Box Press Podcast

Cigar Making with Caldwell Cigars’ Robert Caldwell | Ep. 71

Secrets behind making cigars revealed! Join us on the lanai at Robert Caldwell’s private home for a real talk with the founder of Caldwell Cigar Company. Hear from the character behind Blind Man’s Bluff, Long Live the King and Anastasia cigars. Recorded in Miami with Box Press host Rob Gagner.

Launched in 2014, the brand creates sticks using well-aged, rare tobaccos. In the industry, Robert is known for collaborating with other cigar makers to blend tobacco for small-batch lines, including Lost & Found.

Rocky Mountain Cigar Club Says: This was one of the best interviews I’ve ever seen

– There’s a story inside every smoke shop. With every cigar and with every person. Come be a part of the cigar lifestyle of Boveda. This is Box Press. Welcome to another episode of Box Press. I am your host, Rob Gagner I am sitting next to no one other than Robert Caldwell, he cannot be confused with anyone else. He’s probably one of the taller people in the industry, definitely has a style and a swagger to him. And I appreciate him because he makes really great cigars with Henderson Ventura at William Ventura Cigar Company. You’re kind of a world traveler.

– Yeah.

– So gimme your top three places to travel.

– To visit or live?

– Let’s go visit first. We’re just gonna travel. We live in America. Let’s go visit.

– Istanbul, Turkey.

– [Rob] That’s number one or three.

– Number one, visit.

– That’s number one.

– For visit.

– Istanbul, Turkey. Why?

– There’s like 20 million people spread over like rolling hills. And then you have a culture that’s thousands and thousands of years old. And then it’s the, where Europe and Asia connect is right there. So part of Turkey’s in Asia, part of Turkey’s in Europe, and then, yeah

– [Rob] That’s interesting, kind of like a melting pot of culture.

– And it’s like a very European, but yet like Middle Eastern culture, which is similar to Morocco

– [Rob] Okay.

– and Lebanon, or similar kind of vibe, but amazing food. Great music, great people. Beautiful. Like everything’s gorgeous.

– [Rob] Wow.

– Yeah, but I could never live there.

– Couldn’t live there. Okay.

– No.

– Second place to visit.

– Santa Marta, Colombia. There’s a park there called Parque Tayrona that’s like on, I think the eastern side of the coast. And it’s like a rainforest. It looks like you’re in Thailand or something. Just absolutely stunning nature.

– Wow.

– Just un-fucking-believable.

– Thailand in Colombia.

– Yeah.

– Amazing.

– That’s number two.

– [Rob] Good food too.

– Wait, no that’s number three. Number two is Sagres, Portugal, which is where, when they thought the earth was flat, that’s where they thought it fell into the- like that’s where they thought it fell over. Sagres, it’s like hundred foot tall cliffs, 100-foot tall waves or 80-foot tall waves, really violent sea. And then the whole area there is like a very otherworldly ecosystem.

– And you can’t see land off the coast.

– No, you, you can’t see land.

– They think, “Well, yeah.”

– And it’s violent. Like you hear boom, boom of the waves. It’s just weird. Special.

– Those are the places to visit. Traveling 101 with Robert Caldwell, you heard it here first. One, two and three. All right. Now we’re gonna uproot ourselves because we live in this world where we can work from home. Where am am I going to live? Number three, number three.

– Oof, that’s, you know, that’s a much harder-

– Well, you’re the one who said it, so, okay. Gimme your number one then. you said, “Live or travel?”

– Number one.

– You have to have some idea of somewhere else you’d wanna live.

– So it depends if you’re working or not working.

– Okay. I’m working. I gotta work from home.

– Madrid, Spain.

– Madrid, Spain. Absolutely. I’ve been there.

– Now, work from home, also Florence, Italy.

– [Rob] Really?

– Yeah.

– Isn’t it more expensive in Italy than it is in Spain?

– No, no.

– Really?

– It depends where you go, but no.

– [Rob] Okay.

– They’re very similar price.

– [Rob] So both of those, Madrid or Florence, Italy. Great places to work.

– From home.

– Home. What about, you’re not working. You’re independently wealthy. You just sold Robert Caldwell a cigar brand and you’re gone. You’re done. I’m out, cashing in, I’m living somewhere else. Number one spot.

– Where will we find Robert?

– Somewhere in the coast of Chile where it’s cold, like Patagonia area. And I ride a fuckin’ horse, like Gaucho style, like have a knife and shit

– Why cold? You are living in Miami. You said Minnesota was too cold.

– Minnesota’s too cold.

– Minnesota’s too cold. But then you’re doing the opposite end of the equator, but still going too far south to the point where you hit the other polar plex and you’re going, you’re going cold.

– No offense, but Minnesota’s not Chile.

– [Rob] Really?

– Like, I would never live in Minnesota.

– [Rob] Why?

– It’s too cold.

– But Chile is-

– It’s not as cold.

– [Rob] It’s not as cold. Okay. What are we talking? What’s average, like, gets down to the zeroes?

– Depends where you are. I mean, it gets real cold up in the Andes, like super negatives, but by the beach not so bad. So you could be like very far south, have like, kind of maybe like a coastal New York type of cold. That’s like fucked up for a little while.

– Chilly, windy.

– Not that bad, yeah.

– Good food.

– Good food.

– Pretty nature.

– Yeah. Are you a hiker, rock climber, adventurer?

– Hiker, not rock climber. I button my shirt to look professional.

– That’s not the Robert Caldwell Way.

– I know.

– [Rob] I mean, come on.

– Here we go.

– Like what, what gives? I’ve never seen

– I felt like it was too low.

– I thought you removed the buttons at least halfway up.

– No, but they button weirdly, like up there.

