Gary Jobson

Sometimes in the races you lose, you learn far more than the races you won.

- Andy Schell

Gary Jobson is an America’s Cup-winning sailor and one of the most vocal—and opinionated—supporters of the sport. His story is an inspiration to sailors young and old alike.

How did you know you wanted to make a career in sailing?

The defining moment was when I was 12. I got a little dinghy called a Penguin. Family came over and were thinking of getting into sailing, and I was this 12-year-old explaining what sailing was and giving them lessons. At that moment, I thought, gee, I could get people enthused about sailing. I’ve been on that mission ever since.

It’s rare to turn a passion into a career—how did you do it?

In the late ‘60s and early ‘70s, it was very uncool to be a professional sailor. People didn’t get paid to race. It was kind of dirty. So the only way I could make a living was to talk about it, write about it, do seminars and clinics. I didn’t get paid to race, but I made my money by doing all this and I became a sailing coach. But that got interrupted by Ted Turner.

You don’t just meet Ted Turner!

Ted is 12 years older than me. He came up to [Robbie Doyle and me after a collegiate regatta] and said, “I don’t know who you guys are, but someday we’re gonna sail together.” Oh, OK.