In Southwest Florida, family-owned businesses tend to come and go. As trends and tastes change, and as private equity increasingly buys out the founders of successful entities, watching family-owned businesses continue operations from one generation to the next has become the exception, not the rule.
But Charlotte, Collier and Lee counties have such exceptions.
The exceptions include businesses that have met and exceeded 30-, 40- and 50-year milestones — and a few even older. They include an assortment of enterprises, from restaurants to hardware stores to a lawn mower manufacturer that made a pinpoint pivot to maintain relevancy.
Generational baton handoffs have happened, are happening now and are being planned for the future. Some of these businesses have shifted, evolving as times and technology change; some of them have stayed relatively the same.
John and Billie Resnick have led The Resnick Group, a Naples-based, family-owned financial advisory firm, for nearly 30 years and co-organize the annual Resnick-Wynn Family Business Conference at Florida Gulf Coast University, where professionals discuss leadership and family enterprise.
Brian Tietz
John and Billie Resnick know what it takes to sustain a family-owned business. For almost 30 years, the husband and wife have owned and operated The Resnick Group, a Naples-based, family-owned, financial advisory company. For the past five years, they also have helped organize the annual Resnick-Wynn Family Business Conference at Florida Gulf Coast University. National business luminaries, including Steve Forbes, chairman of Forbes Media; James Tisch, executive chairman of Loews Hotels and co-owner of the New York Giants; and Jim Perdue, chairman of Perdue Farms, have spoken at the conference. Billie Resnick said the guest speakers and owners of family-run businesses share a common thread.
“Families aren’t expected to always agree with each other, but successful family businesses have grown by respecting each other’s viewpoints,” Billie Resnick says. “Mutual respect and synergistic teamwork is a hallmark of successful family firms. During a recent visit with Steve Forbes, he shared that most family business fortunes weren’t built by creating something new, they were created by making an existing product or service better.
“Making tough decisions takes leadership, but when you treat the business as a business first, it makes those choices a little clearer.”
Gulfshore Business is putting the spotlight on Southwest Florida’s family-owned businesses. Those featured here are by no means a definitive list. But they have spanned multiple generations, having navigated challenges and seized opportunities along the way.
All of them will have to continue innovating in a rapidly changing world, full of competition, pitfalls and chances for advancement.
Charlotte County
Don Berini, seated, is surrounded by employees at The Bean Depot Cafe, a multigenerational, family-owned business in Charlotte County that has served as a community hub since 1923. The former El Jobean Post Office and General Store continues its legacy just north of Boca Grande.
Brian Tietz
The Bean Depot Cafe & Museum
One of the oldest surviving buildings in Charlotte County has more than a century of history behind it and has had just three families at its helm: a father and son, a death-defying daredevil and his wife, and one of Southwest Florida’s founding entrepreneurs of the 1920s — the founder and namesake of El Jobean.
The Bean Depot Cafe is one of the few family-owned businesses with ongoing, multigenerational ownership in Charlotte County. It’s located at 4370 Garden Road, just north of Boca Grande, and it’s listed — as well as the once adjacent but since-destroyed Grand Hotel — in the National Register of Historic Places. Since 1923, when it was first built by Joel Bean as El Jobean Post Office and General Store, it has been a community hub. It’s a tradition that legacy and current owner Don Berini doesn’t want to change.
“The Bean Depot used to be the last train depot,” Berini says. “It was the post office, the general store and one little jail cell. It was pretty much the hub of the area. The Grand Hotel was there, which Hurricane Ian did quite a bit of damage to.”
Berini said he rode out Hurricane Ian on Sept. 28, 2022, eating hot dogs and drinking whiskey inside the cafe, which survived. But whatever was left of the Grand Hotel was washed away by hurricanes Helene and Milton in the fall of 2024. Berini has salvaged some of the remaining wood, and he hopes to partner with Charlotte County someday on resurrecting the hotel.
More than a century prior, Joel Bean bought a 1,071-acre tract of land in 1923 and began development by building the hotel and the post office. He named the development El Jobean, an anagram of his name.
