Sir Ben Ainslie likes to defy the odds but his latest race against time could even test his skills of generating something from nothing.
Last year Britain's most able seaman since Admiral Nelson masterminded one of the greatest sporting comebacks of all-time, calling the tactics as Oracle Team USA sailed back from a virtual Dead Sea to win the America's Cup in San Francisco.
But sailing with a Stars and Stripe on his sleeve took something off the moment for the four-time Olympic champion.
Britain has staged the Olympics, finally won the men's singles title at Wimbledon and seized yellow at the Tour de France twice...in two years.
But the Auld Mug is arguably the last sporting summit to be conquered and it's time to end 163 years of maritime misery, with Sir Ben at the helm and a nation providing the wind in his sails.
However, turning a required investment of £80 million into a success will not be easy, new teams rarely succeed on their maiden voyages - indeed it took US software billionaire Larry Ellison two attempts – a reported $200 million - before his success in Valencia four years ago.
"It is never easy, but it is about bringing together the right people who have built successful corporations, designed successful America's Cup boats, sailed on winning boats, brought the Olympics to Britain and we have those people," said Ainslie, who is being backed by London 2012 deputy chairman Sir Keith Mills and Carphone Warehouse co-founder Sir Charles Dunstone in his campaign.
"Winning last year was more powerful that anything I'd previously achieved but it would have been so much more fulfilling with a British team and that's the goal.
"Since childhood I've had this burning desire and ambition to be part of a winning British America's Cup team. We don't just want to take part, we're here to win and we've got a budget that will make us competitive."
Next week Ainslie will seek to capture one of his sport's most famous records as he seeks to set the quickest monohull circumnavigation of the Isle of Wight at the JP Morgan Asset Management Round the Island Race.
He already holds the multihull record from last year and the event has deep rooted historical links to his America's Cup campaign.
The race was first contested as a 52-mile circuit sail on the Solent in 1851 - the schooner America won - claiming trophy naming rights - and a British boat has never won it back.
Ainslie - who has already raised 40 percent of his required budget - could have named his price to be involved with another campaign but wanted to fly the British flag, though he's drafted in experienced Kiwi Jono McBeth to the key role of sailing manager.
"For me, it is probably not the easy option, but it is certainly the right option," added Ainslie, who received a royal seal of approval to his challenge from Team GB ambassador the Duchess of Cambridge.
"It is about righting a wrong and bringing the cup back to British waters for the first time ever.
"I know what it is like to be successful but I'd like to do that under the British flag - with a boat the whole country can get behind. All of us are here to win the America's Cup and we will do whatever it takes to achieve that goal."
© Sportsbeat 2014