Hey everybody, I have a guest with me today: Robert Caldwell of Caldwell Cigars and Lost and Found Cigars. Today, we discuss Robert's experience of pipe smoking as a cigar smoker primarily, and how he has found his favorite pipe tobaccos, pipes, and methods for smoking.

[Robert Caldwell]: Nice to see you.

[Shane Ireland]: Good to see you again. I wanted to chat just a little bit because you and I have had a lot of conversations like this over the past couple years. Basically, the crossover between pipe smoking and cigar smoking: I'm primarily a pipe smoker and have been exploring cigars a ton the last few years, and you had the opposite experience. So, remind me, when you got started with pipes, it was it right about the time that we met?

[RC]: Well, it was around 10 years before that, I bought a couple pipes. And, then, I don't know why, but I thought, well, I said I'm going to try smoking pipes. And, then I had this romance of how when I get older, wiser, have a little bit more gray hair, and look distinguished, I was going to do that.

[SI]: Mm, hm. Distinguished.

[RC]: And, actually, even my wife, when she found out I had them, because I got them before her, I was like, "Ah, I don't really," and she's like, "Well, when you get older," you know? So, it was one of those things. And then I would smoke them, only I didn't know how to do it, and I consistently kept burning my palate, and it was a really awful experience. I feel like with cigars, as long as you know how to light a cigar, you can smoke it.

But, I had a very bad experience, I guess, in the beginning, so that didn't really work out for me. And, then, when you and I first started talking, I loved the idea of enjoying tobacco this way, but I didn't know how to do that.

[SI]: Right.

[RC]: So, over the last year or something, I've gotten much better.

[SI]: Well, I was going to say, I think for me, what I remember being a breakthrough moment for you was when we were both at the Muletown Pipe Show, in Columbia, Tennessee, at the BriarWorks factory. That was March of '22, I think? You were there because you had done an event at their shop and kind of just stayed and hung back for the show. And we spent a lot of time that weekend: you, me, Pete Prevost, and Jeremy Reeves, smoking and talking about stuff and trying different things. I feel like that's when, after that, you started hitting me up a lot more, asking for recommendations on stuff and started buying more pipes. So, as a cigar smoker coming to pipes, first and foremost, what would you say were maybe the most challenging parts there? Maybe technique wise, and knowing where to start?

[RC]: Yeah. Well, you guys have been incredibly helpful with guiding me on understanding my palate and what I like with cigars, because the experience is far different between a pipe and a cigar. However, I like what I like.

[SI]: Right.

[RC]: And I think that what I like is consistent across the spectrum.

[SI]: Right.

[RC]: So, understanding my palate and which tobacco to guide me to I think was very relevant. But, I wouldn't have enjoyed those tobaccos if I didn't know how to pack a bowl.

[SI]: Yeah.

[RC]: Light the pipe, use the tamp, and all these types of things that go with it. And, then I do find myself, as well, when I'm lazy, kind of regressing back to bad behavior, I guess. Like last night, I was smoking a little fast while jet lagged. And I started burning my palate because I wasn't doing it the way that I know how to do it. But, it's been really helpful for me. And, by the way, I get all of my stuff only from you guys. True story.

[SI]: Thank you.

[RC]: But, you know, I found that I like smaller bowls. So, in the beginning, I got a bunch of pipes and I had a lot of larger bowls, which I didn't like. I got a lot of, I'd say the wrong tobaccos, or wrong tobaccos for my palate.

[SI]: Yeah.

[RC]: Then I came to understand what I like with the pipes and then dually with the cigars; there's a lot of overlap there. For example, I didn't know you could age pipe tobacco. When I found that out and I started tasting some of the aged tobaccos, it became really brilliant. And, for me as a cigar smoker, there's a couple great utilities for me with a pipe, one of which is that you could take a few puffs and enjoy it, or you could smoke a 15-20 minute bowl and have a very well-rounded tobacco experience. Whereas with a cigar, I would never light a cigar and smoke it for 15 minutes; that's just a waste of a cigar to me. But a pipe, you can enjoy in that way, which I don't feel like you can do with a cigar.

[SI]: Yeah.

[RC]: That's part of it. And, then secondly, sometimes when I'd like a tobacco experience, I don't feel like a cigar. That's something that's new. So, in the beginning it was like, I've got 15-20 minutes. I want a little tobacco or whatever, and fun, let's light up a pipe for a little while. But then, once I started smoking a pipe a little bit more regularly, now sometimes I want to have a pipe instead of having a cigar. I'll always be a cigar smoker first. I mean, I love my cigars.

[SI]: Of course.

[RC]: I just went about three weeks without having a pipe. But I smoked cigars over that three-week period. And then, I came here yesterday and I smoked a pipe. I didn't smoke a cigar when I got in last night. And then, so now for me, there's times I want a pipe. And then, the other thing that's helpful for me is my wife.

