Episode 63 Robert Caldwell

Episode Summary

Episode 63 of A Cigar Hustler's Podcast welcomes Robert Caldwell, founder of Caldwell Cigars, for a wide-ranging, unscripted conversation recorded in the hosts' new downstairs studio (landlord smoking rules be damned). Caldwell opens with the story behind his viral social-media stunt — challenging retailers and shop crowds to shave sales rep Miguel's beloved beard, with a Dominican Republic blending trip and free boxes as the bounty — a campaign born from a one-on-one meeting where Miguel told him his social media game was weak.

The centerpiece is Caldwell's now-legendary story of losing his Global Entry and TSA PreCheck. A trip to Lebanon turned into "extreme tourism" when he drove south instead of north, ended up in a Hezbollah-controlled town near the Israeli border (notes on dashboards so cars don't get blown up, mortar-scarred houses, iPad rocket footage), then flew out of Beirut on the airport's evasive takeoff maneuver. By the time he landed in Miami, his trusted-traveler status had been revoked — an early lesson in smartphone tracking and government oversight that still costs him line time across 100+ flights a year.

Caldwell then walks through his path into the industry: a bad restaurant cigar on his birthday sparked the idea for a hospitality-focused cigar distribution business, which grew into private labels and custom blends, a dirt-cheap warehouse in pre-boom Wynwood (from $2,500 a month to $45,000 today), and the Wynwood Cigar Factory partnership with Christian Eiroa built on a roll-pack-ship-same-day concept. Two alpha personalities couldn't coexist, so Caldwell walked away with nothing and, within about six months, launched Caldwell Cigars with partner Hernando in the Dominican Republic. He'd hoped to sell 80,000 cigars a year; he sold that in five weeks and now moves well over a million, which brought its own operational chaos.

The pair close with market talk — younger 25-to-40 smokers driven by the craft-beer mindset versus older smokers who won't stray from their go-to — plus the show's standard four questions (Clint Eastwood, Raphael the Ninja Turtle, and a favorite cigar answer that lands on Davidoff Millennium Petit Corona after disqualifying his own Anastasia), and news of Caldwell's five-year anniversary retailer trip to the DR.

In This Episode

1. 01
   New studio, no smoking allowed
   The hosts christen their new downstairs room while ignoring the landlord's no-smoking rule and riffing on Disney going smoke-free.
2. 02
   The Miguel beard challenge
   How Caldwell turned a rep's request for better social media into a nationwide campaign to shave Miguel's beard and head at retail events.
3. 03
   Lebanon and losing Global Entry
   Caldwell's trip into Hezbollah-controlled southern Lebanon, the harrowing Beirut departure, and the revoked Global Entry and TSA PreCheck that followed.
4. 04
   How he got into cigars
   A terrible restaurant cigar on his birthday led to a hospitality distribution idea, private labels, and custom blends in Miami.
5. 05
   Wynwood Cigar Factory with Christian Eiroa
   The cheap pre-boom Wynwood warehouse, the Louis Vuitton Design District domino effect, the roll-pack-ship-same-day concept, and why two alphas split.
6. 06
   Launching Caldwell Cigars
   Rebuilding back-pocket blends in the Dominican Republic with partner Hernando and going from an 80,000-cigar goal to over a million a year.
7. 07
   The changing cigar market
   FDA regulation, consolidation of independents, and why 25-to-40-year-old craft-minded smokers explore while older smokers stay loyal to one blend.
8. 08
   The four questions
   Clint Eastwood, Raphael the Ninja Turtle, Davidoff Millennium Petit Corona, and the best advice he ever got: 'don't do it.'

Brands & Cigars Discussed

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Transcript

Welcome to episode 63 of the Cigar Hustlers Podcast. This week we sit down and talk to Robert Caldwell of Caldwell Cigars. Enjoy the show. Mike, Mike, Mike, Mike, Mike, Mike Squared, Mike Squared.

