Benjamin Alexander, 38, only started the sport six years ago but is now set to compete in Beijing 2022.
The Wellingborough native was inspired by watching the 1993 film and has now been taken under the wing of Dudley Stokes, one of the Jamaican bobsleigh team from Calgary 1988.
Speaking to the Daily Mirror, he said: “Being nine or maybe 10 years old when the movie Cool Runnings came out and that being the coolest thing since sliced bread, and even cooler because I am half-Jamaican.
“To now, maybe 27 or 28 years later, trying to fly the very same flag Dudley and the rest of the team held high in the 1988 Games is almost a bit of a dream come true.”
Alexander was a troublemaker before receiving a scholarship to a private school where he flourished academically.
He took up DJing in 2000 and played in nightclubs that were “incredibly violent at the time” he says.
Two years later, he was queuing to get into a London nightclub and someone was shot and killed.
Touring the world, the athlete played in cities as far-ranging as Hong Kong and Ibiza, also enjoying a career in tech and finance.
On a trip to Canada in 2015, Alexander’s interest in skiing was sparked after years of avoiding the slopes.
In 2018, he was in Asia and visited the Pyeongchang Games in South Korea and the idea of becoming a skier took root.
However, it is tough to finance his new sporting career with money being one of the major obstacles to overcome.
“As an up and coming skier, I’m paying out of my pocket to travel to these remote locations to get to races,” he explained.
“I’m staying at budget hotels to try and manage the crazy budgets that Olympians are normally faced with.”
He was even faced with the possibility of giving up on his Olympic dream when the Covid pandemic hit.
It prohibited him from travelling to different countries in the southern hemisphere during last summer.
The resilient Alexander made the most of it and resorted to backcountry skiing, which he says put him in the best physical shape of his life.
“I did a slightly different element of the sport which is backcountry skiing where you put the skis on your back and walk up the mountains and ski down them,” he continued.
“This time last year I would say I was in the fittest shape that I had ever been in my life, after 90 days of climbing mountains.”
Alexander competes in the giant slalom, one of the four main categories of alpine skiing, navigating between various poles or gates at speeds of almost 70mph.
An initiative from The International Olympic Committee (IOC) aims to have as many nationalities represented at the Winter Games, to generate more interest around niche sports such as skiing.
Therefore, every country is allowed to select a male and female representative to compete as a “B criteria” athlete.
It means it’s unlikely they will compete for a medal but are skilled and up to a high enough standard to take part.
Despite not having a full-time coach, he remarkably managed to qualify for the games after finishing seventh in the giant slalom at the Cape Verde National Ski Championships last week.
Despite entering the sport at a later date than most, Alexander draws on inspiration from the likes of US alpine skier Bode Miller, who won his last gold medal at the age of 36.
“There are always these incredible stories about age not being too much of a factor. If it‘s possible to win a gold at 36, then it’s highly possible to compete at 36.”
Alexander hopes he can be a key figure of representation and inspire those both in Jamaica and the black community as a whole, as he edges closer to becoming an Olympian.
He said with a huge grin: “I hope I can encourage other people to get involved in the sport, where otherwise they might have felt that it wasn’t for them, and I want to show that it’s absolutely not true.”
“If I can inspire people to follow in my footsteps then that’s great and I’m very happy to be doing it for Jamaica.”
The Beijing Winter Olympics begins on February 4.