Scott MacGregor: A Lifetime in Hospitality and Timeshare Leadership

From Culinary Arts to the Front Desk

MacGregor’s professional story starts in the early 1980s when he graduated from the University of Massachusetts at Amherst with a degree in finance. Like many young graduates, he was unsure of his next steps. He initially pursued a career in classical French cuisine, training on the job rather than in a formal culinary school. This led him to the Springs Club in Rancho Mirage, California, where he worked in a setting frequented by celebrities like Frank Sinatra, Bob Hope and Gerald Ford.

However, his career took a dramatic shift when Paula Monroe, the club’s general manager, introduced him to an opportunity at Watt Industries. Intrigued by the prospect of something new, MacGregor transitioned into hospitality, accepting a front desk position at the Palm Springs Tennis Club in 1984. “I loved the fast-paced environment of the kitchen, but I knew that long-term, I wanted a career with more stability and growth potential,” MacGregor said.

Learning from the Best: Woody Cary, Watt Industries, and Ed McMullen, Sr.

Watt Industries, founded by real estate mogul Ray Watt, was a dominant force in the high-end residential and resort development industry. The company had pioneered some of the first purpose-built timeshare resorts in the western United States, including San Diego Country Estates, Laguna Surf, and Desert Breezes.

One of MacGregor’s earliest and most influential mentors was Woody Cary, then the CEO of Tricom Management, a Watt subsidiary managing resort and residential properties throughout southern California. MacGregor vividly recalled his first encounter with Cary—an early morning shift when he noticed a man planting flowers alongside the landscaping team. That same individual later emerged from the back office, still dressed in work clothes, and introduced himself as Woody Cary, the person responsible for signing MacGregor’s paychecks. “That moment defined the kind of leader Woody was—deeply involved and always hands-on. He led by example, and I was fortunate to learn from him,” MacGregor shared.

Another key figure in MacGregor’s career was Ed McMullen, Sr., a respected leader in resort management and hospitality operations. McMullen, who had a long and influential career in the hospitality sector, played an integral role in shaping the Marriott Vacation Club during its early years. As a senior executive at Marriott, McMullen helped develop best practices in timeshare sales, operations, and customer service that became industry standards. His expertise in guiding resorts through operational transitions made him a sought-after consultant and mentor. “Ed had a way of simplifying complex operational challenges and focusing on what truly mattered—delivering value to owners and guests. His insights helped me understand the intricacies of resort governance and long-term planning,” MacGregor noted.

MacGregor swiftly rose through the ranks under Cary’s mentorship and with McMullen’s guidance. Initially hired for front desk operations, he soon played a pivotal role in bridging the gap between resort operations and sales teams, ensuring a seamless experience for owners. His efforts were noticed, and within a few years, he was managing rental operations across Southern California.

“It was a time of tremendous learning. The industry was evolving rapidly, and I had a front-row seat to some of the most innovative developments in hospitality and timeshare,” he said.

Graduate Studies, Meeting His Wife, and Interval International

In 1999, MacGregor took a brief hiatus from the industry to pursue a master’s degree in international business and organizational development at Suffolk University.

“Returning to school after so many years in the industry gave me a fresh perspective,” he recalled. While at Suffolk, he met Valeria, who was also completing her master’s degree. “Meeting Val was the highlight of my graduate experience. We shared a passion for business and travel, and she has been my partner in every sense of the word ever since,” MacGregor said. Shortly after graduating, he and Valeria married.

Another notable event concerning the Palm Springs Tennis Club was a meeting involving Jon and Christel DeHaan, who were pioneers in the timeshare exchange industry and the founders of Resort Condominiums International (RCI), the first major timeshare exchange company. Also present at the meeting were Mario Rodriguez, then CEO of Interval International, and attorney Craig Nash, who would later play a key role in the industry.

Their discussions reinforced MacGregor’s belief in the power of exchange programs in shaping the future of timeshare ownership. Recognizing MacGregor’s talent and leadership, Interval International recruited him as the regional manager for the northeastern United States. “That opportunity expanded my perspective on the industry, from individual resorts to the broader landscape of vacation exchange,” he said. "While at Interval, I reconnected with two longtime friends from the 1980s, Billy Curran and Dennis Ducharme. Billy was a marketer and developer, while Dennis was a developer and operator. Though they worked together as business associates, they were not formally business partners. Recognizing an opportunity to collaborate, I left Interval, moved my family back to Cape Cod, and co-founded In Season Resorts with them. Working with Mel Weinberger at Holland & Knight, we developed the In Season Vacation Club, a flexible and dynamic timeshare product. Unlike traditional clubs, this structure allowed developers to add and adjust inventory based on demand, addressing a common industry challenge where properties, once dedicated to a club, became difficult to remove. The model provided both consumers and developers with greater adaptability, ensuring long-term sustainability and value."

