Naples Family Business: 20 Years of Success & Navigating Challenges

by Chief Editor

Southwest Florida Family Businesses: Navigating Tradition and Innovation

Ninety percent of businesses in the United States are family-run, yet less than a third survive to the next generation. This stark statistic underscores the unique challenges faced by family enterprises. As Southwest Florida business owners prepare for the fifth annual Resnick-Wynn Family Business Conference at Florida Gulf Coast University, the conversation centers on how to overcome these hurdles and ensure lasting success.

The Reinvention Imperative

The story of Christopher Shucart and his father exemplifies a key trend: constant reinvention. Their Naples-based JCS Realty Group, established in 2004, has thrived by repurposing existing properties. Their latest venture, the Cheeky Tiki, transformed a shopping center parking lot into a vibrant entertainment destination. This adaptability isn’t merely opportunistic; it’s a necessity.

“Our expertise has been repurposing. Taking something that’s already existing,” Shucart explained. This approach is increasingly vital as operating costs, like insurance and property taxes, continue to climb – reportedly increasing by almost 500% in the last 15 years in some areas.

The Emotional Landscape of Family Business

Successfully blending family dynamics with business demands is a perennial struggle. Shucart acknowledges the inherent difficulties: “Family business is as difficult as it gets. As 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.”

However, a strong foundation of respect can mitigate these challenges. Shucart credits a respectful working relationship with his father for strengthening their bond, even amidst the pressures of business ownership.

The Role of Technology: AI and Problem Solving

The 2026 Resnick-Wynn Family Business Conference highlights “Timeless Values in Times of Rapid Innovation,” signaling a growing recognition of the demand to embrace new technologies. The conference agenda includes sessions on leveraging Artificial Intelligence (AI) for business problem-solving and strategic decision-making. This focus reflects a broader trend of family businesses exploring AI to enhance efficiency and gain a competitive edge.

Key Speakers and Conference Details

This year’s conference, held February 20, 2026, at Florida Gulf Coast University’s Cohen Student Union, will feature Jim Perdue, Chairman of Perdue Farms, as the keynote speaker. Other featured speakers include David Diamond and Brett Diamond of DeAngelis Diamond, Bill Daubmann of My Shower Door, and Mark Bole, an instructor at FGCU’s Daveler & Kauanui School of Entrepreneurship.

The event runs from 9:00 AM to 2:00 PM, with registration beginning at 8:30 AM. Attendee pricing is $250 per person, with proceeds supporting student scholarships and local family businesses.

Looking Ahead: A Cautiously Optimistic Outlook

Despite economic uncertainties, Shucart expresses a cautiously optimistic outlook for 2026, anticipating “sluggish and steady growth.” This sentiment reflects a broader trend of Southwest Florida entrepreneurs remaining resilient and adaptable in the face of evolving market conditions.

Frequently Asked Questions

Q: What are the biggest challenges facing family businesses today?
A: Balancing family dynamics with business needs, adapting to changing market conditions, and managing rising operating costs are key challenges.

Q: How can family businesses improve their chances of long-term success?
A: Prioritizing open communication, fostering a culture of respect, embracing innovation, and seeking external expertise are crucial steps.

Q: Where can I find more information about the Resnick-Wynn Family Business Conference?
A: Visit the conference website at https://www.fgcu.edu/familybusinessconference/.

Did you know? Family-owned businesses contribute significantly to the U.S. Economy, generating approximately 64% of the nation’s GDP.

Pro Tip: Regularly schedule family business meetings to discuss both business performance and family concerns. This proactive approach can prevent conflicts and strengthen relationships.

Stay informed about the latest trends in family business management. Explore additional resources and connect with other entrepreneurs to share insights and best practices.

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