Kevin O’Leary: Net Worth, Wine, Watches and House

by / ⠀Blog / July 1, 2022
kevin o'leary

Early Life

Kevin O”Leary was born Terence Thomas Kevin O’Leary on July 9th 1954 in Montreal, Quebec, Canada. His parents were a small-business owner, investor, and salesman. His parents divorced when he was a child and his father would later pass away when he was seven-years-old. O’Leary’s mother would then run the business as the executive and would later marry George Kanawaty, an economist. Kanawaty also worked for the UN’s labor division, causing the family to move around the world frequently to places such as Cambodia, Cyprus, and Tunisia. However, O’Leary would go to both Stanstead College and St. George’s School in Quebec. Although he wanted to be a photographer, he instead went to university for business and investment. In 1980, he received his MBA in entrepreneurship from Ivey Business School at the University of Western Ontario on the suggestion of his stepfather.

Much of his investment skills and lessons came from his mother who operated a secret investment portfolio. He didn’t know about her investment portfolio until after she had passed away.

New Beginnings

During his MBA program years, O’Leary had an internship for Nabisco in Toronto and was the assistant brand manager for the cat food brand that they had. Afterward, O’Leary had many business ventures. In fact, he was briefly a television producer and then started a software company called Softkey. However, the day before the signing of documents, a major donor dropped out, forcing O’Leary to find alternative backing in the form of selling his SET share and convincing his mother for a lend of ten thousand in seed capital. Softkey would later buy The Learning Company in 1995 and would change its name to TLC and move its HQ to Cambridge. Massachusetts. Then in 1999, Mattel acquired TLC. O’Leary left when sales began to go down.

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O’Leary moved on to forming other ventures such as O’Leary Funds and O’Leary Ventures. He would also get into cryptocurrencies and wrote several books. However, he is perhaps best known for being on the reality television series of Dragons’ Den in 2006 and Shark Tank in 2009. Dragons’ Den was one of the most successful shows in Canadian television history with nearly two million views an episode. Much of this is credited by O’Leary’s blunt and rude persona that he became known for.

As for Shark Tank, he joined the show when it started, however, he left in 2014. Because of his television appearance, he was nicknamed “Mr. Wonderful”, something that he is often referred to he claims. Besides his attitude on the show, he also became known for preferring deals where he loaned money in exchange for royalty payment rather than taking a share of the company.


In 2017, he even had his attempt to run for the Conservative leadership race. He was often compared to the then-President Donald Trump as they were both wealthy business men who were both on reality television shows about business. However, O’Leary dropped out in April of the same year when he realized that he did not have enough support in Quebec and it would lose him the race.

Watch Collector

Kevin O’Leary is worth around $400 million as of 2o21. An avid watch collector, he owns many luxury watches such as Patek Philippe Nautilus 5711 worth thirty thousand dollars at the time. He also has a Rolex Daytona in steel, along with the ultra-rare gem-encrusted rainbow version. In fact, when he buys watches, he likes to buy two of them to show his commitment to the brand that he is not a time waster.

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Wine Head

He is also a huge wine lover and after several business experiments, he created the Shop Mr. Wonderful website and partnered with the Vintage Wine Estates. Vintage Wine Estates has become one of the largest wine producers in the United States with over 2 million cases sold annually. His website sells wine at a much more affordable price He learned a lot about wine from his stepfather when they moved all over the world and became very knowledgable about wine. He then began collecting and trading wine and has five cellars across the planet.

Kevin’s Home (Alone)

Kevin O’Leary’s main home is located in Toronto, Canada. However, he has additional properties in Boston, Massachusetts, Geneva, Switzerland, and Muskoka, Ontario. He also has a lake home on Lake Joseph, Ontario that has over three thousand square feet and comes with its own boat house, boat garage, and dock. O’Leary spends most of his time between his residence in Toronto and in Boston. In fact, he has lived in Boston for over 20 years and working there as well. They had moved in the 1990s. He also has a property down in Florida where it offers a nice ocean view.

Kevin O’Leary married his wife Linda in 1990. She is the VP of Marketing for O’Leary Wines. They have two children, a son and daughter in their 20s.

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About The Author

Tristan Anderson

Hello! My name is Tristan Anderson and I live in Manhattan, Kansas. I enjoy being in nature and animals. I am also a huge geek who loves Star Wars and has a growing collection.