The Flyin’ Bulldog is a chef-owned restaurant in Dunedin that opened in 2025 with a simple promise — sandwiches by day, something more elegant by night. Behind it are Jason and Monique Vasilakos, who left the Northeast to build their first restaurant from the ground up. On this episode of Palm Harbor Local, Jason walks through the leap, the food, and why this small Gulf Coast town is the place they chose to plant roots.
From Brooklyn Kitchens to a Dunedin Storefront
Jason has spent close to 28 years in the culinary world. He came up through fast-paced line cook jobs, moved into fine dining for the last eight years, and trained through both a butcher program and culinary school. That last step wasn’t his idea — his mother-in-law pushed him to earn his culinary degree, and he credits it with changing how he sees the work entirely. She didn’t get to see the restaurant open, but her fingerprint is on it.
Born and raised in Brooklyn, then a decade in New Jersey, Jason and Monique reached a point where staying put stopped making sense. Something clicked in the summer of 2025, and they decided to stop waiting.
Why the Gulf Coast — and Why Dunedin
They married in Naples fifteen years ago and always pictured themselves on this coast. When the time came, they looked everywhere — Naples, Sarasota, Tampa, back and forth. Jason was a day away from signing paperwork in Siesta Key when it just didn’t feel right. He walked away. Dunedin was the one that fit: a small, walkable downtown with its own character and no big chains to compete with.
What sealed it wasn’t the real estate. It was the people. Jason describes being genuinely taken aback by how welcoming the community has been — a stark contrast, he says, to the head-butting he was used to up north, where other business owners here actually want you to succeed.
What a Chef-Owned Restaurant Does Differently
Ask Jason what sets a chef-owned restaurant in Dunedin apart from a chain, and his answer is immediate: attention to detail. They make their own sauces. They smash their own burgers. Nothing comes out of a freezer bag. That obsession with consistency — getting the same thing right every single time — is the part diners feel without always being able to name it.
He’s quick to share credit with his staff, including a sous chef he trusts completely and a line cook who once ran his own sausage program in Hawaii. Different backgrounds, one standard.
Sandwiches by Day, Dinners on the Horizon
The sandwich menu was the front door on purpose — a way to show the town how they do things before expanding. Weekend breakfast is next, kept deliberately simple: egg and cheese, pork roll, grab-and-go. Down the road comes the dinner concept — family-style, set menus a few nights a week, seasonal plates like a fried chicken dinner.
And yes, it’s dog-friendly to its core. The restaurant is named after their bulldogs. The “Smashington” burger is named after one of them. They recently launched a “Yappy Meal” for four-legged guests. This isn’t a marketing angle bolted on — it’s who they are.
Advice for Anyone Chasing the Same Dream
Jason’s advice for someone at the start is plain: get in the kitchen and don’t leave. Stay humble, cut your onions, find someone willing to teach you, and make yourself vulnerable enough to learn. You’ll burn yourself and make mistakes — that’s the job. It’s advice that holds up in just about any career, not just behind a stove.
If you haven’t been yet, go. Grab a smashburger, a Philly cheesesteak, or the roast beef — and if the chicken sandwich shows up, know it’s got a kick. Bring the dog.
Want more stories like this from the people building our community? Subscribe to the Palm Harbor Local newsletter and follow along on the podcast — we sit down with a new local every week. You can also find us on Instagram @palmharborlocal.
Learn more about The Flyin’ Bulldog at theflyinbulldog.com. And if you’re curious why choosing local actually matters, independent restaurants return far more of every dollar to the local economy than chains do.
Show sponsored by Valley Bank — valley.com
