Island Lifestyle Importers is the exclusive designer, manufacturer and distributor of Tommy Bahama cigar accessories and Island Lifestyle Cigars.

SARASOTA — Island Lifestyle Importers was born, quite appropriately, in a cigar bar, when two strangers with radically different backgrounds struck up a conversation about their shared passion for well-aged, premium cigars.

Rick Louis, now the firm's CEO, is a self-described "serial entrepreneur" with a financial business background.

Ryan Frailing, vice president, worked for the Sarasota County Sheriff's Office — a seasoned deputy with patrol, civil and undercover narcotics experience.

"But he was born to be an entrepreneur," Louis said of his business partner.

Both are serious connoisseurs, or "leather-tongues" as they are known, who are always searching for the next great cigar.

"We started talking about why no one has made quality accessories that fit the lifestyle of a true cigar connoisseur, and then we looked at each other and said 'Why not us? Let's create some of the things that are missing in the marketplace,'" Louis said. "It started off as kind of a hobby job, but one we took very seriously."

Frailing recalls a lot of coffee-table-top conversations when they first started talking back in 2009.

"But we put action behind it," he said. "We had no idea what kind of endeavor lay ahead of us, but we knew there was room for better products, better accessories — products that speak to us."

The partners began building cigars and critiquing their own creations while brainstorming ideas for must-have accessories.

"When we were sitting around testing, we talked about how we were going to break through all the clutter," Louis said. "The concept of 'Rick and Ryan's Killer Cigar' really didn't catch a lot of attention, and then we looked at each other. Both of us were wearing Tommy Bahama shirts, Tommy Bahama shorts, watches and shoes. We said 'Hey, have they ever done a cigar?'"

Smoking parrots

The first year after their affiliation with the Seattle-based upscale sportswear and home-furnishings company, Island Lifestyle Importers became its largest-selling category after clothing, Louis and Frailing said.

They've seen double-digit growth every year since.

Today, their company is the exclusive designer, manufacturer and distributor of "Tommy Bahama Luxury Cigar Accessories," which are sold online and at the more than 160 Tommy Bahama stores in North America, the Middle East, the Pacific Rim and Australia, as well as at other retailers, specialty shops and fine tobacconists.

Adding cigar accessories to the Tommy Bahama brand was a natural fit.

"Their style really tapped into the cigar community — smoking parrots whisking people away to an imaginary paradise — we were able to capture that," Frailing said. "That brand — both Rick and I really loved it. We wanted to be associated with that."

Island Lifestyle Importers' creations became so popular at the Tommy Bahama retail stores that the company reached consumers "who weren't necessarily looking in Tommy's direction for cigar accessories," Louis said.

"We brought in other channels of distribution, negotiated worldwide licenses, and we effectively became the Tommy Bahama cigar accessory company," Louis said. "We can take it wherever we want, within certain guidelines. They've given us a free hand. Right now, we're pushing a couple hundred deals."

The Sarasota company's lighters, cutters, ashtrays and other products are embossed with Tommy Bahama's signature logos and original artwork.

"We created a way to print 3D onto metal — full color, patent pending," Frailing said. "We can take any artwork and include it into the design of lighters and cutters. We're able to produce some really neat stuff."

Best in show

Island Lifestyle's aged reserve cigars are handmade at a factory in Nicaragua using Cuban seed and Nicaraguan tobaccos from three valleys — Jalapa, Condega and Estelí — that have each become internationally known for producing their own distinctive flavors.

The Connecticut, Sun Grown and Maduro blends come in four sizes: Robusto, Toro, Churchill and Gordo.

All have been aged five to seven years.

They range in flavor from smooth — the Connecticut — to the full-bodied, spicy Maduro.

Individually, they retail for around $10.

They were first introduced to a national audience in 2016 at the International Premium Cigar & Pipe Retailers Association annual trade show in Las Vegas.

Neither Louis nor Frailing knew what to expect.

They were on the main floor when the association's president, board and a crowd of onlookers surrounded their booth.

"I thought we'd done something wrong," Frailing recalled.

The association presented the two stunned Sarasotans with their "Best of Show — New Exhibitor Award."

"It was a real balloons-and-confetti moment," Louis said.

Cigar dinner fundraisers

Island Lifestyle Importers is known in the veterans community and beyond for its largess. 

"It's really, really important to know that we're both men of faith, and we said from the start that if the Good Lord blesses us in this endeavor that we are going to give to charities, not only to veterans but to the Salvation Army," Louis said. 

The idea of the cigar dinner was born.

"A lot of cigar guys are like-minded and, sure, we have the ability to donate, but we had the ability through our community to do something that was a blast," Frailing said.

They partnered with Sarasota's Founders Club and had the first charity dinner on its back porch.

They planned on 40 people coming but ended up with 80.

Now, they have to cap the diners at 100, and they sell out quickly.

Recently, they raised $13,000 in just four hours for the daughter of a Sarasota deputy who needed a diabetes alert dog.

Some of the guests flew in from Texas and Georgia just for the evening.

The dinners have also helped raise money for the veterans' charities Operation Second Chance and Operation Patriot Support.

Retired Sarasota County Sheriff's Office Maj. Kevin Kenney is the Florida Coordinator of Operation Second Chance and serves on the board of Operation Patriot Support.

"Over the last years, Rick and Ryan are one of the top businesses in the county contributing to both charities, not only in monetary donations but in personal volunteer time," Kenney said. "They are truly dedicated to the welfare of veterans in our community and show it day in and day out."

"Our military — as citizens we owe them a debt we'll never be able to repay," Frailing said. "Doing little things like these dinners is just the smallest way of paying back."

No strangers

Both partners realize they would never have met, much less gone into business together, without their shared passion for cigars.

"If you walk into a cigar bar, you'll find people from all walks of life — attorneys, $10-per-hour guys, you name it. It's very diverse," Frailing said.

Said Louis: "You never meet a stranger over a cigar. It brings all mixes together. There are no strangers for long over a cigar. It's really kind of cool."