So we're finally downstairs. Downstairs, new studio. There's no smoking permit in the downstairs room. That rule went over really fucking well.

Yep. As we're sitting here smoking. How about a big can of air freshener? The landlord is quite the prick.

But whatever. I'll hose the room down when we're done. And you're afraid of the camera? I'm not afraid of it.

It's still charging. The batteries didn't come charged. And then we only have the one working plug apparently in here, so it was charging overnight. Look, it isn't all fucking glitz and glam, you know what I mean?

It's not perfect. Don't look behind the curtain over there. You don't even want to see the bathroom. We're going to have to hire somebody to clean the bathroom.

But we're making some progress. Yes. All right, so you're not afraid of the camera? No, no.

I did a whole show by myself yesterday. Did you really? Yeah, that's why the batteries, they're dead. Oh, very nice.

So we have Mr. Caldwell with us. Thank you, happy to be here. Should I not smoke?

No, no, no, you're fine. We're all smoking. I brought down the ashtray. I feel kind of bad, because when I got here, they didn't have an ashtray.

No, so the landlord is myself and my brother. Ah, fuck. " There you go. So, fuck 'em.

However, Disney is now moving to no smoke. Yeah, it's no smoking at Disney. How fucked is that? You know what the weirdest thing?

No loose ice in your cooler either. No, and also restricted stroller sizes. That's the best one. But that makes sense, because you can imagine guys are pushing a stroller with one kit in it with like seven compartments.

Right. Cutting through the traffic that way. That's what I used to do with mine. Disney is such a fucking process at this point.

It is horrendous. I mean, you can't even fucking smoke there. You can't even drink at Magic Kingdom. It's a totally dry part.

I thought that just changed too. Uh, well, I mean, I don't, I haven't been there in that long, so. Well, everybody goes to, uh, what's, uh, Epcot. You go drink it around the world.

Yeah, you go get fucked up at Epcot. But you can't get fucked up at Magic Kingdom because there's too many goddamn people and it's gonna put complete misery. And if you go in the summer, fucking forget it. No.

You get to ride two rides and then your day's done and then you go home. Right. Do you, you want to introduce the missus? Yeah, sure.

So I'm here with my wife, Paula, and she's shouting away from the microphone. Say hi. Hi. So, I mean, that might be all we get from Paula, but...

That's probably it. She's gonna pretend like she don't speak English now. So, we got Fuck Disney, and I marked that off, 'cause I actually wrote that down. Dude, so, not too long ago, I saw that you did a Facebook post in regards to Miguel's beard.

And it was a bit of a challenge to get people to knock off little portions of his beard, huh? So how was that going? He's fully shaved. Is he?

Yeah, so a retailer was very intelligent, because Miguel, I mean Miguel's a scrappy guy, so people don't really want to fuck with him. And he called me and he's like, "The thing is, I love my beard, my beard is my identity," which is a dramatic position to have. " How much do you buy from Miguel via all brands? So he tells me the number.

I'm like, well, that's a lot of money. He just got a new house and he's got to pay for the new house. So here's the deal you're going to make with him. You shave his beard and you get to come to DR and you can blend your own proprietary cigar from the store.

Oh, no shit. Oh, wow. So then he said, cool. So then he called Miguel and he's like, look, I'm done unless your beard comes off at my store.

So he shaved off the beard. And then two nights later, I'm in the Bronx at Papa Juan's. I don't know if you've been to that store. You know, they have a nice crowd, and then so, kind of get somebody to block the door for me, and then I mentioned that if they could get his beard off, excuse me, his head shaved that night, and whoever got the most hair, but including scalp, I would accept that too by weight, won, and then they would get whatever amount of boxes, but everybody in the store would get a 10 count box, and there was like 30 dudes in there, and they were tough, but then I think they felt bad for him, so they let him, let him have it.

