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An Interview with Robert Caldwell


​​​​​By: Bryan Ott

Earning ratings as high as ‘93’ by Cigar Aficionado, Caldwell Cigar Co. is quickly becoming one of the hottest boutique brands on the market. Adorned with unique names, artistic bands, and featuring rare tobaccos, they take great pride in the quality of each and every one of their cigars. Recently, we sat down with Robert Caldwell, the founder of Caldwell Cigars, to find out more about his brand.

Bryan Ott
: What did you do before starting your own cigar company?

Robert Caldwell
: Commercial real estate in Miami. I have been in cigars about eight years now. I started in the industry by building a hospitality cigar distribution company in Miami. From there, the ball kept rolling. It’s an uphill roll.

: Your excellent Blind Man’s Bluff cigar is made at Agroindustrias Laepe, better known by most as the home of Camacho Cigars.  How did you get hooked up with that famous facility?

: Thank you. I have worked closely with those guys for many years through my other company. They and their parent company have been great mentors of mine, and always gracious with help and advice. We began discussing the project right after the 2014 tradeshow. We needed a cigar that was built for speed; a real volume product. Our production capacity in the Dominican Republic is nowhere close to Laepe. It was a great fit for everyone.

: What makes your Dominican factory different than others?

: The factory in the Dominican is all about the people. It is Tabacalera William Ventura — a father and son team. William is pure finesse. Henderson is the guy you want on your side going into a war. They fit with us like a glove. They have love, respect, and passion for cigars and are consistently pushing themselves to improve.

: I heard about the cigar Nothing You Ever Heard Of.  Do I have to call it something else now?  Seriously, tell me a little about this cigar.

: [Laughs] that turned out to be The Last Tsar. We just didn’t want to release the name, and wanted to have a bit of fun at the same time.

BO: Is it your most expensive release?  Do you think you’ll go higher in the future?

RC: If I go higher, I’ll get stoned to death. We are in fair price points with all of our products. The Last Tsar had to be higher. The tobacco is very special, extremely rare, and well-aged.

BO: Opposite end of the spectrum—what are your thoughts on economical, bundled cigars?

RC: I think they’re a great product. The beautiful thing about this passion is that no matter who you are, there is a cigar for you. It’s all about what you like.

BO: Caldwell blends excluded, if you could only have only one cigar while deserted on an island (albeit an unlimited supply), what would you choose?

RC: Davidoff Millennium Petit Corona. I’d trade you my remaining food for a 5-pack.

BO: The artwork and design accompanying your brand is totally different than 99% of the rest of the industry. Is it all your vision or is it more a collaboration?

RC: We try to do things how we see fit when it comes to branding and marketing. We work with some very talented, big artists who are also friends. It is my vision, but the credit goes to Jaclyn Sears and Evoca1.

BO: Your team seems close knit, almost family like, and fun-loving. Can you tell us about some of your team members, their roles, and what it’s like working with Caldwell Cigars?

RC: I’ll tell you about my current All-Stars. I have Jaclyn Sears. She does design work for me and manages the Iberian lines. She is a complete pain in the ass, but she gets the work done. Jaclyn is a very important part of the team. Jeremy McDonald is my sales manager. He is the slowest, most lackadaisical person I have ever worked with. It takes him an hour to boil water. But by the end of the day, he out-smoked, out-drank, and out-sold everyone in the room. Lastly is Richie Riot. Richie dresses like an N’Sync groupie. He is fun to mess with. I have never seen heart like he has. He eats, sleeps, and drinks Caldwell. It is amazing for me to have someone believe in us like he does. We could go out of business tomorrow and, 20 years later, he will be hand-washing his Caldwell t-shirts.

Working for us is a challenge. We are super laid back, cool, then people get real comfortable, and then they get their heads ripped off. We shoot from the hip a lot. It’s high speed tackle football, but don’t spill the beer.

: Have you achieved your ultimate goals in life yet?  If not, what still needs to be done?

: You know what? I am very happy with what we have been able to achieve. We did it. Then we did it again. Success and victory to me don’t include numbers. I am proud of what we have fought to earn. In terms of still having things to do - of course there’s more; I’m always scheming. I like the hard road.

: Anything you’d like to say before we wrap up?

: Yes. There’s several important people in my life I’d like to take an opportunity to thank. I would not be where I am today without Jonathan Drew, Davidoff, Jaclyn Sears, Jeremy McDonald, and Ernesto Carrillo.

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