Rich Dudes│Kevin O’Leary's $400M Net Worth, the 2nd Richest on Shark Tank

Terence Thomas Kevin O'Leary, also known as Mr. Wonderful, is a Canadian businessman, investor, and television personality with an estimated net worth of $400 million. Kevin O’Leary might be best known as the bluntest cast member of ABC’s Shark Tank and CBC’s Dragon’s Den, but he’s as much of a serial entrepreneur and investor off camera as he is on TV.

So how did Kevin O’Leary turn tens of millions of dollars into a nearly-half-billion-dollar net worth? Below we break down his multi-million dollar investment portfolio, his biggest wins (and losses), as well as the core principles that Mr. Wonderful has used to build his wealth over decades.

Kevin O'Leary net worth at a glance:

Kevin O’Leary was born in Montreal, Quebec in 1954 by the name Terence Thomas Kevin O’Leary. His mother, Georgette, was a huge inspiration in his business life and investing strategy.

Georgette would often set aside 20% of her paycheck into a portfolio of large-cap stocks and Telco bonds, something that O’Leary later did in his own investment portfolio.  Her other smart money moves include keeping a secret bank account from both her husbands and buying classic Chanel jackets that are worth considerably more today.

Kevin O’Leary education

Before college, Kevin O’Leary aspired to become a photographer and rockstar.

But O’Leary ultimately heeded his stepfather’s advice and attended university—receiving his Bachelor's in environmental studies and psychology from the University of Waterloo in 1977 and an MBA from the Ivey Business School at the University of Western Ontario in 1980.

Kevin O’Leary & The Learning Company 

Kevin O’Leary became an entrepreneur in 1986 by co-founding the educational software company SoftKey, which later became The Learning Company. Much of Kevin O’Leary’s early personal wealth was made by selling the company to toymaker Mattel in 1999 for $4.2 billion (and pocketing $11.2 million). 

Some of his other career highlights include:

• Investing in StorageNow, a self-storage company that was later sold for $110 million.
• Having a stake in Vintage Wine Estates—a top U.S. wine producer that sells over 2 million cases of wine annually.
• Investing $8.5 million across 40 Shark Tank deals. 
• Founding O’Shares Investments, a mutual fund with $1.5 billion in assets under management as of 2022.

Kevin O’Leary is primarily known for being a venture capitalist on ABC's Shark Tank, but he actually invests in a variety of assets beyond startups. While we don’t know the exact composition of his $400 million dollar portfolio, we can break down much of his wealth based on the information he's shared.

Mr. Wonderful is known for his strong belief in diversification. He invests no more than 5% in one name and no more than 20% in one sector. That’s a principle he says he applies to all assets, whether that’s stocks, crypto, gold, or collectibles. No wonder the bulk of Kevin O’Leary’s investment portfolio is in diversified ETFs.

The Shark Tank investor has naturally invested in numerous startups, plus holds about 20% of his portfolio in crypto and 5% in gold.

We also know that he’s invested $8.5 million in Shark Tank deals and is an investor in other companies like StartEngine, O’Shares Investments, and Vintage Wine Estates—which also produces his wine label, O’Leary Wines.

Finally, he has several investments in collectibles like watches, guitars, cameras, and even NFTs, although he isn’t as upfront about these collections as he is about the rest of his investment portfolio.

1. Kevin O'Leary stock portfolio

Kevin O’Leary is the chairman of O’Shares Investments (originally called O'Leary Funds), which focuses on balanced investments that are designed to preserve and grow wealth. If we go by the companies in O’Leary’s O’Shares U.S. Quality Dividend Index (OUSAX), we can get a sense of the types of companies that O’Leary might hold in his own portfolio.

With over 100 companies in the index, it certainly fits Kevin O’Leary’s first investing principle—diversification. If you look at the top 7 holdings, you’ll see that they're all under 5% (except Home Depot, which is just above 5%). That fits with O’Leary’s belief that you should never invest more than 5% in any one company or name.

O’Shares also has two other indexes—O’Shares Global Internet Giants Index (OUSMX) and O’Share U.S. Small-Cap Quality Dividend Index (OGIGX). If we assume that Kevin O’Leary holds 20% in each index, then that means he holds 60% of his investment portfolio in stocks (though this isn't necessarily true of his personal stock portfolio).

2. Kevin O'Leary crypto holdings

Mr. Wonderful wasn’t always a fan of crypto, but over the years he has grown to become one of its biggest advocates—slowly increasing his crypto portfolio to 32 positions and 20% of his net worth. We can also assume that Kevin O’Leary holds a max position of 3-5% for each crypto.

While we don’t know every coin he holds, or if he’s sold any positions recently, he has confirmed owning the following cryptos:

3. Kevin O'Leary watch & guitar collection

Besides his investments in stocks, crypto, and startups, Kevin O’Leary is an avid collector of luxury watches and other collectibles like classic guitars and vintage cameras.

While he views his collectibles as investments, he’s also clearly very passionate about each individual item. Unfortunately, he doesn’t go into much detail about how many watches or guitars he currently owns after an incident where he was stolen from by an insider.

Though we can’t say what percentage of Kevin O’Leary’s net worth is in collectibles, we can assume it makes up no more than 20% of his investment portfolio (likely much less). In addition to owning several guitars, Kevin O’Leary owns high-end watches by brands like Rolex, F.P Journe, and Omega.

