Episode 100!!! Secret Special Guest Matt Booth 101 Cigars

Episode Summary

For the 100th episode of A Cigar Hustler's Podcast, the hosts sit down with Room 101 founder and designer Matt Booth for a loose, freewheeling, often profane conversation about the state of the cigar industry. Booth, in the middle of a podcast media run, opens with a candid look at the manufacturer/retailer relationship — why "mutual support" (his running "reach around" gag) has to flow both ways, why products don't sell themselves, and how big accounts like Smoke Inn or a department-store partner such as Nordstrom each demand a different kind of attention. He and the hosts also debate Abe Dababneh's philosophy of stocking whatever the customer asks for versus a retailer's obligation to educate consumers on boutique blends.

The heart of the episode is Booth's history of the boutique movement. He describes the "golden age" of boutique cigars around 2008–2009, when he was working at factory level and launched the original Room 101 line, followed by what he calls the "Ed Hardy era" — a flood of name-on-a-band brands that eroded retailer trust in anyone who looked like them — and now the "nuclear winter" of FDA uncertainty and market oversaturation. He pushes back hard on the word "legacy," arguing only houses like Fuente and Padrón truly earn it, while joking that Room 101's revived Big Payback qualifies as a "legacy sub-brand." Booth also explains his move away from Caldwell distribution to self-distributing with logistical and infrastructure support through La Palina, insists he and Robert Caldwell remain friends and collaborators, and shares why genuine collaborations produce cigars that taste like nothing either maker would build alone.

The back half turns personal. Booth talks about four years as a Marine machine gunner in 3/7 India Company, how enlisting was a deliberate "vicious rearrangement" of his life, and the toll road life takes on time with his young son. He traces Room 101 from men's jewelry into cigars and spirits, inspired by his obsession with Alfred Dunhill's 1920s luxury lifestyle model, and gets into the technical side of jewelry design using ZBrush, Maya and Rhino. He closes with the now-legendary New Orleans blackout story — waking up in an alley with no wallet, glasses or memory, a kind cab driver, a sales rep named Duke bailing him out of a bar, and a standing ovation at the Room 101 sales presentation hours later — plus a nod from Jerry Catrone that he's now "Matt Booth 4.0." The episode wraps with the hosts and Booth sipping Casamigos Añejo and teasing that the conversation continues in Episode 101.

In This Episode

1. 01
   Manufacturer and Retailer Reciprocity
   Booth argues brand-building requires mutual investment from both maker and retailer, and that boutique cigars don't sell themselves without shop-floor education.
2. 02
   Servicing Big Accounts vs. Boutique Shops
   Why large retailers like Smoke Inn and department-store partners such as Nordstrom require the same level of attention as a major chain, and a friendly disagreement with Abe Dababneh's stocking philosophy.
3. 03
   The Golden Age, the Ed Hardy Era, and the Nuclear Winter
   Booth's timeline of the boutique boom from Room 101's 2009 launch through the flood of vanity brands that burned retailers, to today's FDA uncertainty and market contraction.
4. 04
   Who Actually Gets to Call Themselves a Legacy Brand
   The hosts and Booth debate the word 'legacy,' landing on Fuente and Padrón as the real thing while joking about Big Payback as a Room 101 legacy sub-brand.
5. 05
   Leaving Caldwell Distribution for Self-Distribution with La Palina
   Booth clarifies he didn't jump ship but moved to self-distribute with logistical and infrastructure support, and remains friends and collaborators with Robert Caldwell.
6. 06
   The Case for Real Collaborations
   Booth compares co-branded blends to writing music with other people — if everyone genuinely participates, you get something none of them would have made alone.
7. 07
   Marine Corps, Fatherhood, and Life on the Road
   Four years as a machine gunner in 3/7 India Company, why he enlisted to rearrange his life, and the cost of trading days with his four-year-old son for sales trips.
8. 08
   Room 101 as a Luxury Lifestyle Brand
   From hand-sculpted jewelry to ZBrush and Rhino design files, Booth explains his ambition to build the Alfred Dunhill of 1920 for 2020 across jewelry, cigars and spirits.
9. 09
   The New Orleans Blackout Story
   Booth recounts waking up in an alley with no wallet or glasses, piecing the night together from friends' accounts, and delivering the Room 101 presentation hours later.

Brands & Cigars Discussed

Linked items are in our shop. Mentions without a link aren’t currently stocked or couldn’t be matched with confidence.

Transcript

Welcome to the 100th episode of a Cigar Hustlers podcast with our secret special guest, Mr. Matt Booth. We've made it. We're also the number one show.

So sit back and relax. And here it comes. Mike, Mike, Mike, Mike, Mike, Mike Squared, Mike Squared, Mike Squared, Mike Squared. Let's go.

Here it is. We're missing out on all this. Here it is. We can revisit that subject as well, I think.

Because I think it's very interesting. You know, because I was addressing something initially from the manufacturer's standpoint, but you also, but you brought it into. We brought something I think very pertinent to the retail side as well. Yes, yes.

So we were having, it was like a conversational coitus. It was reciprocal. Right. Reach around.

It's deep, yeah. It's so deep. I felt a little dirty watching it. I do.

I enjoy a reach around because it is in the truest spirit of partnership. This is an activity in the spirit of true mutual benefit. Yes, I agree. This is how I treat all my retailers.

With reach arounds. Reach around. Full. Is there a number, or it doesn't matter, like a box, like how many facings is it?

Just a bundle? What's the requirement there? I just had a savage case of deja vu right now. Yeah?

With this reach around conversation. Really? Yeah. Energy of the universe is upon us right now.

Oh, I like that. I believe that. That's fantastic. Maybe it's just the headset.

Well, as we kind of get going. Welcome to episode 100 of Cigar Hustlers Podcast. Are we recording with the camera? Are we going to do the thing where we stop?

Are we gonna do that, or is that not gonna occur here? With what part? He wants to be 100 and 100. We're not gonna do that?

Oh, so fuck me. That's cool. No, it's good. I'm glad my input was taken.

This is my show, goddammit. You can't just come over and run things. You're right. It's actually Palmer's show.

My apologies. I'm just here, you know. I retract. I retract for this.

For one facing. Yes. Big payback. The payback.

The $6. I have a big payback! Our special guest here is Matt Booth today. The real one.

Yes. Bitches. He's on a media tour. I mean, ish.

