When I was a kid, the number sixty-five always carried one meaning— retirement. That was the finish line. My maternal grandfather retired at sixty-five after a long career at AT&T, and everyone treated it like the natural order of things. You worked hard, did your time, then traded in the briefcase for a gold watch and a fishing pole.
I turned sixty-four last week, and retiring is the farthest thing from my mind. Seriously. There’s too much still percolating—ideas, plans, half-scribbled notes that I hope will turn into something tangible one day. Truth is, I wouldn’t know what to do with myself if I stopped creating. Work has never been a burden. It’s a blessing. It’s the thing that keeps me curious, grateful, and grounded. I love what I do. All that I do.
Maybe it’s because entrepreneurship runs through my veins and is deeply embedded in my DNA. My great-grandfather St. John owned the general store in the small town of Brooksville, Mississippi, back in the late 1800s and early 1900s. Folks said it was the Walmart of its day—a one-stop shop for flour, sugar, overalls, tools, winter coats, and gossip. It wasn’t just where people shopped; it was where they gathered. Every handshake, every conversation, every bit of news passed across that worn wooden counter.
That same spirit carried on through his oldest son—my grandfather—who took it and ran with it. After playing baseball at Mississippi College, he came to Hattiesburg in 1907 and started working for his cousins at a drugstore. Just errands and sweeping floors at first. But he paid attention to the business aspect of the store. Before long, he was at the Hattiesburg American, our local newspaper, working his way up to business manager, and eventually buying in as a partner. From 1918 until the early 1960s, he helped steer that paper through wars, booms, and busts. He kept the presses running, the bills paid, and Hattiesburg connected to the world.
My father followed the same current. He earned a business degree from Vanderbilt, came home, and stepped into the paper, taking over as the business manager until my grandfather passed away. He had the same spark, the same quiet dream of running something of his own one day. But his time was short. He died at thirty-six. I was six years old. That kind of loss leaves more than sadness—it leaves a charge. A sense that there’s always work waiting to be done.
My brother caught that same spark early. The day he graduated from college, he went straight into business for himself. Since then, he’s owned, operated, sold, and started more ventures than I can count. He’s almost sixty-eight now and still at it—still dreaming, still building, still chasing new ideas. That drive clearly runs deep in our family, and I’m grateful for it.
So, when I was nineteen, the only thing that made sense was opening a restaurant. Not for fame or money—just to build a place where people felt welcome. I didn’t know the word entrepreneur then; I just wanted to be a businessman and turn an idea on a cocktail napkin into something real. Over the years, I’ve opened several—each different, but all with the same heartbeat. Every one starts with a rough idea, some willingness, and a lot of faith in the people around me. Then the lights come on, the kitchen hums, and the first guests walk in. That moment never gets old.
But the funny thing is, my travel business didn’t start that way at all. It wasn’t planned. Strangers asked if I’d take them to Italy, to show them the places and people I’d discovered. I said yes, figuring it’d be a one-off adventure. Then another group asked. And another. Before long, it grew into something real.
Now, as I sit in Milan with twenty-five Americans, I realize just how far that accidental idea has come. By mid-November, I’ll have hosted over 1,400 people on more than sixty tours across Europe. I still don’t think of it as a business. It’s just something I love to do. I spend over three months a year here—walking cobblestone streets, eating long lunches, introducing people to chefs, waiters, and winemakers who’ve become dear friends.
There’s joy in watching someone taste real Pecorino on a sheep farm for the first time or seeing their eyes widen over a sip of espresso in a tucked-away Roman café. Two ladies in this group are on their eighth trip, and they’ve already signed up for Ireland in a few weeks—their ninth. That kind of loyalty can’t be bought. It’s built on shared moments and a sense of belonging.
No matter the setting—restaurant, bakery, or tour bus—the part that keeps me going is creation. Building things from scratch. It’s not about ownership; it’s about life. Taking an idea that doesn’t exist at sunrise and seeing it take shape by sunset. That process—hands-on, unpredictable, satisfying—is what lights me up.
And the truth is, I’m not slowing down anytime soon. With seven new restaurant openings planned over the next five years, there’s plenty to keep me busy. I’m also restarting the food products division I mothballed a while back— bringing back sauces, mixes, and seasonings that blend Southern roots with what I’ve learned abroad. There are a few more projects percolating too. Some will take flight. Some won’t. That’s part of the fun.
People sometimes ask when I’ll slow down, or if I ever think about retiring. I smile and tell them I’ve never been good at sitting still. For me, work isn’t a countdown to freedom—it’s part of living. The creative process, whether it’s drafting a menu, walking guests through a Tuscan vineyard, or jotting down notes for a new project, keeps me sharp and thankful.
Looking back, it all connects—the general store, the newspaper, the restaurants, the tours. My great-grandfather’s handshake behind the counter. My grandfather’s press deadlines. My father’s business degree he never got to fully use. My brother’s ventures. My own restaurants and stories. And now, my son—he’s got that same gleam in his eye. He’ll be home one day to work with us, and I can already see him thinking ten steps ahead. That feels right, and I’m grateful to see it continue.
Entrepreneurship wasn’t something I learned in school. I’ve lived it one decision, one mistake, one small victory at a time. It’s staying late after the last customer leaves, looking around a quiet dining room, and feeling thankful that people chose to spend their time with you. It’s waking early in a Tuscan villa, pastry in hand, sun rising over the hills, thinking about what’s next—and smiling that you still get to do it.
Sixty-five might still be the traditional retirement age. But the way I see it, the number doesn’t set the pace—the purpose does. As long as there are people to feed, places to explore, and ideas to bring to life, I’ll keep showing up.
Because the love of creating isn’t something you age out of. It’s not a phase, and it’s certainly not a job title. It’s a calling. A way of seeing the world that keeps you wanting to shape it. One grandfather traded his briefcase for a gold watch and a fishing pole at sixty-five, but I’ll take the next idea over the next nap any day.
That number—sixty-five—still marks a finish line for some folks, and I’m happy for them. They’ve earned it. For me, it’s just another mile marker on a road I’m grateful to still be traveling, thankful each day for the chance to keep building something new.
Onward.
