A Rhode Island Upbringing and a Determined Path
Richard Winkler’s story begins in Cranston, Rhode Island, where a strong work ethic took root early. At just 11 years old he was delivering newspapers, and at 16 he began working at a neighborhood grocery store. “I worked every job you can imagine – except cutting meat,” he says, smiling. “You needed to be in a different union for that.”
That early responsibility taught him discipline, drive, and a deep appreciation for hands-on problem solving. He enrolled at the University of Rhode Island, majoring in both political science and economics and minoring in speech. “Becoming a lawyer was always the goal,” Winkler explains, “And if I was going to be a litigator, I figured I’d better learn to think fast and speak clearly.”
He went on to study at New England School of Law in Boston, only to discover that courtroom litigation didn’t match his personality or values. “I loved advocating for people, but I hated the delays, the paperwork, and the constant motion-filing. I remember telling my mom I couldn’t stand it because I wanted to get things accomplished and didn’t have the patience for the constant delays. She laughed and said, “Why didn’t you ask me? I could have told you that and saved you the time.”
From the Courtroom to the Boardroom: Embracing Timeshare Complexity
Seeking a better fit, Winkler took a leap into the unfamiliar world of real estate development. He joined a firm in Newport, Rhode Island - Inn Group Associates - that happened to be in the timeshare business. “Within days of starting, the sales manager dropped a foot-high stack of attorney general complaints on my desk,” Winkler recalls. “I thought, “What did I just sign up for?”
What he found was a chance to make a difference. He quickly became involved in helping shape public policy at the state level, working alongside lawmakers to develop what would become the Rhode Island Real Estate Timeshare Act. He also helped reform how timeshares were assessed for property taxes, which led to a high-profile legal battle with the City of Newport. The case ultimately went to the Rhode Island Supreme Court - and Winkler’s name remains on the landmark decision.
“That’s when I realized how the law could create real fairness,” he says. “That was the moment I saw the power of structure and governance in an industry that desperately needed it.”
A Career Rooted in Loyalty and Deep Experience
For the next two decades, Winkler served as General Counsel through a succession of acquisitions - from Inn Group to Eastern Resorts, then to Equivest, and eventually to Cendant. He played an essential role in overseeing timeshare operations throughout Rhode Island and Massachusetts, including properties like Newport Overlook, Bay Voyage, and Jiminy Peak. He also pioneered a timeshare license model at Newport’s Inn on Long Wharf.
Later, as a partner in Sterling Resort Group, Winkler shifted toward legal strategy and sales and marketing operations in Minnesota, New York, and Rhode Island. “There weren’t any templates for what we were building,” he says. “So, we just built it ourselves.”
Creative Detours—and an Entrepreneurial Spirit
After decades of legal and executive leadership in the timeshare world, Winkler chose to step away and explore his creative side. He launched a travel club, dabbled in consumer product development, and even wrote and published a humorous book under a pen name. His creative work included a jewelry line that turned names into musical notes.
“I wasn’t making much money, but I was happy,” he says. “It was a chance to invent, imagine, and pursue ideas just because they were interesting. You can’t always have everything, but creativity gave me something new to love.”
A Conversation That Changed Everything
During the COVID pandemic, Richard Winkler reconnected with longtime colleague Scott MacGregor, now part of the Lemonjuice Solutions team. What began as a casual discussion about potential investments quickly took a more meaningful turn. MacGregor encouraged him to schedule a call with Lemonjuice CEO Alexander Krakovsky.
“I told Scott, ‘If I’m seriously going to consider this, I need to meet Alex face to face,’” Winkler recalls. So, he made the drive from Rhode Island to Maryland - masked and cautious - to sit down with Alex for what would become a pivotal conversation.
“What impressed me most wasn’t just Alex’s grasp of the business,” Winkler says. “It was his constant focus on fairness. He kept saying, “That’s not fair to the owners. And it was clear - he truly meant it.”
More Than Repurposing: A Holistic Vision for Legacy Resorts
Since joining Lemonjuice, Winkler has been instrumental in helping reshape perceptions by emphasizing an important message: Lemonjuice works collaboratively with resorts not just in times of transition, but to uncover value, improve operations, and create long-term solutions.
“That couldn’t be further from the truth,” Winkler says. “Lemonjuice is not a liquidation firm. We’re not here to strip resorts for parts. We’re here to evaluate what’s right for each unique property.”
Sometimes, he explains, that means repositioning the project because it has outgrown its useful life. Other times it means revitalization. And often, the answer lies in a creative hybrid - part timeshare, part full-ownership, or a shift in usage models that better reflect today’s realities.
What sets Lemonjuice apart is the comprehensive nature of its services. The company assists with legal restructuring, document modernization, voting analysis, and title updates for every owner. It offers strategic guidance, capital investment, and practical solutions to help boards make informed decisions. Most importantly, it walks beside each resort through the entire journey - from initial assessment through implementation and beyond.
"We’re not the kind of company that just delivers a report and walks away," Winkler explains. "We work as true partners with our clients.
Property Management with Integrity and Experience
In addition to repositioning work and strategic management services, Lemonjuice’s operations team handles everything from budgeting and reserve planning to maintenance, staffing, and board relations.
“Property management is about more than keeping the lights on,” Winkler says. “It’s about understanding the community, communicating transparently, and creating a structure that works.”
Lemonjuice’s management philosophy combines operational rigor with a human touch - ensuring that even during times of transition, the owners feel seen, heard, and supported.
A Message to Boards: Don’t Wait to Start the Conversation
Facing tough decisions, board members often hesitate - but Richard Winkler urges them to act before it’s too late. “You don’t need to commit to anything today,” he says. “But talk to someone who understands the challenges. Don’t wait until you’re out of money, out of insurance, or underwater on ownership support.”
He understands that resorts carry deep emotional value. “We’re not asking people to walk away from places that matter to them,” he says. “But when the numbers don’t work - or the property can’t keep up - it’s time to consider real options before the situation gets worse.”
Many legacy resorts face mounting insurance costs, stricter regulations, aging infrastructure, and a shrinking pool of paying owners. “Deferred maintenance doesn’t fix itself,” Winkler notes. “And governing documents written 30 years ago can’t address today’s problems.”
Boards may feel pressured to keep maintenance fees low, but that approach can do more harm than good. “It might seem like a win in the short term,” he explains, “but it weakens the resort’s long-term stability. Eventually, service declines, reviews suffer, and value disappears.”
Lemonjuice helps boards tackle these challenges head-on - with clear assessments, thoughtful planning, and realistic solutions that protect owners and preserve what matters.
People, Purpose, and a Plan That Works
Winkler’s deep commitment to Lemonjuice is grounded in the strength - and sincerity - of the team. “Our leadership brings more than 150 years of experience,” he says. “We’ve faced every kind of resort challenge, and we care about doing right by owners.”
That combination of know-how and principle is what sets Lemonjuice apart.
"We believe in fairness, transparency, and community," Winkler adds. "Legacy resorts - and the people who love them - deserve nothing less."
About Lemonjuice Solutions
Lemonjuice Solutions is a leader in strategic management and reimagination for legacy timeshare resorts. With a team of industry experts and a proven track record, the company offers comprehensive and tailored solutions. To learn more about Lemonjuice’s commitment to preserving the value of timeshare resorts, visit lemonjuice.com or contact Jan at 863-602-8804 for a strategic consultation.