Canadian Millionaires and Billionaires Who Started From the Bottom

Lilly Singh is one of the highest earning stars on YouTube. She has more than 13 million subscribers and, according to Forbes, earned $10.5 million in 2017. She's won numerous fan awards and released her first book last year. Singh stated things weren't always so peachy for her. She started making YouTube videos as a way to deal with feelings of depression.

Love him or hate him, October's Very Own, has certainly made a name for himself, and the phrase "started from the bottom" is ubiquitously associated with him and his brand. It, by the way, is estimated at a cool $120 million, making him one of the richest rappers. Talking about his humble beginnings, Drake has been quoted saying, "[My mother] wanted the best for her family. She found us a half of a house we could live in. The other people had the top half, we had the bottom half. I lived in the basement, my mom lived on the first floor. It was not big, it was not luxurious. It was what we could afford."

Robert Herjavec was 8 when his family moved to Canada, fleeing political oppression in what was then still Yugoslavia. When the family arrived in Halifax, they had all their possessions in one suitcase and $20 to their name.

Herjavec graduated in 1984 and then took on minimum-wage jobs to help support his family. He then started working behind the scenes in the film industry before convincing Logiquest to give him a job if he worked the first six months for free. He founded a cybersecurity firm in 1990, sold it for $30.2 million in 2000 and founded the Herjavec Group in 2003. According to Investopedia, he has a net worth of $200 million.

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Justin Bieber’s mother was only 17 when she gave birth to him, so his grandparents helped raise him. When he was 12, he came second in a local singing competition in Stratford, Ontario and his mother uploaded the video of his performance to YouTube.

Soon it wasn’t just family and friends who watched videos of the boy singing. A year later he had a record deal and the rest is history. With an estimated net worth of $265 million, according to Wealthy Gorilla, The Bieb is hot on the heels of the 20 richest singers of 2019.

Born in Quebec City, Guy Laliberté knew early on that he was going to have a career in showbiz. He started out as a street performer, then joined a performing troupe, tried his hand at full-time employment and when that didn’t work out, he went back to performing on the streets. In 1984 he co-founded Cirque du Soleil, got a government grant and took the company on tour. Cirque du Soleil is now world renowned and Guy Laliberté is worth around $1 billion, according to Forbes.

Aldo Bensadoun was born in Morocco and grew up mainly in France. He came to Canada to study and worked in a shoe store. In 1972, he opened a shoe stand in Montreal’s Le Château store and had a huge bestseller with an Italian clog. In 1978 he opened the first freestanding ALDO store. These days his company has more than 3,000 stores worldwide and, reports Forbes, Bensadoun is worth $1 billion.

Born in Romania in 1920 as Marcel Abramovich, Marcel Adams was the son of a tanner. From 1941 to 1944, he was forced to work in Nazi labour camps. He managed to escape and flee to Turkey and then Israel before coming to Canada in 1951. Here he worked in a tannery but in 1955 he started investing in real estate. He opened his first mall four years later and these days he has a net worth of $1.7 billion, according to Forbes.

For the first few years of his life, Stewart Butterfield lived in a log cabin that didn’t even have running water. Growing up, he taught himself to code and during his university years, he designed websites for extra money. He was 27 when he and a friend built a startup and after it was sold, he became a freelance web designer.

Two years later, he started Ludicorp, the company originally behind photo-sharing site Flickr, with his wife and a friend. These days he’s CEO of another company he co-founded, Slack, and according to Money he has a net worth of as much as $2.1 billion.

Jean Coutu didn’t come from a dirt-poor background, since his father was a pediatrician. However, his riches didn’t come from a big inheritance either. He trained as a pharmacist and opened his first pharmacy in Montreal in 1969. He and his associate gave customers what they didn’t know they wanted: discount prices, longer business hours and professional service. By 1973 there were five branches in Montreal and the group started franchising.

Today Jean Coutu is worth an estimated $2.3 billion, according to Forbes, and is the patriarch of one of Canada’s richest families.

Lululemon may be one of those companies you didn’t realize were Canadian. It was the brainchild of Chip Wilson, who was born in California but later moved to Canada. Wilson founded his first clothing company in 1979, a year before he graduated from university with a degree in Economics. This company catered for the surfing, snowboarding and skating markets.

He sold it in 1997 and founded Lululemon Athletica in 1998. While he isn’t active in the company’s management anymore, he’s still the biggest individual shareholder and has a net worth of $3.5 billion, according to Forbes.

Alain Bouchard’s family lived in a mobile home after his father’s business went bankrupt. When Bouchard was 19, he started working as a stock boy in his brother’s milk store. He went on to work for a grocer and in 1980 he founded his own convenience store, Alimentation Couche-Tard. These days the business has expanded to some 15,000 stores all over the world. Forbes estimates Bouchard’s net worth at $3.6 billion.

Sales representatives can have one of the highest-paying in-demand jobs in Canada. For Jim Pattison, his sales skills made him a billionaire. He used to work a variety of menial jobs, one of which was washing cars at a gas station that had a small used-car lot. When the regular salesman was away one day, Pattison sold one of the cars. He then moved on to a part-time job at a larger lot in Vancouver.

In 1961 he sold his house and got some loans to open his own car dealership. Today the Jim Pattison Group owns a variety of companies and Pattison has a net worth of $5.7 billion, according to Forbes.