You know. Are you getting caught up with this shit yet, or what? It's ruining my life. Yeah?

Actually, no. Oh, the reach-around. No, I actually enjoy it, man, because, I mean, okay, so, all the funny business aside for a second, I very much appreciate and enjoy this because it's critical for me to get my message. That's a huge challenge out there, man, and you know, it makes, this is what makes that happen, so I appreciate this.

Yeah, well, thanks. Oh, I mean, you know, the one cool thing about, no, it's definitely not serious, is like, you know, the Kiss My Ash one that you did, that was definitely off the fucking wall, totally unorthodox for what they normally do, and then you did the Cigar Obsession, those are the two that, have you done other ones this week? Well, last week they aired The Lounge Experience also. Oh, the two young ladies.

Yes. Up in Chicago or something? Yeah. And I think all of these, and to identify them as well as you guys, I think that there's a certain cluster of folks that are all doing their part to really generate more momentum, energy, and awareness for our community as a whole.

And everyone has their own little spin on it. And so their shows take on their own individual personality. Yes, I was going to say this is definitely different than what you've done. It's a very different, I like.

Yeah. Oh my God, I'm so nervous, how's it going to be different? I don't, I have no idea. But I can tell you that it's not like, so how'd you get, what'd you do for a living, and shit like that.

It's more, I mean, what's really cool. I'm so nervous. Is I, I have the opportunity to kind of, I'm a little bit of everything. I don't, I don't do well.

So I obviously do retail, I obviously do online retail, and I obviously do wholesale. So, you know, pornography. Right. And porn.

So I, you know, I have my hat in many things. And, um, we haven't even addressed my shirt yet, I mean, jeez, we're just like, I saw it last week, yeah. You need that bang. This is my official bang shirt.

Oh, such an effervescent beverage, full of, what is it, it's, look at the top though, the one, and I, and I ingest this product myself frequently, but if you look at the top, it's talking about the, the amino acids and the, but, but wait, there's one that I very much enjoy, just pull it around. The cock ten? Keep, keep turning. The cock.

It's cock. It's just cock ten. That's it. I'm like, for real?

I'll take two. I'll drink. I'll drink it. It sounds invigorating.

How much cock is in this can? It's amazing. But it's almost French and fancy with the C-O-Q as le coq. It's nice.

So we have a pretty good relationship with Bang, even though I said that the birthday cake tastes like diabetes. I mean, for real though. Yeah, it's super, very, very sweet. " They're like, "Hey, really appreciate the support.

" Did I say bad things for me, wouldn't it be a problem? So yeah, we were talking a little bit about industry jive prior to, and like, you know, one of the things that you were talking about on Kiss My Ass Radio was the fact that, you know, Abe's like, "Hey, you know, I'm not going to bring in products. I'm in the service business. " And I don't entirely agree with that statement, you know, and I don't believe in dealing in absolutes.

Well, you know, I agree with that as well. Now, the one thing I will say about Abe's store that I've always understood it to be in respect, So we deal with shameless self-promotion. We've dealt with Nordstrom as a retail partner for about five years. And the larger the machine, there become different ways that you have to attack it to make sure that your merchandise effectively pulls through.

And I look at a chain like Smoke Inn and you really have to give it the level of attention that you do to a department store. It's just a larger animal, you know. So I do understand where he's coming from piloting an entity of that scale, you know, but at the same time... This is like Attorney Matt, we're getting the official diatribe of...

Very happy for the opportunity. Thank you very much. I'd like to thank my mom. Thank you.

Thank you. Hi, mom. My mom thinks I'm... well, she thinks I'm crazy.

She does, yeah. She loves me. I wonder why. You can't see it at all.

She's the best. But Abe, he's obviously really good at what he does, and he obviously has his own kind of mindset, and yeah, Big Delicious, or whatever the hell you call him. Oh my God. Big Delicious.

It's kind of weird. Just juicy. Whatever. Yeah.

Oh, that's weird? That's weird. That's weird. I'm just checking.

I'm just checking. It's cool. Shit, what the hell were we just talking about? No, no.

Abe's big and juicy. I believe in that to a certain degree. I just don't believe in an absolute equation. Absolutely.

No, no, 100%. You know, it's like, hey, I just believe in educating consumers on different products and, you know, kind of holding them by the hand and saying, hey, you know, you really should try this, you really like this, right? You know, you ever heard the saying, it ain't gonna suck itself? Yeah.

Okay, so it ain't gonna sell itself either, all right? It's just not. And there are certain products that do, genuinely. The baccarats, the big payback, things that organically pull off the show.

No, no, for real, right? And then, you know, you also have this cachet, this bevy of these beautiful artisanal products that are all very different from one another, and made by people that genuinely care about what the fuck they're doing, down to like a myopic level, and so you, you know, it's not, I guess your job is whatever you want to make it to be, but at the same time, like, if you want to educate and endear these products to your people, your folks, your kinfolk, your kinfolk, as they come into your your retail location, you know, it's going to take a little bit of, it ain't going to sell itself. It ain't going to sell itself. It ain't going to sell itself.

And it ain't going to suck itself. It ain't going to suck itself. Viva low. You're a move, Patrick.

I've been telling them all week, this is not taking care of itself. So just one room for you guys? It's so lonely on the road. Dude, it's tough.

I don't know how, you know, I don't know how anybody does it, to be honest. The fucked up reality is legitimately every day I'm out here, I'm trading a day with my son. Yeah. I genuinely am.

How old's your boy? He's four and a half. Okay. Oh, wow.

That makes it hard. It makes it very challenging, man. And look, it's rewarding to be active in a business where I genuinely feel part of the community and people actually care. Right.

But then, you go out on the road and, you know, just, you sit down with someone and say, well, you know, Roma Craft is giving me 25% off, and Foundation is giving me 150% off, and what do you do for me, Matt Booth? And I'm like, so, this is very good for you, your relationships must be forged, if you forge these relationships to where these people will accommodate you in such a fashion. It's a very interesting model. Maybe I'll just send you some boxes and a check for a G and we'll be cool.

Yeah, but so how many of those guys do you think are actually full of shit, though? All of them. All of them. Yeah, that's a fair statement.

But you have to tell them they're full of shit in a nice way because then you get into, you know, the other conversation. Right. I just tell them to go fuck themselves. I kind of do, but I do in a comical fashion.

