In 2006, a 12-year-old Madison Shirley sat behind the hostess stand at Great Southern, her father’s just-opened restaurant in the relatively new and not-yet bustling Seaside, greeting customers as they trickled in. Sometimes that trickle slowed to nothing, and she would retreat to the office, open the latest Harry Potter book and devour it. The servers, bartenders, chefs, and cooking staff would flicker in and out of Madison’s youth, offering companionship, advice, and even cooking lessons.
“I spent most of my life as a kid in the restaurant,” Madison, now 30, recalled recently. “My babysitters were the servers and bartenders and the people working in the back of the house.”
When it was time to go to college, she and her dad, Jim Shirley, agreed she should venture out to another part of the world and another field of study. After 10 years of trekking up and down the West coast, Madison decided to return home. In the fall of 2021, she became director of brand and storytelling for her father’s restaurant group, which has burgeoned into a small empire of eight restaurants scattered across the 30A area.
“Being able to come back full circle was an important experience for me,” Madison said. “I get to again be a part of the story my family is trying to build and the community they are continuing to establish and maintain.”
Madison’s parents split up when she was two. Her mom decided to leave the restaurant business for the fashion industry in San Francisco. Madison grew up dividing her time, half the year in Florida and half in California.
In California, she lived with her mom and stepfather. In Florida, her dad raised her alongside her Southern grandmother, Nona, and her ever-prim-and-proper Aunt Kim. “They taught me so much about what it was like living in the South and how to be a proper adult, if you will,” Madison recalled. This was very different from her mother’s lifestyle, which Madison said gave her a well-rounded upbringing.
When Great Southern opened in Seaside in 2006, it was Jim Shirley’s first restaurant in the area. He’d spent years running successful joints in the Pensacola area, some of which still stand today. But, he was venturing into uncharted territory when he opened shop in a tiny shaker cottage in the then-sleepy and quiet Seaside.
Madison remembers going hours and hours without seating a single customer. Then, as Seaside started slowly growing, they had some busy weekends around the holidays. Then those weekends turned into busy weeks. A busy day back then is like a slow lunch service today, and the restaurant often has a packed house.
Through it all, Madison roamed the restaurant, pitching in and learning to make her way through a non-traditional childhood.
She picked up basic cooking skills and prepared food for herself at home at a young age. She learned to talk to people and entertain herself when needed. Her bedtimes were a little later than other kids. But to her, it was all normal, and, she says, it was instrumental in helping her become who she is today.
“It taught me at a really young age how to interact with people of all different shapes, sizes, and ages,” she said. “And it’s what helped make me as independent of a person as I am today.”
And even though her dad was busy and her day-to-day life was distinct from other kids, Madison said she never felt she was second to the business. “When he needed to be there for me, he always made himself available for it.”
When it was time to head off to college and forge her own path, Madison decided to go all in. She chose Oregon State University, about as far away as she could get from Florida while still stateside. The quiet college town of Corvallis is tucked in rural Willamette Valley along the west coast. Though perhaps baffled at times by her decisions, her family was ever-supportive as she zigged and zagged along some unexpected paths over the next decade, trying to find her way.
Pursuing a passion for the natural world, she entered an environmental engineering program. She soon realized she needed to pivot. “Vector calculus did me a little bit dirty,” she joked.
She shifted gears to digital communications, minoring in business. “I realized it wasn’t the actual engineering that was my passion. It was more about bringing people together and using evocative storytelling to inspire folks to be more thoughtful about their approach to the environment.”
She started a music festival almost by accident. She and some friends invited people they knew to play music for each other at the park. They called the gathering Funk in the Forrest. About 20 people showed up. It was fun, so they thought, let’s do this again in a couple of weeks.
150 people showed up, and they realized they were on to something. The festival has carried on as an annual tradition with big-name funk bands but still the home-grown vibe. In 2022, after a two-year Covid-related hiatus, they had their largest turnout yet, with about 2,000 people. “So many people came back, saying how integral the festival was to the community,” Madison said. “It was a really heartwarming and humble experience.” The festival will return in the fall of 2023.