In 1942, Leo Simon, a circus daredevil who performed stunts such as dousing himself with gasoline and setting himself on fire — he was nicknamed both “Captain Leo” and “Suicide Simon” — bought both buildings from Bean. For a couple of decades, the hotel became a haven for other daredevil types, with the flying Wallendas, the Flying Valentine Brothers and more practicing their acts in the hotel’s back yard, according to a history compiled in the 1990s by El Jobean Historical Properties Inc., which was looking to refurbish both buildings.
By 1996, with interest in the property waning, Tom Berini paid $50,000 for the post office building and converted it into a museum and restaurant, the Bean Depot Cafe, which operates to this day. It serves “Suicide Simon” burgers, hot dogs, salads and sandwiches.
“My father really set up a solid business model with comfort food,” Don Berini says. “He was very smart about the designing of the menu. And the location. We were really fortunate during the hurricanes to be a pivotal part of the recovery in that area. It’s been a blessing.”
When Tom Berini died in 2019, ownership of the Bean Depot Cafe passed to Don Berini, his mother Ruth Anderson and Chris Meyer. With Anderson living in Fairbanks, Alaska, and with Don Berini entrenched in his career as an engineer, commuting to Tampa from his home in North Port, management of the restaurant has shifted to Erin McCormack, a childhood friend of Don Berini and, like him, a Lemon Bay High School graduate.
“It’s been a blessing but at the same time extremely challenging, physically and mentally and financially,” Berini says of owning the restaurant. “Once I get into the weeds on some of the details, it stirs up a lot of emotion.
“The beauty of it is how much it’s allowed me to be a part of the community and continue on the legacy of being the hub of the community.”
Clay Roberson and his father Kenneth Roberson, founder of Roberson Funeral Home & Crematory, continues to work daily as the family-owned business marks its 50th anniversary. The firm is now operated across multiple generations, with Roberson’s sons and grandsons.
Brian Tietz
Roberson Funeral Home & Crematory
Kenneth Roberson’s business will be celebrating its 50th anniversary this year, having opened in 1976 in Port Charlotte and adding a Punta Gorda location in the 1980s. Roberson, 82, still works every day.
“One day, I plan to,” Roberson says of retiring. “My mother lived to 102, so it might be a few more years. We’ll continue to run it as a family business.”
Roberson has two sons, Mark and Clay, and three grandsons, Hayden, Trent and Zack Roberson, who all work in the business. Asked how they get along, Kenneth Roberson, a former state representative, says, “Well, I’m the CEO and the boss. But we get along well. We’ve been here a long time, serving families in Southwest Florida and Charlotte County and the North Port area.”
Collier County
Kelly Ellis and his son, Keith Ellis, represent two generations behind Kelly’s Fish House Dining Room, the oldest continually operating restaurant in Naples. Founded in 1953 as a net and gear shop for local fishermen, the landmark has remained family-run for 55 years.
Brian Tietz
Kelly’s Fish House Dining Room
In operation since 1953, the restaurant has its origins as a net and gear shop frequented by shrimpers and fishermen. Kelly Ellis and his family have operated the local business for 55 years. His mother, Kelly McGill, took over the Fish House Dining Room in 1971, renaming the local restaurant Kelly’s Fish House Dining Room. It’s the oldest continually operating restaurant in Naples.
Ellis moved to Naples from Hawaii at age 14 in 1962. His restaurant is at 1302 Fifth Ave. S., on the east bank of the Gordon River in Naples. “I’ve been fortunate enough to have a lot of people working with me for a long time,” Ellis says. “I’ve had three or four generations at one time in here. The menu and the recipes are basically the same as they were in ’53.”
From left, Timothy Stready Jr., Timothy Stready Sr., Quintina Stready, Justin Stready and Cassandra Stready represent multiple generations of Cleveland Bass and Movers in Naples. Founded in 1969, the family-owned moving company continues under third-generation leadership at its headquarters on Linwood Way.
Brian Tietz
Cleveland Bass and Movers
The area code has changed three times over the past 57 years, but the rest of the phone number — 744.4848 — has stayed the same. The headquarters at 2363 Linwood Way in Naples has lasted for multiple generations, as well. Cleveland Bass founded the business in 1969.
