How did The Cigar Guys start, and when did it go from a hobby to a podcast and media company?
The Cigar Guys started in April 2022, when we began sharing cigar content on TikTok. We were building Besa Cigars around that same time, so we were getting involved in the industry from both the product and media sides. We had a passion for cigars, a foundation of knowledge, and access to experienced people we could learn from.
On January 14, 2023, we launched our weekly podcast. That gave us more room for conversations, interviews, and the personalities behind the cigars. The dynamic between me, Jared, Mark, and Zach became a big part of the show.
The transition into a media company happened gradually. We kept showing up, publishing consistently, and expanding into articles, short-form videos, industry news, and event coverage. As partnerships and business opportunities developed, we started building the team and systems to support that growth.
Launching the podcast was a clear milestone, but becoming a media company came from treating it like a business every day. What started with a shared interest became a commitment to building something bigger.
You wrote The Cigar Guys' Ultimate Guide to Cigar Smoking. What did you want a beginner to take away from it?
I wanted a beginner to walk away feeling comfortable stepping into the cigar world. When you’re first getting started, the terminology, the selection, and even walking into a cigar lounge can feel intimidating. The goal was to make that introduction approachable.
Beyond the basics of choosing, cutting, and lighting a cigar, I wanted readers to feel confident asking questions and discovering their own preferences. You don’t have to pretend to taste everything someone else tastes, and you don’t have to buy the most expensive cigar to appreciate the experience.
For me, cigars have always been connected to conversation, relationships, and taking time to slow down. I wanted the book to give people a foundation so they could feel comfortable joining that conversation.
What is the most common mistake new cigar smokers make?
I’d say the biggest mistake is jumping in without taking a little time to learn the basics or asking someone experienced for guidance. A little research in the beginning can save you a lot of frustration, whether that’s learning how to cut and light a cigar, understanding its strength, or knowing how to pace yourself.
You don’t need to become an expert before you start, but don’t be afraid to ask questions. Visit a knowledgeable tobacconist and be honest about your experience level. That guidance can make a big difference in your first experience.
Who has been your favorite guest so far, and what did they teach you?
It’s very hard to pick just one, but if I had to, I’d say Alex Weghorn, National Brand Ambassador for Davidoff Cigars.
That conversation meant a lot for a couple of reasons. First, it was a subtle reminder that the work we’ve been putting in for years is paying off. Having someone representing a brand like Davidoff join us showed that larger brands take what we’re building seriously and want to be part of the conversation.
Second, Alex’s knowledge of tobacco history is incredible and it extends well beyond Davidoff. We recorded for over two hours, and we only stopped because we had to. We could easily have kept going.
The biggest takeaway was how much there is still to learn. You can spend years working in this industry and still sit down with someone who gives you a whole new appreciation for the history behind it. Those are my favorite conversations.
What is your go-to cigar and whisky pairing, and why does it work?
Shameless plug, but it’s true: ever since we released the Besa Maduro, my go-to pairing has been that cigar with The Macallan Double Cask 12.
I used to be more of a bourbon guy, but over time I’ve gravitated toward Scotch. My palate has come to really appreciate a great Scotch alongside a medium- to full-bodied cigar at the end of the night.
The Besa Maduro is full-bodied, with rich notes of cocoa, espresso, and mild spice. For me, those flavors balance beautifully with the sweetness of the Macallan. Neither overwhelms the other, and that balance keeps me coming back to the pairing.
How has cigar culture changed since you started the show?
Since we started the show, one of the biggest changes has been how visible cigar culture has become. Every year, we see new brands entering the market and more creators building content around cigars. There are more voices, more conversations, and more ways for people to discover the culture.
We’re also seeing cigars appear more frequently in luxury and entrepreneurial lifestyle content, especially on Instagram. People are incorporating them into conversations about travel, business, style, and taking a moment to enjoy what they’ve worked for.
What interests me is how that exposure translates into community. Someone might discover cigars through a lifestyle post, then become curious about the craftsmanship, history, and people behind them. That gives us an opportunity as a media company to take that initial interest somewhere deeper.