And I also actually almost offered the retailer a huge incentive, like a major credit to make it happen, but then I felt kind of bad. And I think I had Miguel right at his breaking point, so then I let him be. Really testing the boundaries of when he could snap. Well, here's the thing.

Miguel says to me at the beginning of the year, we have one-on-ones with our salespeople, so I'm always like, what can I do for you? Because I want to make my corporate initiative, but at the same time, you've got to tailor things to different markets. So what can I do for you, Market X? And they're like, oh, well, you know, you offer your incentives in the summertime, but I'm selling in Arizona, and Arizona's a wintertime market, or Florida's a wintertime market, so can you reverse the incentives?

No problem, that makes sense. Oh, can you come out into this event? Can you call this retailer? Whatever I can do within, you know, the box that fits for me, yeah, we'll make that happen.

So Miguel's like, bro, your social media game's weak. So I'm like, the minute he said it, I'm like, well, it just got really strong. Yeah, it was pretty impressive, man, like the breaking news and shit. " Yeah, we put it together.

And actually, the best thing is, he sent me these really dramatic messages, and then I called him, and his voice was cracking like he was 12 years old. Literally. He was terrified. So, that was fun.

Yeah, that was awesome, man. That was very well done on your part. So actually, I don't know if you remember this, but we were hanging out at Stogie's, I think it was like a year or two ago. Probably two years back.

Yeah. And you actually told us an awesome story about how you lost your global entry. Mmm. So, I don't know, are you comfortable with hearing that story?

Yeah. That is a fucking great story. So, I went to Lebanon for work/vacation, but mainly vacation, just for shits and giggles, and met some people, and then I ended up in the south of the country. And so, when I got there, I have a lot of Lebanese friends, so they kind of told me, like, stick to Beirut and go north, because if you go south, you get to all, like, Hezbollah.

controlled territory so i'm like cool so i end up down in the south literally so close that you could see the lights of like the israel border and so park the car and little note written on a paper left in the front of the car it had the phone number and the name of like the local guy i'm like what is that no i gotta put the name of the phone number on the dashboard so that they know that i'm here visiting this person and i'm like well why and they're like well if they don't They recognize the car, they assume it's got a bomb in it, so they drag it out to the floor and they blow it up. Oh, wow. What the fuck. So, I'm like, alright, so then we roll up.

It was very nice. I like, I like extreme tourism. So, so anyways, you know, we go in the house and we walk in this house and it's a very nice big house, but there's, I mean, very obvious war scars on it. As in like, racket holes in the wall and stuff?

Well, bullet holes, I mean, like mortar. I mean, they're serious, like artillery fire. Right. On the outside of the house.

Whew. So I get inside, so there's a ton of dudes with beards, and they're all like more or less my age. And I'm like, alright. So, getting a little bit, not quite nervous, but curious.

I'd be fucking nervous. Yeah, I was kind of like, well, I'm kind of like, you know, these guys, I don't think they'd fuck with me, but whatever. So then I just kind of break the ice, and I'm like, well, I was under the understanding that this area of Lebanon was Hezbollah controlled. And the guy's like, well, of course.

I'm like, well. So I was also under the understanding that everyone in this town was Hezbollah. And they're like, well, yeah, of course. And I'm like, no, but like that everyone was Hezbollah.

And the guy says, we are. And these guys all have beards and, you know, they kind of looked the part. And then they kind of got my drift a little bit by it, but they started fucking with me. And the guy's like, well, we are all Hezbollah.

And I'm like, no, no, but by we, I mean, you would assume that it was everyone. " Right. " So that was very interesting. So I spent a very long amount of time there.

I think I got there like at eight at night and I left like at three in the morning. And I went straight back to Beirut. It was like an hour and a half, two hour drive. Got straight back to Beirut, straight to the airport, get on the plane.

And that's an ordeal too, because when a plane takes off out of Lebanon, all the airspace around the airport, basically you have like five miles and then it's all enemy controlled airspace to them. Right. So the plane takes off in basically this maneuver, which is like a, like it just goes like that. So the plane is jerking and squealing and going everywhere.