– [Rob] For you.

– Yeah, well, all my shirts, all my dress shirts are tailored.

– [Rob] Really?

– Try to find shirts that fit me.

– Yeah, I know. You’re about the same size torso as me and about like 16 inches longer.

– So I have a very good friend in Turkey that owns a tailoring company,

– [Rob] Mm.

– so then he makes my shirts. But then they make them so that they wear openly well. Custom.

– Well, he’s always like, you know, “Try it on.” I’m like, “I don’t wear it like that.” So then I open it up. But then when you actually close ’em like, they’re a little weird in the chest area.

– [Rob] Yeah.

– They’re not made to be closed. They’re made to be like that.

– “Miami Vice” style. Love it. So do you think you’ll live in Miami for the rest of your life?

– Absolutely not.

– Really?

– I hate this fuckin’ city.

– [Rob] Really?

– I hate it.

– Why, why are you here then? Why are we in Miami?

– I’m born and raised here. I’ve lived here my whole life. I like my house. I like, I have privacy and stuff. I work here. The airport’s convenient.

– [Rob] Yep.

– It’s convenient city to live in, but it was the coolest city in the world until like 10 years ago. It’s the people.

– What did you call it, “shiny-“

– Shiny shit syndrome.

– Yeah. Shiny

– Yeah.

– shit syndrome. Which is, define.

– People come here,

– [Rob] Urban Dictionary.

– People come here from other places. They see all the shiny shit and then they want that.

– Like this and that and the cars.

– But there’s no economy here.

– Cell phones.

– So like Miami’s the most unaffordable city in the country because nobody makes shit, and it’s so expensive to live here.

– It’s all imported. So there’s economy there. It’s all importation of product from basically-

– That’s more like Port Everglades, Fort Lauderdale.

– [Rob] Okay.

– Miami, the port, you have a lot of stuff coming in, yes. But a lot of it’s- Port Everglades is much

– [Rob] Cruises, people.

– So Miami’s like real estate, tourism and tax law. And the crazy thing is you have, there’s nothing you can rent in the county for under like $1300 a month. And you’re talking like a 250-square foot efficiency, piece of shit, no kitchen, $250. Or $1250 a month.

– [Rob] Wow.

– It’s incredibly expensive. And then you’re driving an hour and a half to get to Miami City. So it’s just real weird, man. It’s real weird.

– So just a lot of shiny objects to distract you, but it’s real no value.

– Yeah, and there’s no way to get there. Like there’s no ladder to climb in Miami. Like, and so always we’ve had a brain drain where intelligent people in art, finance or law have always left to California or New York.

– [Rob] Really?

– Always, like-

– I thought this was new York’s playground. Like you come down from New York, get away from the city-

– For the weekend and then you go back up.

– [Rob] To make your money.

– Yeah. So it’s always been that. It’s never been the guy

– It’s their cabin.

– Yeah. It’s never been the guy that makes money here. So then with COVID what’s changed is that you’ve had a lot of businesses come in that then bring, not find locally, but bring people with them to work for them.

– [Rob] Sure.

– Because nobody in Miami will hire anybody that’s from, like if you come from New York, you’re not hiring local. You’re importing your workforce from New York.

– Really, why?

– Education, people are not educated here.

– Well, that is kind of a direct response to the taxation problem.

– Mm-hm.

– [Rob] The taxes pay for.

– Favorable climate. Well that, and then again, it’s like, people are distracted by like the ambition in Miami is just to make it, but not to climb the ladder to get to the top. I just want to be on top. So then it’s like the shortcut city where everybody’s like, “Dude, I got this deal for you.”

– But you know, what I think is interesting about that, there is a retailer named Terry and I don’t know his last name, but he wrote a book called “The Border,” or something like that. He was a border patrol agent in the eighties in Arizona. And you know, they didn’t have cameras back then. So you had to do like personal stakeouts. He has all these different stories in the book, and it’s absolutely amazing. One of those books that you just can’t put down, like it’s good. I should send it to you.

– And a retailer? A cigar retailer?

– He’s a cigar retailer in Arizona. They call him like, he’s real grumpy. He came up with a cigar too, his own cigar for the shop. But he is very hard. Like you could just, you can hear it in his voice, you can see it, that he’s lived through some thick stuff. And the stories in there, like, you know, you talk about like dogs protecting a spot and they’re like injecting, sleeping or tranquilizer into the meat. And he’s throwing meat in there. The dog’s finally getting affected. And then he goes in.

– Whoa.

– And he’s not, there’s no, like, search warrant, right? So he’s like undercover going in, basically behind enemy lines, to try to figure out what’s going on, and who he needs to basically target. He’s got tons-

– That’s cool.

– Tons of cool stories in that book. You would absolutely love it. It’s an easy read, too

– Yeah.

– What got you excited about cigars even in the first place? I mean, you smoked really young.

– Yeah.

– So you like, you know, we’re not gonna say any ages, but you were very young. You were getting cigars. But like at what point, whether you’re, I mean, were you smoking really good cigars back then? Or were you just kind of smoking eh?

– Both, but I think back then it was a weird time because I mean, it was like the early 2000s. So you had, like the boom that had been had busted and there’d been a ton of product, I think during that boom.

– Right.

– But they were really good cigars from major brands back then. So now people complain about the big guys, you know, like I don’t smoke X or Y brand because they’re very big and they’re, I’m not gonna name anybody.

– Right.

– But you know what I’m talking about, but back then, there was good shit.

– I still think a lot of it is good.

– I would agree with you. But I think that those that don’t try those products are never gonna, they’re not ever gonna be like, “Oh, I’m gonna pick this up.” Like they got a new something.

