The Story Behind Key West Shawn
Our Story
From the mountains of Tennessee to Mile Marker 0 — and one dinner that changed everything.
Chapter One
From the Tennessee Mountains to Key West
I was born and raised in Southeast Tennessee. For about 44 years, the mountains were home, the kind of place where you know your neighbors, the seasons actually change, and life moves at a pace that feels right.
I wasn't unhappy, but Jeannie and I knew that at some point we were going to live near the water. We visited a lot of beach towns over the years, but we kept noticing the same thing. Get half a mile away from the beach, and it was just a regular old town.
Then we discovered Key West, and we loved it. Here, when you get half a mile away from the water, you're already starting toward the other side of the island. You never really leave that beach vibe.
Shawn on The Price Is Right, 2015 — with Drew Carey
Chapter Two
A Winning Spin on The Price Is Right
In 2015, I appeared on The Price Is Right with Drew Carey. I wore a shirt that said 'I flew my Mom to The Price Is Right for her 75th birthday' — because that's exactly what I did.
I won nearly $40,000 in cash and prizes. Arms in the air, Drew Carey right there, the whole thing. It was one of those moments that doesn't feel real until you're standing in it.
I didn't blow the money. I did something that seemed a little unusual at the time — I invested it in original 1985 Garbage Pail Kids trading cards. I displayed them around my home like small treasures, because that's exactly what they were to me.
won on The Price Is Right
Chapter Three
The Garbage Pail Kids Gamble
About six years after The Price Is Right, the pandemic hit. And something strange happened to the collectibles market.
Sports cards, Pokémon cards, vintage trading cards — everything exploded in value almost overnight. The market went from a niche hobby to front-page news. People were paying serious money for things that had been sitting in attics for decades.
My Garbage Pail Kids collection — the one I'd bought with Price Is Right winnings and displayed like art — had become genuinely valuable. I sold the collection, and those proceeds helped fund the purchase of a home in Key West.
A game show, a bunch of gross trading cards from the '80s, and a pandemic. That's how I got to Key West.
Chapter Four
Making Key West Home
In December 2021, we made Key West our permanent home.
After spending more than 44 years in the mountains of Southeast Tennessee, we found ourselves living at Mile Marker 0, the end of US 1, just 90 miles from Cuba and surrounded by water on three sides. It was everything we had hoped it would be. The weather was warm, the sunsets were even better than we'd imagined, and the sense of community was stronger than we ever expected.
For the first few years, we simply lived the island life. We explored restaurants, met incredible people, discovered hidden gems, and learned the rhythms of a place that doesn't rush for anyone. We weren't checking things off a tourist list. We were becoming locals.
After about three years, I picked up a camera and started making videos. The first ones didn't go anywhere. I was still figuring out my style, finding my voice, and learning what people actually wanted to see. Looking back, those early videos weren't failures. They were just the beginning.
Mile Marker 0
Chapter Five
The First "Hey Babe"
One evening, Jeannie and I were having dinner at the Boathouse in Key West. We'd been talking about the videos — what was working, what wasn't, why nothing was really landing.
"Hey, babe, what's for dinner tonight?"
— Jeannie, at the Boathouse, Key West
I explained what we were eating. I described the Boathouse the way I'd describe it to a friend — as one of the best happy hours in Key West, a place worth knowing about. Casual. Honest. Specific.
That was it. That simple moment became the beginning of the 'Hey Babe' format — and everything changed.
Chapter Six
And the Rest Is History
The format grew from that one dinner into something neither of us planned. Restaurants, attractions, local businesses, events, hidden gems, honest recommendations — all delivered the same way: Jeannie asks, Shawn answers.
Jeannie is an essential part of what we do, even though she's usually behind the camera. She asks the questions that visitors actually want answered. She keeps the conversations real. Without her, there's no 'Hey Babe.' Without her, there's no Key West Shawn.
Viewers experience Key West through our conversations — not through a polished travel segment, but through two people who actually live here, eating the food, visiting the places, and telling you exactly what they think.
"What began with one simple question has become our way of helping people experience the Key West we know and love."