[SI]: Yeah, sure.

[RC]: There's a lot of times where it's a little stronger. If I have a little more facial hair, I'll go to bed, I get in bed, and she's like, "Can you go wash your beard again?" That type of thing.

[SI]: Right, right.

[RC]: So, she very much likes the pipe, because she loves the way it smells.

[SI]: The aroma, mmhm.

[RC]: Which I think 99% of people can resonate with.

[SI]: Yep.

[RC]: And then it's not a heavy time commitment. I mean, you smoke a pipe, you brush your teeth, and your palate is pretty good.

[SI]: Pretty fresh, yeah.

[RC]: You smoke a cigar and you brush your teeth, you're going to brush your teeth again, and again, and again to get it out. So, not a knock on cigars, but I think the utility of a pipe is that it's an added utility.

[SI]: Yeah.

[RC]: And so, for me, it's interesting because I always saw them as unobtainable for the experience. Just because I didn't know how to use them. I'll go through times, like I had, I think in May, three weeks where I didn't smoke any cigars. I just smoked pipes. And, the other thing that I like with a pipe a lot is, I do take time off from smoking cigars, because I like to let my palate rest.

[SI]: Of course.

[RC]: And, if I were to spend three weeks taking time off of a cigar to let my palate rest, if I smoked an occasional pipe in that period of time, it doesn't really bother.

[SI]: It doesn't have that impact.

[RC]: But, if I smoked a cigar during that period of time, it probably would affect it, where I wouldn't get back to the virgin palate that I'm looking to get when I'm blending cigars.

[SI]: Interesting. Now, you made a point a moment ago. So, what I was trying to get at, too, is that I have been for a while a firm believer that if you enjoy premium tobacco, in general, that these do occupy two different spaces in your rotation, or in your enjoyment of premium tobacco. And, I also believe that, being honest, I had the opposite experience.

So, pipes were something that I was enamored with, and romanticized, mostly because aesthetically I love the design element. I love the idea that it's this tool that's an heirloom item, that doesn't just get burned up and gone, you know? And, when I was a young guy getting into pipe smoking, it also seemed more economical to buy a tin of pipe tobacco that could be like 20 bowls, versus a cigar that is $10, $15, $16, especially if you lived in California at the time. They're just gone in a moment. So, it wasn't until way later that cigars became something that I was smoking more regularly. And, it wasn't just like a special occasion kind of thing.

But, I do believe firmly that learning more about cigars and smoking more cigars made me a better pipe smoker, and vice versa. I think that the more experience you have with tobacco, in general, and with tasting different types of tobacco, different curing methods, and different regions, you do tend to enjoy whichever of those things was your primary focus more. It's just more experience, right? And, I don't know if you've found that too, I don't know if you've found that smoking the aged pipe tobaccos, or just wrapping your head around pipe tobacco in general, informs a little bit more of how you're tasting other premium tobaccos. Because that was my experience.

[RC]: One hundred percent. And then, in addition to that, I think that when I was first experimenting with tobaccos, years ago, I thought all pipe tobaccos were flavored. So, I think the first tobaccos I smoked were the Davidoff Rolls.

[SI]: Flake medallions.

[RC]: I would just jam the tobacco in there and I couldn't get it lit.

[SI]: Yeah.

[RC]: And then, the other thing, I got cherry or vanilla tins of tobacco and I just kept burning my palate. I don't smoke flavored cigars. So, I thought it was really kind of gross, but so much of what I knew about the pipe world was like flavored stuff. So, for me, as a cigar smoker, it was very unenjoyable to try to do that. Then while getting to know you and Jeremy, and understanding the process, and the romance that goes behind it, and the different countries of origin, and the different processes and flakes, the processes to provide different flavor experiences, and all of those elements made it go from this thing that you jammed down and lit on fire to a much more sophisticated activity, which is what I always thought about cigars.

[SI]: Sure.

[RC]: And you've been around me with other cigar makers that are always curious.

[SI]: It seems that almost every cigar maker that I've met at this point, at some point, tried a pipe 10 years ago, 20 years ago, 40 years ago, if they've been in the game that long. And, almost all of 'em are like, "Meh."

[RC]: Yeah.

[SI]: "It was too difficult." The learning curve is steep, and we say that all the time. Like, I was determined, when I decided that I was going to smoke a pipe, to get it right. And, it took forever for me personally. At that time, there were less resources to guide you, and I wasn't in a place where I had a lot of guidance from people around me. If you have a local tobacconist with pipe smokers around there, it's going to speed up your enjoyment. Kind of like when you were with us at the Muletown show, one weekend of hanging out with guys that really know what they're talking about, is going to really help you on that learning curve.

[RC]: Yeah.