– Yeah. They want something that is either shinier or newer and more boutique.

– Exactly. So the people that don’t trust big business are never gonna trust big business, you know?

– Yeah. Okay.

– So.

– But isn’t there some power there to getting really good quality stuff? Because you got a lot of buying power, you got a lot of access to quality tobacco.

– Yeah. But then the question is how much volume.

– I was just gonna say, you got a smirk on your face, so where are we going?

– So you can get the best tobacco in the world. But what if you’re gonna only make 50,000 cigars? And what if you’re a huge company, that does nothing for you.

– Sure. Okay.

– You either use it or you sell it. But I mean a lot of bigger companies are buying for quantity

– [Rob] Mm-hm.

– or they’re growing and when you get something very, very special or a unique varietal or

– Can you have quantity and quality at the same time?

– I think so. But you have to age the shit outta the tobacco. So then you have price.

– [Rob] Okay.

– So I think to have like quantity, quality and consistency.

– [Rob] Yeah.

– You gotta age it.

– You gotta age it. Well, that would make sense.

– Yeah. But you gotta age it long time.

– Which I recently smoked the Davidoff Oro Blanco $500 cigar, which was very unique. Have you smoked it?

– I have.

– [Rob] It’s unique, right?

– Yeah.

– Like I’ve never tasted anything like that, but I mean, what are they talking about? Like 2012 is when they were saying like tobacco and aging and it’s been there that long.

– Yeah.

– So that would make sense. You know, kind of almost like really high-end wines.

– Mm-hm.

– I don’t drink, but I hear that high-end wines are like no longer fruit forward. It’s more like mineral, earth, leather, cocoa, or you know, just these complex flavors. That’s what I felt like was going on on my palate. Like this complex flavor I’ve never tasted before. Like this, great cigar, but I’ve tasted this before in a cigar. Like I taste cigar, I don’t know what I’m tasting as like, I’m not a good palate, like I’m like, “Ooh, I taste plum.” I just, this is good, balanced. And I hate that word sometimes because it’s like so cliche to say, “Oh, it’s balanced.” But it is. Like anything that starts to go

– Yeah.

– It’s like, whoa, whoa, whoa. My palate’s like all over. It’s like chaos in a smoke shop. It’s just alarming.

– Yeah.

– And I used to be a funeral director. So chaos in general is not good. Like you want the family nice and calm and like nothing can be outta order. It’s gotta just make it all very nice. Speak slowly. What other crazy jobs have you had?

– I’ve never had a job in my life. Ever. Well, when I was in Minneapolis, in college, I bartended for like six months. And then

– How did you do that, being in rehab? I didn’t even like it. I tried to be,

– Had to pay the bills, man.

– I know. But I tried to do that. I tried to be a barback in Fargo when I went to school and I was like, I gotta get outta here. This is just horrible.

– The only job I ever had, job, because I’ve been an entrepreneur my whole life. Even before that, like I had a car washing business in high school, shit like that. The only job I ever had was when I left rehab, I went to bartend

– Bartend.

– Like immediately, because I had to pay tuition. My mom cut me off. She’s like, “I’m not helping you with anything.”

– At some point you have to do that to a drug addict.

– So, yeah. I think that your ambition in life should to be, have something that it doesn’t feel like you’re working that hard. You know what I mean?

– Right. Do you think that that either that spending or that kind of like just basically buying stuff that leaves you empty at the end of the day, kinda like drugs, right? Drugs will leave you empty at the end of the day. Don’t really fulfill anything other than a quick high or something. Do you think that’s pretty common in American culture?

– Yeah, a hundred percent.

– Yeah, do you feel like you’re subject to that now?

– Never.

– Or after you got clean?

– No. I’ve never been like, a pointless consumer.

– [Rob] Really?

– Never.

– You never got like really obsessed with something and wanted to buy it. And a lot of it.

– For different reasons, but not obsessed. So I’ll buy, like if I go to the grocery store and they got a buy one, get one free I’ll load the fuckin’ cart. Like toothpaste, buy one, get one free. I’ll buy 20 things of toothpaste to have inventory. Because my theory is toothpaste is $3.79. You buy one, you get one free. Now they’re half price. So you doubled your money. So you gotta work like real hard to double your money, but not if you buy right. So I buy a lot of stuff like that.

– But what about cash flow? If I buy 20 of those, that’s enough toothpaste to probably last me a lifetime. Doesn’t it go bad?

– No, it’ll last you a couple years.

– Let me go check your toothpaste. How long have you been brushing your teeth with Colgate from 1973?

– No, I use Arm & Hammer.

– [Rob] Me, too.

– That’s the shit.

– Because of the baking soda.

– Yeah, makes your mouth like

– And the peroxide. Yeah, it kind of does the scrubbing bubble thing.

– And then like with consumption, like I don’t buy anything, I’m very rarely an impulse buyer.

– Unless there’s a deal.

– If there’s a deal, but that’s strategy.

– [Rob] Mm-hm.

– But like I’m not a guy like, “Oh that looks cool. I’m gonna buy it.” Like I think real hard before I buy something.

– [Rob] Really?

– And I’m super cheap.

– Well, yeah.

– Like I’m incredibly fuckin’ cheap.

– You like to pinch a penny?

– I don’t like drive around looking for deals, but I mean like, I’m like, “Do I really need this?” And it’s like 70 bucks and I’m like, “I don’t fuckin’ need that.” And then my wife, like, she’ll get a package. I’m like, “What’s in the box?” She’s like, “Oh these pair of shoes.” I’m like, “Where are they from?” And then she buys, well, she buys from some of these like companies that resell like, gently used.

– Oh yeah, yeah, yeah. Like secondhand, like.

