Take, for instance, Deanna Wallin, the founder and CEO of Naples Soap Company. After finding herself unhappy with her job in 2009, a friend recommended that Wallin consider a new career in retail. While brainstorming concepts for a business, another friend pointed out the wide array of body soaps and skincare products stacked in Wal- lin’s bathroom. “I’ve always been a skincare junkie from the time I was very young; I’ve always had dry skin,” she explains. Her friend suggested that she simply sell what she knew, and in Wallin’s mind, “It just made sense,” she says.

Naples Soap Company started up in a 300-square-foot space in Tin City and drew a large crowd almost immediately. “I had people driving from Boca, from all over the state,” Wallin recalls. Naples Soap outgrew its quarters within months, and eight years later, after the flagship store took a hit from Hurricane Irma, the company needed to expand. Wallin acted fast—she secured a space on Fifth Avenue, signed the lease within 72 hours and opened the second Naples location eight weeks after the hurricane swept through. The retail giant, Dillard’s, now carries the line.

Naples doesn’t stand alone as a spot that’s hospitable to female entrepreneurs. The rate of women-owned businesses around the country has steadily increased over the last decade. In 2018,women-owned companies made up 40 percent of all businesses in the United States, according to the American Express 2018 State of Women-Owned Businesses report. The trend is reflected in this year’s statistics for Fifth Avenue, provided by The Greater Naples Chamber of Commerce: out of 237 total businesses on Fifth Avenue, 24 of them—about 10 percent—are women-owned. Downtown Fort Myers is similar in what it offers—arts, dining, and entertainment—but out of the 600 businesses reported in that zip code, only 18 are women-owned.

SVETLANA KOGAN

Each business venture represents a gamble for success—even if you’re deciding to downsize. Like Wallin, Dr. Svetlana Kogan reached a point where she questioned how content she was in her career. In her New York internal medicine practice, she felt a disconnect from the city and its constant fight-or-flight energy. She was hooked on the tranquility of Naples after a couple of visits and moved her practice into a suite on Fifth Avenue in 2018.

Naples’ smaller population enabled Kogan to establish a concierge practice, which isn’t easy in a metropolis like New York. “I want- ed to keep it very small and cap it at about 250 patients,” she explains. “I want to invest myself into every case. It should be how it used to be where the doctor was a family friend.”

Kogan credits her time in New York for shaping her character and developing a great appreciation for her new hometown. “Naples is a thriving community, very cosmopolitan and diverse,” she says. “The people, business owners and residents are always out, strolling. The weather is great—being out there, not cooped up in the office but being able to go outside and connect with people.”

Fifth Avenue’s lively atmosphere makes it receptive to new businesses. While the close proximity of storefronts makes it easy to know your neighbor—and even those far- ther down the road—there’s an undeniable sense of community that seems to ward off competition with each other.

CATHY CHRISTOPHER

Just ask Cathy Christopher, the director of sales and marketing at Inn on Fifth. Her friendliness might be the product of her years in the hospitality business, but it’s also the sign of someone invigorated by her career. “I do feel very much at home here,” Christopher says. “It’s very much a part of me. It’s like walking into a comfortable place.”

Christopher helped open the inn 22 years ago, and over time has become well-acquainted with the other players along Fifth Avenue.

“The one thing that has been constant is that Fifth Avenue then and now is the main street of Naples,” she says.

“Fifth Avenue has thrived because of the character and personality of the street and the town. Naples has maintained that aura of being a magical place to be without being glitzy or pretentious.”

She cites the special events that take place on the avenue throughout the year, like the St. Patrick’s Day Parade and the Christmas Fest that features a visit from Santa himself, as a major component behind the avenue’s liveliness.

Mayor Bill Barnett notes that the women’s influence has been all positive and credits their determination. “They’re all special individuals that have worked their way into entrepreneurship, that have worked their way up the ladder,” he says. “They are where they are today because of hard work. They all add to the ambiance and charm, plus the business acumen.”

BETH RESSLER

Beth Ressler is the owner of Wind in the Willows, the dandelion-yellow store at the intersection of Fifth Avenue and 8th Street South. She was a department store buyer before eventually owning her own clothing store in Ann Arbor, Michigan.