But if they continue on their route at any point in time, they'll get shot out of the air. And basically it's been said, we don't care if it's a commercial aircraft filled with people, you're not getting in our airspace. So they have this very interesting maneuver, but before you get on the plane, there's just bomb-sniffing dogs and all this shit everywhere, so they tear apart your shit, check everything for explosives like five times and get on the plane, so it's really comforting. And then I landed in London, and I checked my email, and then I'm like, alright, and so I had an email from a United Kingdom border entry or some shit, which is like their global entry, and then it got rejected.

" I was just in transition, so go to the terminal, get on my American Airlines flight, fly to Miami, land in Miami, check my email, global entry rejected. And so this is like seven years ago. " But back then this was new shit, and it's like you can't believe that the government knows where the fuck you are when you're the fuck out of the country. So this was, actually I'm very, I very much hate that, I really hate that, but this was the beginning of it for me to realize how much government oversight there was and everything and how they could track, and I was trying to figure it out, and finally I realized it was the smartphone, so they're tracking you with a smartphone, they know you're in like a Hezbollah controlled area, and that's, that's the only explanation for it, so, and then I went in, and you get nowhere with them, they're just like, no, no, no, we know where you were, yeah, so you still don't have global entry to this day, no, and they took away my TSA.

So I don't have that either, so I can try to wait. Holy shit. And you know, I travel on any given year over 100 flights, so I wait in line every single time. Oh, that sucks.

How brutal, man. So what the hell made you want to get into the cigar industry in the first place? So I've been an avid consumer since I was very young. I used to say the age, but then FDA started interfering with that shit.

So let's just say I've been smoking for a very long time, multi-decade smoker. So, about ten years ago, I was at a retail store that I often visited, and there was a guy working there, and he was a friend of mine, and he was a friend of mine, like socially, but I'd met him at the cigar shop, and he just hated working there, so then I had this brilliant idea, situationally, a couple nights later, I went out to eat, it was my birthday, left the cigars in the car, ordered cigars off the menu, sold out, sold out, sold out. cigar comes out cracked the next one dried out the next one bugs so I finally get up and I go to the humidor they had a big double door cabinet and they had one box of cigars in decent shape and so I grabbed the cigar I had no idea what it was grab the cigar like all right how much is it 12 bucks fine whatever go out smoke it so then the next day pre-smartphone go on the computer and I tried to find a restaurant or hotel like hospitality cigar distribution company to sell these guys cigars because of course that existed and of course it didn't so I'm like oh little light goes off in the head and then so I call this guy I'm like hey this shit doesn't exist and I think this is a brilliant idea because we live in Miami and you can smoke everywhere and all these tourists are here and they all want to smoke but there's nowhere to buy cigars and he's like great idea so then we kind of made an agreement where he was going to run it and I was going to put in the money because I had a career at that point and then after a couple weeks he said I can't work I need to get paid. I can't just do a sweat equity thing with you.

And then I was like, well, this is a kind of startup thing, and I'm sure as hell I'm not going to pay you. So then I just started doing nights and weekends. And then I started doing private labels and custom blends for some of the accounts and then for my own product to put into the accounts. And then that kind of snowballed.

And then I rented a warehouse in a neighborhood of Miami called Wynwood. That's now a very famous neighborhood, but at the time it was just like the hood, like it had no name. Right. The people are like, where are you?

And I'm like, well, I'm like between Alapata and Little Haiti and like the middle of Schittsville, and I was the only business there. So I rent a warehouse and it was insanely cheap. So now actually the space that I was in was paying $2,500 a month. It's rented now for $45,000 a month.

Jesus. Yeah. So property value at that point in time, you could buy a warehouse in a neighborhood, 5,000 square feet for 80 grand. Now 5,000 square feet runs about $7 million.

