🎙️Beyond the Timeshare: The Jim Gissy Story
A podcast that goes deeper than deals, dollars, and destinations.
This is the untold journey of a man whose name may be synonymous with success in the resort industry — but whose vision and ventures extend far beyond the world of timeshares.
🌟 Who Is Jim Gissy?
In this podcast, we explore the remarkable life and multifaceted career of Jim Gissy — from his humble beginnings as a record-breaking sales agent at American Income Life Insurance Company to becoming the Chief Executive Officer of Westgate Resorts, one of the largest privately held timeshare companies in the world. But make no mistake:
This is not just a business podcast.
This is a human story.
A story of transformation, vision, and purpose.
🧭 Where It All Began
Our journey starts in 1984, when Jim joined Westgate Resorts as a sales representative. With sheer determination and natural sales talent, he rose rapidly through the ranks — becoming Executive Vice President of Sales and Marketing by 1990.
- Led thousands of sales, marketing, and operations professionals
- Played a pivotal role in Westgate’s explosive growth
- Honored in 1996 with the ARDY Award for Top Sales Executive
We’ll uncover the strategies, mindset, and leadership philosophies that propelled Gissy to the top.
🏞️ More Than Resorts:
A Real Estate Visionary For over 30 years, Jim Gissy has quietly built a massive and diverse real estate portfolio across Central Florida.
- Owns 2,500+ acres of vacant land
- Controls over 2 million sq. ft. of commercial property
- Includes offices, hotels, RV parks, billboards, and historic landmarks
- Is the largest private landowner along Florida’s iconic Rainbow River
Notably, he owns Gissy Springs and the Rainbow River Ranch — hundreds of acres of pristine natural land, including thousands of feet of river frontage and over a dozen natural springs.
🌿 From Development to Conservation
One of the most compelling arcs in Jim’s story is his evolving relationship with nature. Initially, he considered building an ecotourism resort on the Rainbow River. But after facing local resistance and reflecting on the ecological value of the land, Gissy changed course. Now, in partnership with Conservation Florida, he’s working to permanently protect this land through conservation easements — a move that could create an unbroken corridor of protected lands between:
- 🌳 Rainbow Springs State Park
- 🌲 Withlacoochee State Forest
This decision marks a significant pivot in Jim’s career — from developer to environmental steward. 💡 A Multifaceted Investor Jim Gissy’s business interests span far beyond real estate and resorts.
- 🎯 Board Chair and largest investor in Starboard Cruise Services
(a global leader in cruise ship retail, now expanding into land-based resort retail at Westgate properties) - 💰 Investor in First Green Bank, originally for financial reasons — but over time, he embraced its mission of environmental sustainability and community impact
Jim’s outlook now blends capitalism with conscience, balancing profit with preservation. He is a strong advocate for public land purchases, believing nature should remain accessible to everyone, not just the wealthy.
🔍 What to Expect in This Podcast
Beyond the Timeshare is a deep dive into:
- 📈 Gissy’s rise in the high-pressure world of sales and timeshare leadership
- 🏢 His influence as a dominant force in Florida’s real estate market
- 🛳️ His strategic expansion into cruise and resort retail through Starboard
- 🌊 His personal mission to protect Florida’s springs and preserve the Rainbow River
- 🌎 His evolution as a businessman who now champions sustainable development
We’ll unpack the values, decisions, and defining moments that shaped Jim Gissy — offering a rare look behind the curtain at a man who continues to influence Florida’s future in both business and conservation.
Become a supporter of this podcast: https://www.spreaker.com/podcast/florida-real-estate-deep-dive--6429387/support.
