Sandy Stilwell took one look at the restaurant business and thought she'd never look back.
She recalled her first foray into the industry when, at 12 years old, she was a dishwasher for her uncle's restaurant on Fort Myers Beach.
"I decided I didn't want to be in the restaurant businessI would never do that," she said with a laugh.
Sandy (front row, right) with her family and boyfriend Jon Finstrom (to her right).
Seven restaurants later and an eighth on the way, Stilwell has become one of the largest independent restauranteurs in Lee County. Her newest creation, S.S. Hookers, broke ground on a new building just off the causeway in Punta Rassa, where she will attempt to establish her first franchised restaurant.
"I've become confident in what works and what doesn't, I'm developing the menu myself," she said.
The location will be a fishing inspired restaurant and fish market. Stilwell and her family have always been avid fishermen.
Her original dream was to own a hotel like her father, Tom, who moved the family to Fort Myers Beach when Sandy was 12. He built a hotel, now the Ramada Inn on the beach. Back then it was called the Even Tide.
"I worked as a maid and desk clerk at my parent's hotel. We were struggling, it was a family-owned business and 10 others were being built. We rented our rooms for $12 a night," she recalled.
They eventually sold to Mariner Properties, the group that owns South Seas Island Resort on Captiva, according to Stilwell.
She bought her first hotel, the Sandcastle Island Resort on Fort Myers Beach, when she was in her early 20s. She worked the Inn for a couple years before selling it with the help of realtor James Newton, author of the book Uncommon Friends and close associate of some of the most celebrated minds of the 20th century, including Thomas Edison, Henry Ford, Harvey Firestone, and Charles Lindbergh.
"He owned the company that sold my inn. He wanted to get to know this young girl, he wanted to sell a bunch of condos," Stilwell said with a laugh. "We started a property management company with over 400 rentals. He really taught me a lot about business."
While the business venture was short lived (they sold it to Caldwell Bankers), the friendship she forged with Newton and his wife, Ellie, became a lifelong bond.
"Around Christmastime he and Ellie would give me a Christmas Card and it was kind of heavy. He would give me a gold krugerrand coin," she said. "He'd tell me, 'put it some place safe, because you never know, this might get you out of trouble someday!'"
Through these experiences and friendships, Stilwell set out to find her next project. She always dreamed of finding a place where she wanted to go on vacation. After growing up on Fort Myers Beach, she wanted a place a little off the beaten path, with a little more serenity and privacy.
"I always loved Sanibel and Captiva, it was a place that jut captured my heart. I set my goal to buy something on the islands."
She almost ventured to Vanderbilt Beach in Naples, but she pulled her offer at the last minute. While the hotel was profitable, the attached restaurant was not, and she still wasn't eager to jump into that side of hospitality. She made way for another notable investor.
"I didn't have partners, didn't have knowledge of the restaurant business, so I turned it down. I knew there was a backup offer on it. It turned out it was the golfer, Jack Nicklaus!" she exclaimed. "He wanted to put in a whole country club community and offer the beach component, it made sense for him."
She always regretted not pulling the trigger on that purchase, so she set out to learn more about hospitality, traveling to Cornell University over the summer, at the time a single mother, to learn more about the Food & Beverage Industry.
"I learned a lot about the numbers of the business, the book knowledge, accounting part of restaurant management. Really, it has to be good service, good food, and you have to pay the bills, and marketing!"
The Captiva Island Inn became available for purchase with a small restaurant attached with a tenant already in place. She pulled the trigger this time.
"There were only 6 rooms at the time. The restaurant went up for sale 2 years in, I felt it was the right time to try the restaurant business," she recalled fondly. "I gave myself one year, if I could do it, great. I changed the name to Key Lime Bistro. That was 15 years ago."
The rest is Islander history.
Stilwell, owner and CEO of Stilwell Enterprises and Restaurants Group, has since transformed the Captiva community into an oasis of destination dining and resort hospitality with a home-grown feel. She has since purchased and created RC Otters, Cantina Captiva, Sunshine Seafood Cafe and Wine Bar, Latte Da Coffee and Ice Cream Shop, Captiva Pizza, and the Sunshine Grille in Fort Myers. S.S. Hookers will be her eighth establishment and first brand new building.
But her impact on the islands and the rest of Southwest Florida may be even greater through her charity work.
"One of my greatest strengths is being able to hire good people and trust them to do their job, and not micromanage them," she said. "We're now up to 17 rooms and I built the shopping center for more parking."
"I'd say half of my time is in the community doing charity work. We do a lot of events," she proclaimed.
Stilwell's presence has been felt in such charities as the PACE Center for Girls (currently the president), the CCMI Soup Kitchen, Ronald McDonald House, the Salvation Army, Fort Myers Chamber of Commerce, Barba's Friends, and Hope Hospice, just to name a few. The Uncommon Friends Foundation has also been a cause near to her heart, a foundation inspired by the work of Jim and Ellie Newton.
Her first foray into nonprofit work was when her now-grown children, Chauncey and Erik, were still in school.
"I was doing PTA, everything around the school, I was team mom and all that stuff for every sport you can imagine!" she said. "Then I got involved with Ronald McDonald House. I was the President there and helped build it, it's been over 17 years now. I got involved with the Children's Hospital through that. It's been wonderful."
Her charities have raised millions for various causes, including a recent Martina McBride/Billy Dean concert that raised $500,000 in one night for the Heights Foundation. As President of the PACE Center for Girls in Lee County, she's orchestrated the organization into a new school and raised hundreds of thousands to update the facilities.
"In 20 days we'll be moving into our new school. It's a school for troubled girls that get off track a little bit, we give them counseling, help them get their self confidence back," she said.
Sandy Stilwell also is on the Resort & Hospitality Board at Florida Gulf Coast University, the Board of Trustees at Hodges University, worked for local chambers of commerce, on the editorial board for Gulfshore Magazine, among numerous other causes and organizations that have benefitted mightily from a woman's touch.
"My role is to help guide the whole organization in a positive way. I don't think it's a privilege, it's a responsibility."