Whitney Smith walked into Fleet, Smith & Freeman as a fresh law school graduate in 2005, when the firm was just three years old and in its early growth stages. Twenty years later, she stands as an equal partner alongside founder Fleet, having built a successful practice while never losing sight of what matters most: family and community.

• It all began with a recommendation from CPA Larry Reeder, who had watched Whitney grow up in Fort Walton Beach. Whitney went to high school with Reeder’s son, and when she graduated from the University of Florida Levin College of Law, Reeder knew exactly where she belonged.

“You need to hire this young lady. You won’t regret it,” Fleet remembers Reeder saying. The advice proved golden.

“She was eager to learn, very bright, and had inherently good problem solving skills,” Fleet recalled of Whitney’s early days. “She is not someone who simply accomplishes tasks that are assigned to them, but makes the effort to analyze the problem and come up with solutions.”

Those qualities distinguished Whitney as partnership material early on. Fleet recognized her exceptional work ethic, straightforward communication, and ability to engage in what they coined “the truth tunnel” – honest conversations about firm direction and concerns essential for good partnership.

• “Her practice has grown rapidly,” Fleet said. “She and I are now equal partners. She pulls her own weight, develops her own clients, has her own reputation and has her own ability to bring in work.”

Whitney’s professional journey included a significant evolution. Starting as a litigator handling business disputes, fiduciary litigation, and trust contests, she transitioned to estate planning about five to seven years ago when Fleet decided to narrow his practice scope.

“She expressed an interest to do that,” Fleet said of the estate planning transition. “She started doing the training, going to the workshops and the continuing education programs.”

The shift proved strategic and personally fulfilling. Whitney’s focus on estate planning for blended families and families with young children filled a market need, attracting clients who connected with her as a fellow parent.

• “She has the ability to attract younger couples with children,” Fleet explained. “I see more files opened up for younger families than we were getting before she started doing that.”

Freeman, who joined the firm in 2012 and became a shareholder in 2020, experienced Whitney’s mentorship from day one. Freeman’s own path to the firm mirrored Whitney’s – both came through Larry Reeder’s recommendation, and both chose to build their careers in their hometown.

“Whitney actually interviewed me for the job,” Freeman said, describing their first meeting at the old Neighborhood Cafe location. “It didn’t feel like an interview at all. It felt like two girls catching up and learning about each other.”

Freeman found herself working under Whitney initially, learning litigation and civil matters before developing her own real estate practice. She quickly discovered Whitney’s remarkable productivity and mentoring approach.

“She can have a to-do list that’s two pages long and somehow she makes her way through most of it in just one day,” Freeman said. “I never feel like I can’t walk down to her office and ask for assistance on a matter. It’s always an open door policy with her.”

Whitney’s support extends far beyond professional guidance. When Freeman and her husband struggled through three years of fertility treatments, Whitney provided unwavering encouragement.

• “I remember Whitney always asking how I was doing, feeling, what she could do to support us during our treatments,” Freeman recalled. “When I finally got pregnant, she was one of the first people I told. I went into her office with so much joy, hopefulness and tears in my eyes and when I told her, she immediately jumped up, told me she was so happy and started crying too. It meant the world to me.”

Freeman continued: “To have your colleague and partner show that much happiness and love for something that was so important to me was truly special. She has continued to show that kind of love and excitement with every step of our journey to complete our family. It’s really unheard of to have that kind of support in an office, much less in a law firm.”

This personal support reflects the firm’s broader culture, which Whitney has helped shape over two decades. Fleet established a “families first” philosophy that Whitney embodies and champions.

“If your kids are sick, you don’t come to work. You stay home. If your children have some kind of event at school, you need to go watch that event,” Fleet explained. “Whitney’s family has always come first, and she has still done a great job of developing a significant law practice.”

Whitney’s strength shows in professional settings where others might hesitate. Freeman says she admires her colleague’s approach in challenging situations and notes that Smith can “be very tough” when needed.

• This strength extends to mentoring the next generation, particularly her girls. “I’ve heard her talking to both girls about how you choose your profession and you keep your head up and you stay strong,” Freeman noted. “Just because you are a female, doesn’t mean that you can’t show that you deserve that spot that you’ve worked so hard for.”

Whitney’s commitment to Fort Walton Beach runs deeper than professional success. Her community involvement spans the Florida Bar Association, Okaloosa Bar Association, Fort Walton Beach Chamber of Commerce, and the Mardi Gras Club. In 2021, the Krewe of Bowlegs crowned her their sixty-sixth Queen. She has also served as Honorary Commander for the 4th Battalion at the 7th Special Forces Group (Airborne) and as Air Combat Command Civic Leader for the 53d Wing at Eglin Air Force Base.

“You are only going to get out of a community what you’re willing to put in it,” Fleet said. “If you don’t show up, you can’t make a difference. Whitney shows up, without hesitation.”

The local roots shared by all three partners create something distinctive. Fleet, Smith, and Freeman all grew up in Fort Walton Beach, attended local high schools, pursued law degrees, and returned home to build their careers.

• “We’re committed to the community,” Fleet explained. “Our lives, our roots are deep here. Our family history is deep and we have a responsibility to the community to do our work in a professional manner and be an asset to the community.”

For Freeman, this shared background created immediate comfort when joining the firm. “Right from the get go, this firm felt like that hometown feel,” she said. “It didn’t feel scary, it felt like home.”

Client feedback over two decades reflects Whitney’s impact. “We get lots of comments and emails and people tell me how much they enjoy working with her and how good a job she does,” Fleet said. “Whitney developed her practice and it has grown dramatically in 20 years. That’s a result of doing a good job and people talking about how good a job she does.”

The significance of Whitney’s 20-year tenure extends beyond personal achievement, according to Fleet. “Twenty years for an employee, and a lawyer, in one firm is significant,” Fleet noted. “It is rare at law firms for people to stay for that long of a time.”

As the firm evolves, Fleet sees Whitney assuming greater business leadership responsibilities. “She not only was going to be a good lawyer, she was gonna be a good business person,” he said. “I was pretty sure that I was going to pass the torch to her at some point in time to continue this legacy of what we’ve done here.”

Freeman shares that same optimism about their continued partnership. “At some point it’s probably going to be just Whitney and I,” she said. “I look forward to her and I being able to continue to conquer the legal profession in this town and work together and hopefully continue to build on the practice.”

Fleet’s assessment of Whitney’s two decades carries the weight of a mentor’s deep pride.

“Whitney is without a doubt one of my absolute best success stories as far as someone who came in, listened, adopted her own approach and techniques, has a good moral compass and sense that we provide a service here and has done a good job.”

For Freeman, Whitney’s impact reaches beyond professional excellence: “She really made me feel like this was the place that was going to be right for me when I came back to a town that I swore I would never come back to. I think she is a great inspiration for working hard, working your way up, making a place and a name for yourself in a small town.”

20 years later, that fresh law school graduate has become the embodiment of Fleet, Smith & Freeman’s founding principles: exceptional legal service rooted in community commitment, delivered with the understanding that families come first and success is measured not just in billable hours, but in the lives touched and the community served.