How does a birthday dinner lead to the creation of one of the leading boutique cigar companies? It started with an entrepreneur identifying a problem, offering the marketplace a solution and then letting that idea evolve and develop into something unique and creative. That’s the story of Caldwell Cigar Co., founded by Robert Caldwell in 2014—and it’s a story of innovation and risk-taking that led to big gains and a loyal following.

To carve out a place in the crowded cigar industry, Caldwell has done a lot of things differently than the typical brand owner. From how he approached blend development to the people and companies he has collaborated with, Caldwell is in many ways an innovator in the tobacco industry. Tobacco Business recently talked with Caldwell about the role innovation plays in his company and how he took an idea for a boutique cigar brand and helped it rapidly grow and evolve into something beyond his expectations.

Tobacco Business: What does innovation mean to you and what role does it have in Caldwell Cigar Co.?
Robert Caldwell: Innovation is actually one of our core principles. We have three: create, innovate, ambition. It is a principle that our company was founded upon and will forever be the backbone of what we do.

What’s your definition of innovation?
Creation is from zero to one. Innovation is from one to infinity. It is the refinement or redirection of a proven approach.

What was your earliest experience with cigars and how did this influence your own brand’s creation?
My first experience with cigars was visiting Ernesto Perez-Carrillo’s factory when I was about 12 years old. I immediately fell in love with cigar manufacturing. I remember watching the rollers roll cigar after cigar in an almost effortless fashion. The attention to detail that they had and their seamless process really enamored me.

Many see you as a trendsetter rather than a follower within the cigar industry. What’s the key to being unique and paving your own path in such a competitive environment?
We have always marched to our own beat at Caldwell Cigar Co. Since day one, we have set out to do things our own way. A lot of people along the way told us we were doing it wrong, but we just kept on pushing forward. I think our uniqueness is bred out of having an independent vision and following it, not listening to the contrarian views or the naysayers.

What would you say is the biggest misconception people have about you?
That I am an asshole. But this is two-fold, because I am. But I am not the asshole that people think I am. My greatest enjoyments in life are good conversation, art, music, food and traveling. I have never liked being in the limelight.

To what do you attribute your brand’s success?
Our success has been bred from trusting our judgment, moving forward and never looking back, working with friends and enjoying what we do every day. I believe that our energy and principles have resonated with consumers and retailers and drawn them to our brand. We make good cigars, and that has kept them with us.

How do you determine what you’re working on will be a hit among your customer base?
Originally, it was what I liked. Then I realized that what I like, some other people liked. I started developing products that I knew were great products but might be different than what my palate enjoyed. So some of our products I love because I love them. And some I love because you love them. We have built brands to meet the needs of consumers outside of ourselves. Outside of that, we have focused on the top-selling sizes. These are cigars that are in the 50-60 ring range with five- to seven-inch length.

How will your company remain innovative and competitive in the face of challenges like the U.S. Food and Drug Administration’s regulations?
I love a challenge. We have to maintain our agility and move in line with what we are required to do. We may suffer some hardships in terms of product development and creation, but we can also redouble our efforts on brand awareness and continuing to strive to perfect our products.

When it comes to marketing your brand, what advice do you have for other companies?
A lot of what we have achieved on a marketing level has been the result of luck. We made cool cigar boxes and bands, and people took pictures of them and put them online. We made cool hats and shirts, and they did it again. Most of our brand awareness has been because of our consumers and retailers. We just hired someone to handle marketing, but we have flown the last four years by the seat of our pants. The advice I would have would be to be original and do that every day. Trust in your judgement and push through until you get where you want to be.

This story first appeared in the May/June 2018 issue of Tobacco Businessmagazine. Members of the tobacco industry are eligible for a complimentary subscription to our magazine. Click here for details.

– Story by Antoine Reid, an editor and digital content director for Tobacco Business Magazine. You can follow him on Instagram @editor.reid.