This episode of Clear the Air features the Simply Stogies crew reflecting on Matt Booth's transformative role in the cigar industry, from his bold Room 101 brand to his provocative marketing that redefined premium cigars. They discuss how Booth and similar trailblazers injected irreverent energy, driving innovation in blends and branding that elevated the culture.

James and Nick welcome Matt Booth of Room 101 Brand. Recorded LIVE for our Patreon supporters, Matt fields questions from them as well as discussing several topics with James and Nick. Matt talks about his time in the Marine Corps and how it shaped his career. Matt discuses being "on" all the time and whether or not it's a grind. Matt keeps James on his toes throughout the delightful and in-depth conversation.

Dive into the latest episode as the team unpacks the shifting buying patterns in the cigar industry—spotlighting who’s getting it right and who’s missing the mark. Explore the realities of rising cigar prices and the looming risk of pricing out loyal customers. Ever wonder what it means when sales are down but revenue is up? The crew breaks it all down, then brings it back to Dave and the appeal of Small Batch. Tim shares insights from a military mindset, drawing parallels to how Small Batch and Avowed approach the market compared to other industry players. It’s a candid, no-holds-barred look at the business side of cigars, and why some brands continue to stand out.

Dave West joins James and Nick to catch up on everything that's been going on throughout 2025. Dave addresses if the industry is seeing a slow down in sales or a shift in buying patterns. He tells us what he thinks it all boils down to. Dave tells us why some cigar shops are thriving and why others aren't. We discuss Avowed Cigars' growth and their plan for the future, how they find lounges to invite, and what Avowed has done in their inaugural year. Dave discusses cigar reviews, changing the game for the industry, and much more! Dave West is one of the most positive people in the industry. We hope you enjoy listening to this conversation as much as we enjoyed having it!

Tim, James, and Jimmy return to Clear The Air to unpack the latest Simply Stogies Podcast with guest Brian Desind of Privada Cigar Club, taking on free speech in cigar artwork and the myth that edgy designs are marketed to kids. They dig into Privada’s collectible info cards, debate the good and bad of gatekeeping in cigar culture, and make the case for why cooler-dors still deliver despite industry pushback. Stick around for bonus questions that keep the conversation candid and fun.

Join our Patreon and watch us record LIVE beginning Dec 2!

James and Jimmy welcome Privada Cigar Club owner and founder, Brian Desind, back to the podcast. The two catch up with Brian and find out what he, Privada Cigar Club, and the LCA have been up to. Brian discusses being passionate about cigars and the industry, as well as being good at marketing. Brian talks about working with factories and blenders as they are the true force and artists in the industry. Brian tells us he's more "seasoned" and how that's help him face some of the changes that 2025 brought to Privada Cigar Club.

James, Jimmy, and Tim opine on the recent news of How Bout That Cigar, a cigar media outlet, closing their business. What does this mean for the cigar industry? What is "cigar media?" Who's responsibility is it to define "cigar media?" The three give their opinions and thoughts on what all of this means for the industry.

Tim, James, and Jimmy return for another episode of Clear the Air to dive deeper into the last episode of Simply Stogies Podcast with guest Zack Van Ginkel of HDA Cigars. The crew dive into a range of topics from their conversation with Zack — including how brick-and-mortar shops can better support homegrown brands, why HDA chooses to maintain consistent pricing by avoiding discounts and sticking to MSRP, and what really separates micro cigar brands from boutique ones. Tune in for an insightful discussion on authenticity, brand identity, and the evolving cigar market.

James and Nick welcome Zack Van Ginkel of HDA Cigars to the program. The trio discuss how Zack and his business partner, Andray, got into the cigar industry. We find out that Zack is a good 'ole Iowa boy who is making his way in the cigar industry. We discuss Iowa retailers and retailers in general, we also find out about Zack's military background. Zack talks about working with James and Angela Brown at Oveja Negra and wanting to blend their own cigars that stand on their own. Zack then touches on milestones for HDA, the cigar industry, and retailers in general.

In this episode of Clear The Air, Tim, James, and Jimmy return to the microphone for another engaging discussion. This time, they take a closer look at the latest episode of Simply Stogies. Tim handles the intro and outro with a bit of self-deprecating humor. James and Jimmy step in to guide the conversation, diving deeper into the content and themes presented. The episode ultimately shifts into a thoughtful discussion about the need for greater transparency and knowledge across the entire cigar industry, from consumers to manufacturers. The hosts argue that fostering this openness can help the industry not only survive but thrive in the future.

With Nick Syris on vacation, James welcomes Jimmy Dailing to the show. In addition to being a reviewer at simplystogies.com, James announces that Jimmy is a new host at Simply Stogies Podcast. Jimmy also manages a brick & mortar called The Drawing Room in Davenport, Iowa. The duo discuss the cigar industry, cigar lounges, the proper etiquette while at a cigar lounge, cigar media, and much more. Join us in welcoming Jimmy to the roster of hosts at Simply Stogies Podcast!