So it's some of the highest priced real estate in all of Miami. It's like the art district now, right? Yeah. And the dirt is worth more than luxury condos on South Beach on the sand.

It actually makes no sense. And it will come down. But so I rent this cheap space, it's super dangerous. " And this was the cheapest rent in Miami.

" So we built a cigar factory called Wynwood Cigar Factory and so what happened then immediately was all the businesses that were in that design district that Louis Vuitton had taken over, they were all month-to-month leases and none of them knew why and then all of a sudden Louis Vuitton came in and all of them got kicked out and now all those guys needed somewhere to go and we were immediately adjacent. So immediately the rents went up times 10 and everything got leased out and then so now Wynwood is Wynwood. It's a very well-known neighborhood but back then it was even for the next year and a half, two years, two years, two years. So for a few years, it was like dead and super dangerous.

So I got started there with that cigar factory with Christian and we had a concept which was like roll, pack, ship cigars, same day. So we make cigars till three. Those cigars are really good. Really good.

So the factory would open at six. I'd show up at 11:30 because that's how my life was at that point in time. And then we'd roll cigars basically from six in the morning till like three in the afternoon or something like that. And then from three to five, they'd package and pack the cigars.

And then at 5:30, we were on the route where we were the last stop with UPS or FedEx, whoever it was, they'd pick it all up and it would get overnighted to retailers, so the next day they'd get fresh cigars. So it was a really cool concept, and we did very well with it, but the problem was that we didn't get along for shit. I mean, we were both alphas, and we both have two very different ideas of what the industry is, how to navigate within it, how to break the rules, and then so it was like we were head-to-head on everything, and I didn't see that. Because the way that it was presented to me was, or the way that I interpreted it, rather, was, okay, well, this is yours, and I'm doing this.

So he had CLE, and he was doing Asylum with Tom, and this was like my project, but we were partners, and then, but when you have an alpha personality, they're going to be involved. And so we were actually, we were at our, at our height, so we were only in business six months, we were doing 25,000 to 30,000 cigars a month sold, with a production capacity like 20 so we're just living off this back order right and the brand was killing it and it was like how do we get more rollers how do we do this um and then just it got to the point where i just was so unhappy with the partnership and then i said you know what i don't care i'm done right and then i approached him and i said i'm done and then i called my friend hernando who's now my business partner i'm like i'm done he's like what do you mean i'm like i'm done but the thing is in addition In addition to the Cigar Factory, we were operating a bar at night, we were having special events, we had sponsorships, like we had a sponsorship from Lincoln, we had a sponsorship from Kind Bars, we had Montana Spray Paint sponsorship, Kid Robot, I don't know if you know Kid Robot, like the little figures, we had all these weird sponsorships, because we were like in the mix suddenly, and everyone wanted to come do shit, we had a, I don't remember his name, but Jamie, whatever, from the group, the XX, come and do a concert, we had all sorts of just crazy shit. um occurring there so my boy hernando's like well i'll just buy christian's share and i said no i'm done so then i completely walked away from it within a month it just like just ceased to exist um and then i was having a couple conversations kind of to do a license deal with a couple different companies or looking into it because all of a sudden people were like approaching me He's like, hey, we could do something. And I was about to sign one, and then I just said, no, I'll do it myself.

So I called my friend, Hernando, and I said, hey, I think I'm not, I was literally going to sign a deal. And then I called him, I'm like, I don't think I'm gonna go. I was like, do you want to get in this? And he's like, yeah.

And then, so we started out, flew down to Dominican Republic, immediately started attacking with packaging. I already had some kind of back pocket blends that I had, So we rebuilt them in Dominican Republic, tweaked and modified them and then started developing new stuff and then we launched Caldwell. I think, I want to say that Christian and I kind of broke up, August, September maybe, and we launched Caldwell at the end of April. So it was immediately, I mean, we were within six months in the market with Caldwell.

