Key Points About This Article:
- Kevin O’Leary is among the most outspoken multi-millionaire investors in the market, who has used his celebrity status to promote certain ideals.
- Here are the three investments O’Leary made to get to where he is, and a deeper dive into his back story.
- If you’re looking for some stocks with huge potential, make sure to grab a free copy of our brand-new “The Next NVIDIA” report. It features a software stock we’re confident has 10X potential.
Kevin O’Leary was born Terrence Thomas Kevin O’Leary on July 9, 1954, and has become among the most prominent businessmen many investors follow. A TV personality known for his roles on prominent television shows such as Dragons’ Den and Shark Tank have prompted his nickname as “Mr. Wonderful,” a sarcastic moniker given O’Leary’s frequent crass takes on business ideas.
O’Leary’s entrepreneurial journey began with the founding of SoftKey Software Products in 1986. The company specialized in educational software and became a major player in the industry through aggressive acquisitions. Notably, O’Leary sold SoftKey to Mattel (NASDAQ:MAT | MAT Price Prediction) in 1999 for approximately $3.8 billion, making him a multi-millionaire. This move has allowed O’Leary to venture into a number of new spaces, many of which have garnered the investor much more attention among the broader finance community.
With a current net worth of around $400 million, O’Leary isn’t a billionaire yet. But his investing and communication style are certainly intriguing, so let’s dive into the story of how he got to where he is, and where he thinks the market could be headed from here.
This post was updated on October 21, 2025 to clarify details of the sale of Softkey to Mattel and O’Leary Funds AUM growth.
SoftKey
As mentioned, O’Leary’s founding of SoftKey Software is really the starting point to this iconic investor’s origin story. Founded in 1986 as SoftKey Software Products Inc. in Toronto, Ontario alongside John Freeman, this company’s extensive product range in the software space, alongside a number of relatively new innovative products at that time, garnered significant interest among other players in the market.
This interest ultimately led to a 1993 merger with WordStar International and Spinnaker Software to form SoftKey International. This move significantly increased the company’s market presence and established a much larger company from which SoftKey could continue to acquire software applications from developers. Furthering the company’s diverse array of software products without the high costs typically associated with internal development helped SoftKey ride the tech wave in the 1990’s to a significant valuation. O’Leary sold The Learning Company (formerly SoftKey) to Mattel in 1999 for about $3.8 billion in stock. The deal made O’Leary wealthy, with his personal payout in the tens of millions.
Given that SoftKey began with a modest investment of $10,000 from O’Leary and Freeman, this company is among the most impressive success stories in the tech sector at that time and indicates how well many tech personalities did during the run-up to the dot-com crash. The company’s innovative model led many larger competitors to pull from its playbook, which included effective merchandizing techniques and eye-catching graphics to sell its various products.
StorageNow
StorageNow Holdings is a Canadian company that specializes in the development and management of climate-controlled storage facilities. Founded by Reza Satchu and Sanjil Shah, the company has become the leading self-storage provider in Canada. With more than 6,300 units spanning multiple cities, this major investment from O’Leary has certainly signaled his bullishness in the North American consumer, and a bet that consumers will continue to store the goods they don’t need outside their homes.
The temperature-controlled storage market is one that has grown considerably in recent years, as consumers and businesses require ever-increasing space. And with significant pricing power in most markets, this model has worked particularly well in Canada, which is a market that hasn’t had the same kind of building activity as in other markets such as the U.S.
In March 2007, StorageNow Holdings was acquired by InStorage REIT for approximately $110 million, marking a significant milestone in its operational history. The acquisition allowed InStorage to expand its footprint in the Canadian self-storage market, leveraging StorageNow’s established brand and infrastructure. Moreover, this deal allowed O’Leary to rake in more than $4.5 million from the sale of his shares. This marks another big win for O’Leary in his portfolio, though it would be considered a small win for many other wealthier CEOs (everything is relative).
O’Leary became a co-investor and corporate director in 2003, investing approximately $500,000 for nearly 13% of the company. So, the ROI on this investment in this combined entity could still generate much greater returns over the long run, if his bet on the self-storage space works out.
O’Leary Funds
O’Leary Funds is a mutual fund management company co-founded by Kevin O’Leary in 2008. The idea behind this mutual fund business is to focus on global yield investing, a model which has trailed growth investing mandates by a rather wide margin. However, the inception of many of his funds following the 2008 financial crisis has led to rather impressive returns over time and led many initial investors to stick with his funds over time.
Notably, by 2012, O’Leary Funds managed over $1 billion CAD in assets before being sold to Canoe Financial in 2015. O’Leary serves as the chairman and lead investor of the firm.
O’Leary Funds specializes in various types of investments, primarily focusing on income generation and capital appreciation. The fund categories include Canadian Equity Income Funds, Canadian Balanced Income Funds, Canadian Fixed Income Funds, and more. These funds invest in corporate bonds and dividend-paying equities, adhering to a value-yield investing philosophy. The firm emphasizes diversification across its portfolios to cater to different investor needs while maintaining a focus on income and capital preservation.
As for Kevin O’Leary’s personal investment in O’Leary Funds, specific figures regarding the exact amount he has invested are not publicly disclosed. However, it is clear that he has a significant stake in this endeavor as its lead investor, with O’Leary Funds currently making up a significant chunk of his current $400 million estimated net worth.
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