Simply Stogies
A podcast for both new cigar smokers and veteran cigar aficionados.
Episodes
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.
The hosts unpack Booth's lasting impact, celebrating how his unfil...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 ...
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 th...
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...
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 "sea...
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 ...
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 ...
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 ne...
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...
Tim, James and Nick are back for another installment of Clear The Air, this time about Aaron Paoletta of LaVega Cigars. The three talk about creative types in the industry, the hardships in starting a new cigar company, and much more all at Tim's expense. James and Nick try their best to make Tim cry the entire time.
James and Nick welcome Aaron Paoletta of LaVega Cigars to the show. Aaron tells us how he went from culinary school, to chef, to music producer, to a heavy metal band, and then the cigar industry. We discuss LaVega Cigars, The LaVega lounge, the industry, and Aaron's views on all of it. We find out what skills Aaron brought to the cigar industry from each of his previous careers.
In an unusual episode of Clear The Air, Tim and James are back to dive a little deeper into the stories told by Sean Brown and Jillian Hinton of Dogs Inc from the latest episode of Simply Stogies Podcast. The conversation jumps through a few other key points from the episode including how service members may look at companies that say they are all about the veterans, cigar communities that support causes such as Dogs Inc, and much ...
James and Tim kick off National Service Dog Month by welcoming Sean Brown and Jillian Hinton of Dogs Inc. to the show. Jillian and Sean share their stories and how Dogs Inc. helped them during some of the toughest times in their lives. Dogs Inc. provides guide dogs, service dogs, therapy dogs, and companion dogs to gold star families and veterans who need them. Jillian and Sean tell us how Dogs Inc changed their lives and why they'...
Back to the microphones after last week's episode of Simply Stogies Podcast where Tim brings James and Nick back to the microphone to talk behind Zino Brand Ambassador, Law Ream's back. The three talk a little bit more about the Republic of Debauchery and how the industry really needs some more laughs. They spend time talking about the amount of time and effort it can take to produce such content. They end the episode with some con...
James and Nick welcome the Zino Cigars Brand Ambassador, Law Ream, to the show. The former host of the Republic of Debauchery talks cigar media and content creation. We pick his brain and get his thoughts on comedy in the cigar space, how news is covered, and his transition from content creator to brand ambassador.
James is holding Cigar Apocalypse in Livermore, IA at Smoldering Cigar so Tim has no choice but to find a replacement. Tim and Nick welcome first time guest host Jimmy who is not only a video reviewer for Simply Stogies but a lounge owner. Jimmy owns and operates The Drawing Room in Davenport, IA. Anyway, Tim, Nick, and Jimmy dive deeper into the discussion that Nick and James had on the last episode of Simply Stogies Podcast with ...
James and Nick welcome Les Mann from ST Dupont to the show. Les discusses how he came to work for ST Dupont and the challenges that came with it. We ask Les how he's developed the relationships in the cigar industry and the importance of trust with each of his clients. Les gives us his perspective of working with some of the big names in the cigar industry and beyond, what it's like to work with pop culture icons, the care and thou...
Tim brings James and Nick back to the microphone to discuss some of the topics that were discussed in the latest episode of Simply Stogies Podcast with guest Robert Caldwell of Caldwell cigars. Tim digs a little deeper into the back story of how Nick and Caldwell became friends before digging into the science behind how your cigars are presented to you in a humidor. They talk about LE's and Core Lines and how cigar enthusiasts choo...
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