– Yeah, and I’m like,

– Like “I’m getting rid of my Louis Vuitton’s because my husband bought ’em for me and we’re divorcing.”

– Exactly. So almost everything she buys, but she also buys that way. Not because it’s cheaper, but because it’s more ecological. Like she doesn’t agree with like.

– She’s wise with her dollar.

– Yeah. She’s more of a consumer than I am, but she’s also very mindful of like, “Just because you wore that purse doesn’t mean I can’t,” because a lot of girls like want something new. She doesn’t give a fuck if it’s new or not.

– Right. She just, if she likes it, she likes it.

– Yeah, and she doesn’t want to be like the first line of waste, which is the person that buys it from the store. So she’s very good about that.

– That’s an interesting philosophy: The first line of waste.

– We’re real weird with shit like that. Like we don’t use plastic at all. There’s no trash, my trash cans have no bags in them.

– What do you do? You just throw it in the bin?

– Wash it out, put it in the trash bin. But the only thing that we throw away here, like I was saying earlier, all the organic stuff, even meat, I take it to the corner. There’s a possum family that lives in the corner. So I’ll go throw meat and sausage and shit to them. Because normally you wouldn’t throw out that.

– Yeah.

– But they’ll eat it, and then everything else.

– That’d be a nightmare. Yeah.

– If it’s bread or nuts, we put it out here for the birds and the squirrels. So the only thing that ends up in the trash is, well, trash is trash. So like cellophane and shit like that, that doesn’t recycle. And then everything else is recycle bin, but we just clean it out and dump it. Nice.

– Yeah. Word to the wise, no more trash bags.

– Trash bags are overrated.

– So.

– So then like once a year, like you gotta clean out the trash can. You gotta put it with bleach in there, spray it down with water.

– [Rob] Right.

– Make sure it doesn’t smell. And like once a year you just dump the old trash can, which is recyclable. And then you get a new trash can,

– [Rob] Sure.

– but then you’re not wasting.

– Yeah. Way more.

– 400 plastic bags.

– Way more better for the environment. Would you call yourself an environmentalist or do you just try apply common sense?

– I hate plastic.

– [Rob] Yeah.

– Everything else, I’m kind of okay with. Like diesel truck? That’s cool. Like plastic just fucks with me. And I think it’s from growing up here, like in a coastal environment.

– Where the trash can wash up on the shore.

– You go to Miami Beach. There’s not more than two inches without trash. It’s fucking everywhere.

– And what’s crazy is that they can actually dump that stuff legally into the ocean.

– Well, and for years, and I think we still do, but we would send our trash to Haiti. Like we used to send trash as a country. We would send it to China, but we used to send in Miami they’d fill like big ships with shit and send it to Haiti.

– Aren’t we nice.

– And then a ton of that shit would end up in the ocean and then it just, but not just from Haiti. I mean from all the islands. So a lot of the pollution in Miami’s local, but a lot of it’s just ocean currents, carrying trash from the Caribbean up.

– Right.

– But I mean it’s fucked. So then the permanence of plastic made me have a problem with it, but nothing else bothers me I guess.

– That makes sense. How did you meet your wife?

– We met in a bar in Madrid.

– [Rob] Ooh.

– Mm. We got the same, we met the day after our birthday.

– No wonder why you like Madrid.

– Yeah, we met the day after our birthday and then she started talking to me and she said, “What are you doing in Madrid?” I said, “I came for my birthday.” And she’s like, “When’s your birthday?” I said “Yesterday.” And that hers was yesterday also. And that was that.

– You guys have the same birthday?

– Yeah.

– Are you the same age?

– No, she’s 10 years younger. I wouldn’t marry a woman my age. Crazy.

– [Rob] Really?

– Come on.

– How old are you? 39.

– Yeah, that’s not old.

– Mm-mm.

– I’m 36.

– How old’s your wife?

– She’s five years younger than me.

– You see?

– But I did for a while. I dated somebody who was 15 years older than me. That was interesting.

– Yeah.

– [Rob] Culture shock almost.

– Yeah.

– She was talking about stuff I didn’t even know, but it was fun.

– You were a boy toy.

– I actually proposed to my wife in Spain at La Tomatina festival. Have you ever been there?

– No, I’ve seen it though.

– [Rob] Throw the tomatoes?

– Yeah.

– You should go.

– Where is it?

– It’s right outside of Valencia.

– Okay.

– But Italy’s got a tomato festival and it’s the same thing. Just everybody goes in the street, throws tomatoes at each other.

– Madrid is a cool place. Barcelona is cool.

– Madrid’s way cooler.

– Why?

– Barcelona you feel the tourism, Madrid you don’t. So you can go to Madrid, walk down the street. Nobody fucks with you. You go to Barcelona,

– No, I felt it in Madrid because we got an Airbnb. So we felt, we were like right in the middle.

– Oh, you were like by Sol. Like the train station.

– Yeah. We were kind of like right in the middle. And if I went to the east, there was like an art center and like a bunch of hotels and like food, the quality of food went down and the price went up. And then if I went to the left, which was to the west, like that was where all the tapas were. That’s where all the locals went.

– So you stayed in Gran Vía

– [Rob] Maybe, maybe.

– area for sure. And then to the left would be a La Latina probably.

– Okay.

– It’s a really cool neighborhood. Like lot of little bars and shit.

– Yeah.

– Yeah.

– And you just walked down the down basically this road, and there’s just stuff all everywhere, everywhere. And the locals don’t go out there until like late at night.

– Yeah, they eat at 11:30.

– Like we were like hungry at 6:00 and they’re like still preparing the food. We’re like, “Do you have anything to eat?” And they’re like, “What?”

– 9:00?

