Keeping Up with the Leonards

Back in summer 2011, we shared the story of a local family that left their home to embark on a multi-year sailing adventure. We reconnect with that family four years and many life-changing experiences later.

Scott Leonard is an adventurous entrepreneur with an equally adventurous family. He and his wife, Mandi, along with sons Griffin, Jake and Luke recently returned from a 2½-year sailing trip. While at sea, Scott continued to run his wealth management company and wrote a book (The Liberated CEO, Wiley: 2014) about the business model that allowed him to remotely run his company, Navigoe, and make the trip. I met with the Leonards before their departure to write the July 2011 cover story “Anchors Aweigh.” That article chronicled the inspiring story behind their trip, which has now reached its final chapter.

Scott and Mandi created a detailed 10-year plan that mapped out the goals they needed to achieve in order to make the trip. In addition to shopping for their sailboat, their preparations involved selling their home and all their belongings, securing a homeschool program, receiving medical training, establishing remote technology to service the boat, as well as Scott preparing his business for his time at sea. By the time they departed Florida in 2011, they had downsized their life to fit their 50-foot catamaran, Three Little Birds—a faithful floating home.

The Leonards visited 22 countries and more than 100 islands while Scott ran his business from the boat. They began in the Bahamas, sailed through the West Indies, over the top of South America, through the Panama Canal, to the Galapagos Islands, then westward across the South Pacific.

They visited notable places like Tahiti, Fiji and New Zealand, and New Caledonia. Along the way they experienced a diverse array of cultures, battled typhoons, swam with marine life and peered into the depths of an active volcano.  


Mapping the Leonard’s adventure from Florida to the South Pacific. Inset: The family’s boat graces the cover of our Summer 2011 issue. (Photographed by Bo Bridges)


During their travels, Scott made quarterly visits back to the U.S. to meet with clients and check on the business, while Mandi acted as teacher, cook and co-captain for their three-boy crew. For Scott, sailing had always allowed him the downtime he needed to recharge his battery and think creatively about work. Thanks to the benefits of remote technology to keep him connected, the trip was never a working vacation but a way of life.

The Leonards value the trip for exposing them to different ways of life. They interacted with native islanders whose communities were timeless and untouched by modernity; many of the villages lacked running water or sewage systems.






While the boys studied about the history of other people and places in their homeschool program, they had the chance to experience them firsthand. Mandi says that as a result, the boys appreciate and enjoy different cultures. She adds, “I really feel like they’d have no problem traveling anywhere.”

Scott and Mandi are often asked which ports of call were standouts among the many incredible destinations they visited. Scott named Fiji as a favorite for its ample boat-friendly locations, world-class resorts, great surfing and numerous islands.

Mandi mentioned Vanuatu as an especially exciting locale. It was in this archipelago in the South Pacific that they got to walk along the ledge of an active volcano without so much as a slicker to guard them against flying bursts of rocks the size of cars. It was an unforgettable—and precarious—view.

They also enjoyed scuba diving among one of the largest fully intact shipwrecks, the Calvin Coolidge—a former cruise ship converted to a cargo carrier for World War II. Scott notes that the wreck’s remains are untouched. “There are guns and tennis shoes and tanks, all the cargo they never took out of it.”

"There were 2½ days where we were trying to keep the boat from flipping over. At that point our sails were pretty ripped up, and we were running low on fuel. We were taking full waves over the boat.” 

They also enjoyed scuba diving among one of the largest fully intact shipwrecks, the Calvin Coolidge—a former cruise ship converted to a cargo carrier for World War II. Scott notes that the wreck’s remains are untouched. “There are guns and tennis shoes and tanks, all the cargo they never took out of it.”

Mandi also mentions the walled city of Cartagena, Colombia, as the most beautiful city they visited.

Alas, theirs would not be an epic sailing adventure without some perilous weather. Scott recounts a storm that hit as they sailed to New Zealand, where they had specifically planned to wait out typhoon season.

