New SkyRun Location Opens in Jacksonville, FL

SkyRun’s Newest Addition will be led by Jacksonville local and Navy veteran, Mike Massey

After more than two decades of decorated service in the United States Navy, Mike Massey, retired as a Chief Petty Officer, and made Jacksonville his home. After visiting 21 countries during his time in the Navy, Massey—who met his wife in Japan while in the service—chose to pursue his two primary passions: travel and entrepreneurship. Upon retirement, the Jacksonville resident became part of SkyRun Vacation Rentals and is now dedicated to accomplishing a new mission: developing a carefully curated portfolio of vacation rental properties to accommodate a wide range of travelers, while also providing local, high-quality management services for homeowners. 

Sailing Into Port

When Mike Massey made the decision to retire from the Navy, he did so with a clear vision of what he wanted to do with the next chapter of his life.

“For 23 years, I worked on aircraft, which played a vital role in the Global War on Terror,” said Massey. “In doing so, I gained a broader understanding, not only of the complexity of interconnected systems, but also the importance of keeping the end-user in mind with every repetition and rotation. In the Navy, the end users were the pilots; when I decided to retire and pursue entrepreneurship, I applied that same principle: the customer must always come first. I always loved to travel, but at this point in my life, I wanted to settle down with my family and Jacksonville was the ideal place. This city has played a pivotal role in the history of the United States military and is home to a vast community of active duty and retired personnel.”

Massey became part of the SkyRun Vacation Rental team and will manage homes located in and around Jacksonville and the surrounding area. 

“When I looked at the Jacksonville region, I felt there was a gap in the quality of management services—both for the homeowners and the guests,” Massey added. “I wanted to provide our neighbors with trusted, high-quality care for their homes, along with a guest experience that travelers will tell their friends about.”

SkyRun was created in 2004 and manages nearly 1500 vacation rental properties across the country. Massey will draw on his military leadership and training—along with SkyRun’s vast network of resources and best in class capabilities—to develop the Jacksonville region. 

“Homeowners deserve a property manager who listens to their concerns and provides tailored solutions to meet their needs,” Massey added. “It’s incredibly frustrating to deal with large-scale, national management firms; you never speak to the same person twice. I want to change that broken paradigm. As a locally owned and operated business, I will work directly with the homeowner and the vacation traveler. For the homeowner, I will personally create a customized plan to maximize their rental income and minimize their workload; there are no expensive third-party tools and frivolous fees. For the traveler, I am intensely committed to the guest experience. By being located in the same region—as opposed to a call center, three states away—we’re able to provide a level of responsive, customer service that is really needed across the Jacksonville region.”

From Service to Civilian Life

In the Navy, Massey specialized in aviation and worked on a variety of aircraft—from the P-3, to the C-130, to the C-9 Bravo, to the MH-53. Throughout his 23-year career, he traveled to more than 21 countries, and even met his wife during a trip to Japan. Ironically, or perhaps inevitably, it was this combination of travel and systems management that led Massey to SkyRun.

“When you leave the military, a lot of guys are left to just ‘figure it out’ and frankly, that doesn’t always work out for the best,” said Massey. “I knew that I wanted to run my own small business, but I also knew that doing so without a catch net would be even more difficult. After months of extensive research, trying to figure out my next chapter, I felt franchising would provide the best of both worlds—it gives me the autonomy to build something from the ground up, but also provides a support system, run by an American-owned, nationally-recognized, industry leader in this space. In the military, we’d call that a ‘force multiplier.’”

As Massey continues to curate and expand his vacation rental portfolio, he is utilizing SkyRun’s top-tier systems and technology to manage the properties. This will ensure up-to-date pricing, excellent guest experiences, and smooth stays.

“Jacksonville is one of the crown jewels of the Sunshine State,” said Cord Thomas, President of SkyRun. “By landmass, it is the largest city in the United States, and it has more than 1,100 miles of shoreline, which is more than any other city in Florida. We are excited to welcome Mike Massey to the SkyRun team. After more than 20 years of service to our country, Mike brings a variety of admirable traits, including discipline, focus, work ethic, and a team-first, mission-specific approach to accomplishing every task. More than that, he understands that the customer is the most important part of the process. We are proud to have Mike, his wife, and their two children, in the SkyRun family.”

“I was proud to serve my country, and defend the freedoms we hold so dear,” added Massey. “At this point, I want to live the American dream I fought so hard to defend.”

To learn more about Mike Massey, as well as the SkyRun offerings in and around Jacksonville, please feel free to contact us and schedule a chat.