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How Did Kevin O’Leary Get Rich?


Sometimes known as “Mr. Wonderful”, Kevin O’Leary is a venture capitalist, entrepreneur, and politician. He is best known for being one of the investors on ABC’s Emmy Winning business reality show, Shark Tank. The show features entrepreneurs making a pitch to a panel of five investors or “sharks,” who decide whether to invest in their company.

On the show, he is often direct and abrasive with entrepreneurs who enter the shark tank looking for investment. Fans of the show are often divided on O’Leary because of his direct approach. But like him or not, it is clear that O’Leary understands business and money. 

If you’ve ever wondered how “Mr. Wonderful” was able to build an empire worth over $400 million, this article will explain exactly how Kevin O’Leary got rich. 


O’Leary’s Upbringing and Background

Kevin O’Leary was born on 9 July 1954, in Montreal, Quebec, Canada. O’Leary’s mother, Georgette, was a small-business owner and investor of Lebanese descent, and his father, Terry, was a salesman of Irish descent. 

O’Leary may have gotten his love of investing from his month. Georgette practiced the habit of investing a third of her weekly pay into dividend-paying stocks and bonds. This was very similar to Kevin O’Leary’s current strategy as O’Leary has famously stated that he doesn’t invest in public companies that do not pay a dividend.

After receiving a bachelor’s degree in environmental studies and psychology from the University of Waterloo in 1977, O’Leary went on to acquire an MBA in entrepreneurship from the Ivey Business School at the University of Western Ontario in 1980.


How did Kevin O’Leary Make His Money?

Many people who watch Shark Tank are unaware that O’Leary started out as a film maker in college. His first business was an independent production company called Special Event Television (SET). He co-founded the business with two former MBA classmates. The company produced minor television shows, sports programming, and commercials. 

Photo credit: Kevin O’Leary-Youtube

SET was a minor success but O’Leary sold his shares to one of his partners for $25,000. With his time as a producer behind him for the time being, O’Leary had the time to focus on this next business which would prove to be his opportunity to make a fortune.


With a $10,000 investment from his mother, O’Leary launched SoftKey Software Products. SoftKey specialized in distributing software on CD-ROM. Throughout the 90’s the company acquired most of its competitors including a company called The Learning Company (TLC) for $606 million. SoftKey adopted TLC’s name after the acquisition.

After 1999 is when O’Leary made the majority of his money. In 1999, he sold TLC to Mattel for $4.2 billion. Soon after, he became a co-investor in a company named StorageNow Holdings, a storage company in Canada. Mr. Wonderful was able to pocket $4.5 million when SotorageNow Holdings was sold for $110 million.


How He Continues to Make His Money

Biggest Shark Tank Successes

Wicked Good Cupcakes

One of O’Leary’s most successful investments on Shark Tank. Wicked Good Cupcakes pastry company based out of Boston. The mother-daughter team of Tracey Noonan and Danielle Vilagie was able to land a royalty deal with O’Leary for $75,000. 

The deal stated that for every unit sold, O’Leary would get $1 until the investment was returned. From there, his royalty would drop to $.50/ unit. It only took 75 days for him to get his money back.

Before making a deal with O’Leary, Wicked Good Cupcakes was bringing in about $350,000 in sales. Those numbers quickly rose to over $8 million annually. Although he did not gain any equity from the deal, Mr. Wonderful has often called the deal one of the best he’s ever made.



During Season 5 Brian and Julie Whiteman pitched their business called GrooveBook to the investors on Shark Tank. Groovebook is an app and service which lets you print photo books from your cell phone and then ships them to you monthly. The couple was able to make an 80% licensing deal with Mark Cuban and Kevin O’Leary for $150,000.

After appearing on the show, Groovebook’s paid subscriptions increased from 8,000 subscribers to 500,000. In 2014, the company was acquired by Shutterfly for $14.5 million.



Bottle Breacher


O’Leary also invested in the husband-and-wife entrepreneurial team of Eli and Jen Crane. Their company is named Bottle Breacher. Bottle Breacher makes unique 50-caliber bottle openers, made from recycled bullets. 

The investment would cost the Cranes 20% of their company but it seems like it was worth it as they were flooded with more than 20,000 orders after the show aired and brought in $2.5 million in 3 months.

You can check out all of Kevin O’Leary’s Shark Tank investments here.


Wines, Money Management, and other Investments

Although all of the sharks on the show are investors, Kevin O’Leary often boasts that he is the only professional venture capitalist. He founded O’Leary Ventures which is a private early-stage venture capital investment company. He is also the owner of O’Leary Fine Wines. The company is marketed as a premium wine brand at an affordable price. 




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A post shared by Shop Mr. Wonderful (@shopmrwonderful)


In 2015, O’Leary launched an ETF through O’Shares Investments. O’Shares Investments provides ETFs for long-term wealth management, with an emphasis on quality. The O’Shares ETFs are designed for investors with objectives ranging from wealth preservation and income to growth and capital appreciation.

The ETF is a division of his investment fund, O’Leary Funds Management LP, where O’Leary serves as chairman. O’Leary has also ventured into gold investing, with five percent of his financial portfolio invested in physical gold. 

He has also been a big supporter of cryptocurrency investing. O’Leary owns coins in the cryptocurrencies Ether, Polygon, SOL, and Bitcoin.

Thomas Martin
Tom is a member of the Editorial Team at StartUp Mindset. He has over 6 years of experience with writing on business, entrepreneurship, and other topics. He mainly focuses on online businesses, digital publishing, marketing and eCommerce startups.

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Tom is a member of the Editorial Team at StartUp Mindset. He has over 6 years of experience with writing on business, entrepreneurship, and other topics. He mainly focuses on online businesses, digital publishing, marketing and eCommerce startups.

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