Sir Russell Coutts has hinted he may not be involved in the America's Cup beyond the imminent regatta.
Writing in the London Telegraph, Coutts admitted he gets "bored pretty quickly" and isn't sure what he might do in the future.
"There's always a time to move on," he said. "I've never wanted to outlive my abilities and motivation.
"Most people don't move on soon enough. I've always taken pride in bringing new people into the roles I vacate.
"Plus I like new challenges; I can get bored pretty quickly."
Coutts, the current CEO of Oracle Team USA, has won the America's Cup five times. He skippered New Zealand to victory in 1995 and 2000 and Switzerland in 2003 before switching to a CEO's role with Oracle and winning again in 2010 and 2013.
Now as chief executive of the America's Cup Event Authority he has, along with Oracle's Larry Ellison, been committed to turning a niche event into a mainstream, premium sport.
Coutts used his Telegraph column to laud Ellison's contribution to the Cup, saying the Oracle boss had "changed everything for us".
"Larry Ellison is a visionary," he wrote.
"He aimed to make the America's Cup more televisual from day one - more exciting and more understandable for the casual viewer. That was not easy in sailing.
"David Hill, chief executive of Fox networks in Australia, told us: 'It's just white triangles on a blue background'.
"But Larry pushed us to find a way to superimpose the race graphics over the television images, in a similar style as had recently been applied to the NFL.
"We developed that and it changed everything for us - things like course boundaries and even the sponsors' names on the course came from that vision."
Coutts said the most valuable lesson he had learned from Ellison was to never give up.
"You can't ask too much of newcomers if you want growth," he said.
"It's a daunting business starting an America's Cup team from scratch so allowing existing teams to sell their technology - as Oracle have done to Softbank Japan - is one of the best moves we've made.
"I once asked Larry Ellison what the key things are to being successful in business. He started with quite an elaborate answer and must have seen my eyes glaze over.
"So he stopped himself and said: 'Forget all that. None of that matters. The only thing that matters really, is... never give up'.
"And he's dead right."
Coutts also revealed the Olympics were an interruption to his studies and he had never anticipated sailing and the America's Cup would become a lifelong career and his livelihood.
"It wasn't a given that sailing would be my life," he wrote.
"I was studying structural engineering when I entered the Olympics in 1984. It was a good interruption to win a medal [a gold in the Finn class sailing] but it was an interruption all the same, so by the time I graduated the 1987 crash had happened and there wasn't a lot of work.
"It was my father's suggestion to get involved with New Zealand's America's Cup bid in 1990. He thought it would only be for a few years, but it turned out to be a bit longer than that."
Coutts said Dennis Conner was his inspiration as a young sailor.
"When I was growing up the America's Cup and the sailing world was dominated by [four times winner] Dennis Conner," he wrote.
"It was said he'd sail at least 320 days a year - his approach was to leave no stone unturned. He set the standard and was very much my inspiration. My other hero was the Danish sailor Paul Elvstrom.
"He won four Olympic Golds and I wasn't alone in thinking his record would never be beaten. Then Ben Ainslie came along and won four golds and a silver.
"I was lucky to be sailing during the era that the America's Cup became professional.
"Now sailors and the shore crew get paid properly but before 1990 the best anyone could hope for was a food allowance.
"It was an amateur competition and only really became fully professional in 1995."
Coutts also said foils are here to stay and will soon permeate all forms of sailing.
"Growth never comes with an ageing demographic," he explained.
"If you talk to junior sailors it's the new generation of foiling boats below the America's Cup boats that captures their imagination.
"I'm 55 so perhaps what I have to say is irrelevant. Foils on boats are here to stay. And not just on racing boats but on pleasure boats too - there's a water taxi being developed for Paris that's on foils.
"America's Cup certainly fast-tracked the development of the technology."
Sailing: Sir Russell Coutts may be competing in final America's Cup
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