Operation: Cigars for Warriors (CFW) is proud to announce the second cigar manufacturer that has committed to the Operation: Cigars for Warriors Synergy Program, Caldwell Cigars. CFW’s president, Storm Boen, interviews brand owner Robert Caldwell about his company, its cigars and the upcoming exclusive collaboration, Mad Mofo CFW Limited Edition.
Storm Boen: I’m excited to do this interview and appreciate you taking the time out of your busy schedule to do it. Of course, I’m even more excited about the upcoming collaboration of the new Mad Mofo CFW limited edition. We will visit more about that later. What I would like to know is more about you. To start things out, where were you born and raised?
Robert Caldwell: It is my pleasure to do this interview with you. Operation: Cigars for Warriors has a big place in my heart. I was born and raised here in Miami.
What did you do before Caldwell Cigars?
I went to college through my sophomore year, got bored and dropped out. After that, I got my commercial real estate license and worked everything from sales to development. Around the end of my tenure of doing real estate, I was doing a side job. I started selling cigars to hotels and restaurants, and surprisingly I did very well.
Why did you go from the lucrative business of real estate, especially during the boom in Miami, to selling cigars to hotels and restaurants?
I get bored easily, and I hate over-structure. Dealing in real estate was all that and more, not to mention, I did not like all the shadiness that goes on in that type of environment. Plus, I was really enjoying my side business of selling cigars. I think this was my coming-to-Jesus moment: the freedom of schedule, no structure and seeing as far as I could.
When did you enter into the world of premium cigar manufacturing?
In 2011, I went to work with Christian Eiroa for a year at the factory. Christian and I had very different business and life philosophies, so I left and started Caldwell Cigars. I left on friendly terms, and I still consider him a good man and friend.
Tell me something about you that most people may not know.
Well, I don’t think a lot of people like me. [Laughs].
Why do you think that?
Many feel I’m not emotional enough and/or that I’m not empathetic, or even that I’m emotionally detached. Also because of my size, my natural quietness and my habits of being a bit standoffish, many are intimidated by me. On top of having a dry sense of humor, I think I’m misunderstood a lot. Once I do get to know and like you, I really enjoy talking trash. Typically those who I get along with love talking trash too. [Laughs.]
What else do you think most people would be surprised to learn?
I absolutely love to read. At heart, I believe I’m an introvert. I try to read four to five hours every day.
What genres do you like best to read?
Mostly biographies, books on business, even science books and manuals. I’m not really big on fiction. I love to learn, just not in a structured way like college was.
Since we are doing Zoom, I can tell you are in a lounge somewhere. Tell me about it.
I love this place. It is called Terrible Cigar Company. They have this great shop and lounge, and they have a digital subscription service. The owner loves the military and first responders so much that she offers them a 25 percent discount here in Miami.
That is very impressive. I think the biggest military discount I have seen is 15 percent, and even that is rare these days. Robert, tell us about the Lost & Found line.
I started it with a close friend of mine who owns La Barbra Cigars, Tony Ballato, in 2012. You know him well—he has been attending C.A.T.S. Festival for several years now, even before I did. We both enjoy finding these great stashes of cigars at factories that, for whatever reason, never got put on the market. These are the quality of cigars that if we didn’t sell one of the blends, Tony and I wouldn’t be concerned about it, as we would get to smoke them. [Laughs]. Lost & Found is also the line that we have historically done our charity drives with. Tony, my wife and I are really big about giving back.
So when did your dream of Caldwell Cigars become reality?
I started Caldwell in 2012, which I believe is about the same time Operation Cigars for Warriors and C.A.T.S. began.