So was it everything that you thought it would be, the cigar industry, or more or less? So, honestly, my original assumption was that if we did really well, we could sell 100,000 cigars a year. And actually not even 180, that was my number, 80,000 cigars, but that was the number to get to, not to start at, and so we sold 80,000 cigars in the first five weeks, and then through the course of the next year, we got up to probably a half a million cigars, and now we're well over a million cigars, so in terms of the business side of what the cigar business is to us, it took off in a way that I never foresaw and never could have anticipated, which caused the shitload of problems. Right.

But then the other side of that is that we wanted to do other stuff. Right. So we launched Caldwell Cigars as a segment of an overall company that was called Down and Back, that we were going to make leather goods and that we wanted to do coffee before coffee was kind of a cool thing. And we had a whole bunch of stuff we wanted to do, but we were so successful immediately with the cigars that all focus went on the cigars.

So in the business sense, it was beyond our expectations. But then, in the other side of the business, the business is a lot more complex than I had known it to be, because I was in it for such a short amount of time with Wynwood, and all we were doing was filling the pipeline, so it was like, orders, orders, orders, orders, sell, sell, sell, sell, sell, and then with this business, the difference is like, sell to sell, turn the product, a product's not turning like you thought it would at XYZ Retailer, go out and make it turn, and then you build the brand, and you build the company, and you've got to get more manpower, bigger offices, more investment, more power. More of this, more, more, more, more. So the actual operational back-end of our business is also very interesting and more dynamic than I thought it would have to be.

Yeah, it's a fucking pain in the ass. Yeah, it's a pain in the ass. And then, of course, FDA hits. And then, of course, all the great independents get gobbled up and a lot of the long-timers aren't going to build brands anymore.

And then a lot of the newcomers know how to identify a good product, which means they'll pick it up, which means guys will buy it because it's popular, but they don't know how to sell it or they don't know how to push it through the system or they don't know how to build the brand. So the marketplace, I feel like, has been constantly changing since we entered it with a lot of hurdles. The good thing, the good part about it is you start to build confidence because when you keep jumping hurdles, you know how to jump them. So when new hurdles come in front of you, it's like, yeah, well, we haven't encountered this yet, but we know we can clear it.

Right. But it's definitely a much more complex business now than it was five years ago when we first started. Right. What's kind of crazy to me is like, I mean, I'm always looking on Instagram, kind of looking at the pace of consumers in general and see what's really moving.

And even to this day, I mean, a fuck ton of Cubans are being smoked, you know, because that's something that you look at on a global level, especially your Cohibas. And then, you know, I think I still see that Fuentes and kind of Olivas and shit really still dominate the market in many sense, whereas a lot of these boutiques, there's, my point is that like, there's, there are a lot of consumers where it's really still untapped, you know, and to kind of still see the volume that, that, that's being consumed that isn't some of the better, you know, smaller production cigars, it's kind of fucking boggles the mind, you know? Well, and there's something to be said for that, too. So we see a lot of growth in our brand, at least, with like the 25-ish to 40 sector.

And that's a very much a part of the market that's growing. Whereas like the older sector that's more set in their ways is a part of the market that's not necessarily growing because you don't see a ton of 60 or 65-year-old guys going and starting smoking. You do see it, but you don't see a lot of it. But you see the younger guys being more interested.

And the older guys are the guys that particularly are going to say, no, you know what? I've been smoking Monte Whites for 20 years. That's my cigar. Right.

Whereas the younger guys, especially with the craft beer movement and the more involvement in like the local craft boutique, everything that exists now, they're willing to try stuff. And if it tastes different, that's not a bad thing. " Right. I don't know why that's my example today, but that's it.

But that's usually the go-to. " That's not the same. " Right. It doesn't taste like nothing.

And so this is a similar profile, and he's like, yeah, but it was more flavorful, and I'm like, well, stronger or spicier, or more flavorful? No, it just, it had too much flavor. I'm like, that's a fucking great thing, Matt. Yeah, when does that become a bad thing?

