Rebecca Maddox has what she calls “a junkyard mind.”
“I’m a very curious person, a learner, and I love the creative process,” says the Naples entrepreneur. And for her, creation means developing—as in real estate. “Some people have a talent for singing or playing piano. My talent is to look at a vacant piece of property and an idea pops up.”
Five years ago, she beheld six such acres on Bayshore Drive, located in East Naples, just off US 41. “It was a pretty rough street then,” she explains.
Her first idea was to renovate and then sell the property. But wait. She had a vision: a multifaceted, 18,000-square-foot entertainment campus.
Her impetus for the endeavor sprang from a simple devotion: “I love to drink wine and eat great food, like anybody,” emphasizes Maddox. “And I love meeting people. If I wasn’t around people, I’d shrivel up.”
First came Three60 Market and later food truck destination Celebration Park, boasting a four-sided full-service outdoor bar. Following was Three60 Wine, where each bottle of wine is marked up just $3.60 above cost. Maddox’s next concept was Rebecca’s, a wine and cocktail bar across the street, which also gave Three60 Wine a new home in the same building.
As if this wasn’t impressive enough, there was more to her expansive plan. Enter The Maddox, her membership-by-invitation social club and event venue, which opened last fall.
“I wanted to meet other people, and I thought a social club was an opportunity,” says Maddox, a former accountant who settled in Naples in 2001 after often visiting with top clients when she worked for Citibank, among other employers.
“A lot of people who move to Naples are older,” says Maddox. “But, if you’re in your 50s to 70s, you don’t meet people at your kids’ school. And not everyone likes golf.”
The Maddox rectifies that by bringing people together, with an ability to accommodate 600 members by way of 300 two-person memberships. “It could be a husband and wife, significant others, a gay couple, or two friends,” Maddox says. “And members can bring guests.”
Though yearly memberships cost $18,000 plus tax, Maddox says she’s “not motivated to make money. I’m motivated by a vision to turn The Maddox into the SoHo of Naples.” (The latter refers to SoHo House private clubs in Miami and New York.)
“I’d never choose people [as members] based on money,” she explains. “I want a whole bunch more from them. But, I do want to run a successful business because no one wants to work for a team that doesn’t do well. So, there’s that balance.”
When she began considering members, she looked for people who not only were interesting but also interested. “You can be very interesting, but if you’re not interested in me, we won’t have a very long relationship,” she relates.
She also wanted people “who could deal with diversity of thought, education, and life experiences.”
She tells, “I’ve invited people who are interracial, straight, gay, Black, white, Asian. If you can’t deal with diversity, this club isn’t for you.”
Maddox also says tolerance is big on her list. “I’m sad that so many of us hate,” she says. “I wish I could help people understand kindness.”
That’s in part why she likes clearing tables. “That’s for my guests, and I’m happy to be of service,” she relates. “I don’t feel it’s beneath me. Being of service and being kind is the highest calling.”
Yet, beloved dogs aren’t allowed at The Maddox, and children are discouraged. “I have three dogs and love dogs,” she says. “But sometimes with dogs and kids, people are focused on them. I want an adult environment, where adults talk to each other.”
She also discourages phones and televisions for the same reason. “There’s one TV that’s used as a monitor in a boardroom,” she says. “With phones, you can bring them, but I want people to laugh, dance, drink some good wine, and get to know each other.”
To facilitate this, The Maddox hosts events, speakers, and activities, all noted and updated on The Maddox app that each member receives. Upon opening, she had 284 such events lined up for the first 90 days.
“With lots of private clubs, you eat dinner and then leave, and you might wave at friends on your way out,” says Maddox. “Not here.”
She hopes most members will come frequently—thus “the first one’s on us”—and stay for hours.
“If I was a member, I’d go to the middle room, The Atrium, where most of the people are,” Maddox shares. “There, the bar seats 60. But there also are quiet nooks, where guests can read a book, play cards, or meet a business associate. There are lots of ways to use the property.”
The decor affords a breath of fresh air—with windows that open onto courtyards where orchids hang from the trees. Bamboo in the ceilings and light cypress wood walls and furnishings evoke Bali.
Above all, she wants The Maddox to be back to basics.
