Benjamin Alexander: ‘I spent $150k family inheritance on my dream to ski for Jamaica in the Olympics’

Financier turned DJ turned Olympic skier on how becoming a skier was both his best and worst financial decision.

A report by Susan Gray for London’s Telegraph.

Benjamin Alexander is Jamaica’s first Olympic competitor in Alpine skiing. He took his initial ski lesson six years ago, aged 32, and lines up for the Giant Slalom in Beijing today. He is coached by Dudley Stokes, the Jamaican bobsleigher immortalised in the film Cool Runnings.

Born in Northamptonshire, he grew up with his Jamaican father and English mother. He DJ’d in clubs across Asia, America and Ibiza, including a 15-year stint at Burning Man. He currently lives in Austria, where he has been training for the 2022 Winter Olympics.

How did your upbringing shape your attitude to money?

My father, Keith, was one of ­Jamaica’s “barrel children”, where parents working overseas sent home barrels of goodies to extended family providing care. In 1961, he joined his parents in west London. My parents met while working in a factory. They moved to Wellingborough, Northamptonshire, to afford a property.

My father worked damn hard for very little money, and this inspired me to never be in that situation. The first time I worked in a factory holiday job, it was on a higher hourly rate than him. There was fire in my belly to do better based on not wanting the same income as my parents.

What was your first wage?

I had paper rounds earning about £5 per week, and at 12 I cleaned the shelves in our local corner shop. I was also good at convincing my parents into highly sophisticated loans. I ran rings around them mathematically from very young.

What was your first real job?

While at university, I was pulling 40 hours a week at an IT firm. Three days after my last university exam, I had a one way ticket to Thailand, with £250 in my bank account. I spent 10 years in Asia. I moved to Hong Kong, working in finance, and that’s where I started DJing, having abandoned it at uni.

Then I ditched the finance to DJ full time. In finance I earned low to mid six figures, but it’s a grind and you’re selling part of your soul. It doesn’t compare with being in a nightclub, playing music you love for other people, and to be the centre of attention and paid to be drunk.

How much did you make DJing?

I could make about $20,000 turning up with a USB stick for a night, playing someone else’s music. Flights and accommodation are paid for and typically dinner is included. After two or three days, you jump on a plane and do it again somewhere else.

DJ night club
Benjamin quit finance to DJ full time

What was your most lucrative piece of work?

In 2016, I earned low five figures for a New Year festival in Thailand that never happened, because the organisers did not pay off the cartels.

How much has your Olympic dream cost you?

I’ve buried my head in the sand about costs, but roughly $150,000. I have sponsorship from Atomic skis, Leki poles and Stio skiwear.

Despite the pandemic, I kept training by climbing a mountain to continue skiing. Stio was impressed with my work ethic and it became my first and one of my biggest financial sponsors.

Some of my funding is from a family loan, as my paternal grandmother died leaving £100,000 in savings. From 40 years of labour, my first generation immigrant grandparents were able to squirrel away an impressive sum.

I’ve had sponsors helping me along the way, covering a lot of really expensive equipment costs – the biggest line items on the budget of any winter sports’ athlete.

Competing, I’m wearing maybe close to 10 grand’s worth of stuff. Boots are $1,000, and you spend another 1,000 bucks on customising and modifi­cations. Race skis are $1,500; the race suit, plus the suit that goes over the top, another couple of grand; and my helmet is two grand.

Then you have backups, so even if you only use one pair of skis, you’re looking at $10,000 worth of equipment, which is why the sport is unattainable for most people.

Training at the Schild Skiracing school in Austria wasn’t insanely ­expensive – in the range of €200 to €300 a day. What I wanted to do was work with top 10 coach Will Gregorak, who trains the Philippines’ ski team. But covering tuition and his living expenses would cost $12,000 a month. For a team of six, that’s totally manageable, but by myself it is not realistic.

Skis are $1,500 and the helmet is two grand

The Winter Olympics is the biggest Hail Mary of my life. I knew media interest would attract sponsors, and then I would recoup costs. I just had to keep the belief to get across the ­finishing line.

I’m pretty much on the way to recouping costs. Because of my former life as a DJ and in the finance world, I have a strong Rolodex of people to reach out to. For the Olympics, I’m offering sponsored logos on my ski jacket to a billionaire hedge fund guy, an Ibiza DJ and record label, a global translation company, a ticketing platform, a heli-ski operation, and Gaingels, a New York diversity and inclusion hedge fund. And I’ve started to do a lot of public speaking. I was hired twice by a Silicon Valley firm last year, which is five figures for an hour’s work.

What is the sagest advice from Your mentor, Dudley Stokes?

When I couldn’t train in the southern hemisphere because of the pandemic, and my chosen Austrian resort was too warm, I had 10 days at another resort, stealing coaching from six different coaches. They had different methodologies, and I was treading water.

Dudley said: “Benji, you’re smart enough to take an amalgamation of what they’re offering, throw away the nonsense. It’s probably better than having one bad coach all the way through. For the first six years of our professional bobsleighing career, we didn’t have one single coach, either.” Dudley repackages my frustrations and sends me on my merry way.

What was your best financial decision?

Becoming a skier was both my best and worst decision.

Do you own a property?

No, I rent wherever I am. No properties, no wife, no children, no headaches.

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