The 46-year-old Kiwi then signed on to take part in the domestic kite-racing series, Laglunitas, hosted by the local St Francis Yacht Club's on Thursday nights.
Bore clearly remembers the date of his first race on July 15, 2013: "I had never ridden a race board before and never raced. There were world champions there. I came last in every event I did, for four Thursday nights in a row."
During this period, he often found himself kiting alongside Emirates Team New Zealand training on the water for the Louis Vuitton Cup in the build-up to their challenge for the America's Cup. That was but a sideshow for Bore, who had become focused on his own progress.
"It was a real enlightenment on how much I had to learn. Any egocentric ideas of how much I had of getting on the podium were pretty much squashed. I was thinking, after coming last after my third race, 'What have I done?' So I just changed my attitude, decided just to have fun.
"[From there] I started to catch the pack, I wasn't coming last any more, improving at a really fast rate."
With this newfound confidence growing daily, Bore travelled to the Canadian Kiteracing National Champs in Vancouver and began winning.
He began to appear on world rankings and was also pleasantly surprised at being voted "friendliest competitor" at the Canadian event. The novice was a quick learner.
Meanwhile, someone had certainly been noticing the rise and rise of the plucky Kiwi lad and another pleasant surprise arrived by mail: an invitation to represent the New Zealand team at the upcoming World Cup in China, where he learned there was another Far North local in the five man/one woman squad, Ben Turner from Mangonui.
With the America's Cup over, Bore quit his day job and moved to San Diego to participate in the America Kiteracing Nationals at the end of September. He was now a regular on the circuit.
After two days of intense racing at in the seeding rounds of the World Cup, Bore was relegated to the third tier bronze fleet.
From his results over the following days, his world ranking jumped from 307 to 117 to 102 to 91.
He finished the bronze fleet in 12th place overall. Next stop was Sydney for a training camp during the first week of December, then it was on to Melbourne for Sail Melbourne, an ISAF World Cup event.
Bore eventually returned home to take part in the New Zealand nationals, hosted by the Kohimaramara Yacht Club, on Auckland Harbour, from December 20-22 - finishing 6th overall.
while kitesurfing was regarded in some quarters as a young man's game, Bore said there were no plans to quit anytime soon. In fact, he's just getting started. Besides, there's a grand masters division which is apparently just as competitive as the open, featuring "guys who have been sailing since they were kids".
As an active Project Jonah member, Bore was last seen holding fort on the barbecue and looking after the sausage sizzle lunch for the Far North Whale Rescue class held at the Rusty's Surf Lodge situated on the Kaka Street ramp to 90 Mile Beach on Sunday.
The plan now was to get back to training in order to be ready to represent the Far North in the Sail Auckland regatta being held in the first week of February. Meanwhile, reflecting on a quite remarkable journey over the past few months, Les Bore admitted even he was a bit overwhelmed by it all.
"That I actually did all this, seems like a dream now."