“I spent $150,000 in family heirlooms for my dream of skiing for Jamaica at the Olympics”

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Benjamin Alexander is Jamaica’s first Olympic competitor in alpine skiing. He took his first ski lesson six years ago, aged 32, and is now lining up for the giant slalom in Beijing. He is trained by Dudley Stokes, the Jamaican bobsledder immortalized in the movie Cool Runnings.

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

How did your upbringing shape your attitude towards money?

My dad, Keith, was one of Jamaica’s “barrel kids,” where parents who worked overseas sent barrels of treats home to the extended family who cared for him. 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 dad worked very hard for very little money, and that inspired me to never be in that situation. The first time I worked in a factory vacation job was at a higher hourly rate than him. There was fire in my belly to do better by not wanting the same income as my parents.

What was your first salary?

I had rounds of paper making around £5 a week and at 12 I was cleaning the shelves in our corner shop. I was also good at convincing my parents to give very sophisticated loans. I have run rings around them mathematically since very young.

What was your first real job?

During my university studies, I worked 40 hours a week in an IT company. 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, after dropping out of college.

Then I gave up finance to become a full-time DJ. In finance, I made six to six figures, but it’s a grind and you’re selling part of your soul. It doesn’t compare to being in a nightclub, playing music you like for other people, being the center of attention, and getting paid to be drunk.

How much did you earn in DJing?

I could make like $20,000 by showing up with a thumb drive for a night, playing someone else’s music. Flights and accommodation are paid for and dinner is usually included. After two or three days, you jump on a plane and start again somewhere else.

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