– Yeah, we did a 9:00 dinner and everyone was out. And then by 10:00 it was over.

– Yeah.

– [Rob] They eat fast. There’s not a lot of lounging.

– Here?

– [Rob] Yeah. It depends where you go.

– Okay. I went to the wrong spot. I like the experience, I like the ambience. I mean, that’s why we smoke cigars, right. We stop, we’re like in your yard, that’s like a tropical paradise, and I’m just relaxed. I’m hungry right now, but I’m relaxed. Like I could get up and go get something, but I don’t want to, like, I just want to just chill. That’s why I smoke cigars.

– There you go.

– Why do you smoke cigars?

– I don’t know. That’s a great fucking question. I guess I just like ’em. Sometimes I smoke ’em because I have to, like, I’ll be at a cigar event.

– What? That’s a job, dude.

– Yeah. Sometimes it’s a job.

– You have, have a job. You do have a job.

– So, yeah. Sometimes like if you’re sampling lots of blends.

– [Rob] You’re just a liar.

– Well, it’s not having a job.

– Okay. All right.

– Smoking lots of different blends is work sometimes. Well, especially actually that’s work. And then like, you know, you’re visiting all these cigar shops and you have an event at night and people are like, “Why aren’t you smoking?” It’s like, “I had 13 cigars today.” So you always have to have one.

– Right.

– But then I got very good at slow smoking. So I’ll like light something and then leave it.

– Well and you should actually.

– Yeah.

– Because it tastes better.

– And like myself, I’m actually smoking somewhat quickly right now. But a Corona will take me like two hours, two and a half hours typically. Like that cigar will take me, it’s a little smaller than a Corona. That’ll make an hour and 45 minutes typically. Like if I’m enjoying, but then if I go to a cigar event, you feel like you need to puff and puff and puff. And then I don’t enjoy ’em.

– No. I had a hard time when I worked in tobacco retail, smoking on the job because, okay. Yeah, there’s a lull, great time to light up. Great. And then something happens or rush happens. And then you set the cigar down for too long and then it gets acrid you know,

– Mm-hm.

– it gets that build-up, and then I just ruin the whole stick. So I stopped smoking while I was working, which is very, like, weird.

– Yeah.

– It’s weird to be in a smoke shop and not be smoking.

– Yeah. But I do that in my office. Like I used to go in work a little while, light a cigar, but normally I’ll help like in the warehouse and do that type of stuff. And then in the afternoon I’ll do computer work. And then so now I don’t smoke until like after lunch, when I’m done helping in the warehouse, then I’ll go sit down with my computer and then I’ll light a cigar.

– Right, because you know you can commit.

– Yeah. But I used to come in and light one right away. Like not right away, but.

– Right, or driving with one.

– No, I don’t smoke in my car.

– Why? I think you might be,

– I got married.

– Oh, same thing happened to me. I was smoking in my car all the time. Got married. She kind of put up with it. She didn’t like it. She put up with it and then we had a baby and she’s like, “You can’t smoke in there. And I don’t want my daughter to have that smell in there.” So, you know, you gotta like chlorine bomb the car, get the smell out, vacuum it. That’s the key. Like most people think like the smell is in the fabric, which it is, which is why you would chlorine bomb it. But the actual smell is coming from like the ash. You gotta vacuum all that stuff out. Otherwise you’ll never get the smell out. You can chlorine bomb this, but it’s still gonna smell like ash.

– Yeah.

– So that’s my 2 cents. If you’re trying to clean your car, get the smoke out, get a $30 chlorine bomb. You’ll be good. What’s next for Robert Caldwell? Where do you wanna be in five years? That’s a really typical question.

– Not living in Miami.

– All right, in five years?

– Less.

– I asked you if you were gonna flip this house and you said no.

– I’m not gonna flip it. I’ll rent it.

– Oh.

– You know.

– High-end rental.

– Yeah. The thing is,

– How much are you gonna charge it?

– A lot of money. I’m not gonna say that, because nobody will buy my cigars. So I wouldn’t want to sell it because I love the house.

– Because you wanna come back.

– Yeah. But like I’ll leave for a while.

– I wanna save some of this content for playing PIG with you. Because you have an indoor basketball, half court.

– Half court.

– And it’s awesome. And you say you’re really good.

– I never said I was good.

– Yeah you did. You bragged to me.

– I’ll beat you at PIG though.

– You bragged to me that you could do the far door all the way in the corner.

– Oh I could.

– And you can sink a shot.

– Yes.

– Which I think is, after looking at it, that’s good.

– I can probably do that.

– “Probably”?

– It might take me a couple tries.

– All right. Well, we will let you warm up and you got boat shoes on. We’ll let you warm up with the boat shoes. We’re not playing basketball. I don’t wanna play basketball. I can’t even shoot well. But shooting is kind of fun and therapeutic though.

– Mm-hm.

– Just kind of, do you get ideas? Like what’s your like, when you’re jamming on an idea, like what do you do? Where do you go? What do you, what do you like? I gotta go think about this.

– Yard work.

– Yard work. Yeah. Yeah. We were talking about that. You just like,

– Yeah.

– You’ll go out and kind of trim the trees and the palm.

– Yeah. If it’s during the week I listen to music and I do yard work.

– What kind of music are you listening to? What’s the Robert Caldwell playlist?

– There’s a DJ called Ash.

– Ash?

– He’s fucking amazing.

– DJ called Ash.

– Yeah. That’s like the epitome of what I listen to. But it’s like a hybridization of like, house music and Middle Eastern music. It’s amazing. He’s the best guy in the world.

– Ashnikko?

– No, A-S-H.

– A-S-H.

– Let me see.

– Oh, artist. Is that him?

