Feature | By Jocklyn Mundy | Photos Provided by the Family
From Left to Right: Jac Caglianone, Elli, Jack, Kerry and Matt McKissock. Matti, soon to be born, Cameron Alexander, Charley, and Tobias Oliver. Photo by Isabel Crist Covey.
Some families you admire from across a room. The McKissocks you want to pull up a chair beside.
They are easy to love and easy to root for; their lives have been built on hard work, determination, sacrifice, and, most of all, faith and gratitude.
Matthew and Kerry have never been the kind to take the easy road. He chose a military college and the active-duty years that came with it. When dental school came around, he took out loans and put himself through. There were seasons spent apart, while he continued his education and later deployed to Kuwait with their firstborn, only months old. Faith made the hard road the right road, every time.
Two Kids From Orlando
Matt and Kerry were introduced by mutual friends; it was a blind date. She was unimpressed.
"She kind of quickly blew me off a little bit," Matt remembers. "But I rallied. And here we are thirty years later."
He says it the way a man says a thing he is still a little proud of. The rallying is the part worth knowing. It would become a pattern, this habit of his of seeing a closed door and quietly deciding it was open. Kerry, for her part, was already on her own steady track, with a way of watching how things worked before she committed to them. Years later, that instinct would point an entire family toward its future. They were two Central Florida kids who had no idea what they would build together.
Solid Ground
Matt grew up all over Central Florida. His mother was a registered nurse. His father remodeled houses, and the family lived in each one while he worked on it, moving again when it sold. Altamonte, Longwood, College Park. Each new house meant a new school and new friends.
Disciplined and organized by nature, Matt is the kind of person who takes to structure. When a teammate's father, a graduate of a Virginia military college, started talking about scholarships, Matt was all in. He heard about The Citadel and applied almost on a whim, not even knowing where Charleston was. He thought it might be in West Virginia. When he finally visited the beautiful campus in Charleston, South Carolina, on the Ashley River, six hours from home, he made up his mind on the spot. There was talk of West Point and Annapolis, but those required a congressional appointment. Matt smiles as he recalls, "My family did not know any congressmen." So he let that door close. The Citadel, with its ROTC scholarship, was the one.
At the Citadel, the plans Matt arrived with kept giving way to better ones. He began as a quarterback and came out as a safety. The offense ran the wishbone, a run-first scheme with little use for a passer, so he switched to defense. He went in a business major and came out a biology major, for the simplest of reasons. He fell asleep in english and math. He stayed awake for cell biology. The switch cost him an extra year of coursework crammed into the same four years, and he did it gladly, because for the first time, school felt like something he wanted rather than something he was enduring.
Biology turned out to be a pre-med track, and a family friend who happened to be a dentist became the quiet hinge of his whole life. What struck Matt about the man was not the work. It was the schedule. The dentist followed his daughters, competitive swimmers, to every meet they ever swam. He arranged his life around being there. Matt was a teenager when he decided that was the kind of life he wanted, and decades later, he would recognize it as the life he got, the one where he never missed Matti or Elli or Jack at a single thing, because he had built a practice that let him take Fridays off when needed to travel and be present for his family.
First, though, came his education. The Army deferred his service so he could earn his dental degree at the University of Florida. Then he reported for the four years of active-duty service he owed under his ROTC scholarship. In his first year in the Army, he completed a one-year residency, an intensive program where he did nothing but root canals, extractions, and surgeries alongside specialists, and he loved every minute of it. He was then deployed to Kuwait, where he was placed in charge of the dental care of twenty-five hundred cavalry soldiers, a young dentist barely out of training, the nearest help a helicopter flight away.
"You just don't feel like you know enough," he says of those days. "But you get thrown in." The work gave him years of experience in a fraction of the time.
He was in the desert over the turn of the millennium, treating eighteen and nineteen-year-olds who had never seen a dentist in their lives. He came home a different professional than the one who had left. When people ask him about those years, he does not talk about sacrifice. He talks about gratitude.
"I got more out of the military than I gave it," he says. "It's a great springboard for people's lives. And for families."
He is careful with the word "service." He served four years, not a career, and he will not let anyone dress it up into something it was not. The honor he claims is a smaller and truer one. The Army was the ground he stood on while he became the man who could build everything else, most importantly, family.
5th Generation City Beautiful
Kerry's roots in Orlando go back five generations, a family that helped build the city in more ways than one. Her great-great-grandfather, Dr. J.N. McElroy, a pharmacist, opened the first drugstore in town, McElroy's Pharmacy, on Orange Avenue downtown, serving Orlando from 1881 to 1942. Her grandfather, Captain James N. McElroy, known as Big Stoop, flew P-51s over two tours with the Army Air Forces and came home an American fighter ace. Kerry’s dad, Paul Shirley Jr. served the City Beautiful on the Orlando Police Department motorcycle unit for 26 years, and still rides today. Her uncle Jimbo started the first pizza delivery in Orlando, Jimbo's Pizza, and that was where Kerry got her first job as a teenager, taking orders over the phone.
Kerry chose her own direction early. She started at the front desk of a dental office and worked her way to a degree as a registered dental hygienist. She set out on that path before she ever met Matt. What she could not have known was how naturally that choice would one day meet Matt's own, two lives bending toward the same work without either one planning it.
