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Happy business owner hanging an open sign at a cafe

Let’s say you’re having an issue with a coworker. You could go to your boss to resolve it. But what if your boss is your father? And the co-worker is your brother? Then things get a little tricky. Working for a family-run business means work life slides over into family life, and family life slides into work life. Or they end up being one and the same.

Nationwide, about 20% of small businesses are family owned, according to a study by the SCORE mentorship organization. In Southwest Florida, family-run businesses are ingrained in the fabric of the community, whether that’s the Galloways of Fort Myers or the Wynns of Naples. Some are entering the third or fourth generations of leadership—which is rare considering only about 13% of family-owned businesses last longer than 60 years, according to that SCORE survey. Here are the stories of five local companies that have found success mixing family with business.

Galloway Family of Dealerships

Whether it was washing cars or answering telephones, the Galloway siblings always had a role in their family’s dealerships.

“We all grew up in the business,” Robert Galloway says. “It was something that was ingrained in us from a young age.”

Photo By Brian Tietz

Now, the fourth generation—Robert, his brother Sam III and sister Katherine—is running the Galloway Family of Dealerships that includes Sam Galloway Ford and Coconut Point Ford.

The Galloway name has been associated with selling cars for nearly 100 years in Fort Myers. Sam Galloway Sr.’s parents bought a dealership in downtown Fort Myers in 1927. Henry Ford and Thomas Edison would often stop when they were down on vacation. According to family lore, Ford would come in and chat with the mechanics, picking their brains about the serviceability of the cars. From an engineering standpoint, he’d ask about how he could improve the cars to make them easier to service. And then, the namesake of the world-changing auto company would slide under the cars to take a look for himself.

It’s a mentality that lasted in the dealership for generations: Ownership should be present and have a healthy respect for all areas of the company. “No one worked for us, they worked with us,” Robert says.

After spending most of his youthful years working jobs at the dealership, Sam Galloway Jr. took over in 1971 at the age of 27, making him the youngest Ford dealer in the nation, and he quickly turned it into one of the top 100 dealerships in the U.S. He also became a fixture of the community, supporting myriad causes. He helped start the Edison Festival of Light and drove his 1906 Ford Model N in the parade every year. He founded the Fort Myers Soup Kitchen, now known as the Community Cooperative. “It wasn’t about selling cars,” Robert says of the family’s charitable causes. “It was about helping other people.” Sam Jr. died at age 76 earlier this year.

A successful family business means transparency, Robert said. That’s one of the main lessons he got from his father. “We talked about everything,” he says. “We’d talk about success; we’d talk about challenges. It was an ongoing dialogue. No subject was off limits. We’d even talk about cars at the dinner table. The business was just so deeply ingrained for us from the beginning that those things were just normal.”

Ruth Messmer Florist

The art of floral design has run through the Messmer family for generations. Jeff Messmer had his own floral business in Chester, Pennsylvania, but moved to Fort Myers with his wife in the early 1950s. Ruth Messmer Florist started as a modest husband-wife business in 1953 in their home near Page Field, back when that area was considered the edge of town. In 1958, they opened a shop on Cleveland Avenue just south of downtown. When Jeff died in 1975, Ruth kept the business thriving.

Photo By Brian Tietz

She also became a leader in the Fort Myers community; she was the first female Rotarian, a president of the Alliance for the Arts, a longtime board member for the Lee County Public Schools foundation and the first female president of the Metropolitan Fort Myers Chamber of Commerce.

Her daughter, Heather, grew up in the store. Heather remembers watching as her mother and her employees carefully arranged bouquets. Her mother had a flair for design, and Heather soon picked up on it. By 18, she became the store manager. She actually wanted to be a veterinarian, but the family business ended up being the better fit, she says now. “It wasn’t the dream—it just came naturally,” she says.

Heather worked with her mother for 40 years until her passing in 2000. After that, she worked alongside her brother until she bought out his share of the business. Her daughter, Jessica Gnagey, also grew up around the store. Initially, Jessica didn’t want to get into the family business, either: She went to business school with the intention of venturing out on her own. But she found much of the business world too dry and started to miss the old shop. “I missed the creative process of floral arranging, even just how the flower feels,” she says. It was what came naturally for her, too.

She and her mother butt heads occasionally, but they’re family so they have to work it out, they said. “I usually get my way,” Jessica says with a laugh.

They moved the shop out of the old Cleveland Avenue location in 2019 to a spot on Boy Scout Drive. It was hard to leave the old store and the memories there, but it ended up a more convenient location for customers, they said. Like all retailers, they’ve had to contend with competition from Internet sellers, but once they hired a company that specializes in florist sites, they doubled their business. They say their strength comes from decades’ worth of connections in the community. Their customers know they’ll put together a fresh bouquet customized to each order—more so than what any online florist can do. Just like the ads her mother would run in the News-Press decades ago, they’re still “your extra touch florist.”

The Wynn Family

The Wynn name carries a lot of weight in Naples. Don Wynn started one of the city’s first grocery and hardware stores; he’s credited with helping usher in a new era in Naples. But the Wynn name doesn’t get you too far within the family business.

“You were going to work twice as hard and get paid less,” says Michael Wynn, Don’s grandson. “Then if you really wanted it, you’d have discussions about moving up in the company.”

Photo By Brian Tietz

They’ve had family members interview and not get hired for promotions. Michael himself applied for other jobs in the area when he wasn’t advancing at Sunshine Ace Hardware. It could be frustrating, but it’s helped create a culture where employees know that opportunities will be available for them no matter their lineage, he said.

