Our History

A Commitment to Transparency and Legacy

The Conversation That Started Everything

Our company’s founding is rooted in a deeply personal experience. It began not in a conference room, but in a chemotherapy center in February 2025. Joe and his wife, Michelle, were there for her treatment. Joe had recently stepped away from the property management industry in November 2024, but the sight of a gentleman working intensely on his laptop across the room sparked a crucial conversation. Michelle turned to Joe and remarked, “That used to be you. Working all the time, being a passionate advocate for your clients, ensuring properties were meticulously cared for, and that you were fully aware of every detail.” Joe had to admit it was true. She then asked him the simple, powerful question: “Do you miss that line of work?” 

The Shared Vision

The conversation quickly turned into a discussion about the systemic issues plaguing the rental market. Michelle, who had worked alongside Joe at his previous company as a guest services manager, brought her own invaluable perspective. Joe’s experience gave him direct insight into the challenges and complaints of homeowners, while Michelle understood the pain points and issues faced by guests. This shared, comprehensive knowledge base—seeing the industry from both the homeowner and the guest perspective—benefited them immensely. 

Defining Our Core Values: Transparency First

The guiding principle for their new business was simple: be a boutique-style vacation rental property management company defined by unwavering transparency. Joe and Michelle firmly believed that to fix a broken system, you must first bring everything to light. This commitment is central to our operations. We chose to partner with a technology provider to handle the back end, allowing us to focus entirely on day-to-day operations and authentic guest communications. This partnership resulted in our unique Owner’s Portal—a platform designed to give homeowners total visibility into their investment. Unlike other industry portals, ours provides live updates on guest communications, full access to rental calendars, and most crucially, absolute control over daily rates. While we provide expert recommendations using AI-driven dynamic pricing, the final decision always rests with the homeowner.

Redefining Profit and Payouts

We took several steps to fundamentally change the financial relationship with our homeowners. Standard industry practice requires homeowners to wait until the 10th or 15th of the following month to receive their previous month’s rental income, often with hidden fees deducted. We eliminated that delay and those fees. Our homeowners are paid out within 24 to 48 hours post-reservation. Furthermore, costs for essential services like linen, cleaning, and guest damage protection are paid directly by the guests, meaning these expenses are not deducted from the homeowner’s rental income, creating significantly more profit for them. Michelle was deeply involved in establishing this financial fairness, thrilled to see the company developing into a premier service guided by a Five Diamond approach.

the sun is setting over the water at the beach
A Family Promise and Legacy

As our first season concluded, we faced a difficult and emotional turning point. Michelle sadly passed away on August 1, 2025. She got to see the company take off and begin to grow, and one of her final wishes was to Joe: “No matter what, don’t close the company up.” This company is part of her enduring legacy. Today, Joe, alongside their daughter Lauren, is committed to upholding that promise. This is more than a business; it is a family venture dedication to Michelle.  We promise to remain true to our core values, acting as tireless advocates for both homeowners and guests, ensuring fairness, maintaining total transparency, and delivering the Five Diamond experience that was set to change the rental market.