An Evolution of Vision: Alex Krakovsky’s Journey from Timeshare Owner to Industry Leader

A Family’s Introduction to Timeshares

It began in the early 2000s when Alex’s parents purchased a three-bedroom unit in a charming timeshare resort just steps from the beach in Ocean City, Maryland. Their ownership of Week 25, during the height of summer, allowed Alex and his extended family to enjoy memorable vacations together. “This timeshare was perfect for us for some time,” he recalls. “It was a place where our family grew, bonded, and built traditions.”

However, as time passed, the family’s priorities shifted. By 2013, they decided it was time to sell their timeshare. That decision, and the unexpected roadblocks that came with it, set Alex on a path that would ultimately lead him to revolutionize how legacy resorts are managed and valued.

A Spark of Curiosity

“When we decided to sell the unit,” Alex explains, “I assumed the value would be proportional to the real estate market—at least $15,000. After all, it was a summer week in a prime location in a unit that would be worth at least $750,000.” To his surprise, the best offer they received was around $3,500—a figure further reduced by substantial commission fees.

Shocked and intrigued, Alex began questioning why the timeshare market undervalued properties compared to their underlying real estate. “I had coffee with a local broker and asked why this disparity existed,” he recounts. “He couldn’t explain it, but he did suggest buying more timeshares instead of a full condo. It would be cheaper, and I could potentially rent them out.”

Alex’s initial interest wasn’t in rental income but in understanding the system.

“I bought a few weeks, started attending board meetings, and soon realized that management inefficiencies were a significant part of the problem,” he says. That realization marked the beginning of Alex’s intensive analysis of the inner workings of timeshare ownership and governance.

From Owner to Advocate

One of Alex’s early purchases included weeks at other Ocean City properties, including The Waves and The Bay Club. His growing involvement led him to run for board positions at The Bay Club and The Waves. However, his candidacy was met with resistance.

“When I first ran for the board, my application wasn’t even distributed to owners,” Alex says. “I wasn’t allowed to enter the room during meetings, and my requests for budgets and management agreements were ignored.” Frustrated but undeterred, Alex filed a lawsuit to access the information he was legally entitled to.

The following year, he successfully ran for the board. “I approached existing board members and explained why transparency was essential,” he shares. “Eventually, I earned their trust, and we began addressing the property’s challenges

Transforming The Waves

The Waves, was in dire straits. “There was mold everywhere, the building wasn’t safe, and only 30% of owners were paying maintenance fees,” Alex recalls. “Most owners just wanted out.”

Alex proposed an unprecedented solution: terminate the timeshare regime, sell the property, and distribute the proceeds among owners. While the idea was met with skepticism, Alex’s persistence paid off.

“We replaced the existing management company” Alex says. “Then, we worked through the legal requirements to terminate the timeshare—including obtaining 100% owner consent, a process that involved education, communication, and even court intervention for one holdout.”

Ultimately, the property was sold, and owners received checks ranging from $7,500 to $15,000. “For most, it was a relief,” Alex says. “Some were ready to pay exit companies to take their timeshares off their hands. Instead, they walked away with cash.”

Founding Lemonjuice Capital Solutions

The success at The Waves revealed a broader opportunity. “I realized that many legacy resorts faced similar challenges,” Alex says. “Deferred maintenance, aging owner bases, and unsustainable fee structures were common. But these properties also held untapped potential.”

In 2017, Alex founded Lemonjuice Capital Solutions to address these issues. The company offers a comprehensive suite of services, from reimagining resorts and restructuring governance to managing rentals and resolving deferred maintenance.

“Lemonjuice takes a holistic approach,” Alex explains. “We look at each property individually to determine the best path forward—whether that’s repurposing, better management, arranging for an infusion of capital, or a combination of solutions.”

Shaping the Future of Legacy Resorts

The challenges facing legacy resorts have only grown in recent years. Aging infrastructure, new statutory requirements, declining owner engagement, and changing travel trends have put pressure on many properties. However, Alex remains optimistic.

“There’s growing awareness among owners, boards, and industry leaders that change is necessary,” he says. “Sometimes that means selling all or a portion of a property to the benefit of the owners. Other times, it means implementing better practices to ensure sustainability.”

Alex emphasizes the importance of transparency and communication. “Owners need to understand their rights and options,” he says. “Many don’t realize they own a share of the property and have a say in its future.”

Looking ahead, Alex sees a bright future for Lemonjuice.

“We’re expanding beyond timeshares to work with condominiums and other community associations facing similar issues,” he says. “Our expertise in governance, maintenance, and strategic planning makes us uniquely positioned to help.”

A Vision of Sustainability

At its core, Lemonjuice’s mission is about creating sustainable solutions. “Whether we’re helping a resort reposition itself for long-term success or facilitating a sale, our goal is to deliver value to owners and communities,” Alex says.

The company also focuses on fostering partnerships within the industry.

“Collaboration is key,” Alex explains. “We work with boards, management companies, and other stakeholders to identify and implement strategies that benefit everyone involved.”

Results That Matter

Alex’s vision for Lemonjuice has been proven through measurable success. With an experienced team and robust resources, Lemonjuice returned over $83,000,000 to timeshare owners, many of whom were frustrated with their ownership and ability to sell. and were prepared to pay an exit company because of the perception that it was their only way out. Lemonjuice has also invested $31 million into revitalizing Legacy Resorts.

If you’re a timeshare owner, board member, or property manager facing the challenges of managing a legacy resort, now is the time to discover innovative solutions. Lemonjuice Solutions is ready to help you overcome these obstacles and unlock your property's full potential.

To learn more, contact Jan Barrow, Sr. Vice President of Development, at 863.602.8804 or visit LemonjuiceSolutions.com.