We had the good fortune of connecting with Robert Caldwell and we’ve shared our conversation below.

Hi Robert, what do you attribute your success to?
My brand’s success has been driven largely by breaking from the norms of the industry. I came into an industry that has been dominated by pedigree and tradition. I had neither when I came into this industry. I had different approach, which centered heavily around contemporary art, yet maintained tradition in my manufacturing. Prior to my company’s arrival, very few risks had been taken (in regards to packaging, design and direction). We delivered a product that immediately competed in terms of quality, but also struck a chord with consumers due to it’s approach. 

What should our readers know about your business?
I am most proud of my team. When we launched our company, we came out with a BANG, We were a threat to the industry in every way. We had, and continue to have, alot of naysayers and people who did not understand wht we were doing. My guys fearlessly pushed out the company’s message and kept there eye on the ball. They not only believed in what we were doing, but also did an excellent job of communicating our message on to our retailers and consumers.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Coconut Grove. Dinner at Le Bouchon and then have a drink at Greenstreet. I am getting old, Miami is changing.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
Ernesto Perez-Carrillo. My first premium cigar experience was smoking a La Gloria Cubana Cigar in Little Havana at Ernesto’s factory. He is a manufacturer who is obsessed with quality, and who has been a great mentor to me. Davidoff of Geneva. Davidoff makes the highest-quality cigar in the world. They set the bar so high that by reaching for it, my business has improved dramatically. They have been very generous with us from day 1. They manufacture some products for us and distribute our brand in Switzerland. Along with being reat business partners, they have always been great friends. Jonathan Drew. Jonathan came out and broke the mold when he entered the cigar industry 20 years ago. The trail that he blazed allowed brands like mine to emerge. Without him coming into the space before us, we never would have had a shot.

Website: caldwellcigars.com
Instagram: caldwellcigars
Facebook: caldwell cigars
Youtube: caldwellcigars

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