– Yeah, that, fuckin’ amazing.

– That guy?

– He plays every instrument himself and makes his own music.

– What’s your favorite song? You got a favorite song there?

– I mean, they’re all good, but this shit’s like, all of them are good. His shit’s fuckin’ amazing. That guy’s so good. It’s very good. So he’s got like a little Middle Eastern thing, then it’s electronic. Kid’s like 22. He’s from Canada.

– He’s got a lot of followers, almost a million.

– Mm-hm.

– It’s over 800,000.

– But he didn’t.

– Monthly listeners.

– Yeah. No, that kid’s fuckin’ amazing. He’s like the number one artist in the like Middle Eastern music.

– His first EP is out now. He doesn’t even have an EP out, or album out, just music. He makes music, let it go.

– He’s very good.

– That’s like making a cigar without a brand, or like a commitment to stay there. i.e., insert Lost & Found.

– That works.

– Isn’t that neat? Did you know that you did that?

– Lost & Found was meant to be like, like a one-time thing.

– Why?

– The cigars were bought by Tony Bellato for his store as bundles and then they didn’t know how to sell them. So then Jacqueline that was working with him at the time, came up with the idea of like, just coming up with like kitschy stupid branding.

– Yeah, like have fun.

– Yeah, we just sold him to his store and then people found out they had ’em and then they took off and then it became a thing, but it was never intended to be,

– A real organic takeoff.

– Yeah. So then after it takes off, what do you do? You’re like, “Oh, wait a minute. We should do something more here.”

– Yeah. And then we did like another one and then that one did well. And then we would like sporadically do them, but it was never organized

– [Rob] Mm-hm.

– Until actually two years ago we started organizing it. Because until then it was kind of like, I always thought it was a fluke. Like I never thought every time we’d bring something in and we’d sell it, I was surprised that it sold.

– Really? Why, quality?

– No, just because like I’m like, I don’t see the branding appealing to everybody. So I thought it was like a really niche market.

– Right.

– Which it kind of is, but it’s really not. because I mean, we sell a lot of cigars, but in the beginning I’m like, people aren’t gonna get this. They’re like, which was a fair argument. And then like two years ago we started organizing and started like amping it up and we still can’t get, like, we just did a project with Bolívar. It’s a lot of cigars and they sold them all in like two weeks.

– So you did something with them?

– Yeah, and it sold, like.

– They just didn’t sell underneath the Bolívar brand.

– Wait, Bolívar Lost & Found edition.

– Okay, so I thought the Lost & Found was to say these cigars are lost. They’re in the back of the blah-bitty-blah aging room. Nobody, it was a thing that the whoever first commissioned it didn’t want it. So kind of like your wife, “I don’t wanna be the first consumer of it.” They let it go, and then it goes to you because you’re like, “Hey, what is this?” And you smoke it. And you’re like, oh it’s good.

– So that’s what it is. And that’s what it was. But then now we started pivoting towards manufacturing, using really aged or rare tobaccos. So the deal with them, like you said, these big companies have all this tobacco, but it’s not enough for them to do something with.

– Okay. So it’s not gonna get their 50 million cigars.

– No, so then we plugged in with them and then we said, “Okay, let’s do a project, blend the cigar together.” But using really old lost tobacco, which isn’t necessarily lost.

– Is that the Antique Line?

– No, that’s the Bolívar Cofradia I think.

– But your Antique Line is super old.

– Yeah. But those are lost and then found.

– Okay. So those aren’t, I’m gonna make these with age tobacco, or really gonna age. This is like, this has been sitting there for a long time.

– Yeah.

– How long? Like what’s the longest?

– ’98 Antique Line.

– Wow.

– Yeah. Those haven’t come out yet though. I think the oldest we’ve done so far is 2004.

– Okay.

– But we have some 1998 vintage stuff too.

– You’re the one guy in the industry that I know has black, oh we have to find the black liquorice stash. Is there one here?

– I got some in my kitchen.

– Okay. We gotta, Matt, we need to catch that because I actually did a cigar and candy pairing episode on Unboxed Live and you sent me,

– It worked, right?

– It does work. But you were very picky about, like I got on Amazon and I was like, “Hey Robert, these are the ones I can get.” And you’re like, “Ah, those are all sugar.”

– Yeah.

– Like if you get real into it, like you want the licorice, licorice.

– Pure licorice extract and nothing else.

– Right.

– Because if it’s sugar, it’s shit. It’s candy. And then a lot of times they put anise or clove or mint.

– Yeah. That’s different.

– Yeah. Well then it fucks up the flavor instead of enhancing it.

– Of the cigar.

– Yeah.

– And will you do this with any cigar and just like put the candy in your mouth and then smoke and go, “Oh, that’s good.” Or “Whoa, that’s not good.”

– No, it works with any cigar, but it’s better with lighter cigars. Like mild to medium body.

– That’s the secret.

– Yeah.

– Lighter.

– Fuller body cigars is not the same effect.

– Do you think it’s because it’s like competing strength?

– So the licorice effectively amplifies the natural flavors that you’re tasting, but works again on a mild to medium body cigar, the fuller body cigars I think they’re already full flavor enough that it doesn’t have the same enhancement effect.

– Like, Too much full.

– Yeah, and it doesn’t make it that much fuller. It just doesn’t have much of an effect.

– Got it. Now, you know. Where could somebody go and get this type of licorice? It’s like hard candy.

– Italy.

– It’s not soft, but like online.

– I have no idea.

– So you actually go to Italy to get it or you go,

– Well, when I’m in Italy, I buy it.

– You don’t own a factory. You don’t own any land to grow tobacco. And you’ve worked with more than one producer, right?

– Mm-hm.