“When I was growing up, if you had some popcorn, Kool-Aid, and a deck of cards, you could have so much fun,” she says. “I think a lot of my peers and members feel the same way now. We want to not have all these things that divide us and get back to enjoying family and friends.”
Maddox did just that in September, when she celebrated her birthday with her nieces and nephews on Isle of Palms, South Carolina. She didn’t fret about work because she and her entire staff take off the whole month to rest and reboot. “I pay them their full wages,” Maddox says.
Her life as an accountant was highly successful when she retired from corporate work in 2008 to fully focus on entrepreneurship. A self-described type A, she remains “very goal oriented at my ripe old age of 70. I absolutely love working. I can’t sit around. But I never feel like I’m working. I’m accomplishing—interacting.”
And from being a “supergood employee” to being her own boss, she’s looking to the future—and not only hers.
“I want my vision to be successful and to share it with other people,” Maddox says. “I want to give back, build a legacy, and help people when I can.”
Her embrace of work, change, and challenges can be traced to a nomadic childhood when her father’s business spurred many moves, from Indiana to states including Ohio, Illinois, New Jersey, and North Carolina. They eventually settled in Atlanta, Georgia, where some of her family is now.
“As a child, I hated moving all the time. As soon as my mother hung pictures and found us doctors and my three brothers and I made friends, we’d move,” she says. “But now I realize how beneficial that was. I can go up to anyone in a room.”
She sees her life as “a hell of a tapestry.” Interwoven are accounting, finance, marketing, serving on public boards of directors, public speaking, and writing female-empowerment books, such as Inc. Your Dreams: For Any Woman Who Is Thinking About Her Own Business.
“I never did anything I hated,” she expounds.
As for buying real estate, a turning point was 2008. And, unlike the timing of The Maddox (delayed by the pandemic, supply-chain shortages, and Hurricane Ian), it was perfect. “When real estate crashed—well, everything crashed,” she recounts.
“My father said, ‘If I were you, I’d buy real estate in Naples. If Naples doesn’t come back, nothing is coming back.’”
And the rest, as they say, is an ongoing history.
“Many people who retire get involved with the SPCA or a hospital,” she says. “But I’m still a very good businessperson. What if I could make money and then give it to my employees and charities? That got me sucked into the streak I’m on.”
Just as she cannot limit her range in careers, she cannot limit her goals. “I want to do creative things, create employment, revitalize underserved neighborhoods, be intellectually stimulated—and have fun.”
Opening Doors, Closing Circles
Rebecca Maddox lives not only to invent—but to connect.
So, when she first had the idea of adding Three60 Wine stores beyond Bayshore Drive, she sought a commercial real estate expert as ambitious as she.
She found Duke Kassolis, a commercial real estate investor with 33 years of experience in Naples. “We met, hit it off, and formed a partnership,” Kassolis says.
The dynamic duo are relying on three ingredients to succeed: a great concept, a first-class management team, and the right locations. And, perhaps they should add unexpected pairings and grand plans.
Kassolis proposed that the two open a wine store in North Naples—next to a 10-year-old Tide Cleaners, for which Kassolis holds the local franchise. “We knew it was a strong location,” he says.
But what could wine and dry cleaning possibly have in common?
“They both are strong concepts offering basic services that up to now have mostly been mom-and-pop businesses,” he explains. As an established brand for 65 years, Tide has 96-percent name recognition. “Three60 Wine doesn’t have that history, but it’s quickly gaining strong name recognition.”
Fueling its success is the experience. “People love to come in, browse, and talk with staff who know wine,” Kassolis says. “Customers also are exposed to labels they may not be familiar with but can buy at a great price.”
Having flourished in North Naples and on Bayshore Drive, two new Three60 Wine stores are planned, one at Logan Landings in Naples and one in Estero. Kassolis envisions additional locations, too, including in Palm Beach County and Broward County.
“Great word of mouth is important to the process,” Kassolis says. “That’s how you prove the concept and grow.”
If expanding businesses—and managing them for decades to come—seems unrealistic for two people in their 70s, realize that’s not their intent. Maddox and Kassolis are investing in the future.
“Rebecca and I are in the mature part of our careers,” Kassolis says. “Our goal is to create opportunities for others to blossom to their full potential. We want them to realize their American dreams, as Rebecca and I have.”
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