Yeah, but you're not gonna train that guy away from what he's used to. But the weird shit is, here's the other thing, it's like, well, what do you drink? And they're like, red wine. Oh, I got a wine cellar, I have 1800 bottles, and I'm like, yeah, but you smoke one cigar?

Right. Yeah. It's this weird, like, I don't even know. It's a comfort thing.

Yeah. Yeah. They just don't want to change. It's like it's their go-to.

Right. And they don't want to fuck with it. Right. Well, there's so many options out there, some guys don't want to try something new.

Yeah, but even when they do, it's too much. It's too much, right. Exactly. It's too much.

Where's my Monty White with the bland flavors? Fucking crazy. Did you get really drunk last night or something? No.

You're pretty quiet. I had coffee. That's very interesting. I was doing a monologue, though.

I'm good at that. Yeah. You're an easy guy to interview. You just, you know, lob it up and just fucking sit back.

Let it go. That's it. My mom used to call it verbal vomit. Verbal vomit.

" They ain't got nothing good to say. They haven't been to Lebanon. Exactly. They're not on the no-fly list.

Well, I mean, that pretty much wraps it up for me. What about you? You got anything else to add? We got the questions.

We can do the questions. Yeah. You know, there's really only four. There's not really five.

There's four. Okay. Okay. What one person living or dead would you like to share a cigar with?

Ooh. One person. One person. You can interpret the question any way you want, and you can fucking respond accordingly.

It's not like it's etched in stone, you know? I mean, you could say, like, the Beatles. Yeah. No, I'd have to say, like, Clint Eastwood.

Yeah. That's a good one. Yeah. He's getting up there, man.

I just saw the mule last night. " So it's living and dead because he's kind of like in transit. Yeah, it's kind of like both. He's never going to die.

All right, what one fictitious person would you like to share a cigar with? Book, movie, comic? Anybody you idolized? That's a hard one for me because I don't pay attention to any of that shit, but I'd say one of the Ninja Turtles.

I like the one that had the size, Raphael. I'd pick him. I've never seen a turtle smoke a cigar. My girl would like that, too.

She likes animals. What's your favorite cigar? Favorite cigar, I'm biased, and Anastasia is a cigar that we make with Ernesto Carrillo, and I'm gonna say that's my favorite cigar because it was built exactly to my palate specifications, it hits everything that I love, but I think it's unfair for me as a cigar maker to name my own cigar, so that one's disqualified, so if it's not that, the Davidoff Millennium Petit Corona, I think it's a fucking perfect cigar. That's a really good cigar.

All right. What's the best piece of advice anyone ever gave you? Don't do it. Yeah?

So, when did that save you? It saved me because every time I do it, because I'm a spiteful motherfucker. So, every time someone said, "Don't do it," I'd do it anyways, or I'd do it twice. Right.

And so, that's kind of been, and actually, usually, it's my family with everything. So, I mean, my family, they're very cautious people. Right. And I've made a lot of decisions in my life, against the guidance of my family, It always kind of, for better or worse, helped me on my path, so a lot of times it was very bad things that, you know, that you learned from, and then sometimes it was like, yeah, but I'm gonna do it, and then you just do it, and it's a life experience, and then, you know, or even with business, like, I've been a serial entrepreneur since I was younger, and every time I've had something good, I've decided to go a step further, a different direction, and always against the guidance of my family, and...

Not that I succeeded because I was good at it, I succeeded because of the fucking spike that I had, because I had to make it succeed, because I had to flick off my family, so I'm very much driven by those things, and I don't know, I think that a lot of people live somewhat in fear of don't do it, you know, a lot of people choose that pathway in life, and I've always gone very much against the grain, and for that I have a lot to thank, you know. So don't do it pushes you in that direction of fuck you, I'm gonna do it anyways. I don't wear Nikes. Right.

I don't know. Just do it. Deodoras. " Yeah.