But you do it so much nicer than me. I'm like bluntly. " And I'm like, "You know what, dude? This is a waste of my fucking time.

" And I go, "Mike, get the car! " I do it with intelligent, yet biting humor. I've been kicked out of worse places than this. Come on, Tal.

" What did he say before you left? " So, do you think that some retailers are a little bit more resistant on taking on some of the boutiques because of the fact that some of the boutiques that have been created in the past weren't necessarily really good cigars? Dear God, where do I start? Okay, I was very fortunate to be active, becoming active in this business at a period of time that I consider to be the golden age of the boutique game.

Okay. And this is when it was fresh and new and there were bunny rabbits and daffodils and flowers and--oh, yeah. What were your era issues? We dropped Room 101, the initial product, in market in '09.

Okay. And I was working at a factory level from '08. Okay. Right?

To develop that. So the game was changing and that trend wave was beginning to rear its head, to cascade. And this is gonna dovetail into what is to become the answer to your question. Yes.

You have to remind me what the question was, because I started rambling a bit and all that. He's got to bring him back. But this, as everything does, becomes a trend. Yeah.

Okay? There's the trend makers, and then there's the trend takers. Right. And so then this metastasizes into what I then call the Ed Hardy era of the cigar business.

Ooh. Where everyone had a cigar... well they they probably you know some of them i would imagine had some bundles they got off ci and then printed some bands at kinko's and put them on them but they surely had a cigar with their name on it and and so but what this does is you know you're dealing with people of varying levels of capability right to in in well i mean in every uh in every way possible you could imagine But some of these guys can't support you, because to go back again, reach around, must be reach around, must be mutual support on both sides of that retailer and manufacturer equation. So now confidence and trust is shaken and begins to erode, but not just with Vendor X, with anyone that looks like Vendor X.

C. area, and the retailer shall not be named because this is my joyous moment that I share with people. I could figure this out. I could start rattling names, but I won't, I won't.

So, I'm with my dear friend, Joe Holtman, cigar industry legend, and this was years ago, and he's, you know, he's having a phone conversation in the car, and we're driving, you know, And, you know, he's talking about a retailer that I happen to notice in my notes because I do keep notes, I do, you know, actually have some method to this madness. You write that down? Write that down. Write that down.

" And he said, "Oh, no, man. No, no, no, no. " And I'm like, well, okay, well, tell me why, what happened, like, did something happen, or, he's like, oh yeah, yeah, yeah, no, he hates John Huber, and I said, well, Joe, what the fuck does that have to do with me? And he's like, exactly, and I was like, cigar business.

This is quite possibly one of the most amazing, and I love John, shout out to you, I love you, and he knows it, because I called him about this, and I was like, do you know the conversation I just had, Jay Hube, you're Why are you fucking up my flow out here, Ben? As a joke, right? Right. But any guy that, you know, any tattooed white guy was just not happening in that shot.

Right. That's insane. Because they had some sort of, I don't know. You look nothing like him, though.

I've been called John Huber many times. Really? And by the way, many people enjoy my Monsters series. They do.

And I say, no, no, no, no, I'm not, I do some of his stunts in the more aggressive scenes, but I don't, it's not me. Yeah, it's like, hey, you're a lot shorter in person. But I, but I graciously accept, you know, all compliments, you know, I do. So to get back to the question.

Oh, dear God, what was, what was the question? What the hell was the question? So you, I mean, you, so the whole boutique thing, retailers being burned. Yeah, I think, I think that that, you know, there was this, this chain of events that led.

Do we need something on his bracelet? Is it echoing? Oh, here, I'll just take it off. No, no, you're all right.

Just a little jingle jingle. Yeah. Okay. Oh, jingle jingle, baby.

I noticed you're looking. I was like, oh, he's peeping my link. But then it was an audio thing. And I'm like, oh, no, I feel-- He can't even hear it either.

He's like, he's looking at me. This dude wants me. And then I was like, oh, no, I'm making too much noise. So, yeah.

And then now we are in what I call the nuclear winter of the cigar business. The nuclear winter? Okay. Yeah.

And look, man, there are all these things coming at us from every angle, right? The gray, the, the, the giant gray cloud of uncertainty surrounding FDA, there's things that we absolutely know, there's things that we're just kind of figure out as we go, and they don't fucking know, of course they don't, right, but they're making the rules as they go, so they hold all the cards, right, and that's true, and then you have the fallout from the supersaturation of the boutique-esque type products, right, which, I mean, look, the, the guys that were active in the beginning are typically the ones that put down their tent pegs, right, in, in the, in the, in the. Soil of longevity. Sure.

Got my tent peg in there. 2009, what do you know about that? I love going into humidors because like as a designer first, you know, you see, like I love to go into humidors and I'll look at products and I'm like, you stole that from Jonathan Drew. Right.

Didn't you? You know, 'cause you recognize the authentic plagiarism or the plagiarism of authentic design genetic, if you have that eyeball, you know? You know, and I mean, I've kind of been going a little ham, I would not normally behave this way, I'm a little more reserved, as you can tell. Yeah, you're holding back, that's cool, I appreciate it.

Yeah, I do, I do, I, you know, but I also monitor what I say. Right. First of all, sometimes, I, right, but I like to be-- If there's a mic in front of you, you're gonna monitor what you say. Well, first of all, I just simply like to be respectful of whomever I'm talking to, right, and if they're gonna dislike me, I'm gonna earn that.

It's not just gonna be some-- This guy's a dick. Yeah, some whim, you know, it's going to be genuine, like, oh, fuck Matt Booth, like, I genuinely, he's given me enough substance, I know I dislike him. Right. I'm just a barrel of disappointment, just whisking around the pit.

I mean, I think some of the mainstream shit's falling off, too, big time, you know. Well, it's all falling off. I see a lot of these guys are kind of hitting the panic button, you're starting to see scale back in production in Nestle, and you're starting to see the, like, I've seen reps adamantly ask, hey, is there anything you can buy right now because, you know, I really could use it. Yeah.

Right, yeah, exactly. Take three more boxes. Like that type of thing. So.

Bro, it's insane. Yeah. There's a lot of... I'm sorry, I cut you off.

No, you're good. I feel like I'm giving... I just, I'm so... Take it over.

It's your show. Oh my God. I really like it when I can just kind of lob it up and just, I'll just sit back. Well, I mean, look, this is the most hostile.

