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How this Army Veteran Found Success as a Caring Transitions Franchisee

Jayson Sweet, an Olympia-based Army veteran, is channeling his passion for service and holistic health into a successful Caring Transitions franchise, becoming a beacon of hope and support for families in need.

By Luca Piacentini1851 Franchise Managing Editor
SPONSOREDUpdated 2:14PM 04/21/23

From the battlefield to the business world, Jayson Sweet's journey is proof that perseverance, dedication and a strong desire to serve others can transform lives. Retiring from the Army in 2020 after 20 years of service, Sweet embarked on a new mission: to make a meaningful difference in the lives of families facing challenging transitions. His life had always revolved around service and helping the community, and he knew that his next venture needed to uphold those same values. After discovering Caring Transitions, the nation’s top senior relocation and downsizing franchise with 280 locations, Sweet realized that this was the ideal path for him to continue his mission of making a difference, while also achieving his entrepreneurial dreams. 

“Franchising is an exceptional option for veterans,” said Sweet. “The qualities that make military members successful — discipline, focus and teamwork — translate well into the business world. It is a great way for veterans to demonstrate their work ethic, follow a mission and accomplish goals. If you can find the right company, like I did with Caring Transitions, you will have all the coaching and mentorship you need to succeed. All you need to do is trust your instincts like you did when you were a soldier.”

The Journey to Caring Transitions

Before franchising, Sweet had an extensive career both in the private sector and Department of Defense. “My background is actually in psychology, specifically holistic health, fitness, sports psychology and physical education,” he said. “I began my career as a counselor in the state of Washington, specializing in substance abuse disorders.” 

In 1994, Sweet decided to take a different route — while still serving others — and enlisted in the Army. “I served between ‘94 and ‘97, and then took a break for a few years to attend graduate school,” he said. “In 2003, I came back to the military a second time, this time as a commissioned officer. Around midway through my deployment, I decided I wanted to make this a career and finish my 20 years.”

Sweet’s impressive and honorable military journey ended with his retirement from the Army in 2020. Never one to slow down, he immediately began thinking about his next chapter. “Business ownership had always been on my mind as a potential path, and I knew this was a great time to look into that,” he said. 

Fueled by this entrepreneurial interest, Sweet went through Boots to Business (B2B), an entrepreneurial education and training program offered by SBA as part of the Department of Defense's Transition Assistance Program (TAP). B2B provides participants with an overview of business ownership, including classes on the benefits of franchising, and is open to transitioning service members and their spouses.

“I became very intrigued by franchising,” said Sweet. “But during my research, I didn’t connect with any particular franchises right away. My entire life has been based on service and helping the community — whether it be through work, military, volunteerism — so I wanted a franchise that could allow me to bring that into my post-military career. After a few months of research, I read an article that highlighted Caring Transitions as a top franchise choice for veterans. I dove in and read everything I could on the brand.”

Despite the abundance of businesses providing medical care and home-improvement services for seniors, only a select few cater to the unique needs of seniors moving them from their homes to care facilities or managing the relocation and sale of their personal belongings. Caring Transitions bridges this gap, offering personalized assistance to seniors by visiting their homes, helping them pack and organize their possessions, and ensuring a smooth transition to their new residences by setting up their belongings in a comfortable and familiar manner. To complete the process, the team returns to the original home to organize and conduct an in-person or online estate sale using their exclusive platform, CTBids.

Although Sweet was eager to invest in the Caring Transitions business that winter, another twist of fate and a call from a former colleague brought him back to working for the Department of Defense, this time establishing a holistic health program for the 62nd Medical Brigade. 

“I was in a suit and tie, not a uniform anymore, so that was nice,” said Sweet. “I made a decision that I wanted to help the troops, and set up that program for the commander. I put Caring Transitions on hold for a few years, but always stayed in touch with the team.”

After about a year-and-a-half, Sweet decided it was time to put all of his focus back onto the business and officially launched his Caring Transitions franchise in Olympia, Washington in early 2023. 

Why Caring Transitions Is Perfect for Veterans

There are several factors that make Caring Transitions an ideal business model for those with a military background. Sweet, for example, says it was the organization's focus on service and its affiliation with parent company Strategic Franchising Systems that resonated deeply with him, as he saw it as a way to reconnect with his counseling roots and serve families in need. 

“Strategic Franchising Systems is an amazing, passion-driven organization, and Caring Transitions in particular is very service-based,” said Sweet. “There are a lot of truly great franchises out there, with solid business models and strong support infrastructures, but Caring Transitions resonated on a personal level. These are families going through a tough time. There has been a triggering event — mom or dad needs to go to assisted living, for example — and helping them during that time really appealed to me. Serving others is something I enjoyed about being a soldier, and I knew I could carry over that passion with Caring Transitions.”

Caring Transitions VP of Franchise Development Jim Stapleton agrees that veterans and Caring Transitions are a match made in franchising heaven. “I believe that there is no one better equipped than the military to come up with a plan and execute the plan,” he said. “That is what they are trained to do day-in and day-out. And that is really what franchising is — develop a plan and set up the actions to make it work.”

But Stapleton agrees with Sweet that Caring Transitions in particular is built to be even more than just a proven business model

“We are in the life-changing industry — we really make an impact on the families we work with,” said Stapleton. “This is a very emotional time for seniors and their families, so being able to take the weight off their shoulders and help them into this new reality is what drives franchisees to the brand. We have franchisees from all different walks of life — c-suite level executives, health care professionals, serial entrepreneurs — but the common denominator for all of them is that caring piece. You get both a hug and a check after every job that you do.”

Why Now Is the Time to Join Caring Transitions

As Sweet looks towards the future, he is excited about the prospects of his Caring Transitions franchise and the immediate impact it will have on the lives of those he serves in Olympia. But his long-term goal is to create a legacy for his family. His son Tyler recently joined the business as the Operations Manager, and Sweet says he hopes to one day pass the business on to him. 

“At this stage in my life, I am thinking about what I want to hand off to my family,” said Sweet. “That is a big part of my mission with this business — to prove to myself that I can do it. Franchising is something I’ve always wanted to do, and I am finally here. Seeing that come to fruition with a brand as meaningful as Caring Transitions is very exciting.”

Overall, Sweet’s story serves as an inspiration to other veterans who wish to use their unique skills and experiences to make a positive difference in their communities, Stapleton says. And as the Caring Transitions team continues to look for passion and qualified franchise owners across the country, they are specifically focused on finding those veteran entrepreneurs like Sweet. 

In line with this strategy, Caring Transitions has increased its veteran discount from $2,000 off to 10% ($4,490) off of the entire franchise fee. 

“We are committed to bringing the right people into the system — we don’t just sell franchises to sell franchises,” said Stapleton. “We are so happy to have Jayson on the team. It is individuals like him, with a clear sense of purpose and a military training behind them, who will be successful with Caring Transitions and will help take this brand to this next level.”

Click here to meet some other Caring Transitions franchisees.

To learn more about the cost to open a Caring Transitions, visit