Naples family business thrives through constant reinvention

NAPLES, Fla. — Ninety percent of all businesses in the United States are run by families, but fewer than a third of those businesses make it to the next generation.

As Southwest Florida business owners prepare for the fifth annual Resnick-Wynn Family Business Conference at Florida Gulf Coast University, local entrepreneurs are sharing insights about the state of the economy and the distinct hurdles family-owned businesses must overcome.

In Naples, a father and son have been in business for more than two decades by constantly reinventing themselves and their properties.

Christopher Shucart opened the Cheeky Tiki in October, transforming a shopping center parking lot into a tropical escape complete with cocktails, full service bar and live music. The tiki bar is tucked into the parking lot of a shopping center that Shucart and his father have owned for 15 years.

"Our expertise has been repurposing. Taking something that's already existing," Shucart said.

That philosophy has guided Shucart and his father for the last two decades. They launched JCS Realty Group in 2004, managing and leasing commercial real estate properties in Naples.

"Family business is as difficult as it gets. Because there's emotion and business involved. Business is tough enough on its own. But throw in some different family dynamics and emotions into it makes it that much harder," Shucart said.

Despite the challenges, Shucart said his relationship with his father is stronger now than it ever has been. He credits that to a working relationship built on respect.

However, the cost of doing business keeps rising. Shucart said operating expenses like insurance and property taxes have increased by almost 500% in the last 15 years.

Still, he said there's nowhere else he would rather be in business than Southwest Florida.

"I see 2026 as being a great year. I'm not gonna say it's a banner, right out of COVID years. But I think it's going to be a slow and steady growth which I think is healthy," Shucart said.

Shucart will be at FGCU on Friday, Feb. 20 for the fifth annual Resnick Wynn Family Business Conference, where local business owners meet and share ideas about how to navigate the unique challenges that family-owned businesses face.

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