– And every producer seems to have a, “Well, we do it different.” Right, do you get that?

– Yeah.

– Do they tell you that? “Well, we do it different.”

– No, “We do it better.”

– Well, yeah. Okay. Yeah. What they’re saying is, “We do it differently than the other guy who doesn’t do it right.”

– Yeah.

– [Rob] How much of that is actually true?

– Okay. So they think they do it better, but they do it differently. And then everybody kind of does the same shit.

– What’s one thing that people do not know about cigar making that if they knew they’d be like, “Wow,” and no one’s ever said it before.

– There, so after you make a cigar, it goes into the aging room and the aging rooms have not necessarily a ton of moisture. It depends. Sometimes they’re higher. Sometimes they’re lower. But it’s high enough where you could have mold issues. So you have to mitigate the mold. So you have to treat the wood that the cigars sit on in the shelves. So what do you have to treat it with?

– [Rob] Chemicals?

– Something acidic.

– [Rob] Okay.

– So then that’s open to interpretation. What do you treat the wood with that’s acidic that then could somehow lend flavor to the cigars?

– Lemons, limes.

– Wine.

– Wine?

– Which is another one that everybody thinks is like a fucking secret. But a lot of guys, they dilute wine and they use a dilution of wine and I think lemon juice to counter any effect that they could have from like mold forming. But then everybody’s like, “I know you saw this here, but don’t show anybody.” I’m like, “Yeah, everybody does that.” And it might not be wine, but it’s some iteration of the same concept.

– Right.

– Because you can’t use chemicals Beause the cigars will absorb ’em.

– Ah.

– But then that’s something interesting. Because then you find certain factories where all the blends are reminiscent of each other.

– [Rob] Right.

– Why?

– [Rob] Right.

– It’s not the tobacco, the tobaccos are different.

– [Rob] Mm-hm.

– But then it’s the aging process. They’re absorbing a little something from that aging room.

– So on that same vein, there are certain companies who clearly admit that they spray the tobacco when it’s being fermented with a somewhat sugary solution that amplifies the flavor, and they call it topping, right? “Top the tobacco.”

– Yeah.

– Is that common?

– I think it’s relatively common. I think there’s probably a lot of stuff that happens in various stages.

– Have you seen tobacco being topped?

– No.

– [Rob] Really?

– But I’ve seen like heat treatments. I’ve seen tobacco being boiled, steamed.

– [Rob] Boiled?

– That’s very common.

– Boiling tobacco in water.

– Yeah.

– Why, what does that do?

– Makes the wrapper color more uniform and darker. So like you have a tobacco that color and you want to get it real dark, boil it or steam it. But a lot of guys boil, a lot of guys steam.

– Does that, is that good or bad? To me, if you’re heating up the aging process and quickening,

– If you’re a purist, it’s probably bad. But in reality, I don’t think it has a huge effect. The other thing too is sometimes they’ll make cigars and then they need to age, but then they don’t have time for them to age. So then they bake them.

– In what?

– Like heat, dry heat.

– Hot box, or like create heat in a chamber.

– Yeah, create dry heat in a chamber.

– And that helps age them.

– It accelerates the loss of the ammonia flavor you get off more fresh cigars.

– Yeah, so once you roll a cigar, I was kind of like the rule of thumb is after day seven, it starts to go acrid.

– Yeah.

– And like really bitter until about day 30.

– Yeah.

– And then after that, it’s kind of like, okay, now the tobacco has kind of blended together. The ammonia has gotten released. The oils and sugars are kind of figuring out what they’re doing and they’ve calmed down.

– Yep.

– So you’re saying like, if we apply some heat, that’ll quicken that?

– Yeah. But you can identify that like sometimes you look at a cigar and you’re like, oh look, it’s so dark. Like cigars don’t get that dark.

– Right.

– There’s, I mean, you get like the super black tobacco. Nothing’s that color. Nothing’s that color.

– Like Mexican San Andreas is not super dark. That’s super dark.

– It’s dark. But then you have some that’s like real dark, or some of the Brazilian wrappers that are coming real dark. It’s like this shit’s not possible, like on its own it doesn’t do that. So then something’s happened. And it’s not necessarily that it’s affecting the flavor, which I think it can, but doesn’t mean necessarily it does, but I mean

– Right.

– it just doesn’t get that dark.

– What’s the worst thing about the cigar industry?

– I think the lack of education that’s given to consumers and retailers, if you look at something like the wine industry in the United States, like they went out and they fuckin’ educated everybody, and we’ve done a poor job of doing that. Not because we don’t want to, but because it’s very expensive to do so. Like it’s so small of an industry that you can’t. So I think that’s the worst thing in the industry, is that it’s just so small that it’s almost indefensible because we can’t go out and educate consumers largely. But like, “Hey, this is what cigar smoking’s all about. Here’s the process. Here’s how it’s made.” I mean, I don’t know what percentage of cigar smokers actually know like the process of seed to finish product. And a lot of guys, you meet in cigar shop that are regulars that are around, okay, they know, but that’s not the majority of smokers.

– How is that different than the wine though? I don’t necessarily know how they ferment it all, but I know they ferment it. They bottle it and they ship it.

– Most people don’t know cigar tobacco’s fermented.

– Really?

– Yeah.

– So you ferment it, you roll it, you age it, you ship it.

– Yeah.

– It’s not that hard.

– Or ferment it, age it, roll it, age it, ship it.

– What is the best thing about this industry? What is the best thing about cigars?

– I think the camaraderie, you know, like getting together, smoking, talking to people. I think that’s cool as shit, it’s very unique.

– Do you, I mean, it’s always said it’s a level playing field.

– Yeah.