Now look, I'm junior to many in the business, but now I'm senior to many as well. And I might also add, people have come and gone in my time. And that happened like with the blink of an eye. I remember when I was the most junior dude in the business, running around trying to introduce, I very much like the cigar, by the way, introducing people to our brand, right?

Oh dear God. So you're having a Baca, I'm having a Room 101 Forrest Maduro. I am Baca. Just to kind of slide that in.

Baca. Is it Baca? Or is it Baca? Is it Baca?

I think it's Baca. Can it be Baca? It can be whatever you want. I like it very much.

I like Baca better. Whatever name you want. I very much am enjoying this Bacá, and I enjoy it, and it is very tasty, and I like it. I'm a fan of the factory, so it's good stuff.

Oh, the sponsor to the show. Kind of. I'm a fan of Morris Day and The Time. Nice.

And many other characters. Oh-wee-oh-wee-oh. Yeah, man. It's amazing.

You know what I think is kind of fucked up, too, though? So you're seeing a scale back on, I think, in production, especially from the mainstream brands, But like, who, why did they get to call themselves legacy brands? Which ones? Who said that?

The kind of, in general, you know, if they've been around a long period of time, they get to drop this legacy brand. It's like, and for me, I kind of find that insulting, because like, legacy brand does not, it sounds way fucking cooler than boutique. Way fucking cooler. And the fact of the matter is that I think that some of the smaller production manufacturers are making better cigars than a lot of these mainstream fucking companies.

Well, because there's finite attention to detail, a more monitored level of production, an intimate level of production. You know, all of these things add up to the ability to simply make a better product. Right. You're making a lot less of it.

I just don't think it's fair. Well, so the big payback would be a legacy sub-brand of Room 101. Now, why? Because I've, you know, the brand has been established a certain amount of time.

Right. And that's a sub-brand that's been active, and then less than active, and then revitalized, and relaunched. I consider that to be a legacy sub-brand under Room 101. Gotcha.

But I wouldn't call Room 101 a legacy brand. No. No. Just the payback.

I call it a goat rope. A fucking goat rope. A goat rope. With a legacy sub-brand.

But, you know, and then you have like, you know, La Polina is an example, that's a family, It was started by the gentleman that owns the company, his, you know, one of the forefathers of his family, great-grandfather. I mean, you know what I'm saying, so that is a legacy brand. I believe that that would be a valid-- - It just doesn't feel right to me. - Like, nothing can be a legacy brand.

- I just feel like-- - Nothing. - Like, we shouldn't be called Boutique. If you're gonna call, you know what I mean, like-- - What about Salon Boutique or not Boutique, it's not-- My brand's a salon brand. It's not a boutique.

It's a salon. It's the industry's first salon. It's been-- It's a male barber shop. It's salon.

It's actually been the-- because we innovate and disrupt, and all those other terms that the big corporate marketing guys like to jack each other off with in their offices during their meetings, we do all those things, but we do them actually authentically with soul. And, you know, we are-- and have always been the industry's-- With some form of KY. Yes. If it's available.

If not, you spit, you know. Let's get it done. We are adults here. So, you know, oh dear God, why am I, oh, you know what it is, I'm just, I'm just so nervous.

I like, you're a little nervous, it's fine, it's cool. Well, I mean, I'm just a little, I'm keep, I have so much information that I feel like I want to give. You do. You do.

Like bubbling over. And I'm just kind of like jumping quickly to one, one question to the other, but I have a, I have another great question. You did stay on the microphone. Did that sufficiently cover that topic?

I feel like, yeah, but we, you know, we, we don't agree on it to some degree, but I just don't feel like, They're like, I don't know, it's just legacy, to hear some of these brands call themselves legacy, I'm just like, bro, you haven't made anything relevant in the past decade, you know, like, you're not legacy, so. Yeah, there's a difference between old and stale and legacy, right? Right. Yeah, no, 100%.

Like, I mean, in my opinion, Fuente's legacy, right? Yeah. That was actually one of the first that came to mind. Right, that's a brand that qualifies in that term.

Padrón? No doubt. Padrón, absolutely. So, I think we're on the same frequency with this.

Right, so then there's those two. And then, nobody else. So, you know, recently, you're obviously close friends with Caldwell, and you guys are doing distribution together, but you quit distro with him and you jumped into La Polina. That's correct.

So, what the, why? Well, it wasn't necessarily a jump into another company, it was a move to self-distribute our products, with some support on the back end, related to infrastructure. Okay. Yeah, and logistics.

So, some logistical support, some infrastructure support. So you felt that La Palina would just be a better pair? You know, Caldwell want more money or something? Yeah, all right.

There was waterboarding and hazing at their offices. No, no, look, the Caldwell family, they conduct business in a very human fashion, and I'm like-- He's a great guy. He's amazing. Look, they all are, and they've all become very dear friends of mine.

You know, my friendship with Rosewood predates his activity in the cigar game even, you know, we met one fateful afternoon at the first and only one ever to be Honduran Cigar Festival, up by the big Jesus in Donnelly, no, no, no, no, Tegucigalpa, above the airport, that big Jesus. How long ago was that? It was a hot minute ago. A hot minute.

I want to say 2009. Yeah. Or very early 10. Whenever they had the Umo Jaguar Festival, 'cause they didn't want to call it the Honduran Cigar Fest.

It just doesn't have a ring to it at all. So, but like, you parted ways on good terms. There was no... We didn't really part ways.

I mean, we're still as good of friends as we always have been, and we're going to continue to work on distributing our existing collaborative products as well as developing more. Right. We're talking about developing more. Now that was another thing that you guys brought up at KMIA that kind of was weird for me, so like you were talking about collaborations, and like collaborations are a way, Caldwell said, argued the point that collaborations are a way to get more product into the store, you know, because Ellie's got kind of stale, or yada, yada, yada, but you guys do a lot of collaborations anyways, right?

So it's not a bad thing. Not at all. Back in the day, before anyone other than the face-off, right, we remember this product from back in the day? Other than that, no one, to my knowledge, now, I may have that fucked up, and please correct me.

We don't back check on it. We don't back check. Everything's true here. It's all accurate.

No one had ever made cigars before the big payback. That's too strong, right? It seems legit to me. All right, good.

You can just go with that. Allegedly. Yeah, allegedly, we always throw allegedly. Excellent, excellent.