Millennials and Gen Z are finding cigars through social media. What do you make of that, and what do they get right or wrong?
I think it’s great that social media gives the cigar industry a platform for publicity and outreach, especially with paid advertising opportunities so limited. It gives brands and creators a way to tell their stories and connect directly with an audience.
Where I think too many creators get it wrong is feeling obligated to give a cigar a positive review simply because a brand sent it to them. Receiving a free product shouldn’t determine your opinion of it.
The foundation of The Cigar Guys was built on honesty and integrity. If a cigar is great, we’ll say so. If it doesn’t meet the standard, we’ll say that too—and explain why. There’s a difference between something not fitting your personal palate and something having an actual quality issue.
I’d like to see more creators be honest, even when the feedback is uncomfortable. Your audience needs to trust that your opinion is yours.
What makes a great cigar lounge in your eyes?
For me, a great cigar lounge starts with the people. You can have a beautiful space and an impressive humidor, but the staff and atmosphere are what make you want to come back. Someone walking in for the first time should feel just as welcome as a regular who’s been going there for years.
The fundamentals matter: well-maintained cigars, knowledgeable staff, comfortable seating, and good ventilation. I appreciate a team that listens to someone’s preferences and budget instead of automatically pointing them toward the most expensive cigar.
But what makes a lounge stand out is the sense of community. It’s a place where you can walk in by yourself, strike up a conversation, and leave having made a friend or a business connection. The best lounges give people a reason to stay and a reason to return.
Which cigar do you think is the most underrated on the market today?
I’d say Sans Pareil Cigars. Full disclosure: I represent the brand, so I have a relationship with them, but I also believe they deserve more recognition.
What stands out to me is the time and care behind the product. They work with Jochy Blanco at Tabacalera Palma in the Dominican Republic, with a process that emphasizes tobacco selection, repeated fermentation, and years of aging. There’s a lot of work behind what eventually reaches the smoker.
For me, that translates into complexity and balance. A cigar doesn’t have to overwhelm your palate to have depth, and that’s something I appreciate about Sans Pareil.
When I say underrated, I mean the recognition hasn’t caught up with the quality. I think they deserve to be part of more conversations about exceptional premium cigars.
What is the funniest or strangest thing that has happened while recording?
We’ve had a lot of funny moments, but the one that comes to mind definitely wasn’t funny at the time.
We were interviewing Steve Saka over Zoom and were about an hour into the conversation when a bad storm rolled in. We lost power… not once, but three times while trying to finish the recording. Thankfully, Steve stayed on the call and waited for us to reconnect every single time. He was incredibly patient about it.
By the third outage, we basically said, “We should probably wrap this up before the weather makes that decision for us again.”
Looking back, it’s a good laugh. At the time, we were just trying to keep the interview alive. We’re looking forward to a follow-up in person… hopefully with fewer interruptions from Mother Nature.
If someone could only listen to one episode, which should it be?
I’d point them to our episode with Miguel Schoedel. It’s one of our top-performing episodes, and I think that comes down to how engaging Miguel is.
He’s a walking cigar encyclopedia, but what makes him special is how he shares that knowledge. He draws you into the conversation and makes you want to keep listening and learning. It never feels like a lecture.
For someone who’s new to cigars or simply curious about the hobby, that’s the episode I’d recommend. It also gives you a great sense of what we want The Cigar Guys to be: entertaining conversations where you walk away knowing something you didn’t before.
What's next for The Cigar Guys?
We’ve been doing this for almost four years now, and every year the growth creates new opportunities. Honestly, sometimes I feel like I’m trying to keep up with our own expansion, but that’s an exciting challenge to have.
What’s next is continuing to build The Cigar Guys ecosystem. We have several projects in development, including a national cigar events page, daily industry news across audio, video, and written formats, and new partnerships on the horizon.
The goal is to give people more ways to connect with the cigar community. Whether someone wants to find an event, catch up on industry news, or sit down with us for a full podcast episode, we want The Cigar Guys to be a place they turn to.
I’m proud of what we’ve built, but I’m even more excited about what’s ahead.