His son and daughter-in-law, Timothy and Quintina Stready, ran it for years before ownership continued with the third generation. Siblings Timothy Stready Jr., Justin Stready and Cassandra Stready now operate the business, and a fourth generation also is involved. The full-service moving company also does packing, crating, shipping and delivery, as well as storage for homeowners doing renovation projects.
Michael Wynn is the fourth-generation leader of the Wynn family businesses, which trace their Naples roots to 1938. Today, the legacy includes Sunshine Ace Hardware’s 18 locations, two Wynn’s Markets and the family-owned Wynn Properties.
Brian Tietz
Wynn Family of Companies
Michael Wynn is chairman of the board for Wynn and president for Sunshine Ace Hardware. He’s also the fourth generation to run these legacy businesses in Naples. It began in 1938, when his great-grandparents, Peter Parley and Vida Wynn, opened the Bay Dock Hotel near the city docks. That led to second generation Don Wynn opening the first Wynn’s Market before converting an auto parts store into a hardware store.
Third generation Tom Wynn (Michael’s father) passed the torch to Michael Wynn. The original hardware store evolved into Sunshine Hardware, which today has 18 locations. There are two Wynn’s Markets; the original moved to its current location at 141 Ninth St. N., while a second Wynn’s Market is at Ocean Reef in Key Largo. The family also owns and operates Wynn Properties, a real estate company.
Grant Phelan serves as CEO of Naples-based Phelan Family Brands, a family-owned hospitality company that grew from a single Pinchers Crab Shack in 1997 into a restaurant group with more than 10 dining concepts across Southwest Florida.
Brian Tietz
Phelan Family Brands
What started as a tiny seafood restaurant at U.S. 41 and Bonita Beach Road in 1997 has become an ever-growing restaurant group. Tony Phelan’s first Pinchers Crab Shack expanded to 10 locations along Florida’s Gulfshore. He also started his namesake Texas Tony’s barbecue restaurant in 2010.
Under the leadership of Tony’s son, CEO Grant Phelan, the family’s Naples-based hospitality company — Phelan Family Brands — has amassed more than 10 dining concepts, including Deep Lagoon Seafood and the new Caiman Cantina. These are concepts the family created, but it also acquired many other established local restaurants that now operate under the Phelan Family Brands umbrella, including The Bay House, Chops City Grill, Pazzo, CJ’s on the Bay and others. The Phelans recently converted Yabba Island Grill to Keewaydin’s on Fifth in downtown Naples.
Sheila, Tim and A.J. Zellers represent multiple generations of the Zellers family, owners of Tamiami Ford and related dealerships in Naples. The family business, founded in 1973, continues to expand with a new Genesis dealership under development.
Brian Tietz
Tamiami Ford
Husband and wife Arlie and Genie Zellers opened the car dealership in 1973. In 1986, Tim Zellers, their son, became president of the company and later the owner. He maintains ownership to this day, and there are third and fourth generations of the Zellers family involved.
In 2018, Zellers bought the rights to Genesis of Naples, adding that to the Ford and Tamiami Hyundai dealerships. On Jan. 6, ground broke on a new, standalone Genesis facility on 12 acres at the intersection of Pine Ridge Road and Interstate 75 in Naples. The groundbreaking faced years of permitting delays and legal challenges relating to a roadway easement and a neighboring property.
“This moment carries tremendous emotion for all of us,” Zellers says. “We believed in this project with our whole hearts, even when the path felt uncertain, and the obstacles seemed endless. What pushed us forward was our responsibility: to our family business, our customers and a community that has trusted us for generations. They deserve this facility, and we refused to let setbacks stop us.”
The 30,000-square-foot facility will be the largest Genesis dealership in the nation, Zellers said.
Lee County
Owner Calli Johnson leads Bailey’s, the longest-running family-owned business in Lee County, originally founded in 1899 by Frank Bailey. The multigenerational grocery store is operating at A Bit of Bailey’s at Rabbit Road Plaza while plans move forward for a new store at Periwinkle Way and Tarpon Bay Road.