– Like you and I can sit down and have a conversation over a cigar there’s no prejudgment of socioeconomic status. There’s no prejudgment of maybe political beliefs. There’s no prejudgment on sex, religion, all that stuff.

– Mm-hm.

– And you can wipe all that clean and still have a great conversation with somebody. Or you can have a really bad one. You just walk away.

– Nope.

– Kinda like what you’re gonna do in this interview. “We’re done. I’m walking away.”

– But yeah, for me a hundred percent, that’s it. I mean, it’s just, it’s nice. Like I would never walk in a bar and talk to somebody, but you walk in a cigar shop, someone talks to you.

– Yeah, that’s actually really true because you sit at a bar and most people are just there.

– Yeah.

– Watching a TV, doing this, doing that, drinking, getting their fill.

– Yeah.

– It’s social. It’s so social. Like we’re gonna go to a lounge on Friday and I cannot wait. That’s my favorite thing to do is go to a lounge on a Friday because that’s like the beehive is active.

– Yeah.

– Everyone’s coming in and talking. And “How is your week? What are you doing this weekend?” That’s fun. It’s the people for me. It’s the actual process of connecting with people over, it’s very much a social thing for me, which I know other people, they smoke a cigar in solitude and that’s their thing that they like about cigars. That’s great. That’s not me. I’m an extrovert. I get energy off of conversing with people.

– Mm-hm.

– Are you an introvert or extrovert?

– Introvert. I hate,

– Is it because you get energy being in alone and you need that time or do you get energy from other people, but you just wanna make sure that that person

– I wanna surgically select the people I talk to.

– [Rob] All right.

– So if you put me in a social setting, in business, it’s different. Because like I fuckin’ have to talk to everybody, which is completely outta my element. But then in my personal life, I’m like, I don’t wanna meet anybody new. I do have friends. One’s in Jacksonville, Florida. One’s in Bogota, Colombia. One of them is in Switzerland, but I have very few friends.

– Got it.

– But by design.

– So you’re not calling up your friends on the weekend to get together?

– No.

– What are you doing on the weekend?

– Oh, depends the weekend. I mean like an enjoyable weekend?

– [Rob] Yeah.

– Go to the beach. Hang out at the pool.

– [Rob] With your wife? Or on your own?

– Yeah, sometimes, either way. She works on Saturday, so

– Oh.

– Sometimes I leave her and I go do shit.

– [Rob] Just all on your own.

– Yeah.

– What type of pool? Community pool or private pool?

– I have a fuckin’ pool right there.

– This pool?

– Yeah.

– Over my shoulder.

– Yeah. Why would you go anywhere when you can just sit there?

– Well, I didn’t know. You said a pool and I’m from Minnesota.

– No, I go to that pool.

– So not a lot of people have that in the backyard.

– Yeah, it’s real common here. So, pool.

– Yeah, a lot of people have pools.

– I don’t know, go to the beach. I like to do nature shit. I like to go outside. Ride my bike.

– What can you do nature-esque wise in Florida? Ride? You said ride your bike.

– In Florida there’s a lot. In Miami there is as well.

– [Rob] Really?

– Yeah. But you gotta look for it. You have to kind of know where stuff is, which I don’t. And then I ride my bike.

– Yeah.

– I go walking, beach, boat.

– Boat, you have a boat.

– No, I wish.

– [Rob] But you get on a boat.

– Sometimes.

– Whose boat?

– Various people, like that’s an invitation you don’t turn down. “You wanna go on the boat?” “Yep.”

– Robert, I wanna thank you for the time, hospitality, the whole nine. I appreciate this.

– My pleasure.

– I hope it was enjoyable for you.

– Absolutely.

– I hope they get to learn a little bit about Robert in a different way. What he likes to do, travel fun, going out. What he’s doing with his cigar business. I mean all of it matters, but ultimately I appreciate it.

– My pleasure. Thank you.

– Yeah, you’re welcome. That’s another episode of Box Press. We wrapped it up in Robert Caldwell’s backyard, as always make sure you keep those cigars fresh. If you need anything, head over to or visit your local retailer. Have a blessed weekend and take care.

When you store cigars in a humidor, add Boveda instead of humidifying with a wet sponge or chemical gels and beads. Boveda automatically keeps cigars fresh for months—and it’s all natural. Shop Boveda for tobacco here.

Insider cigar news, including where Robert Caldwell gets his shirts made:

  • 00:50 Top 3 vacation destinations
  • 02:58 Top places to live if you can work from home
  • 06:41 You know you’re from Miami if you know what “Shiny Shit” Syndrome is
  • 09:27 Book recommendation: Sixty Miles of Border: An American Lawman Battles Drugs on the Mexican Border by Terry Kirkpatrick
  • 12:00 Are traditional cigar brands passé? Do today’s cigar smokers only crave boutique or brand new cigars?
  • 24:04 Why do you smoke cigars?
  • 26:35 How do you get cigar smell out of a car?
  • 28:56 What’s on Robert Caldwell’s playlist?
  • 30:34 What are Lost & Found cigars?
  • 33:33 Try eating black licorice while you smoke a cigar
  • 36:25 What’s the one thing most cigar smokers don’t know about cigar making?
  • 39:39 How soon can you smoke a freshly rolled cigar?
  • 40:42 What’s the worst thing about the cigar industry?
  • 41:55 What’s the best thing about cigars?

Who’s on your cigar playlist?

Robert Caldwell smokes cigars and chills out to an artist appropriately called Ash, a French-Egyptian multi-instrumentalist and producer famous for evocative live sessions in exotic locations. Savor a Caldwell Savages cigar and bliss out for more than hour to Ash—Live at Blue Lagoon in Dahab, Egypt.

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