He says, “What was supposed to be a seven- to eight-day trip turned into 11 days because we got hit by a freak storm. There were 2½ days where we were trying to keep the boat from flipping over. At that point our sails were pretty ripped up, and we were running low on fuel. We were taking full waves over the boat.”







The Leonards huddle on familiar shores.


Naturally, Scott grew very anxious when faced with crossing the same stretch of ocean again. When he asked fellow cruisers if the anxiety was typical, they all laughed and said they had been taking Xanax for weeks prior to making that particular leg of their trip.

All of the Leonards are avid swimmers, which made their frequent encounters with sea life a thrill. The boys, who all play water polo, were strong and safe in the water when faced with marine visitors. At one point, they encountered a school of seal pups that would spend the mornings sunning on the deck and afternoons playing catch with the boys.

They also met a large population of jellyfish that surprised them while the whole family was swimming near the boat. Mandi recalls, “All of a sudden they were everywhere! And we were swimming in between them, just like that scene in Finding Nemo! The boys kept their cool and got back on the boat and they were fine—but it was a lot of jellyfish!”

The trip was a formative experience for the boys as they enjoyed the pleasures of sailing while developing valuable skills. They were charged with anchoring the boat, acting as line handlers when entering new ports, operating the dinghy and keeping watch when Scott or Mandi were performing other duties.

The boys had to be especially careful when anchoring the boat. They had to swim among sharp regions of coral reef and keep the boat clear while ensuring the anchor itself was properly lodged in the ocean floor.

Mandi says, “They had real responsibilities, and if they didn’t do their jobs correctly, we could have been in serious trouble. It wasn’t just taking out the garbage or feeding the dog.

They have grown up, and they have maturity and a confidence I don’t think they’d have otherwise.”

As they faced the final chapter of their trip, the Leonards did a bit of a re-write. The trip was timed to come to a close in the summer of 2014 so the boys could resume school in the States that fall.






However, in early winter 2013 (the beginning of typhoon season in the South Pacific) they docked at their final location in New Caledonia. Rather than sailing to Australia to spend six months in a port that resembled a typical American marina, they decided to do something they had missed while exploring so many tropical locations: skiing.

So they put the boat for up for sale and moved to Incline Village in Lake Tahoe. Incline allowed them to enjoy ski season and evaluate where they wanted to live next. Scott and Mandi realized they could choose to live anywhere, and locations like Hawaii made the short list.

They enjoyed Incline, but it was a sleepy town off-season, and they missed friends and family. After taking a trip that allowed them to see some of the most beautiful landscapes in the world, the South Bay beckoned them home.

Mandi sums up their decision to return: “We could have chosen to live anywhere. If people in the South Bay are wondering if there’s a better place to live, I would be hard-pressed to find a better place. You have such a great balance of a beach community, a great school system, a laid-back, friendly attitude and incredible weather. And then you have everything that LA offers culturally and sports-wise at your fingertips. I couldn’t imagine a better place.”

Having lived in both Redondo and Hermosa—and wanting more space—they finally landed in Palos Verdes. They are close to Scott’s office, and the boys have transitioned smoothly back into the school system.

As testament to truly capturing a work-life balance, Scott’s business grew during his travels. He says, “I certainly came back with my entrepreneurial drive completely revived, and I enjoy being back and working. I feel very proud of my employees who had to deal with the day-to-day in my absence. It’s a testament to them and to the business model we put in place, which is what the book talks about. We’re back and rejuvenated and looking forward to growing the business in the South Bay.”

While the trip provided an abundance of sightseeing and remarkable memories, Scott maintains that the main purpose of the trip was to have time together as a family. He says,

“The best aspect of the trip wasn’t so much a place, but every single night we sat on the back of that boat and had a two-hour dinner. In a way it took getting on a sailboat and sailing halfway around the world to do that.”


The family just before departure in 2011.




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