The family first came to Naples when Vida and Peter Parley Wynn arrived from Lakeland after they purchased a small inn in 1938. They later opened a market and restaurant inside. About 10 years later, their son opened a grocery store on Fifth Avenue South, and a few years later, he opened a hardware store. It marked a time when Naples was modernizing; in this case, residents no longer had to travel to Fort Myers for basic necessities.

Wynn’s Market remains a mainstay in Naples alongside Tamiami Trail, with a Sunshine Ace Hardware next door. Sunshine has expanded to nine locations in Southwest Florida; Don Wynn had opened other markets elsewhere but eventually sold most before his retirement in the ’80s. Afterward, his five children ran the businesses, including the real estate and property management company Wynn Properties. The third generation has started to take on a more active role.

Michael Wynn is now president of Sunshine Ace, taking over from his uncle Jerry. He was involved in an early age, remembering handing out hot dogs and soda to customers at the market around the age of 6. He got involved part-time in high school, got a CPA later on and climbed the ranks in the company. “I just fell in love with the family business,” he says.

The company’s culture is based on 10 values his grandfather set. It includes an emphasis on support for employees and the surrounding community, which has led to policies such as giving out $5,000 grants to employees facing hardships. Michael said that list of values has helped keep the family grounded and humble. When challenges arise, he’s found that the family respects each other enough to listen and value each other’s opinion. Another advantage of working with family: He’s found that he can often anticipate questions before they even come up. He says, “We just know each other so well.”

Bartley’s Sporting Goods

Bartley’s Sporting Goods first started as H.A. Bartley Bicycle Shop in 1910 at the corner of First and Hendry streets in Fort Myers. For a while, it sold radios. Then it sold sporting goods. Now, it’s focused on selling uniforms for youth teams and doing custom screen printing and embroidery.

Photo By Brian Tietz

Loring Strickland runs the business now with her husband Steve, making it the oldest family-run business in Fort Myers. She’s the granddaughter of Henry Bartley, who got into the business at age 25. Her uncle Jimmy ran the store from 1972 to 1985. He had four daughters, but none took interest in taking over, so he convinced Steve to come on board in 1980. About seven years later, Loring joined the business.

They have two daughters who work in the store, and a son-in-law who serves as her right-hand man. A granddaughter is the bookkeeper. There’s only one non-family member who works there.

Working with family is “the best of times and the worst of times,” as Steve likes to say. Or, as Loring says with a laugh: “It’s the best that you can see your kids each day—and it’s the worst that you get to see your kids each day.”

Part of their success is due to the basic business principles Henry instilled in the beginning, such as respecting the customer. It’s decades of goodwill and good business that’s kept them around. A phrase of his still adorns the website: “Pay my bills. Treat my customers with consideration, and spend a little time with them.”

The other key to survival: adaptability. During the pandemic, Loring would think through the company’s history. When her grandfather was running it, he had to go through two world wars, the 1918 flu and the Great Depression. At times, he was selling anything from motorcycles to penny candy.

Just before the coronavirus hit, Loring and her family made the decision to permanently get out of selling gloves, bats and other hard goods, and to focus on screen printing and embroidery. “It was the best decision we ever made,” she says.

Youth sports were halted early on in the pandemic, meaning they would have bought a ton of sporting goods they couldn’t sell. However, there was still a demand for custom clothing. Thanks to the help of a Paycheck Protection Program loan, they survived the pandemic and are now just trying to keep up with pent-up demand. “In 111 years, we had to make a lot of adjustments to survive,” she says. “That’s what we continue to do.”

Phelan Family Brands

Sometimes the worst in life can lead to the best decisions. The Phelan family had five restaurants in Texas before an economic downturn put them all out of business in 1987. Tony Phelan had a friend in Naples, who spoke highly of the sunny skies and laid-back vibe, so the family packed up and moved. The family of four had settled into their new lives when the bad news came. Grant Phelan remembers it well: They were outside grilling one day; he was home for a time from college at Cornell University. Dad told him he had cancer. He had two years to live.

The next day, Tony started talking about restaurants again—about how great it’d be to have something here. “You’re crazy,” Grant laughed it off. After all, he was in college, his brother was in high school, mom was a schoolteacher, dad was about to go through cancer treatments. It wasn’t like they were flush with cash.

Photo By Brian Tietz

“Well,” Tony told his son. “I just signed a lease.” It was a little spot in Bonita Springs that would be nice for a seafood restaurant.

“He decided he didn’t want to leave us with nothing,” Grant now says.

That 1,500-square-foot space turned into Pinchers, which turned into one of the most successful restaurant groups in Southwest Florida. And, yes, Tony survived his cancer scare. There are 13 Pinchers locations across the Gulf Coast, plus the Texas Tony’s Barbecue and Deep Lagoon Seafood restaurants. They own a stake in Island Crab Company, where they get their restaurants’ fresh seafood, and they recently bought The Bay House in North Naples. Phelan Family Brands is still family-run, with Grant heading things and his brother serving as controller. His father is still involved in the business along with his mother.

The trick to a successful restaurant business isn’t too complicated, Grant said: Good food and good locations and a good team. Also, their timing was right, starting a restaurant chain right when the population started booming in Southwest Florida. “We were extremely blessed to come to Naples when we did,” he says.

“Dad says the best things that happened to him were once the worst. If he hadn’t gone broke in Texas, he wouldn’t have gotten to Naples. If he hadn’t gotten cancer, he wouldn’t have started Pinchers.

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