[SI]: And, I did it kind of alone for the first many years. I will never forget when I went from maybe 10-20 percent of the bowls I smoked were successful, to like 80-90 percent of the bowls I smoked were successful. Every now and then you mispack, or it's not the right moisture, or something goes wrong. That just happens. But, I remember when it switched for me, when I stopped struggling with it and started enjoying nearly every bowl that I had, more consistently. Then you have the exploration of all the different types of blends, and everything else. But, it takes some determination. I think that's one of the differences between cigars and pipes as a medium. But, like I said, I think a well-rounded and fulfilling rotation includes both, for sure, in my opinion. And, I think you do get better at both of them when you have experience with both of them, as well.

So, you mentioned earlier that you came to the realization that you enjoyed small pipes. I think that's interesting because I also prefer small pipes. Like, some of it is the weight, because if you're a clencher, I really like to have something that's easy to clench, especially while working. But, I know that we also share another thing in common, which is that we prefer small ring gauge cigars. And, I wonder if there's a correlation there. I mean, it seems to be, I hear that from a lot of guys, guys that are into small pipes and small cigars both.

[RC]: Yep.

[SI]: And, vice versa, you know what I mean? Either you want that really long smoke with certain types of flavors, or you want something that is maybe a little more concentrated, and maybe a little quicker. What has been your experience that led you to small pipes, would you say? And, is there a relation between your cigar preferences?

[RC]: So, I bought, well actually, I would correlate the same to me, as when I was a cigar consumer, I just smoked everything. The first 6" x 60 I smoked was a Zino Barrel. It was a nice cigar, my brother-in-law gave it to me.

[SI]: That's a pretty strong cigar, too.

[RC]: Yeah. I didn't enjoy it. I didn't know why. And then, I lit another one, and I didn't enjoy that. And then I realized that it was just too big. From then on, I never really smoked them. I mean, I'll try them when we're blending a cigar, but I dislike large cigars. And so, with the pipes, I bought a bunch of different pipes, and then I noticed, first of all, I had a little bit of an easier time with the smaller pipes. They were more manageable for me to light, keep lit, and pack. And then, it was the same thing with small cigars, I'd rather smoke two Coronas versus a Toro. I'd rather smoke two Coronas, because I get kind of ADD with a flavor. And so, the same thing with a pipe, a large pipe to me is like a big commitment that I'd rather just smoke a cigar if I'm going to smoke something for that long.

[SI]: Or more than one pipe.

[RC]: Yeah, or more than one. But, the smaller pipes for me, I don't know, I just gravitated to them almost immediately. But, I think it was my last trip that I was here, I really identified that.

[SI]: Yeah.

[RC]: Yeah. Or maybe it was at IPCPR that I identified that, because you guys had had a small pipe here that my business partner picked up, and then he was smoking it, and then I went to try it, it was one of these Peterson's, but with a shorter stem.

[SI]: It was a Junior, yeah.

[RC]: And, I was like, "What a cool pipe." And then, I went back, and I actually gave away all of my larger bowls, because they weren't nice pipes anyway. I bought a bunch of different things to try to figure it out. And now I'm just focused on these smaller pipes. And then, I'm not sure if you asked me, I think you did, but in terms of flavor, I was talking with you to understand what to look for, and your guidance in finding out what I would like was very helpful. I think the first thing that I said to you was, "I like that ketchupy taste."

[SI]: Yeah, sure, a tangy flavor.

[RC]: Yeah. The tangy smell of apple cider vinegar and ketchup. I gravitate to that thing right away.

[SI]: Yeah.

[RC]: That's what I like. If it has that, then I'm going to be happy when I smoke it.

[SI]: And you have been gravitating mostly toward Virginias and Virginia/Periques.

[RC]: Yep.

[SI]: I mean, that's the thing with premium cigars, and pipes, and pipe tobacco: they're two sides of the same coin. Like I said, I think that maybe now, more than the past several decades, maybe from the '70s on, it's been an either/or thing. "Are you a cigar guy, or are you a pipe guy?" And maybe you occasionally dabble in one or in both. But there's been this weird division between the two groups.

[RC]: You know why? You pipe guys are weird.

[SI]: Yeah, for sure. I mean, yes. But, what I was going to say is, I feel like more recently I've encountered a lot more people on both sides of the business that appreciate and enjoy both. And it seems like that probably hasn't been a thing, since way before all of our times, you know what I mean? When tobacco use was maybe more widespread in general. But, it seems like there is a bigger group that is interested in both things. And I think that's really cool. I think it's interesting, and like I said, I think it's good for both sides of the hobby.

[RC]: Yeah. And, I think, so back to the difference, you can stumble your way into becoming a cigar smoker. I think it's really hard to stumble your way into becoming a pipe smoker, unless somebody holds your hand and shows you how to do it.

[SI]: Yeah.

