Kevin O’Leary: net worth, wine, watch and home

kevin o'leary

early years

Kevin O’Leary Terence Thomas Kevin O’Leary was born on July 9, 1954 in Montreal, Quebec, Canada. His parents were a small business owner, investor and salesperson. His parents divorced when he was a child and his father later passed away when he was seven years old. O’Leary’s mother then ran the business as a chief executive and later married George Kanawati, an economist. Kanawati also worked for the UN Labor Department, which caused the family to move frequently around the world to places such as Cambodia, Cyprus and Tunisia. However, O’Leary attended both Stansted College and St. George’s School in Quebec. Although he wanted to become a photographer, he went to university for business and investment instead. In 1980, he received an MBA from the Ivy School of Business at the University of Western Ontario at the suggestion of his stepfather.

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

New beginnings

During his MBA program, O’Leary interned at Nabisco in Toronto and was an assistant brand manager for a cat food brand they had. Thereafter, O’Leary had many business ventures. He was actually a TV producer for a while and then founded a software development company called Softkey. However, the day before the paperwork was signed, a major donor dropped out, forcing O’Leary to seek alternative support in the form of selling his stake in SET and convincing his mother to lend ten thousand seed capital. Softkey later bought The Learning Company in 1995, changed its name to TLC, and moved its headquarters to Cambridge. Massachusetts. Then in 1999, Mattel acquired TLC. O’Leary left as sales began to fall.

O’Leary moved on to start other ventures such as O’Leary Funds and O’Leary Ventures. He has also ventured into cryptocurrencies and has written several books. However, he is perhaps best known for appearing on the reality shows 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 episode views. This is largely due to O’Leary’s blunt and rough personality, for which he became known.

As for Shark Tank, he joined the show when it started but left in 2014. Wonderful,” he says, to which he is often mentioned. In addition to his attitude towards the show, he also became known for preferring deals in which he borrowed money in exchange for paying royalties, rather than acquiring a stake in a company.


In 2017, he even had a bid for the conservative leadership race. He was often compared to then President Donald Trump as they were both wealthy businessmen who were both on business reality shows. However, O’Leary dropped out of the race in April of that year when he realized that he lacked support in Quebec and that would lose him the race.

watch collector

Kevin O’Leary is worth about $400 million as of 2021. An avid watch collector, he owns many luxury watches such as the Patek Philippe Nautilus 5711 worth thirty thousand dollars at the time. He also has a Rolex Daytona steel watch, as well as an ultra-rare gem-encrusted rainbow version. In fact, when he buys a watch, he likes to buy two of them to show his commitment to the brand and that he doesn’t waste time.

wine head

He is also a big wine lover and after several business experiments created the website Shop Mr. Wonderful and partnered with Vintage Wine Estates. Vintage Wine Estates has become one of the largest wine producers in the United States, selling over 2 million cases of wine annually. His website sells wine at a much more affordable price. He learned a lot about wine from his stepfather as they traveled all over the world and became very knowledgeable about wine. He then began to collect and sell wine and has five cellars all over the planet.

Kevin’s house (one)

Kevin O’Leary’s main home is in Toronto, Canada. However, he has additional properties in Boston, Massachusetts, Geneva, Switzerland, and Muskoka, Ontario. He also has a lake house on Lake Joseph, Ontario, over three thousand square feet, with its own boathouse, boat garage and dock. O’Leary spends most of his time between his residence in Toronto and Boston. In fact, he has lived in Boston for over 20 years and works there. They moved in the 1990s. He also has real estate in Florida that offers great ocean views.

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

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