Since 2008, OUSAX, OUSMX and OGIGX have returned 325.7%, 356.46%, and 815.9% respectively. Meanwhile, Kevin O’Leary has likely lost money from his crypto holdings as Bitcoin and ETH are down over 70% in the past year. Not to mention, cryptocurrency exchange FTX—which O’Leary had a stake in—recently filed for bankruptcy.

However, since Kevin O’Leary keeps his investment portfolio diversified, these losses have potentially been offset by his other investments in stocks and collectibles.

A standard 60/40 portfolio consisting of stocks and bonds would have returned -15.70% as of November 2022. And while adding in alternative assets like fine wine and Bitcoin would not have been enough to deliver a positive return in 2022, this Kevin O’Leary-inspired portfolio has historically generated almost double the ROI of a 60/40 portfolio over a 5 years time horizon.

Kevin O’Leary credits his business intuition to his mother, who encouraged his interest in money at a young age. Here are the top investing principles guiding The Shark with the Sharpest Teeth:

1. Diversify your portfolio 

If there’s one lesson Kevin O’Leary often repeats, it’s to diversify. Diversification is key to the businessman’s investment portfolio. And not just with how he invests in stocks, either. O’Leary applies the same principles across all his portfolios, whether they are traditional, like stocks and real estate, or alternative assets like collectibles.

One of the toughest collectibles to break into is luxury watches. Prices for brands like Rolex and AP have soared in recent years, making them virtually unattainable for small investors without breaking the bank. For instance, the price of an AP Royal Oak A-Series "Jumbo" with a black dial ranged from $25,000 to $60,000 in 2018 but goes for upwards of $120K today.

In December 2018, the investing platform Rally opened its offering of a Royal Oak A-Series at an initial value of $75,000 with a share price of $75. By June 2021, investors enjoyed returns of over 46% when the watch was sold for $110,000. While you can't buy shares in an AP anymore, Rally currently has watches like an Omega Speedmaster Professional Moonwatch and a "Pepsi" Rolex GMT Master II listed with share prices below $20.

2. Apply the 5-20 rule

Kevin O’Leary has a strict rule of investing no more than 5% in one position and never more than 20% in one sector. That’s why he has capped his crypto investments at 20% and only invests 5% of his wealth in gold. However, it's hard to follow this rule with real estate, considering how a nice house costs an arm and a leg to most investors.

The best way to get around that is with fractional real estate platforms like Arrived Homes and Elevate Money. These platforms let you gain exposure to residential or commercial real estate with a starting investment of just $100. That means you can choose how much to invest and sit back and relax as your portfolio enjoys passive income galore.

3. Take calculated risks

Although Kevin O’Leary invests most of his money in indexes, he also doesn't shy away from riskier investments. But he makes sure they're calculated risks, meaning he does his research and never invests more than he can handle losing.

It’s not uncommon for him to start with a small sum and slowly increase his holdings as he sees how it performs, which is how he approached investing in crypto. Investing in Web3 can be tricky—not only is crypto super complicated, but you also take on a lot of risks by investing in an industry with such a short track record. That's why it might be safer to invest in companies that have already proven themselves valuable.

For instance, Epic Games has been around for over a decade and has hypnotized Gen Z worldwide with their hit game Fortnite Battle Royal. The problem is that Epic Games isn't publicly traded, so buying stock in them is easier said than done. Luckily, Dizraptor is letting accredited investors buy pre-IPO shares in Epic starting at $1000. This is your chance to beat retail investors to the punch and gain exposure to one of the top companies integrating with web3.

4. Learn from your mistakes

Mr. Wonderful doesn’t get it right every time. Sometimes he makes money, and sometimes he loses money. And sometimes, he just makes mistakes, like his exposure to the now-condemned crypto exchange FTX. But the important thing he says is to learn from mistakes, so you don’t make the same one twice.

You don't have to be a gigabrain investor to make good decisions in crypto. You just have to follow your gut—not the crowd—on what sounds promising. Half the battle is getting in on the action early. When you beat the rush, you get to be the first to make a profit while everyone else is scrambling to work their way into the orderbook.

If you want to trade like a pro, you need a platform that does it all. Kraken is the best place for filling your crypto orders and they have a super easy-to-use app. Plus, you can stake top coins through their platform, so no need to find a crypto validator and practice self custody (although it's highly recommended you do so).

How much does Kevin O’Leary make a year?

Kevin O’Leary makes an estimated $50,000 per episode for Shark Tank. With around 24 episodes per season, that’s roughly $1.2 million per year. O’Leary also makes money through his book deals, businesses, and investments.

Is Kevin from Shark Tank a billionaire?

Kevin O’Leary from Shark Tank is not a billionaire, but a multi-millionaire. 

How much is Kevin O'Leary worth?

Kevin O'Leary is worth an estimated $400 million.

Who is the richest Shark Tank member?

Dallas Mavericks owner Mark Cuban is considered the richest member on Shark Tank, with an estimated net worth of $4.6 billion.

Do they get paid on Shark Tank?

Sharks on Shark Tank get paid an estimated $50,000 per episode. However, any money they invest is their own.