Darian “Jack” Jackson enjoys a good cigar.
One or two a day.
He also wants to spend his time with friends who like to relax in an overstuffed chair while watching a game, conversing or just meditating in the smoke.
Unable to find a place fitting his needs, he opened his own cigar lounge: Dapper D’s Cigars.
“The Japanese have high-end, upscale cigar lounges that are geared to really allow people to have the ability to come in and just relax. I think a lot of times we don’t allow people to really decompress from their days. And so that’s what Dapper D’s is supposed to be,” Jackson said.
There are two locations – 725 Skymarks Drive in River City Marketplace and 150 Fountains Way in Saint Johns off County Road 210 in The Fountains at St. Johns. A third is in the works for Downtown.
Jackson displayed an entrepreneurial spirit while serving 10 years in the U.S. Navy. As a recruiter while stationed in Memphis, Tennessee, his office was the second best in the Navy, behind only New York City. He’d unwind after work at a nearby cigar lounge.
The former cigarette smoker wanted to quit so he switched to cigars. At first it was one or two a week. Then he came to enjoy the company of his fellow cigar smokers and he became a regular.
He decided to put his time there to better use. He got a job there as a tobacconist and learned about the business of cigars.
Like many Navy veterans, Jackson’s last duty station was in Jacksonville and he decided to stay. He took a job as a financial adviser but wasn’t fulfilled.
His wife, Ranisha, encouraged him to follow his dream of operating his own business.
When Jackson told his supervisor, Chris Tuttle, about his plans, Tuttle offered to help.
Tuttle, who had five more businesses at the time, served as Jackson’s mentor.
Jackson signed the lease for the River City Marketplace store in July 2020.
The 1,600-square-foot store was ideal for the first one. Working with the landlord, he was able to start it for about $250,000.
Jackson took on a silent partner, pursued funding from the Small Business Administration and invested his savings.
He chose the location near Jacksonville International Airport because he saw its growth potential and that there wasn’t an easy-to-access cigar lounge off Interstate 95 from there to the Georgia state line.
Jacksonville has a history of being a successful cigar town, he said.
In the late 1800s, El Modelo plant produced 6 million cigars a year. There were other producers as well. Today, Jacksonville is the headquarters of Swisher Sweets.
He opened his second location at 150 Fountains Way in 2023. It is 2,400 square feet and has patio seating.
Both locations have a bar and lounge area, walk-in humidor with more than 40 brands and a private members area. Beer and wine is sold at the bar.
He has almost 50 club members at each store. There are three tiers.
The Bronze is $50 a month and includes a private 12-by-12-inch personalized humidified cigar locker, invitations to member events and access to the members’ lounge equipped with TVs with sports packages.
The Silver costs $100 per month and includes the Bronze perks plus a 10% discount, one guest admission per visit and 24-hour concierge delivery service.
The Gold is $200 per month and is topped off with $100 monthly promotional credits, a 10% discount on event booking and unlimited guest admission per visit.
Besides the lounge, customers can order cigars and related merchandise from the website dapperdscigars.com. The mail-order business is about 10% of his sales.
Jackson, 33, lives up to the name Dapper D’s. With about 40 suits in his closet, he stays well-dressed. He also wears shirts with “Dapper D’s” monogrammed, in script, on the cuff.
“I’ve got a suit guy, Arminius Patterson. This guy has done suits for people who have been in Forbes magazine. A lot of Jaguar players are draped in his stuff,” he said.
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