227 What Growing Up On a Boat Taught Remington About Business

Once Upon a Time...

For those who don't know, Remington Begg grew up on a boat. When he was 7, his parents decided to set sail from their home in Bermuda and live independently with their three young children and a dog. All on a boat about the size of two minivans. 

For the next seven years or so, the family sailed through the Caribbean and beyond. 

Remington says the lessons learned and life experiences he had in his childhood impacted his way of thinking and his business sense. You can see it today in several ways.

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An Entrepreneurial Spirit

When you’re on a boat sailing from harbor to harbor through international waters, Remington says, you learn a lot about being an entrepreneur. You don’t have the usual “get up and go to work” life so many of us have in America. 

Instead, you live in the moment, and when you have needs for your family you pull into a port and trade. 

As a young boy, Remington discovered that he could watch the dingeys in port for sailors so they’d be secure. These people were willing to pay him, so he’d make money sitting and watching the small transport boats so no one would steal them. 

As he earned the money, he figured out quickly that he could buy supplies like leather in one port, work on making crafts like belts with it, then sell them in the next port. This is where Remington learned how to invest in the next step.

In addition to the economics, he learned how to look at a problem and reverse-engineer the solution. It wasn’t always about following a well-written plan. It was about finding the best solution. 

While this has served him well, Remington did admit to it hindering his initial math lessons in middle school when his family returned to the U.S.

Why Communication is Key (in Business and Sailing)

When you’re on a boat in open water and the only thing between you and the sea is a railing, listening is critical. 

“Most parents tell their kids not to cross the street without looking and panic if the child walks toward the road. For my mom, it was falling overboard and drowning.” 

So from safety to learning how to navigate with traditional tools—this was before we carried supercomputers with access to the world’s GPS—Remington learned the importance of communication. 

He now carries that into business. Whether you’re working with clients or team members, it’s important to actively listen, ensure communication has happened and move forward with the task at hand. 

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