How Did Kevin O’Leary Make His Money?

Terence Thomas Kevin O’Leary is one of the most well-known investors to come out of Canada. He’s a prolific media personality whose face is all over financial news. He’s also a 66-year-old man with a burgeoning YouTube channel.

Known as Mr. Wonderful, you can find O’Leary playing the heel in both the Canadian and U.S. versions of Shark Tank (known as Dragon’s Den in Canada).

So, how did Kevin O’Leary make his money?

His investment style is familiar to anyone who watches the show. O’Leary loves making licensing deals, and he has a team of lawyers that can enforce any patents or other legal contracts.

O’Leary is a wine connoisseur, author, and mutual fund manager. He’s also brash and resembles The Simpsons character Montgomery Burns in his perspective on money. Having been both rich and poor, he’ll tell you being rich is better.

How did O’Leary got so filthy rich?

How Kevin O’Leary Got Started

O’Leary was born and raised in Canada, and his father died when he was only 7 years old. He originally wanted to be a photographer but followed his parents’ lead to become a businessmen and investor. His first notable job was as the assistant brand manager for Nabisco’s cat food brand in Toronto.

After a short stint as a television producer, he started Softkey. The company filled retail shelves with mostly shareware compilations but made enough money to acquire The Learning Company for $606 million in 1995 and took its name.

TLC also spent $416 million on rival Broderbund before being acquired itself by Mattel for $4.2 billion in 1999. This acquisition lost Mattel $3 billion in shareholder value within a single day, prompting a class-action lawsuit that was settled for $122 million in 2003.

This would be considered the biggest business blunder from the Shark Tank cast if not for Yahoo!’s disastrous $5.7 billion acquisition of Mark Cuban’s Broadcast.com. Of course, both men profited through billion-dollar exits from what turned out to be failed tech companies during the height of the dotcom bubble.

How Did Kevin O’Leary Make His Money?

O’Leary’s fortune isn’t as easy to pin down as it is for many other notable wealthy people. This is because he’s an investing wizard who made money from a variety of sources. Although he sold TLC to Mattel for $4.2 billion, he only reportedly netted about $11.2 million from the deal.

The company was buried in over $1 billion of accumulated debt by the time Mattel took over.

When he left, he invested $500,000 of his payout in StorageNow Holdings, which he later sold for over $4.5 million. From there, he joined Genstar Capital and created O’Leary Funds. He grew the fund from $400 million in assets under management in 2011 to over $4 billion by 2020.

He has stakes in a variety of businesses, many of these deals done through the Canadian and American TV shows. He’s a paid media personality, something he really enjoys, and his YouTube channel has over 300k subscribers and 17 million views. All of this generates revenue.

Altogether, Kevin O’Leary’s net worth is estimated at $400 million in 2020.

Is Kevin O’Leary a Billionaire?

Unlike Cuban, Kevin O’Leary is not a billionaire. He does manage billions of dollars of assets through his funds, and he did create and sell a billion-dollar company to Mattel though.

His net worth of $400 million makes him the second-richest shark beneath Cuban. He’s also the second wealthiest dragon on Canada’s version of the show, behind only Boston Pizza franchising guru Jim Treliving.

It’s important to note O’Leary isn’t himself a billionaire, because he often makes the distinction on TV. When competing with offers from other sharks, he loves to point out that he’s the only one (so long as Cuban isn’t on the show) who made a billion-dollar exit from his company. He fails to mention he’s still only a millionaire.

Perhaps O’Leary could use a bottle of Tres Comas tequila.

How Is Kevin O’Leary So Rich?

Although not a billionaire, O’Leary is undeniably wealthy. He made some of this money by building his billion-dollar software company, and he grew it from there. His mom taught him to invest a third of his earnings, and he had a lot of high-earning jobs.

Inevitably, his investment skills made him rich.

While he often owns equity, he’s known for pushing licensing deals. He loves making deals that put residual cash in his pocket, and he’s a known number cruncher. He learned his investment skills and financial discipline from his mom and his business savvy from his dad.

By diversifying his portfolio, he remains safe from most market events. He’s also a marketing powerhouse who uses his media reach to promote his portfolio of companies.

What Companies Does Kevin O’Leary Own?

O’Leary’s goal is to spend money to make money. He prefers residual earnings and wants licensing or high-interest loans over equity deals. As he discusses on his shows, he doesn’t want to work – he wants his money to work for him.

On Shark Tank alone, he invested $8.54 million in 40 deals. His show portfolio includes companies like Zipz, Honeyfund, Lovepop, First Defense Nasal Screen, and Total Merchant Resources.

He also invested in MacKenzie and Marr Guitars, Dig it Gloves, Last Call, and Vineland Estate Wines through Dragons Den.

O’Leary started O’Leary Ventures to manage his diverse portfolio of startups. He also owns O’Leary Funds, which manages wealth for others. And he launched an ETF through O’Shares Investments.

These investments keep money in O’Leary’s pocket, along with the inheritance he received from his parents after their deaths.

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The author has no position in any of the stocks mentioned. Financhill has a disclosure policy. This post may contain affiliate links or links from our sponsors.