At the same time, Madison plugged away at schooling. She graduated in 2015 and immediately got jobs at Adobe and then Google, upending her life in rural Oregon for the high-speed, techie Silicon Valley. It didn’t take long to realize she needed a change again.
Madison had thought tech would be her next passion project, the thing that would drive her career. “It wasn’t quite hitting the mark.” Less than two years later, she packed up and headed back to Corvallis, taking a job for 2 Towns Ciderhouse. She had found a home.
Over the next six years, Madison made a name for herself in the craft beer industry, becoming second-in-charge of marketing and taking seats on boards of the Northwest Cider Association and other agricultural support groups.
She loved the industry’s deep connection to the environment, not only for moral reasons but because its day-to-day operations are highly affected by changes in the weather and the availability of natural resources.
It was here at 2 Towns that Madison learned that what sold the product was not just how good it was but the story behind it, and the reasons it was made in a specific way. “The story made people feel like they were part of the family we had created at the cider company, and discovering that was what got my communications ethos locked in.”
When she chose, in the spring of 2021, to uproot all that and move home, it was bittersweet because she had become very successful in Oregon, but she also felt confident because she had discovered what drives her. “I had found what I was passionate about, which was telling people’s food stories.” She was ready to apply that to a new venture.
After she decided to move, but before she had relocated, her grandmother, Nona, passed away after battling dementia for many years. It wasn’t a surprising death, but it shook the family and made Madison even more confident in her choice.
“It was a turning point in my mindset,” she said. Her own father was about to turn 60. “It made me realize how important it was to be physically close to family, to be involved in it. No matter how engaged I had been, I was still a whole continent away.”
Today, she does the marketing and branding for the restaurant group, helps facilitate events, and has recently branched out into all other aspects of the business in what she described as a catchall position, somewhat of an apprentice to her father. The varied responsibilities are a perfect fit for her.
“I’m really ADHD, so for me, the hospitality industry is this perfect happy space of controlled chaos.” She said that though it feels cliched to say so, it really is something new every day. One day she is learning all about processing visas for foreign workers, and the next, how to properly prepare a restaurant for a cold snap. And she loves working closely with all the leaders at the various restaurants.
“I’m always blown away with what they are able to do and how as a collective group, we are able to do so much.”
Many people have made much of her move from the “hippie West coast” to the “conservative deep South,” but Madison sees it differently. “There’s a lot of polarization and inflammatory conversation between both states.” But really, she said, the communities are much more similar than many people would assume. People in both areas are very passionate about where they live. They value and work to protect natural lands. They have a deep appreciation for food and are both quite rural.
“People in both places are just trying to be happy and healthy and supportive of their communities,” she said. “Whenever I talk with people in either place, I say, you should just go there and talk to the people. You’d be really surprised. Politics aside or not, you’d be surprised how many similarities there are.”
Madison lives in a house in north Santa Rosa Beach with her fiancee Justin Schepige, a touring musician, their two dogs, and two cats. “It’s a full house. Lots of fur.”
Aside from her work, she has spent the last year planting a native pollinator garden in her backyard. Very little written guidance existed for native species where she lives, so she worked with the University of Florida researchers to figure it out.
She is also striving to visit as many state parks as possible in 2023. With four under her belt in the first week of the year, she had a strong start. She likes to head down a trail until she hasn’t heard or seen anyone else for 20 minutes, pop out her earbuds, and take in the quiet seclusion.
She is involved with the Cultural Arts Alliance, is getting certified in SCUBA to visit the Underwater Museum of Art, and performs spoken word poetry with the Emerald Coast Storytellers.
“I’ve just been delving into all the overlapping opportunities here,” she said. “This really small slice of Florida somehow has a little bit of everything.”