Kerry's heart, her strength, her spiritual grounding, these have steadied every choice the family has made. The proving came early. Their firstborn, Matti, arrived at Evans Army Hospital in Colorado, and she was barely three months old when Matt shipped out to Kuwait. Kerry packed up the baby and drove cross country to Florida to stay with Matt's brother and sister-in-law, who already had two little ones of their own.
From The Ground Up
When Matt finished his service, the plan had been to join an established dentist near home. The arrangement did not come together. He calls it a blessing now, because what he really wanted was to build something from the ground up, exactly the way he wanted it.
So he studied the map. Winter Park, Clermont, Windermere. They scouted each one, looking for the place that felt like it would still be growing in thirty years. Kerry was pregnant with their second daughter when they drove through Windermere. "We just fell in love with it," he says. There was a space for lease at the corner of an intersection in a professional plaza, and he looked in the window and saw a dental office that did not yet exist. He signed a ten-year lease and opened in April of 2002, thirty years old, fresh out of the military, his name on the loans and the equipment. That is where Windermere Dentistry began, online at windermeredentist.com. A decade later the practice had outgrown the space, and they moved across the intersection to the plaza where it still stands today.
Windermere became home in every sense. They bought a house in 2006 on Lake Down where they have raised their daughters Matti and Elli and son Jack. The town they had chosen off a map became the one place their family belonged.
The Work Pays Off
Each of the McKissock kids would find their own way through hard work and discipline. Matti came to volleyball almost by accident. She begged to play, but her parents, for all their love of sports, did not know the volleyball world she was asking to enter. Then a patient mentioned to Matt that club tryouts were that very night, the kind you cannot miss without losing a year, and the McKissocks rushed her to a gym full of what felt like thousands of girls. She made the team.
What always defined the kids was a simple mantra Matt still repeats, “Work hard and do your best.” Matti did both, scrapping for playing time by sliding into whatever position got her on the floor. Setter was her natural spot, but she took whatever was offered and kept at it. The work paid off when she earned the starting setter position as a true freshman on scholarship at Georgia Tech.
She captained the team for four years, set the program's career assist record, and became the first ACC Setter of the Year in school history. The banner they raised still hangs in that arena. Matti also played a fifth season at UCLA.
In 2023, she married Georgia Tech football player Tobias Oliver. When they were ready to settle down, they chose to stay close to family and the town she grew up in. They are now a family of four, with daughter Charley and newborn son Cameron. Tobias is a senior project manager with Amazon Robotics, and Matti is the founder and director of 407 Volleyball Club in Ocoee. She is pouring everything she learned into girls who are exactly where she once was.
"If anybody should be a club director, it's her," Matt says. "She started as a humble club player, had a tremendous college career, and now has built a career out of it. She can look at a discouraged young girl and say, keep working, keep showing up, keep doing your best."
Family First
Elli was recruited by the University of Florida in ninth grade. She committed in August of that year, with Miami, Washington, and Texas also in the mix. She played five years for the Gators as their libero, a digger, the kind of player coaches build a defense around, and she left holding the program record for career digs.
Elli has played professionally since graduating. Now her latest team is bringing her back to Orlando, where she will play for the Orlando Valkyries, close to her family.
What pulls them all together now are the grandbabies. Charley alone was enough to draw her aunt back across state lines. Elli had her pick of teams. She chose the one nearest home.
"I know you think this is about me coming back to see you," she told her parents. "It's about Charley and Cameron."
There is more ahead for Elli, too. This November, she will marry Jac Caglianone, a Tampa native and fellow Gator who plays professional baseball for the Kansas City Royals.
Ask Matt about the two young men his daughters chose, and he does not reach for their résumés. "Both are everything a dad looks for," he says. "Humble. Kind. They love my daughters and treat them like princesses. We are all very blessed to have them in our family." The accomplishments do not move him. What he cares about runs deeper. "They check all the boxes. Faith. Character. The way a man puts his family first. Both measure up where it counts."
Grateful Hearts
The athleticism was not lost on their youngest son, Jack. He played quarterback throughout high school and heads off soon to play football for East Tennessee State University, his story still being written. The game has asked a great deal of him, and he has never hesitated to push through.
"There's nothing that could make him work as hard as he works," Matt says. "It's hard to get your kids to clean up their room, but I've never had to ask twice for any of ours to go to practice, to training, to give everything they have in their sport."
The children are grown now, each one settling into a life of their own. The deepest joy these days comes with the grandchildren. It is the simple things, watching Charley reach for a volleyball the moment she sees one, and now, holding baby Cameron.
Although the McKissocks would never say it, this is what the American dream looks like. Not something handed to anyone, but something earned, with faith, with sacrifice, with work.
That is the country's story too, the one we mark this July. Two hundred and fifty years of ordinary families choosing to serve, to work, to stay, and make something that will outlast them. The McKissocks never set out to embody any of it. They simply kept doing the next right thing, together, for thirty years. And when the fireworks rise this Fourth over the lakes and the rooftops of the town they chose, they will be for families exactly like this one, the ones who built this country the way it has always been built, one faithful, unglamorous, hard-won day at a time.
"For I know the plans I have for you," declares the Lord, "plans to prosper you and not to harm you, plans to give you hope and a future." Jeremiah 29:11 (NIV)