You know, I had approached Sam Lucia to collaborate with me. And at the time, I had just gotten started, you know, and I was, I was, you know, At the time that I started, I was traveling aggressively to meet people, like I said, and introduce our brand of folks, and I was like in his dust trail, like I'd go into a store, I had four facings I was trying to sell people, and, you know, they'd mention that, you know, Sam was just here, he sold 75,000 boxes on Saturday, and I was like, is this Oliva Day or post Oliva? This was Oliva, yeah, yeah, and so, you know, and he, and he had been, you know, one of the first guys to be, you know, somewhat kind and accommodating to me, you know, when I came into the game, and so we had developed a friendship, and I, and I hit him up to, to create some sort of co-branded thing. He worked with a large company, and there was politics involved, so it didn't materialize, but I always felt like a collaborative product would be of interest to folks, you know, and now it's just, again, you know, it's the Ed Hardy era of the collab game now, right?

So the trend comes, it's hot, it's pop, and people jump on it, and then the Johnny Come Lately's come and swarm, and then it's like tired and old as fuck. Right. The thing that I find most interesting about the potential for the collaborative platform is if everyone's actually participating. Yeah.

If they're actually invested, you're genuinely going to get something that tastes nothing fucking like anything any of them would make. Very true. - It's like I said on whichever show, I've said this, maybe it was Cigar Obsession, it's one of the recent, it's all like swarming around you, but I said it's like writing music, you can sit down and you can write music solo, you can play with yourself, or you can play with others, and the byproduct of playing with others in that creative mode is that you're gonna write something that you wouldn't have written by yourself. Right.

Same thing with building a cigar. Okay. You want to take a break right now? Yeah, we can do that.

Yeah, we can do that. Yeah. Shaky breaky. Okay.

We'll be right back. Hey, it's Mike too. Want to be part of the show? com backslash the Cigar Hustlers podcast.

We have tiers starting just $5 a month. For $10 a month, you get a special show swag, and then you're eligible for the weekly secret show. Secret shows cover in-depth cigar reviews, behind the scenes information, and sometimes we just talk shit about people. Which tier works best with your budget and become an official show hustler?

Thanks for the support. It's so cool in certain circumstances and others super whack. Like if you go to a show at a bar and the lead singer of the band is wearing a headset. This is a non-starter for me.

Non-starter. You know what's funny is like- That one got in his way when he would smoke. Yeah, I went on Kiss My Ash, and I was like, I really want one of those. Like, that's kind of what spurred this into kind of action.

Understood. And then when we started using it every day, I'm like, this fucking sucks. I can't smoke. I can't do this.

But Matt has stolen my headgear. I'm making it work. You know, what's really kind of funny is before you got on the show, I was actually thinking, maybe we need to get headgear for the guests so that they can hear themselves. Yeah, add to the list.

And make something, you know, a little bit better and more comfortable for them. You know, we're a low-budget show, so it may take a year or two to get to that. It's not an option, but, you know. You're good.

You're good. Okay. No, you're fine. You're good.

And we're back. We're back. So to briefly kind of talk about your past without going into cigar shit, so you were a Marine. That's correct.

Four years, 3-7 India Company. I was a machine gunner in their weapons platoon. So was it, it obviously wasn't a career for you. You didn't want to go long-term.

No. Was it a good decision for you or a bad decision for you? You know, I was in a, in a, in a very critical need for a drastic rearrangement of my life, right, and I, and I chose to, I chose to enlist, which, you know, I'm very glad that. Was it like a "fuck you mom and dad" thing?

No, no man, it wasn't a "fuck you mom and dad" thing, it was like I'm literally gonna Leviathan my life if I keep doing, I was doing, yeah, I was going, you know, so I needed, I needed a vicious and immediate rearrangement. Yeah, like a wake up call. Yeah, I pulled the chute, I pulled the cord, and so it was definitely not an environment that a guy like me would flourish in, I think, but at the same time, I'm very, very glad that I did it, I'm very glad that it's done, and you and I would not be sitting here today had I not done that. No shit.

Absolutely. I would love to talk to some of the people that you were with over there, just to get some of the stories, some of the real good stories. We could get, I bet we could get someone to call in if you want, if you really want to get crazy. Oh, yeah.

I mean, we have the ability. Yeah. We're still friends to this day, man. I mean, when we started promoting our brand on the fashion side, I mean, some of those guys that were in my platoon were part of, like, our street team.

I mean, we were very tight. Right. How long were you in? Four years.

Four years. Are you not listening? I didn't hear that, no, I'm sorry. Yeah, you said that first.

Oh. Did I say that? Oh, you're paying attention. So that's what made me think that you didn't really love the whole Marine thing.

" But it makes sense if you're like, you know, you wake up naked in a fucking pile of bushes, and like, "I gotta get my shit together," you know? Well, that's the cigar business part. I mean, we can fast-forward to that. Right, yeah.

Yeah, but yeah, man, no. And look, the guys that I knew that chose to re-enlist that felt that they had found where they wanted to, you know, to stick it out and do their life, man, I congratulated every one of them. Right, of course. I think that's amazing.

Everybody's course is different, right? Yeah, man. And to find, you know, where you want your home to be for the next 20 years. If you're 20 at that age, I mean, you're ahead of the game, right?

Yeah, and you're retiring at an early age, too, if you want to. Those guys are now retired, good rank, good benefits, and now going on to do something else. Buying Matt Booth bracelets and shit. Yeah, that's right, you want that chain.

New Cuban links. So the bracelet, the whole jewelry company started before you got into cigars, right? Yeah. So why would you decide to get into cigars?

Because it's just a, man. It's you know it's not easy it's not a I mean it's a fun business to some degree but shit but wait it's not easy it's not easy no it's not easy no it's not so strange I thought I thought have you ever walked into just disillusioned so I'm so oh my god he's done Jerry Springer wasn't real cigar businesses yeah Springer wasn't real I didn't even get to meet Rick James Matt like this is fucked man this is so like what makes I mean, I know nothing about that industry, but it seems like it would be more lucrative in some levels than cigars, right? And you're obviously an established name in men's jewelry, so what made you transition over into saying, hey, let's parlay this into cigars as well? I mean, obviously gin later, but cigars as well.

Zitching. Here's another shameless plug for you. Oh, the thank you. I have always been desperately in love with the brand concept and brand architecture of Alfred Dunhill.

OK, but of 1920. OK, the the old school gentle, the quintessence of old school gentleman luxury collection. Right. All the finest appointments.

