Kevin O’Leary’s Net Worth: The Rise of Mr. Wonderful, From His Software Company to ‘Shark Tank’

Kevin O’Leary is a Canadian businessman, who has been both a dragon and a shark on television. Unsurprisingly, O’Leary has amassed considerable wealth from his business deals and investments over the years. So, what exactly is Kevin O’Leary’s net worth?

Here are the highlights of O’Leary’s life and how the investor and television personality made his millions.

Early Life

Kevin O’Leary was born on July 9, 1954, in Montreal, Quebec, Canada. His mother is of Lebanese descent and his father is of Irish descent. Because of his father’s heritage, O’Leary also holds Irish citizenship and an Irish passport. His parents eventually divorced, with his father passing away shortly afterward.

O’Leary’s mother remarried to economist Gorge Kanawaty, who works with the UN International Labor Organization. Because of his stepfather’s work, O’Leary grew up traveling around the world and lived all over the world, including Cambodia, Tunisia, and Cyprus to name a spots. His mother was a skilled investor, and O’Leary credits her for teaching him what he knows about money, including always saving one-third of his income.

Having initially wanted to pursue photography, O’Leary’s stepfather advised him to attend university instead. From there, he continued to develop an interest in business and investing. O’Leary graduated with a bachelor’s degree from the University of Waterloo in 1977. He earned his MBA at the Ivey Business School at the University of Western Ontario in 1980.

During his MBA studies, O’Leary completed an internship at Nabisco as an assistant brand manager for the company’s cat food brand. The would-be millionaire credits his experience at Nabisco for helping him further develop his skills. After leaving Nabisco, O’Leary had a brief career as a TV producer. He co-founded the independent production company Special Event Television with two former MBA classmates.

O’Leary’s share of their company was eventually bought out by one of his partners for $25,000.

Career

In 1986, following the selling of his share of SET, Kevin O’Leary set up the software company SoftKey in a basement in Toronto with business partners John Freeman and Gary Babcock. After a major financial backer withdrew their $250,000 commitment, O’Leary used his $25,000 SET share and a $10,000 investment loan from his mother to set up the firm. The company was a publisher and distributor of CD-ROM-based computer software for Windows and Mac computers.

SoftKey has developed several educational software products since then, and by 1993, it had become a major player in the educational software market. SoftKey acquired rival companies, including WordStar and Spinnaker Software. Two years later, in 1995, SoftKey also acquired The Learning Company for $606 million and the TLC name. Mattel bought TLC in 1999 for $4.2 billion.

O’Leary left TLC after Mattel experienced a drop in sales and earnings. Both Mattel and O’Leary were sued by Mattel shareholders for misleading investors about the health of TLC. O’Leary disputed all the charges, saying that the drop in sales was due to a technology meltdown and a clash in the management of TLC and Mattel.

In 2003, O’Leary was a co-investor and the director of the company Storage Now, a developer in climate-controlled storage facilities. The company would become Canada’s third-largest owner and operator in storage services, following several development projects and acquisitions. Storage Now had facilities in 11 cities that served major companies like Merck and Pfizer. The company would be acquired in March 2007 for $110 million.

Investments

Kevin O’Leary was previously a vocal skeptic of cryptocurrency until August 2021. At that time, O’Leary announced what was meant to be a “long-term” investment and spokesperson relationship. He took an equity stake and crypto as payment for FTX, which ultimately collapsed in November 2022. O’Leary came under fire for promoting the company that ultimately stole billions of dollars from over a million investors.

O’Leary sought to do some damage control in December 2022. In an appearance on CNBC, he admitted that all of the $15 million in value he received for the partnership went down to zero. Incidentally, when he first announced his investment/partnership, Kevin claimed that it was FTX’s focus on compliance systems that changed his mind about cryptocurrency.

Shark Tank and Dragon’s Den

Kevin O’Leary made his television debut in 2006 when he became one of five venture capitalists for Canada’s version of Dragon’s Den. Three years later, in 2009, O’Leary also joined the famed business reality show Shark Tank. O’Leary remained on both shows until he left Dragon’s Den in 2014.

On both shows, O’Leary developed an on-screen persona of a blunt and bullying investor, which was encouraged by the producers. It was also on both shows that O’Leary gained the nickname “Mr. Wonderful,” not just for his blunt persona but also for his feedback that was helpful to entrepreneurs who appeared. O’Leary has a holding company, Something Wonderful, to manage his investments on the show.

O’Leary’s most notable investments from Shark Tank include Plated and Talbott Teas. Plated was originally fellow shark Mark Cuban’s deal. However, Cuban backed out after due diligence on the investment was done. After running into the Plated founders a year later, O’Leary accepted their offer to come in on the deal. When Plated eventually sold to the grocery chain ALbertson’s for $300 million, O’Leary made $3.5 million on the deal.

Circling back to Talbott Teas, O’Leary initially invested $250,000 for 35% equity. The company was later acquired by Jamba Juice and GrooveBook – which Shutterfly acquired. See the Talbott Teas pitch below.

Other Business Ventures

The millionaire also co-hosted the Discovery Channel’s Discovery Project Earth in 2008. O’Leary also co-hosted a segment on the CBC News Network with journalist Amanda Lang, The Lang and O’Leary Exchange, in 2009.

Additionally, in 2012, O’Leary has also produced and hosted his reality show, Redemption Inc., where he tries to help ex-convicts to start their businesses. The series lasted for only one season on CBC and was comprised of 9 episodes.

O’Leary is also a published author. In September 2011, he published his first book, titled, “Cold Hard Truth: On Business, Money, & Life.” He also released follow-up books in 2012 and 2013.

Personal Life & Politics

Kevin O’Leary has been married to his wife Linda since 1990. They briefly separated in 2011 but have since gotten back together.

Linda serves as the VP of Marketing for O’Leary Wines. They have two children and primarily reside in Toronto but have a cottage in Muskoka, Ontario. O’Leary also has properties in Geneva, Switzerland.

The millionaire also obtained UAE citizenship so he could partner with Emirates on investments.

On January 18, 2017, O’Leary entered the Conservative leadership race after months of speculation in Canada. During his campaign, O’Leary was often compared by the press to then-US President Donald Trump. They cited that both are wealthy businessmen who gained fame through reality television and ran on platforms of tax cuts and lowered regulations.

O’Leary dismissed the comparisons, saying that what sets him apart from Trump was his stance on immigration, noting that he is descended from Irish and Lebanese immigrants. He added that he “wouldn’t exist if Canada had walls.” O’Leary eventually withdrew from the race on April 26, 2017, saying that although he believed he could win, it would be “selfish” of him to continue over a lack of support in Quebec.

Kevin O’Leary’s Net Worth Today

According to Celebrity Net Worth, Kevin O’Leary’s net worth is $400 million. Mr. Wonderful might not have reached billionaire status like fellow shark Mark Cuban, but he’s still considered among the wealthiest.

You can catch Kevin O’Leary on Shark Tank Season 15 on ABC.