Shaping the Industry: Legislative Battles, ARDA, and Innovation

MacGregor’s tenure at Palm Springs Tennis Club coincided with a landmark legal battle—Palm Springs vs. Palm Springs Tennis Club. At the time, the city imposed transient occupancy taxes (TOT) on timeshare exchange guests. Tricom, under Cary’s leadership, challenged this, arguing that timeshare owners were already paying property taxes. With the legal support of Best Best & Krieger, attorneys Doug Kreiger and Lance Eldred, the case ultimately reached the California Supreme Court, which ruled in favor of the Palm Springs Tennis Club. This decision became a precedent, exempting timeshare maintenance fees from TOT across the country.

The following year, Woody led an initiative to get fair property taxation for timeshare owners who were being taxed on the aggregate value of timeshare sales, rather than on a comparable real estate basis. Woody formed the California Timeshare Owners Foundation, appointed Scott as its Vice President, and recruited 40,000 timeshare owners to appeal their property tax assessments, resulting in a change to property assessment procedures and a win for timeshare owners and developers across the country.

MacGregor was also active in the American Resort Development Association (ARDA), working alongside industry leaders to shape regulations and advocacy efforts that protected both developers and timeshare owners. Through ARDA, he helped refine policies on governance, owner rights, and financial sustainability for legacy resorts.

“Industry collaboration is key to ensuring a strong future for timeshare communities,” he emphasized.

In 2011, Shep Altshuler, Publisher of TimeSharing Today, formed the Timeshare Board Members Association, TBMA. Soon after, MacGregor, along with Woody Cary, Jerry Sikes, another prominent expert in timeshare resort governance, became instrumental in helping organize TBMA’s in-person conferences. Recognizing the need for education and support among Legacy Resort Owners Associations and General Managers, they contributed their expertise to create an environment where industry professionals could exchange ideas and access valuable resources. These conferences focused on the challenges, solutions, and fiduciary responsibilities of managing legacy resorts. “The industry was changing, and many legacy resorts needed guidance on governance, financial sustainability, and operational efficiencies.

In 2024, ARDA ROC and TBMA formed a partnership to enhance the in-person conferences — providing a forum where board members and managers could gain insights from experts and share best practices. MacGregor explained, “Through these efforts, the conferences provide a vital resource for preserving and improving the operational integrity of aging timeshare resorts.”

Lemonjuice Solutions: Redefining the Future of Legacy Resorts

Today, as Chief Operating Officer of Lemonjuice Solutions, MacGregor applies decades of experience to help resorts navigate their next phase. Lemonjuice specializes in evaluating properties based on three pillars: hospitality, real estate, and governance. The company has helped numerous timeshare associations restructure, ensuring fair financial outcomes for owners while maintaining the integrity of the resorts.

“Our goal is simple: to help resorts find their best path forward, whether that means revitalization or a transition to a new use,” he said.

Lemonjuice has distributed over $100 million to timeshare owners, ensuring that those who have invested in their properties receive a fair return when a transition occurs. This significant financial redistribution underscores the company’s commitment to protecting owner interests and providing a structured exit strategy for resorts facing sustainability challenges.

Additionally, Lemonjuice has invested $34 million in resort revitalization efforts, breathing new life into properties by improving infrastructure, upgrading amenities, and enhancing operational efficiency. This investment not only preserves the value of viable resorts but also strengthens their long-term success.

At the helm of Lemonjuice is Alex Krakovsky, Chief Executive Officer, whose vision for strategic resort solutions has driven the company’s expansion and impact. Jan Barrow, Senior Vice President of Development, brings decades of experience in property management and redevelopment, ensuring that every resort transition is handled with expert care. Together, they lead a team dedicated to finding innovative solutions for timeshare owners and resorts nationwide. By combining financial expertise, real estate acumen, and a commitment to ethical resort transformations, Lemonjuice continues to set the standard for responsible timeshare repurposing and revitalization.

Connect with Scott MacGregor, Executive Vice President/Chief Operating Officer, Lemonjuice Solutions, (321) 236-6663, scott.macgregor@lemonjuice.biz, or visit lemonjuicesolutions.com.