You could go to their their flagship in Mayfair and sit on their patio and drink their alcohol and smoke their fine cigar. Whilst waiting for your bespoke item to be made for you, or during the ordering process of that, your consultation, I mean it's the shit, it's the shit, so the idea was how, you know, I was very enamored with the idea of, okay, how can I create the Dunhill of 1920 in 2020, by 2020, a luxury lifestyle collection that has a lot of craft, traditional crafted products, but with modern stuff. Mike Szczecin: Right. Mike Szczecin: Right.

Mike Szczecin: So, you know, for example, when I started making jewelry designs, it was all by hand sculpt, right? Mike Szczecin: Mm-hmm. Mike Szczecin: And now we're using, in addition to hand sculpt, we're using some computer programs, even Mayan Zebrush, like they're traditionally for computer animation. Mike Szczecin: Right.

Mike Szczecin: But now we can feed files from those programs into Rhino. Like a 3D printer? Well, it's a 3D software, right, but it's, I mean, you could build a design for a car on Rhino, but when we started using that stuff for jewelry design, you know, it was very, for us, it was very limited, a lot of straight lines, angular things, but Maya and ZBrush allow us to create things that you may or may not even understand had the human touch to them, you know, because you're really sculpting virtually. virtually and so it's really helped us to evolve because now i can make a link design for a bracelet if i want to do like a character driven design and we can feed that into rhino i can either do it by hand first and we can scan it and then scale it right because you can't make the same thing twice right so if you want to make some sort of matching series where there are different scales of the same character this is the perfect way to accomplish that gotcha you know um so you want You want to open a store one day?

Oh, dear God. I mean, that's kind of what they did, right? I mean, I would-- If you're trying to replicate it. I was in love with having the idea of having like a townhouse or a con-- where it's like full immersion, everything in it, from furniture to fixtures to fittings to, you know-- Insane.

Yeah, and I would still love to do that, you know, but I mean, you know, life and branded business get away from you, man, and we are here now. We are cigar hustler. Here we are. Yeah, no doubt.

You ever, you, you, you, you an old school rap fan? Yeah. Like Ice-T? Yeah.

New Jack Hustler song? Like you, we could modify that somehow for your theme song? Yeah, we could slide that in. Absolutely.

Dope. You know, what's funny is we did, we had Rick Ross for a little bit and I'm like, you know, we don't want to get in trouble. Like as, as we kind of progressed, we kind of grew a little bit. We got a little more serious and serious.

We're like, all right, we should probably cut that out. And you know, I mean, don't get me wrong, we don't make any money on this thing, but. Understood. You get banged though.

We get banged. - Yeah, and Mike got this laptop, so. - My man, so, so, but I mean the idea was to have this multi-class brand. And by class I mean like class of goods, right?

Things that fit together that could build this picture. - Right. - And having an affinity for cigars that I earned and learned from my dear Uncle Lee. - That was a good cigar.

- Thank you, man, thank you. Cult favorite, cult favorite, legacy brand. - Legacy brand. So, wow, it's crazy, Room 101 has two legacy sub-brands, wow!

Just so you know, if you go past an hour, if we get like an hour and a half, two hours, you will be episode 101 as well. So we're just gonna filibuster on this microphone. That's the strategery here. The record is three episodes for one guest.

You know what, I just realized why you wanted to be 101. I'm a fucking idiot. Oh yeah. That's so funny.

Duh. Well, there's that. Well, that'll go over. There's that.

Boom. The mic goes off. I'll make sure that we stretch it out. Just for you.

Oh, we're gonna stretch it out. Just for you. Thank you, man. I mean, we got more to talk about anyways.

So did that sufficiently answer your question? Because I get a little chatty sometimes. Yeah, no, that's cool. I feel like you should do that, man.

I think it'd be badass if you built the place and you had like a fire pole. Like a Room 101 fire pole from one store to the next. Skulls and shit. Mm-hmm.

Well, look, man. That'd be amazing. Address would have to be 101, so. Address would have to be 101.

Yeah, the placement would have to be really. Yeah. Really kind of, you know, dumbs it down as to where exactly you can go. It's like, is it address 101?

No, I'm sorry, it's 102. Fuck, bro. No, I just put the numbers on the building. Fuck up the mailman completely.

I'd be like, this is 3715, 37, 101. Mailman. It's like the address is in Mexico. Like, how do you get your mail?

We don't do mail, bro. We don't do mail, bro. We don't do mail. Oh, mail.

You just show up. It's two blocks down from the Blue House. The Blue House is gone. It's been gone for years.

Yeah, man. So that really was the idea. And, you know, honestly, man, like at the level we're offering some of these products, I don't know. Now, please, we don't fact check here.

Right, no. If you want. I don't know of another brand that's operating in those categories at the level we are. Right.

To be, you know, you can have people that offer like a tchotchke item or a, you know, like gift with purchase stuff or, you know, whatever. S. alcohol market, which is a fuck show of a business, it's like Boardwalk Empire realized. Really?

It's actually not that different. I had an industry vet tell me, he's like, "Matt, this business is Boardwalk Empire. " I was like, "Oh, he's right. He's totally right.

Oh, yeah, it's totally. " I want to get into it. I could explain some of it to you. I mean, it's just, it's ridiculous.

We've got time to kill. Go ahead. Yeah, okay. Briefly.

But you ought to tantalize me with questions, please. You know what's funny about this? So I've had, I've done several of these, participated in several of these things, and everyone, you know, I respond to the vibe, I feel like we have a vibe here, right? We're vibing.

Yeah. We're vibing. So I respond direct, I'm like a vibe chameleon, right? I respond directly to the vibe, and I've done ones that are, you know, very buttoned up and very serious, and I rise to that, and I, you know, this, I just feel very, I feel very comfortable with that.

Not that I'm uncomfortable in the other one. Like I was telling you before, you know, what's funny is, I've talked with you twice, right? So I've gotten two versions of you, right? Ah.

So we've got to get this on film, so I'm going to throw it out there. Okay, put it on wax. The first one was, it was IPCPR, you were in the Davidoff booth, and you were straight out of fuckin' Fear and Loathing in Las Vegas, you were Johnny Depp's character, fuckin' apeshit crazy, and my brother had a bracelet on, and, you know, you went, like, right to it, and like, what the hell's, you know, what is, is that a, whatever name you said, and then, you know, my brother looked at you like, I don't fuckin' know, and he said, okay, where'd you get it from, and he's like, eBay, and, like, at that point, the conversation was kinda gone, and you just went away, like, just fuckin'. I floated away like a phantom.