Brian Tietz
Bailey’s General Store
Opened in 1899 by Frank Bailey, the grocery store is the longest-running family-owned business in Lee County, with members of the fourth and fifth generation now involved. Bailey’s is in transition after the 2023 demolition of the most recent store, built in 1965. A new store is being planned for the same site at the southeast corner of Periwinkle Way and Tarpon Bay Road. In the interim, the business is operating with a much smaller footprint, at A Bit of Bailey’s at Rabbit Road Plaza.
Mary Macoy (left) and Joann Mow (right) are longtime employees at Farmer’s Market, the longest-running restaurant in Lee County. Open since 1952 in Fort Myers, the restaurant has evolved into a community gathering place.
Anna Nguyen
Farmers Market Restaurant
Since 1952, this restaurant at 2736 Edison Ave., the longest-running one in Lee County, has seen a lot of change, sitting near the epicenter of the historically Black community known as Dunbar. When it opened, it opened to white people only. These days, it’s a melting pot of greater Fort Myers. Betsy Barnwell has owned Farmer’s Market for the past 11 years, and her father-in-law, Bill Barnwell, owned it before her.
Members of the Bartley family continue operating Bartley’s Sporting Goods in Fort Myers, the city’s oldest surviving business, founded in 1910. The multigenerational company now specializes in printing names on sports jerseys after shifting its business model in recent years.
Brian Tietz
Bartley’s Sporting Goods
Henry A. Bartley opened H.A. Bartley Bicycle Shop in August 1910 in downtown Fort Myers, making it the city’s oldest surviving business. Over the following century, the store has switched locations and shifted its business model, but it has remained in the same family.
Located now at 2555 Cleveland Ave., Bartley’s Sporting Goods no longer sells bicycles or even much in terms of sporting goods. Instead, it specializes in printing names on the back of youth sports jerseys. It also prints names on the backs of jerseys for the Boston Red Sox, Minnesota Twins and Pittsburgh Pirates during spring training; and Florida Everblades hockey jerseys, too.
Rylee Manetta, 30 and Bartley’s bookkeeper, is the great-great-granddaughter of the founder. Steve and Loring Strickland, who is the granddaughter of the founder, co-own the store.
“Even though we’re still Bartley’s Sporting Goods, when you walk in, you wonder, ‘Where are the sporting goods?’” Loring Strickland says. The change happened in 2019, just before COVID-19.
“We had to make a decision of how to stay in business and continue on, so we decided to change and do more printing. It’s more hands-on and better to work with the customer face-to-face. It’s a good thing we did, because I think we would have been out of business if we hadn’t. I’ll tell you what: In this market, it’s getting harder and harder. We celebrated 115 years in August.”
The Galloway Ford dealership in Fort Myers traces its roots to 1927, when the Galloway family began selling Model T vehicles in Southwest Florida. Today, Robert Galloway leads the Fort Myers location, with multiple generations of the family continuing the business at 1800 Boy Scout Drive.
Brian Tietz
Galloway Ford
The Galloway family began selling Model T’s when there were dirt roads throughout Southwest Florida. The year was 1927, and the dealership then was known as Lee Motors. Henry Ford himself would drop in on the store, as would Thomas Edison and tire businessman Harvey Firestone. Sam Galloway Sr. took ownership of the dealership in the 1940s and ’50s. Today, Robert Galloway runs the Fort Myers store, and his brother, Sam Galloway III, runs the Estero location. Members of the dealership’s fifth generation also work for the company. The Fort Myers dealership has changed locations over the past century, but since 1996 it has been located at 1800 Boy Scout Drive.
From left, Madison Henderson, Ranell Henderson, Dennis Henderson, Julia Peckich, Hailey Henderson and Melissa Tindell are part of the team at Skip One Seafoods in south Fort Myers. The family-run restaurant and fish market at 15820 S. Tamiami Trail has operated in much the same setting since the 1960s, maintaining its legacy for more than half a century.
Brian Tietz
Skip One Seafoods
This restaurant and fish market at 15820 S. Tamiami Trail in south Fort Myers shared its name with a boat owned by the original owner. Now owned by Dennis Henderson, it’s been more or less the same setting — a time capsule of an eatery — since the 1960s, having eclipsed the half-century mark of endurance.