Do you have any blue sky goals that you are hoping to achieve over the next ten years with Drunk Chicken?

Desiree: Over the next ten years, my vision for Drunk Chicken Cigars is bold and expansive. I want to see the brand grow into a household name in the cigar industry while maintaining the authenticity and quality that have made us successful.

Another major goal is to expand internationally, making Drunk Chicken Cigars available in more markets worldwide. We’ve will continue to build a strong following in the U.S., but I see potential to reach cigar lovers across Europe, Asia, and Latin America. This would involve strategic partnerships with international retailers and distributors who share our passion for quality and accessibility.

Beyond just business growth, I also want Drunk Chicken Cigars to have a lasting cultural impact. I want to continue breaking barriers in the industry, showing that boutique cigar brands—especially those founded by women and minority entrepreneurs—can thrive and lead. Through mentorship programs and partnerships, I hope to inspire and support the next generation of diverse voices in the cigar world.

Ultimately, my blue-sky goal is to cement Drunk Chicken Cigars as a legacy brand—one that is recognized not just for great cigars, but for fostering a movement that embraces community, inclusivity, and the sheer enjoyment of a well-crafted smoke. The journey so far has been incredible, and I’m excited to see where the next decade takes us!

Jean: Are we going to see the chicken mascot (tell me know the name if there is one please) at PCA? It is always one of my favorite booths to visit because of the fun atmosphere. 

Desiree: Unfortunately, No, our beloved mascot, Cooper, will not make it to PCA 2025 trade show! Cooper has been an integral part of our brand's identity, embodying the fun and welcoming atmosphere that Drunk Chicken Cigars is known for. 

We're thrilled to hear that our booth is one of your favorites, and we're committed to bringing that same lively spirit to PCA 2025. This year, we're especially excited to introduce The Henchman, a bold new addition to our lineup, which will be exclusively available at the event. 

Be sure to stop by Booth #2126 to meet Cooper, experience our latest offerings, and enjoy the vibrant atmosphere that makes Drunk Chicken Cigars stand out. We can't wait to see you there!

Jean: And anything you can tell us about any upcoming releases/launches?

Desiree: The Henchman is a bold, full-bodied cigar created as a PCA 2025 exclusive release by Drunk Chicken Cigars.

Wrapped in a smooth Connecticut leaf, this cigar breaks tradition—offering a surprisingly robust profile thanks to its double ligero filler. While Connecticut wrappers are often associated with milder smokes, The Henchman delivers unexpected strength and complexity, making it a standout in any humidor.

Crafted for cigar lovers who enjoy a powerful and flavorful experience, The Henchman is bold, unapologetic, and unforgettable—just like a true henchman should be.

Jean: Since it is March, I would love to get your input on how you feel about women in the cigar industry. Let’s call it the glows and grows. Where do you feel we are doing well, and where can we get better?

Desiree: I love that—the glows and grows. It’s such a powerful and honest way to frame the conversation.

The glows: Women in the cigar industry have truly been making their presence known, and it’s inspiring. I love seeing more women confidently walking into lounges, owning cigar brands, leading events, and shaping cigar culture with authenticity and passion. We’ve created spaces where women don’t have to shrink themselves to belong—we're bringing our full selves, from our style to our knowledge, and earning the respect we’ve always deserved. Communities like Sisters of the Leaf and more female-led boutique brands are proof that we’re not just participating—we’re leading.

The grows: That said, we still have work to do. There are still pockets of the industry that hold onto outdated perceptions of who a “real” cigar smoker is, and sometimes women have to work twice as hard to be taken seriously. We need more representation at the top—more women in executive roles, more female blenders and rollers being celebrated, and more brands collaborating with women not just as influencers, but as industry partners.

The future is bright, but we get stronger by continuing to support one another, advocate for inclusion, and push the industry to evolve with us—not around us.

Jean: Do you have any dream partnerships for Drunk Chicken Cigars?

Desiree: I’m incredibly proud of the partnerships Drunk Chicken Cigars has built so far—they reflect who we are as a brand and where we’re going. Our collaboration with Boveda has allowed us keep our cigar fresh,  pairing Boveda in our packaging I can relax knowing our premium cigars will maintain its quality. Red Phone Booth has been a beautiful fit, aligning our sweet-tip blend with their upscale, speakeasy vibe. The exclusive Red Phone Booth Sweet cigar is one of my personal favorite collaboration.

At Underground Cigar & Lounge in Forth Worth, TX, we’ve found a true community that supports boutique brands like ours. We were honored to create the Chef an exclusive cigar only found at the Underground. And City of Palms Cigar Distribution has been essential in helping us scale—ensuring our cigars reach lounges and shops across the country.

Looking ahead, my dream partnerships are simply with people and brands who value authenticity, quality, and connection. Whether it’s pairing cigars with premium spirits, collaborating with chefs, or expanding our presence in luxury lounges, I want Drunk Chicken to continue building experiences that bring people together over a great cigar.

Jean: Thank you so much for taking the time to chat with me today! We are excited to see what the future holds for Drunk Chicken, and for you! 

Make sure to support Desiree in Drunk Chicken on their social channels @drunkchickencigars and on the web at www.drunkchickencigars.com