Like just fucking shh, shh, shh, shh. And then the second time-- I was wild back then. The second time that I kind of got to chill out with you was down in Stogies in Houston. And you got more of the chill mat, right?

And it's kind of crazy. I didn't know what to expect when we sat down here with you, but you're right. Your demeanor and the way that you're acting is totally different than one of the experiences that I've had with you. You're saying I'm a changeling.

Yeah, yeah, yeah, yeah, whatever that means, sure. I see. No fact checking. It was 16, Matt, so you have 13 more to go.

Yeah. 0 right now. Golfer6315, my dude. My dude.

That's golfer6315? Yeah. Yeah, that's his Instagram. Hmm.

You know, when he was traveling, he used to come in here, too. No shit. My name is golfer3615 on Instagram and I hate your cigars. Hate you, hate your cigars.

So yeah, Jerry's the man. He is. He is. We work with him.

He pedals our swill in Houston. Yeah. He's a swill peddler. He's a swill peddler.

Solid dude, though, man. He and I have had a lot of good times, a lot of good conversations. At least he's also, too. No, of course, man.

I love them both. 0. 0 was waking up in the gutter, so what do you, I mean, what do you want from me? Yeah, you don't, you know.

I'd prefer to stay alive. I've actually heard that story. Yeah, no, that happened. That was an actual thing.

That's, that's, I mean. New Orleans, right? That was New Orleans. I mean, I woke up in an alley in Okinawa.

I mean, it's happened a couple of times. It's not something, it's not something I make a consistent practice of. And genuinely, it's all in good fun, but sometimes I, you know, I'm having such a good time, I get carried away with myself. Yeah.

And so I'm trying to not do that. That hasn't happened recently? No, sir. Was that the last time, New Orleans?

Absolutely. Well, that's a little while ago. I clipped some behavior in a major way after that. That was a wake-up call.

It was a little scary, man. It was. Like, even for a total maniac animal, it was a little like, maybe I should rethink a couple things. Some of my choices in my life.

As I'm spitting gravel out and not having my personal effects on me. Everything's gone. Yeah. That was wild, man.

, right, so, and there's no whisper of memory that has ever come back to me. It was a very strange deletion of an evening of my life, right? But I have great friends in the business, as we know, and, you know, so every once in a while, I'll go in, you know, you know, I ran into, you know, it started as early as, you know, the first So I ran into one of my friends who worked for Rocky, and he's like, you know, he's coming up and he's talking to me like we had seen each other already, and to me, this is the first time I've seen this cat since maybe like the last trade show, I'm like, yo, did I see you the other night? And he's like, oh, come here, come here, come here.

He like takes me away, he's like, and he downloads me on the chapter that he was part of. I'm like, oh, wow, I was off the hook. And then, so I get these updates from people. From time to time.

Or you go visit a retailer and they say, you know, it's been with your pants on. It's a couple. Yeah. Yeah.

It's been a couple of years since we've seen each other, but you probably wouldn't remember seeing me last time. And I'm like, oh, shit. And they're like, well, we're in New Orleans. I'm like, fucking here we go.

All right. Tell me. Here we go. What did I do?

What happened? You know, and it's interesting, like literally being fed your evening to you and like, yeah, having a blackout. I was. Yeah.

But that was it was more. I was like altered beast. No shit. Yeah.

It was. It was. It was pretty wild. Like, let's fucking rage.

Apparently. Like the whole... Apparently, yeah. Allegedly.

Allegedly. I mean, this is America, Jack. I will not be responsible for my own behavior. I don't have to be, apparently, 'cause that's how it works, but...

You didn't wind up in jail, so... Yeah. That's always a good thing. Yeah.

Yeah. So there's that. It might have been better, actually. You know?

I wouldn't know where my wallet was. No face tattoos or anything, so... So you never found your wallet? Okay, so, I'm just very much, I wanted to take more of this Bacá in it, I'm very much enjoying it.

It's very nice, it's very pleasant, it's a good cigar. So, apparently, some, let's not be so flippant to say that there were friends of mine, I think they were looking out for me at the time. Use the term friends loosely. Someone took my wallet on my behalf so I would not lose it.

Oh, there you go. Yeah, yeah, so the glasses were gone. They were lost. Yeah.

Someone's wearing my frames in New Orleans right now. Probably a hobo. " You know, and I did have my phone magically in my pocket. No shit.

Yeah, yeah. And it had battery, and I collected myself. And I remember, I remember, you know, like the Terminators icon. " Where the fuck am I, man?

How did I get here? Pants were on, no strange pains, you know? " You know, give me some rest. Possibly some water.

And I look at my phone, I'm like, oh my, that is far. That is extremely far from my current location. And I look down the way, and a couple blocks down the way, I see traffic going back and forth, a main thoroughfare, if you will. So I hobble my way down there, and I flag down a cab.

And, you know, to this cat's credit, you know, I just, I explained to the guy what was going on, man. And I was like, look, pat my pockets, man, like there's, I woke up back there, like I just, I kinda, I genuinely just need some help, man, I need to get back to my hotel, can't, will you help me? And I understand if you won't, 'cause you have to make a living, but, and this dude took me back to the hotel, now, my one regret, right, as if there are not more, my one regret of this evening was that I wasn't thinking straight enough to get this dude's info, because I would've gladly sent him, Right. Money, cigars.

It's New Orleans. It might not have been his first time that happened. I would assume that this is kind of standard operating procedure. Right.

Or something that happens. They have a fund that he applies to. So were you wearing bracelets or anything at the time? No.

No. They weren't taken. You just didn't have any involved. Yeah, that's correct.

Yeah. De-blinging is an intelligent move when you start to go down a certain road, you know. Any photos on your phone? No.

Nothing. So, in the moment, man, you can't take the pictures, you just gotta look. No, like somebody else did, and then, you know, well, let's take his wallet, but shove his phone way down in his pocket, 'cause he's not gonna be able to figure it out. You wanna talk about operator, okay?