" So we're south by this bombed-in area. Right. Cool. Well, hey man, thank you very much for coming out.

Yes, thank you for taking the time to talk to us. My question. My question. I was thinking question.

Go ahead. Yeah, I got a question. No, I'm just kidding. Thank you guys for having me.

I mean, you can ask us anything you want. How long have you guys been doing the podcast? Over a year now. Yeah, this will be episode 64.

That's very cool. You got to send me a link so I can send it. Fuck yeah, man, absolutely. You know what it is for us, it's just kind of raw.

It isn't about a sale or a purchase or anything. It's just kind of, you know, we bullshit about people in the industry and it doesn't have a format. It's just authentic. That's good.

And because of that, it's been kind of gaining in notoriety and shit. We're the number two cigar podcast on Podbean. I'm number five or eight on iTunes currently. And this just kind of grew at us just doing, somebody told us not to do it.

Well, good, and you know what, the other thing too, like I've done many interviews, and a lot of them, it's the same format, and of course, it's important to have like an introduction to the person or how they got started and all this stuff, but a lot of guys, it's like, it's just, it's almost like they watched or listened to the prior interview and asked you the same exact questions. Right. And the open format, I think, allows it to go in a different direction where guys that are paying attention to this type of media, they've already seen all the other interviews. Right, exactly.

And this lets them connect in a different way. " You know what I mean? That gets old. But how many stories have you heard about somebody getting off the no-fly list, you know?

And that's also kind of an attribute to, like, shit that I pick up along the way, you know? I mean, we've only hung out one other time before him, but it was a great story. It's a great story. " Yeah, that was the first thing he mentioned.

" Yeah, this is gonna be, that's gonna be fucking stellar. Next podcast, I got, I got more stories for you. I know you do. I got a couple of them.

Alright. Well, okay, then that means he's coming back. " I got, I got a good one where I was abducted. Yeah?

Yeah. I spent, like, 24 hours abducted by... Aliens? A paramilitary group.

No shit. Good story. Do you want to tell it now or tell it later? No, no, no.

All right, no. This is the hanging chat. Leave and lingering. All right.

This is Florida. We got hanging chats here. That's it. That's true.

Do you, A, is there any way you want anybody to get in touch with you? Like, uh, Instagram, anything like that? Yeah, my Instagram is Caldwell Cigars. Um, Facebook, Robert Caldwell.

Easiest way to get in touch with me. I don't respond quickly. I'm notoriously slow at responding, and I think that's it, but do pay attention because we're going to be, it's our five year anniversary month, starting like in two days, so we're actually going to run some really cool things, we're going to let guys win five guys, come down on a five year anniversary trip to DR, like we did, and they get to blend their own cigars, so we're going to bring stores and retailers down, so that should be cool. Oh, cool, this will actually go up on Tuesday, so that's right after your contest starts, that's perfect.

And you got Jerry Grouper in the state of Florida, and he's one of the best in the industry, in my opinion, so. Yeah, absolutely. So, all right, cool, man. All right, thank you again.

That concludes it. Later. Awesome, thank you. Hello, this is a prepaid collect call from the Correctional Institution.

This call is subject to recording and monitoring. To accept charges, press one. To refuse charges, thank you for using T-NetX. This has been a Cigar Hustlers Podcast, a Mike and Mike Production.

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Show Notes

This week we have an opportunity to sit down with Mr. Robert Caldwell of Caldwell Cigars!

We skip all the BS about cigars and hear some amazing stories about his life and travels!

Also touch on Disney No Smoking Rules, Industry Information and weekly updates on the show!

As always we welcome your show ideas and thoughts on our FB page "A Cigar Hustlers Podcast".  You can follow the show on IG @cigarhustlerpodcast, Mikey @cigarhustler and Mike too @fcc_mike.

Please make sure to rate, review and subscribe on which ever of our many providers you use!

Thanks for listening!