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Shanna Dickerson: Building a Luxury Travel Empire and Being Her Own Boss

In November of 2009, Shanna Dickerson, a highly successful concert producer from Nashville, cruised across the Caribbean on a small boat with her parents. It was the 30-year-old’s third trip that year to St. John, an almost 20-square-mile piece of land, a dot in the string of the U.S. Virgin Islands. 

The sun was warm on her skin. The sky was blue. On one side of the boat, the clear blue ocean stretched wide. On the other, she could see the shores of Peter Bay, a development of the most exclusive, highest-end villas in the Caribbean.

As she gazed at the villas, something inside her shifted.

She felt a shiver of excitement, the wide-open sense of possibility. She knew then that she would leave her old life behind and start anew.

She wanted to find a way to live in one of those villas, start her own company, be her own boss. She didn’t know exactly what that would look like, but when Shanna Dickerson gets interested in something, she tends to go all the way.

Five months later, she landed in St. John. With only a few personal possessions she had sold her furniture and her car and had spent almost all her savings — she stepped into her new life.

She had walked away from a career many only dream of, producing major concerts and music festivals in Nashville and around the country with Jay-Z, Kenny Chesney, Red Hot Chili Peppers, Green Day, Metallica, Fleetwood Mac, Snoop Dog, and Widespread Panic. She spent a year as tour manager for Steve Winwood, the only woman on a bus full of musicians and roadies crisscrossing the country. She was a concert-producing machine, once doing 23 shows in 30 days. 

“I swear I lived nine lives in those ten years,” Shanna, now 42, recalled.

She thrived in the business. She was great at logistics and details. But she was tired. “I was working very long days, very long nights. It was exhausting.”

Regardless, most of the people she knew thought she was crazy to walk away from a life like that.

“They said things like, how could I leave the best job in the music business? How could I leave this backstage life with all these musicians? People were really giving me the third degree.”

Fast-forward 12 years, Shanna is living the life of her dreams. From almost nothing, she has built Blue Sky Luxury Travels, a multi-million-dollar, global travel agency. The company books leisure and corporate travel for the highest-end clients, the rich and famous, across St. John, where her company started, and worldwide. 

The only people who didn’t think Shanna was crazy were her parents. And that may be because, throughout Shanna’s life, they have watched her throw herself into things that interest her, master them, then not be afraid to scrap it all and start again when her mind, her body, or both need a change.

Shanna started gymnastics at four years old. She excelled, practiced five hours a day, and rose to the top of the field. When that wore on her, she turned to another interest: tennis. She trained tirelessly and became one of the top high school girls in North Carolina. “My parents didn’t push me to do anything like that. I always pushed myself.”

She was recruited to play tennis at North Carolina State University. But before school started, facing more years of grueling training, she knew she needed a break. She turned it down.

While figuring out what to do next, she started attending big jam-band concerts in amphitheaters, and loved it. From backstage, she became interested in how it all worked, how the parts came together. As soon as she graduated, she was off.

Towards the end of her 20s, though, Shanna started having a nagging feeling.

She didn’t want to climb the corporate ladder, retire when she was 65, and then live the life she dreamed of. She wanted it now. 

“I said, screw it, it’s better to do it while you are young and healthy, and you can bust your butt and figure something out.”

With her connections and exceptional resume, she landed the highly coveted gig of a villa manager in Peter Bay, the development she had gazed out at four months earlier. In return for her work, she could live rent-free. She had a roof over her head — a gorgeous, luxurious roof steps from the sandy beach — but not much else. 

Even so, there was a honeymoon phase. “You are amazed at how beautiful it is. You go to every beach. You do everything. And then, after 30 days, I was like, ‘What in the world did I just do? Oh my God!’ Reality set in. I didn’t have any money coming in. I had to build a business. This was all on me.”

She began learning about the luxury travel industry. It took about two years of scrimping and hustling before she knew she was going to make it. 

She started booking villas for clients, then moved on to mega-yachts. Then private islands, private jets, private events. (She once booked a $3 million 40th birthday trip that included The Lumineers playing on a mega-yacht sailing to a private island in the Bahamas.)

Building a global business from a rock in the middle of the sea proved challenging. She couldn’t get reliable wireless service. Her landline went down when it rained, and power outages were regular. In 2014, she decided it was time to relocate back to the States. Now she alternates months between the U.S. and the Caribbean.

Last December, Shanna moved to Santa Rosa Beach, an area in the Florida panhandle. She is excited to expand her business and live a stateside beach life. (The area’s beaches are compared to the Caribbean, and rightly so.) She has also started a non-profit, Blue Sky Relief Foundation, an organization working to eradicate animal abuse, neglect, and homelessness.

“There’s a lot of growth to happen here with the company,” she said. “I’m very excited for this new chapter.”

To learn more, visit Blue Sky Luxury Travels and follow Shanna on Instagram.

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