Ressler opened up Beth’s Boutique on Third Street after moving to Naples, and in 2001, bought the popular gift shop Wind in the Willows. She merged the best lines of both stores before moving onto Fifth Avenue. The store, which sells a funky mix of products like bib-overalls and hand- made ponchos, stays current because Ressler isn’t afraid to let the business evolve. She frequents gift shows throughout the year and consults with her staff to find out what’s trending with customers.

The vibe of the store translates well with the lighthearted atmosphere that visitors come to soak up on Fifth. And for those wanting a dash of sophistication, there’s Arabesque. The combination fine stationery and gift shop pays tribute to a time when personal touches like handwritten cards and letters were a pillar of relationships. Owner Sheryl Sashin opened Arabesque to preserve this tradition, and after years of communication via Facebook, “the tide is turning,” she’s happy to note, and people are returning to more formal notes.

SHERYL SASHIN

“I think people understand the value of having something tangible,” says Sashin. She explains that she’s seen a surprising surge in young clientele, specifically young men. “They are really getting back into fountain pens and to caring about what kind of paper they’re writing on.”

It seems Sashin had exceptionally keen foresight when she established her business on Fifth 20 years ago. She notes that the avenue was quieter then, but still had an upscale flair where “everyone felt very comfortable wearing their diamonds day and night.”

Fifth Avenue doesn’t seem to be slowing down anytime soon. Folks can look forward to wearing their diamonds— or anything else they choose—to a show at the new Gulf- shore Playhouse, across the street from Tin City. Just 17 years ago, the theater wasn’t even a blip on the radar of founder and Executive Director Kristen Coury.

KRISTEN COURY

After arriving from New York in 2003, Coury fell in love with Naples and applied for a 501c3. Performances in the Norris Center followed, as did tight community partnerships. Now, Naples boasts a New York-caliber professional theater.

Reflecting on her endeavors and entrepreneurship, Coury admits that success was earned through perseverance. “You have to be willing to keep rowing the boat amongst the really wild and choppy waves of the business,” she says. “We’ve suffered extraordinary downturns in the market. We’ve taken our licks and kept on prodding through it.”

She pauses a moment before summing up what seems to be any entrepreneur’s key to success, a trait that each of these women has clearly aced over the years: “Ultimately, you grow alongside the business and continue to watch what the company itself needs you to be.”

SHINING A SPOTLIGHT ON FIFTH AVENUE

Highlighting the contributions of some of Naples’ key players is no easy feat, but Bruce Barone is up to the task.

As the executive director of Fifth Avenue South’s Business Improvement District, Bruce Barone juggles a host of responsibilities: he plans—and often executes—the events that take place on the avenue, oversees the landscaping and enrichment projects and directs media and public relations opportunities.

In that same breath, Barone, 38, has already found a new outlet to commemorate the glam-

our of downtown Naples and celebrate the ingenuity of the people who work there. He recently partnered with Gulfshore Business magazine to showcase some of the women entrepreneurs who have shaped Fifth Avenue.

“I’ve been working on how to build awareness about Fifth Avenue and the merchants here and this was in the same vein as the Faces of Fifth project,” he says. “We have a really successful street and some really tenured businesswomen that are pretty much templates for success.”

Fifth Avenue is the vibrant heart of downtown Naples. It offers a generous sampling of some of the best fashion, cuisine and art in the area. The area’s success has much to do with the

overarching support each entrepreneur has for one another. They’ve all shaped downtown by generously sharing their own unique service, but in merging their strengths have created a formidable community that draws thousands of visitors every year.

Take Veljko Pavicevic, for example. The general manager of the well-regarded Sails Restaurant on Fifth partnered with Barone to provide the space for the women entrepreneurs’ photoshoot—and a coastal European brunch on the house—to boot.

Barone acknowledges that the variety of businesses on the avenue enhance the dynamic, and however the community responds, the businesswomen listen.

“They’ve seen the flow of the avenue; they’re masters of their crafts,” he says. Because of this, Barone wants to get the word out. Every new task he takes on is in an effort to enhance recognition of the powerful players on Fifth. He wants to get visitors excited, and, more than anything, wants to get the locals on board with savoring Fifth Avenue, a destination they have access to throughout the year.

The fabric of Naples is a rich one because of the contributions of devoted business owners like those on Fifth Avenue. “I think we’re creating a culture on Fifth,” says Barone. “It’s about sophisticated luxury, a place where you can bring your family. It’s a well-articulated masterpiece.”