[RC]: And anybody can light a cigar: you can light it wrong, you can cut it wrong, but you can figure out what you're doing wrong. You know?

[SI]: And, it'll still smoke.

[RC]: So, if you cut it too much, and you light it the wrong way, it'll still smoke. Pipes, no. If you pack it in there too tightly, you're not going to be able to draw it, or if you suck it too fast, or it's too loose, you burn your palate, or spit into the thing by accident. With a cigar, I mean, if you're a novice cigar smoker, and you suck down a few big cigars, you might get a little bit queasy feeling the next day.

[SI]: Right, right, right.

[RC]: But, a pipe, you could smoke five or six puffs of a pipe this big, and you put in tobacco that's really wet and it's packed too tight, and you're sucking it really hard and it gets really hot, you might not notice, but all of a sudden you blow out your palate. So the punishment is hard and swift with a pipe. Whereas a cigar is much more lenient. We were talking in Germany with another cigar maker that loves pipes, you know? But, his first thing was like, "I wish I knew more about them to understand it." So I think for somebody that's interested, you have to have patience, which I didn't have. You have to give it the time that it needs.

[SI]: Yeah.

[RC]: Which, for a cigar smoker, is really easy. Like, if you're smoking a little too fast, you just slow it down.

[SI]: Right.

[RC]: But, with a pipe, it's the same thing, but it's also a very different thing. So, the experience is if you're smoking it too fast, you don't really know until it's too late. And, a cigar will tell you right away, I mean, it'll start the canoe or you'll get a big cinder on the end of it.

[SI]: Yeah.

[RC]: And you can just set it down on the ashtray, and wait two minutes, knock off the ash, and keep going. But, this, I mean, you're going to hurt yourself, you know? So, that was my experience in the beginning. It was very unfortunate, because I got some cool pipes many years ago, and I was sitting down with you guys at Muletown and really started to understand it, and I still screw up all the time.

[SI]: Yeah, sure.

[RC]: Like yesterday I was forcing a bit, I guess. And then today I've been doing just fine.

[SI]: Yeah, I mean I've been doing this a really long time, and, like I said, I would say that there's still somewhere between a 2 percent to 5 percent failure rate for me. And, it's all user error, always user error. And, it just happens. You just suck it up, drive on, dump it out, and reload another pipe. So, last question on this. I'm curious, because again, we're coming to this from totally opposite sides — as somebody who is primarily a cigar smoker, and who has taken to the pipe, or become interested in it and started going down that rabbit hole, what advice would you give, if any, to guys that are really familiar with premium cigars and might be curious about pipes?

[RC]: Probably to do your research, and try to find what it is that you like.

[SI]: What does that mean?

[RC]: So, if you smoke a cigar, what type of cigar do you like? What size? Which I think you obviously have to correlate that to the pipe. For example, when I drink coffee, I drink espresso. I'm not a tall Americano coffee guy.

[SI]: Yeah.

[RC]: I'm a short shot of espresso kind of guy.

[SI]: Yep, yep.

[RC]: Same way that I am with a cigar, it's the same way that I am with a pipe.

[SI]: Right.

[RC]: So, I like those smaller experiences; they work for me. And, then also, just trying to understand the tobaccos. And, the thing is, it's really easy to make a mistake on a tin of tobacco. If you make a mistake on a box of cigars, you're kind of screwed. I mean, you're losing $300 versus $15.

[SI]: Sure.

[RC]: As you know, I bought probably well over a hundred tins of tobacco from you guys, and probably 10-15 pipes. And then if you don't like it, pass it on, you know? And so, I sent over a lot of my tobaccos that weren't for me. I sent 'em to my uncle. As for the pipes, I gave them away to different friends that wanted to try them. But I'd say, don't be afraid to just go through the same path that you went through to understand what you like with cigars.

[SI]: Experimentation, yeah.

[RC]: And, the old pipe tobaccos are just really good, if you have a chance to smoke them.

[SI]: If you have a chance to smoke some well-aged stuff, it's definitely a game changer. But, no, I mean, I would say that that's one of the purposes of your tobacconists out there, whether they're online tobacconists, like Smokingpipes, or your local tobacconist; hopefully you can find somebody that has experience with both that can give you some direction. You could ask, "I smoke this kind of cigar, this is my profile, this is the kind of stuff that I love. What would it translate to in a pipe tobacco?" And, yeah, you might be pleasantly surprised. And, like I said, I've had phases where I'm smoking two or three cigars a day, and maybe one pipe, and totally the opposite. I think that's the fun of it, too.

[RC]: Yeah.

[SI]: It also prevents me from ever being in a rut on one side of pipes or cigars. And it's also just a nice change of pace every once in a while. Like I said, I think it makes you a better pipe smoker if you're experienced in cigars. And, I think the opposite is also true. But find out for yourself, I guess. Thanks everybody.