Kevin O’Leary: Net Worth, Shark Tank, Dragon’s Den, Watch Collection

Kevin O’Leary, in full Terence Thomas Kevin O’Leary, (born July 9, 1954, Montreal, Quebec, Canada), Canadian entrepreneur, financier, and television personality who was perhaps best known as a panelist on custom dallas stars jersey air jordan 1 low flyease custom nfl football jerseys fsu football jersey custom maple leafs jersey air max 270 women penn state jersey air max 270 women custom stitched nfl jersey nike air jordan 1 elevate low custom stitched nfl jersey custom youth hockey jerseys custom nfl football jerseys custom sublimated hockey jerseys asu football jerseythe reality series Dragons’ Den and Shark Tank.

O’Leary co-founded SoftKey Software Products, a technology company that sold software geared toward family education and entertainment. During the late 1980s and 1990s, SoftKey acquired rival companies such as Compton’s New Media, The Learning Company, and Broderbund. Softkey later changed its name to The Learning Company and was acquired by Mattel in 1999, with the sale making O’Leary a multimillionaire. O’Leary was soon fired by Mattel after the acquisition resulted in significant losses and multiple shareholder lawsuits.

Net Worth

Canadian businessman Kevin O’Leary is said to be worth of $400 million thanks to his software company SoftKey International, which he sold to Mattel for a huge sum back in the nineties. He’s the second richest shark on the show, although we’re still not sure how he earned his ‘Mr. Wonderful‘ nickname.

Kevin O’Leary made the biggest deal of his life when he sold The Learning Company to Mattel at the height of the dot-com bubble in 1999 for $4.2 billion. Since then, he’s become a venture capitalist, mutual fund manager, and television personality, currently best known as one of the investors on “Shark Tank.”


O’Leary and his wife, Linda, have been married since 1990. The couple separated in 2011, but resumed their marriage after two years. Linda now serves as the VP of Marketing for O’Leary Wines. They have two children. Trevor is a music producer and DJ while Savannah is a multimedia producer at the Huffington Post. In a 2016 interview, O’Leary stated: “In a successful growing business, it eats your time alive. Then later in life, you can provide for your family things that many others can’t have. But because you sacrificed, you’re then given the reward of freedom.”

O’Leary’s primary residence and tax residency is in Toronto, Ontario. He also maintains a cottage in Muskoka as well as homes in Boston and Geneva, Switzerland

Dragon’s Den

In 2006, O’Leary appeared as one of the five venture capitalists on the then-new show Dragons’ Den on CBC, the Canadian instalment of the international Dragons’ Den format. On the show, O’Leary developed a persona as a blunt, abrasive investor, who at one point told a contestant who started crying, “Money doesn’t care. Your tears don’t add any value.”  Dragons’ Den became one of the most-watched shows in CBC history, with around two million viewers per episode. Coxe attributed the show’s success in large part to O’Leary’s presence.

Shark Tank

In 2009, the American version of Dragons’ DenShark Tank, began, and Shark Tank executive producer Mark Burnett invited two of the CBC Dragons’ Den investors, O’Leary and Robert Herjavec, to appear on the show. Both have remained with Shark Tank since the beginning. For several years, they appeared on both shows, although Herjavec left Dragons’ Den in 2012, and O’Leary left in 2014. Shark Tank became a ratings hit, averaging 9 million viewers per episode at its peak in the 2014–15 season. It has also been a critical favorite, winning the Primetime Emmy Award for Outstanding Structured Reality Program four times. Besides his blunt persona, O’Leary also gained a reputation on both shows for preferring deals in which he loans the entrepreneurs money in exchange for a percentage of future revenue, rather than taking a share of the company.

Watch Collection

For our Mr. Wonderful, even watch collection is a serious business.

For one, he wears all his watches at least once a month. Like a true entrepreneur, he believes watches are meant to be worn instead of being kept in a vault.

O’Leary is also known for making a statement through his watches.

Rolex Cosmograph Daytona Ceramic Bezel:

The Rolex Daytona ref 116500LN was much awaited by watch fans. It combines the classic look of the stainless steel Daytona with the Cerachrom ceramic bezel – making the bezel less prone to scratching and fading.

Kevin owns both the black dial and white dial variants of the 116500LN, but instead of the Oyster bracelet that comes with them, he has swapped it out for his favorite red strap.

Rolex Submariner Steel Yellow Gold Blue Dial

Kevin counts the Rolex Submariner as one of his go-to timepieces. While the Sub was initially developed for diving, many fans like Kevin have taken to wearing it during business or formal functions.

Panerai Luminor 1950 Acciaio

Another favorite of Kevin’s is his Panerai Luminor Acciaio. The eye-catching 47mm watch comes with a cushion shaped case and circular crown guard, and is made even more striking when paired with his signature red strap.

This watch is outfitted with Panerai’s signature “sandwich” dial, where a luminescent background is sandwiched between the dial’s surface and the movement.

He massive list continues with watches like: Cartier Roadster, Jaeger LeCoultre Reverso and more. You can watch this video to see it more:


The Chairman of O’Shares Investments has a preference for investing in companies with a high dividend yield and those with a strong financial track record and balance sheet. 


Mr. Wonderful invests most of his money in OG manufacturer of software and hardware, Microsoft. The company, founded in 1975 in Redmond, WA, takes up 4.98% of O’Leary’s entire portfolio and has a dividend yield of 1.1%. 


Apple is one of the most popular companies for investors, so it makes sense that O’Leary also invests 3.09% of his portfolio in the tech giant. The largest company in the world by market cap, Apple has a dividend yield of 0.6% and in its most recent quarter, it generated a revenue of $64.7 billion

Johnson and Johnson

Next up is Johnson & Johnson, which O’Leary invests 4.84% of his portfolio in. The healthcare giant has a market cap of nearly $400 billion and is one of the most well-known dividend stocks out there, with a yield of 2.7%.

His other investments are mostly up to date as in the following companies: Pfizer Inc. , Verizon Communication and Home depot and many more.

Bitcoin : Kevin O’Leary, businessman and star of the popular reality show Shark Tank, has done a 180 on Bitcoin. He had harsh words for the cryptocurrency in 2019, when he called it “garbage” and said that it was a “useless currency.” Even earlier this year, he was critical of Bitcoin’s lack of usability and the challenge of buying it.


Following Stephen Harper’s resignation as leader of the Conservative Party of Canada, O’Leary attended Conservative party gatherings in February and May 2016, leading to public speculation about whether he would run for 2017 leadership election

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