Skipper Rich Wilson is the oldest sailor and the lone American taking part in this year’s Vendée Globe race. He began sailing with his dad at the age of three, served on the crew of the winning boat of the International One Design World Championships in 1975, and, at the age of 30, became the youngest winner of the Newport to Bermuda Race. Since then, he has set world records for sailing between San Francisco and Boston, between New York and Melbourne, and between Hong Kong and New York—three routes made famous by speedy trade ships in the 1800s.

Despite all of his success at sea, he recently told Vendée Globe reporters that he didn’t consider himself a professional sailor. He said that what he really thought of himself as was an educator.

It makes sense. When he’s not at sea on the Great American III, the 58-year-old runs an educational company and non-profit organization. Skipper Wilson founded Ocean Challenge nearly twenty years ago to share information about sailing and other adventures with students in classrooms and families at home—work shared through the non-profit sitesALIVE! He and his staff provide information to teachers, and they and their partners write material for newspapers around the country. During the Vendée Globe, Skipper Wilson will spend two hours each day working on material for sitesALIVE!

Earlier in his career, Skipper Wilson, who studied math in college, taught high school for a year. He spent a few years as a defense analyst on B-52 planes and cruise missiles and another couple years working with the Government of Saudi Arabia on a network of power and desalination plants. After founding a firm that made emergency strobe lights for sailboats, he started another that used the blood of the horseshoe crab to test for problems with medical devices and solutions. He returned to school to study Ocean Resources Management at MIT and to specialize in new ventures at Harvard Business School. He invested in the publishing, music, and entertainment industries. He wrote speeches for a presidential candidate. His work took him all over the world.

During those years, Skipper Wilson was still spending lots of time at sea. He completed many long distance voyages and won a couple more races. He bought a boat, the Great American, on which he and a shipmate attempted to sail from San Francisco to Boston by a 15,000-mile route around the southern tip of South America. On Thanksgiving Day, 1990, the 65-foot waves off Cape Horn proved too much, and the boat capsized. Although the boat was righted by another huge wave an hour later, it was too damaged to sail. They were rescued the following night by a huge containership. Skipper Wilson wrote about that adventure and the successful voyage he took along the same route three years later in Racing a Ghost Ship: The Incredible Journey of Great American II.

In his spare time, Skipper Wilson also spends a lot of time working to raise awareness about asthma, an illness he’s suffered from since he was a baby. He has volunteered with the American Lung Association who named him a “SuperAchiever” for refusing to let asthma slow him down. Taking four medications every day to control his symptoms, he has learned to recognize the messages his body sends him and to react accordingly—great training for someone who needs to pay attention to the sea to survive long voyages.

Skipper Wilson lives in Massachusetts, where he swims and runs to remain in top physical shape. He shares his adventures with 300,000 students worldwide at sitesALIVE!