By the time I passed out in my room, all credit cards had been canceled and reordered to the business center of the hotel, expedited shipping, on the credit card companies, by the way, and I had cleaned up, you know, what I thought was a lost wallet scenario, So I passed out, and organically, naturally, I sprung, like, adrenalized awake a couple hours later, and I looked at the clock, and I realized, I gotta do the Room 101 presentation about 10 minutes downstairs for the entire company. So what I'm gonna do is I'm just get my pants on and get downstairs, and I got to the little conference room, and I just Very, very timidly cracked the double door of the conference room, and I peeked in, and the first slide of my presentation was up on the big screen, right? " And the entire room turns around, standing ovation, clapping, 'cause they had heard, 'cause I had sent some text messages to some folks about leaving a soldier behind, and I had very colorfully illustrated how I felt that it was an incorrect move. Yeah, that's kinda fucked up, dude, you know?

It was an incorrect move. Yeah, it's like, how do you bail on your boy that's impaired? It's like, dude, we gotta get him in the hotel room, we gotta make sure he's not laying on his fucking back. And then chain him to the bed.

Right. Yeah, well, you know, you gotta be reaching a point of, you know, about to pass out, right? So, you know Duke? He used to work at a cigar shop in Biloxi, worked for AJ.

He's a hitter. He's a solid sales guy. He works for Davidoff now. Younger cat.

Love him very much. Duke ran into me at a bar that he used to frequent when living in New Orleans, this is his chapter, right, and he said that I was sitting at the bar by myself, and I told him, you know, they won't let me leave the bar, 'cause I had already been without wallet. See, I was apparently going into establishments and continuing to drink with no wallet, right? And so, I mean, this is very much out of my character, but I was on Pluto, and so, And so, Duke knows these cats, talks them into letting me go, he actually, I believe, paid what I owed them, thank you Duke, I owe you an evening, and put me in a cab, and he says, I get back to the bar, and I sit down, I'm like, god damn, man, and he's kind of collecting himself, he's like, Matt's off the hook, and he says, I literally turn my head, and you're sitting there staring at me with a fresh drink ordered.

Like, staring me down, had bailed out of the side of the cab, gone back in, and ordered a drink. Oh, man, yeah. I mean, that was the persistence, you know, so, yeah, man, so I gave a... It would have been a struggle.

I gave a stellar presentation, and then went directly back to my room and fell back asleep, yeah. And that's my, you know, and there are other people that have given me reports, but we've spent far too much time on that. That's a great story, man, because, you know, you only, for me, I only heard, like, little tidbits of it. Yeah, me too.

Well, you've heard, yeah, you've heard more than just tidbits of it. You've heard chapters. Chapter one, the bar. Crazy, man.

But yeah, so that, you know, similar to my choice to rearrange my, ooh, similar to my choice to rearrange my, viciously rearrange my life and go in the Marine Corps, I decided, you know, I needed to viciously rearrange some things, how I was treating myself and, you know, stress takes its hands on you in certain ways, you know, and you wake up in a gutter. I mean, it was like, Dr. Dre fan, are you? You remember the Fuck Easy video where his carcass is stretched out in the gutter at the end of the video?

It was like that. Like, I was that. I was easy. But not the Blue Pendleton, at the time, yeah.

How are we doing on time? I see you keep looking over there. Six. Okay, so you wanna kill it and go for it?

I'm gonna do it again, and then we go to episode 101. We can do episode 101. I got more to talk about. I'm enchanted.

Alright, we're gonna wrap this episode up. This is the end of episode 100. Episode 100, Legacy Boutique Brands, and other topics. Oh wait, before we cut these out, we do have these Casamigos Anejo gifted by my wife, I want to do a quick sip of it, I mean, you know, I know if you don't want to, like, you're good, but I feel like we should.

All right. This is from your wife. Yeah. I will sip with you.

I don't really drink that much anymore, man, but I mean, I'm, you know. I mean, you know, I'm hoping to get you blackout drunk, but who knows, you know. Tequila. It's just the one thing.

The essence of vomit. Let's go for it. It's not the essence of vomit. I'll tell you, when we go to the next show, I'll tell you why I love tequila so much.

Okay. Hey, cheers to episode 100, it's a great show. And on to episode 101. Yes, thank you, Matt, for being here.

You know, man, that's not half bad. I told you. That's actually not really bad at all. This is fucking good.

Yeah, that's pretty, that's pretty fucking good. Anejo, baby. Thank you, Mr. Brittany.

Now, the Reposado and the silver, that shit ain't my style. Does George Clooney put his essence in this? I think he does. Is this why it's so delicious?

He does like a little beard scruff or something, you know, like a little yeast, I don't know. I was thinking of something else, but yeah, no, it's fine. That's actually very delightful. I mean, maybe he does do the other thing, but I mean, he sold that company for- Allegedly.

He sold that company for- Mad paper. $700 million. Yeah, the brand should just be called We Got Paid. That's, I mean, Casamigos has a ring to it, but like, we paid.

Ka-ching. I think that's what it means in Spanish. We got paid. Oh, that's what, no, that is what it means.

That's a translation. That is what it means. And it had a $300 million incentive bonus, so it was worth a billion. Yeah.

That's sold. No, it's dope. It's a, it's a unicorn story of epic proportions. And if that number isn't reached, I just want you to know, it's not because on my behalf, because there have been times where I've tried to acquire this tequila and it's not available in the stores.

Understood. Understood. Yeah. Very tasty, man.

Cool. Thank you. There you go. All right.

All right. That's it. Episode 100. A Cigar Hustlers podcast, its owners and its sponsors take no responsibility for the opinions or statements made by the talk show host or their guest.

Statements or show topics are not necessarily the beliefs of Mike and Mike Productions or the podcast providers, and opinions between talk show hosts may differ. It is not our intention to libel, incite, or hurt anyone's feelings. We invite you to write the show's host, Mike Stefan Kevich, with any feedback or suggestions that you have for their shows. These broadcasts are presented and made public as entertainment in the hope that they will be entertaining to the audience.

This has been a Cigar Hustlers podcast, a Mike and Mike production. m. for all new episodes. Hi, I'm doing, I'm who's Joey Raw?

Yeah, we just don't have to do a single, single podcast ever again. Perfect. I'm good, Mike and Mike. How are you guys doing?

I don't even have to try to end the record. We're gonna cover a lot of ground here, Mike. All right. Try to keep up.

That's a sign of a good podcast. It'd be like four cigars when I walked in a door. All right, end this. Mike, Mike, Mike, Mike, Mike, Mike, Mike Squared.

Show Notes

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