One-on-One with Margaritaville Hospitality's Dan Leonard

An education in restaurants set Dan Leonard, president of Margaritaville Hospitality, on the road to overseeing the company's rapid expansion into a wide range of hospitality.

Leonard calls himself a “prototype of [his] generation.” As a youth in Chicago, his neighbors owned the local bar and needed someone to wash the dishes and take care of  short-order cooking. As one of seven kids, his parents were “pretty pleased” to get him into the workforce, even though he was young. 

Getting a taste for the restaurant industry, he moved from the independent bar to the branded side, taking a job at McDonalds. Once he had graduated high school and decided on hospitality as a career, he determined to “put some education behind it” and spent the last two years of the 1970s studying hospitality administration at Triton College in Illinois. At the school, he learned about purchasing, human resources, menu creation and legal matters from the textbooks but also spent time in the kitchens for a more complete perspective of the business.

While studying at Triton, Leonard got a job washing dishes at a Rusty Scupper restaurant owned by Stouffer’s, where he spent the next 15 years holding “about every position in the restaurant,” from cook to bartender to kitchen manager to front-of-house manager and finally general manager. The various roles made it easier for him to support his teams when he started managing, he recalled, because he knew what they were going through with their different responsibilities. 

In the mid-1990s, Leonard joined Planet Hollywood—at the time, still a growing brand with only three properties open. He opened the Minneapolis property within the Mall of America before moving to Orlando to oversee the 500-seat restaurant at Walt Disney World. He was quickly promoted to the brand’s regional director for the entire East Coast, covering all locations from Toronto to Key West, Fla., as the brand grew from three restaurants to more than 40. The themed restaurants were different from any other property he had worked in before, presenting him with yet a new dynamic to learn. “Opening all those properties in the different cities—you learn so much from the different leaders you work with, the different team members you work with, the different cities and partners you work with,” he said. “So not only was I able to do that, I got a heck of an education out of it.” The most important lessons from that education were to stay flexible and to match the right team with the right leadership, he said.

Related: How a strong brand proposition, CEO keep Margaritaville from wasting away
Dan Leonard
Dan Leonard (Margaritaville)

With Planet Hollywood, Leonard estimates he was on the road 20 days a month, and while that was exciting, he had kids in middle school who he wanted to see grow up. “I didn't want to miss out on that, so ... I needed to find something closer to home that keeps me off the road.” Right around the same time, he met Margaritaville Holdings CEO John Cohlan, who was looking for a GM to open up a restaurant at Universal Studios in Orlando. “At the time, truth be told, I didn't really know anything about Margaritaville, but it was hard to resist his passion and enthusiasm,” Leonard said. “I’d get to be a GM, which is a job I love for a lot of different reasons, and I’d get to stay home and then they have an opportunity to grow.” The nascent company had two restaurants in Key West and New Orleans, but Leonard saw possibilities. “I guess I felt, if we really did this right, and we're smart about our growth, we could do six or seven of these,” he recalls thinking. 

Leonard joined the team as the GM of the new Orlando restaurant, overseeing a handful of team members in various management positions. “What it helped us do is understand the guests' experience,” he said, noting that Cohlan himself “sat at the host desk for three months” to get a sense of what guests wanted. The brand grew quickly, with restaurants under the Margaritaville, 5 O’Clock Somewhere and Landshark Bar & Grill brands opening across the country and internationally, and Leonard was soon COO of the hospitality division.

Leonard became president of Margaritaville Hospitality in 2007, just before the global financial crisis slowed development to a crawl. The experience taught the team to be better businesspeople and how to adapt to new challenges. “How are you going to protect all the things you've built over these years, and then still prepare for the future?” he recalled thinking at the time. “You can't save your way to prosperity.” 


The idea to expand the Margaritaville brand into hotels was Cohlan’s, Leonard said. “He saw the many different segments we could go into and just kept turning over rocks and finding new opportunities for the brand.” In 2010, Cohlan and "Margaritaville" singer Jimmy Buffett were driving down the Gulf Coast and saw an in-development hotel in Pensacola, Fla., that was preparing to open. After Cohlan and Buffett met with the property’s owner, the hotel opened several months later as the first Margaritaville Hotel. “With the help of [designer] Pat McBride and our design firm, our folks were able to convert it in about three months,” Leonard said. 

As the company moved into the hotel space, Leonard and his team wanted to maintain the Margaritaville culture they had built in the restaurants. “We were able to just bring that right onto the hotel side, which was almost like a natural transition,” he said. The company partnered with established operators like Davidson Hospitality, Benchmark Hospitality, DHG and Aimbridge that could handle the logistics of the hotels while Leonard was able to further develop the power behind the brand. Over the next decade, Margaritaville continued to gain ground, announcing the Latitude Margaritaville residences in 2017 and adding the Compass by Margaritaville Hotels and Resorts brand the following year. The company also launched a vacation club and a line of casinos, building its footprint across the U.S. and the Caribbean.

“Our brand is very much an experience, and opening these properties with good GMs and in frontline staff—they delivered,”  Leonard said. “And when they delivered, it created this momentum. And one thing led to another, and here we are now with 18 hotels ... The staff is the wind behind our sales growth. They create the experience and our guests just want more of it.” 

After a lifetime in restaurants and hotels, Leonard feels the hospitality business was the perfect fit for him, with something new to learn every day. “I learn by experience, and there's a boatload of experiences in restaurants, hotels, resorts. It's never a dull moment, and I've never looked back and wouldn't want to do anything else.”