How’d you get into the cigar industry? 

I started smoking really young. Let’s say I was 18 for FDA purposes. I was fascinated by cigars immediately and I remember the romance I had with them from the beginning. I always smoked alone; it was a hypnotic experience for me. 

About ten years ago I started a hospitality cigar distribution company but wasn’t planning on running it. I was just to spearhead and launch it and then be the silent partner, but I ended up captaining the ship. From there I built a cigar factory in the Wynwood neighborhood of Miami. I went there because it was cheap... it then became a very trendy neighborhood and that helped elevate the awareness of what we were trying to do. 

What, if anything, did you bring from your time at Wynwood to Caldwell Cigar Co? 

Wynwood taught me that originality in the cigar business still works. I also learned what doesn’t work. Wynwood thrust me elbow deep into the art world. That, in turn, affected my business and the way that I look at the world. The entire Wynwood experience made me pivot mentally if that makes any sense. 

I’m not talking about cigar manufacturing or the brand, I built that from the ground up with my bare hands. Rather, it was an experience that brought me together with myself. 

You’ve killed the collab game.  What do you look for when someone proposes that you work together? 

Thanks man. 

Synergy. That’s a vague response but, really, I have to like them, know I will work well with them, and also that their interpretation of tobacco is very different from mine. I haven’t worked with people similar to me. That would be boring. 

For us the excitement comes from the challenge of dividing our differences and seeing what that brings us. 

What’s an average day in the life of Robert Caldwell like? 

Weird, probably.

I like to garden.

I grow shit.

I like to mess with my plants.

I like art and animals.

I wake up pretty early and usually read old encyclopedias or back issues of NatGeo.

I don’t do digital. I hate it.

The news is all bad or bullshit.

I’d rather read about the fornication habits of gazelle.

I sometimes go to my office but not usually. I travel 200 days on a slow year and well over 300 on a busy year, so I prefer not to go to the office unless I have to.

I also don’t like computers or cell phones.

I don’t own a tv.

I guess I went off on a tangent there. 

The Caldwell Collection holds some of the most unique tasting cigars on the planet.  Where do you find the inspiration for your blends? 

In just that; I wanted to produce cigars that were multi-dimensional and that tasted different than what was on the market. I don’t like cigars that are too much of anything. Too rich, spice, creamy. Too much of anything is bad. I like balanced and well-rounded cigars that are also dynamic with a lot of character. 

So, with that mindset we procure tobaccos and process them to hit all of those aspects. I love our products. I don’t smoke all of them... I have my favorites, but I am very proud of all the brands that we have built.

How would you characterize your portfolio to someone that’s never smoked a Caldwell cigar before? 

Flavor first. Equilibrium. Balanced. Simple yet sophisticated. 

What can you tell us about your factory? 

It’s called Tabacalera William Ventura. It’s a boutique father and son operation that combines about 60 years of manufacturing and blending experience.  We have been steadily growing with them. They are tremendously proud people and have always put their best foot forward in an effort to deliver an impeccable product (sometimes we trip on our laces... but they have done a great job).

How important is packaging to a cigar brand?  I’ll admit, the Eastern Standard bands had me itching to try them long before they were available at to me or I received feedback from friends. 

That’s what they’re supposed to do ;). And that’s really the idea. Hopefully your desire to try one was matched by your enjoyment of the product. The whole idea of packaging in terms of marketing and branding is creating curiosity and desire, and I buy things on the same premise. 

The backside of that coin is if the blend or quality doesn’t match the marketing, then they've sold you air.  That being said, it is as important as the cigar in terms of getting the brand into someone’s hands.

What can your fans expect from you in the next 12 months? 

We plan to keep pushing forward. We are emphasizing the core this year. That’s King Is Dead, Eastern Standard and Long Live The King. We have made a lot of noise the last few years, so this year it’s back to basics. 

Those brands are the foundation of our company and they’re my babies. I want everyone to try them. 

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