How Benjamin Alexander rewrote the rules to become Jamaica’s first Olympic Alpine skier
Benjamin Alexander is an Olympic athlete and innovation speaker whose career defies traditional pathways to elite performance.
After spending over a decade as an internationally touring DJ, he pivoted in his thirties to competitive alpine skiing and went on to make history as Jamaica’s first-ever Olympic alpine skier at the 2022 Winter Games in Beijing.
Born in England to a Jamaican father, Alexander qualified for the Olympics in just two years, overcoming limited access to competition during the pandemic and training largely outside conventional national systems.
He competed in the giant slalom and was selected as one of Jamaica’s flagbearers at the Opening Ceremony, extending the country’s legacy of breaking boundaries in winter sport.
Today, as an inspirational speaker, Alexander draws on his Olympic journey to explore themes of unconventional thinking, calculated risk and long-term execution under pressure.
He is also mentoring the next generation of Jamaican winter athletes, helping to build a sustainable pathway in a sport where representation has historically been limited.
In this exclusive interview with the Inspirational Leadership Speakers Agency, Benjamin Alexander reflects on what it takes to pursue outlandish goals with discipline, resilience and belief.
Q1: Your journey to the Olympics began in an unconventional way. What moment shifted this from a personal challenge into a serious pursuit of Olympic qualification?
Benjamin Alexander: “Initially, I started to ski just because I saw my friends heli-skiing, and I thought this was probably the most insane thing that I had seen anyone do. My friends had turned into superheroes, so my initial goal was simply to be able to keep up with these guys and to attend the heli-ski events they were attending.
“At the beginning of 2018, I attended a tech entrepreneur gathering of skiers in Revelstoke, British Columbia, Canada. It was at this moment I realised a couple of things. First of all, I was the only Black representative out of a crew of 200 people.
“Secondly, with these friends knowing of my Jamaican ancestry and my Jamaican roots, my father’s Jamaican, the jokes about Cool Runnings and the 1988 bobsled team started right there. The joke of the day, or the weekend, was, “You should go to the Olympics.”
“I took that a little bit too seriously. In 2018, I went to the Olympics as a spectator and absolutely fell in love with the spirit of the Games. As a child who had only seen skiing on TV and knew nothing about winter sports, this was probably the first time I had ever paid any attention to the Winter Olympics.
“I noticed something else. Jamaica, which is a powerhouse in the Summer Games, only had three athletes representing the country at the 2018 Winter Games in Korea. I thought perhaps there was a chance for me to do this.
“In the beginning of 2019, I moved to Revelstoke for a month of ski training, or really just skiing. During that time, I met a former professional ski racer and asked his opinion of this crazy idea.
“In a nutshell, he said I had the worst ski technique he had ever seen, which was justified as I had only skied about 25 days and had taken two lessons. However, he was completely shocked at my ability to keep up with him.
“He said I was fearless, crazy, stupid, or a combination of the three, and that this fearlessness might give me the opportunity to qualify. It was this individual who steered me in the right direction and set me on my merry way to becoming Jamaica’s first-ever alpine ski racer.”
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Q2: Qualifying under extreme constraints tested both your physical and mental limits. What did that experience ultimately teach you about resilience and determination?
Benjamin Alexander: “I nearly failed to qualify for the Olympics, largely because of the pandemic. I had set out on this outlandish mission to qualify for the Olympics in just two years, something most people spend the majority of their lives trying to do.
“Not only did I have just two short years, but I was also coming from zero skiing background. Little did I know that 17 of those 24 months would involve no access to competition because of closed borders, and for a large portion of that time, I would have no access to skiing at all. I had intended to go to the southern hemisphere during their winter months to continue training, but the pandemic made that impossible.
“Qualifying for the Olympics taught me to keep fighting until the very last moment. I contracted Covid over the Christmas break of 2021, with less than 20 days left in the qualification window and still a lot of work to do. I thought I had no chance.
“I decided to keep trying. I had five races booked in the final seven days across four countries, which required 20 hours of driving. I was a one-man show, racing during the day and driving for six hours to the next race. It felt like Mission Impossible until the very last moment.
“Seven to two hours before the deadline, I qualified. It taught me to never give up until something is absolutely impossible.”
Q3: Your story resonates far beyond sport. What core lessons do you hope audiences take away when you speak about goal-setting and overcoming adversity?
Benjamin Alexander: “The highlight for me was walking in the opening ceremony as the flag bearer.
“Because of the 1988 bobsled team and Cool Runnings, there is a cult following and a special energy around Jamaica competing in the Winter Olympics.
“To carry on that legacy 34 years later and hold the flag, sharing that honour with none other than Usain Bolt, was absolutely the highlight of my Olympic experience.”
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Q4: As the first alpine skier to represent Jamaica at the Winter Olympics, which moment best captures the significance of that achievement for you personally?
Benjamin Alexander: “My proudest professional achievement is being the first person to represent Jamaica in alpine skiing and beginning a legacy of alpine ski racers.
“I am currently mentoring 10 young athletes who are fighting for two spots at the 2026 Winter Olympics in Italy. I am also working on a plan to bring Jamaican cross-country skiers to the 2026 Games.
“What I did was just a line in the sand, the beginning of a movement. I am proud of that, but I am even more proud of what is still to come in the next Olympic cycle or two.”
This exclusive interview with Benjamin Alexander was conducted by Chris Tompkins of The Motivational Speakers Agency.
