Salute Larry Gildersleeve – Timeshare Industry Pioneer From RCI Leadership to Best-selling Author

The Timeshare Pioneers series for Resort Trades was created to chronicle and honor the involvement of a handful of true pioneers whose early contributions and entrepreneurial spirit paved the way for today’s nearly $10 billion a year timeshare industry.

To set the stage for this Pioneer feature, envision a flashback to 1974 when RCI became the world’s first timeshare exchange company. The U.S. timeshare industry was still in its infancy and ALDA was formed in 1976 as the precursor of today’s ARDA.

In 1980 Larry Gildersleeve began his timeshare career with RCI in Indianapolis as VP of Resort Affiliation. During his decade of leadership, Larry recruited, trained and managed a 25-person sales team in five U.S. cities, successfully licensed the Australian operation to the industry trade association and managed the growth of its licensed operation in Japan. Eventually, he had corporate oversight of RCI’s European, Latin American and South African operations.

Recalls Larry, “My first U.S. industry event was in California in August of 1980. My first international conference was in Australia in early 1981. Gary Terry, head of ALDA, was also there and there were less than 75 attendees. I was asked to speak about the successes and challenges happening in the US and Europe and to share industry “best practices”, so hopefully, mistakes made elsewhere weren’t repeated on the Gold Coast of Australia. For most of the 80s, because of my global perspective, I was often the keynote speaker at conferences around the world.”

Rising to the position of Senior Vice President, Larry played a significant role with RCI, bringing in new RCI affiliates and contributing significantly to the industry’s global expansion. At the time he left RCI, he led the resort affiliation and resort services divisions and had executive responsibility for all the company’s then 12-country global operations, plus in-house legal and regulatory affairs.

“The biggest challenges everywhere involved introducing the ‘new’ concept of timeshare vacationing to the marketplace plus related regulatory issues. For example at the time and probably still now, Australia is the only place on the planet that I’m aware of where timeshare falls under its securities laws and is regulated by its SEC equivalent, adding even greater challenges.”

By 1990, timesharing was in Larry’s DNA, so it was only natural that he continued to work with other industry pioneers, often leaving his own imprint on the industry he helped create. He joined industry pioneers Ed McMullen, Sr. and Allen Ten Broek in creating Hilton Grand Vacations, now the second-largest timeshare company in the world. Larry freely admits the transition from being an executive with an exchange company to one with a development company revealed a whole new world about the internal workings of a very complex industry. “It was a steep and challenging learning curve,” Larry recalls, “but it was extremely rewarding, personally and professionally.”

“I have the greatest admiration and respect for the early industry pioneers,” Larry says. “It was a Star Trek-like adventure, with courageous developers and other industry professionals boldly going where no one had gone before. I don’t recall any of them questioning will it work, they just went out and made it work. Their efforts, and success created a whole new way for consumers to vacation around the world, and created a trillion dollar industry in the process.”

After Hilton, Larry held executive positions at Interval International, MeriStar Hotels and Resorts and Trendwest Resorts. For a time, Larry was interim CEO of Trendwest’s Australian operation, commuting back and forth from the Seattle headquarters.

“Larry is truly a Pioneer,” shares fellow timeshare pioneer Ed McMullen, whose Hilton Head resort company was purchased by Marriott in 1983 to form what later became Marriott Vacation Ownership. “He has held senior positions with all major companies during the industry’s growth and affiliations with much more developing industry companies. He is the go-to guy for all things considered in the Vacation Ownership business through today. Larry remains a talented, thoughtful, and close friend to the entire industry both old and new.”

Still working full time as a resort industry consultant, Larry directs the activities of Customized Solutions, a division of Gildersleeve Partners LLC, a unique entity brokering third-party merchant services exclusively to the resort timeshare industry. The company is focused on finding ways to increase the profitability of companies in the timeshare industry by lowering their operating costs and enhancing operating efficiencies. They’ve been able to achieve this through relationships with the country’s largest credit card processors. The initial formation and creation of this company were fueled by entrepreneurial/innovative skills gleaned from years of previous timeshare experience. His business partner is Trendwest co-founder, Jeff Sites.

When asked to share his tips to industry newcomers, Larry advised people to engage experienced industry professionals in all disciplines. “Timeshare is like no other industry,” he says, “with countless interrelated moving parts, and success requires mastery of all of them. Nothing will ever be as simple, or as easy, as initially envisioned.”

During his over three decades in key positions within vacation ownership companies, Larry had a front-row seat to the growth of the industry. He believes his “hands-on” exposure internationally and his high-level involvement with ALDA and ARDA were pivotal in shaping his career.

But there IS life after timesharing and Larry Gildersleeve has proven that. From a very young age, he knew he wanted to be a published author, earning a BA degree in journalism and pre-law from Western Kentucky University and an MBA from Indiana Wesleyan University.

“I started numerous books over the years, but never got very far,” Larry recalls, “because, like legions of other aspiring writers, the commitments to family and career intervened. So my dream of becoming a published author was put on hold for several years. Coming home to Bowling Green, Kentucky with Kathleen, my wife of 26 years, ignited both my passion to write and, more importantly, a commitment to actually act on my desire to be a published author. My dream finally became a reality in 2016 with the debut of my first book, Dancing Alone Without Music, published by Amazon.”

Amazon recently awarded Larry Gildersleeve its coveted “bestseller” designation in three categories for his debut novel. The book was released in 2016 and reached #5 nationwide in the competitive Inspirational Fiction category. It was then included in Amazon’s Hot New Releases marketing category and is available in soft cover and Kindle e-Reader, at and it was recently picked up by Barnes & Nobel’s online distribution.

Follow Your Dreams– the sequel to his first book – will be released by both Amazon and Barnes & Noble in June. Larry will also release two works of non-fiction in 2017 and anticipates producing four books a year going forward. And no, he is not finished with timesharing and is still involved in consulting and business development activities. He recently became aligned with NYC-based Morgansheer Hospitality but his professional passion is now in writing and publishing. That is the vacation ownership industry’s loss but the world’s gain. Does the genuine world traveler have his own favorite vacation spot? Larry and Kathleen own four timeshare weeks at Shipyard Village within the Litchfield by the Sea gated resort complex in Pawleys Island South Carolina and have used their weeks every year since 1985. Larry believes that the timeshare product enables “average” American families to

Does the genuine world traveler have his own favorite vacation spot? Larry and Kathleen own four timeshare weeks at Shipyard Village within the Litchfield by the Sea gated resort complex in Pawleys Island South Carolina and have used their weeks every year since 1985. Larry believes that the timeshare product enables “average” American families to affordably vacation in luxury accommodations at highly demanded locations around the world.

“What I personally loved most about the industry are the enduring friendships I’ve developed and sustained around the world over the past 37 years. I’ve had a wonderfully rewarding career, with the privilege of working with professionals in outstanding companies. I took calculated career risks, and each one paid off, one way or the other. Looking back, I wouldn’t do anything differently.