Mobile CEO and Family Stalled By Hurricane Season

A Southern California entrepreneur and his family, who set out on a three-year sailing journey this summer, have docked in Puerto Rico while waiting for hurricane season to pass.

Scott Leonard, CEO of a wealth-management firm in Redondo Beach, says the family planned to reach the southern Caribbean, out of the hurricane track, by September. He's found, though, that sailing from place to place can take longer than expected.

"While I always knew the trip would be dictated by weather, I was not aware how much it would affect our day-by-day sailing," Leonard writes on his blog. "Even though you're ready to go, all you can really do is muster patience and wait for the right conditions to get on your journey."

SecondAct wrote about Leonard, his wife, Mandi, and their three young sons in June as the family prepared to take their 50-foot catamaran, Three Little Birds, to South America and Indonesia.

Leonard, who calls himself "The Mobile CEO," described the adventure as a chance to introduce his sons to different cultures while demonstrating how a complex business could be directed from anywhere, using modern satellite and broadband technologies.

The family spent a few frantic weeks moving out of their home and getting rid of most of their possessions as they prepared for the trip. They set sail from Florida on July 8 and stopped in the Bahamas and the Dominican Republic on their way to Puerto Rico. Leonard also is chronicling their life at sea on Facebook. Here's what he says about the first four months:

On their daily routine: "Snorkel, read the morning paper, email office and clients, build sand castle, conference call, play hide-and-seek. That's my work/life balance." Leonard and the boys exercise together in the morning, which can involve kayaking, stand-up paddleboarding, swimming or water polo. Then, while he touches base with his company, Mandi Leonard conducts "boat school" for Griffin, 11, Jake, 9, and Luke, 5.

On working from the boat: Leonard says he made himself "intentionally irrelevant" to the day-to-day operations of his company, Trovena, to give himself the freedom to sail around the world with his family. He drew up specific plans and timetables and focused on "what was important, even if it wasn't urgent." Now he says he can do what he needs to by getting in touch during the day and flying to California once a quarter. His contacts with the office are "lean and focused," he says, leaving him time to handle the boat and participate in his sons' daily activities.

On hurricanes: "As I write this post, thunderstorms and wind gusts up to 30 mph are hammering our boat," Leonard blogged in September. "And the winds are from the southwest and west; a far cry from the 10-15 mph east and northeast winds that were predicted. Did I mention that this has been going on for the past 15 hours? This is merely the 'aftermath' of Tropical Storm Maria." The family has ridden out Hurricanes Irene and Katia and Tropical Storm Maria.

On achieving his goals: "It's easier than I thought to mix work and family. And, as our lives are much simpler -- no after-school commitments, TV or play dates -- we have more time to spend together."

Spending time with his family was one of the main reasons for the trip, Leonard says, and so far it's working. "One of the best parts of our trip -- and it is by design -- is that there are so few life distractions that we just spend time together," he writes. "I love walking down the beach at night, holding hands with my boys."

The family's catamaran is being hauled out of the water in Fajadro, Puerto Rico, for maintenance over the next two weeks. Hurricane season ends Nov. 30, when the Leonards plan to sail to Mexico.

Read more: How to Move Abroad and Keep Your Job