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The businessman, entrepreneur, investor, author, and famous television personality of Canadian origin, Mr. Kevin O’Leary, is worth $400 million.
So, how did he become a multimillionaire, and how did he increase his portfolio multifold?
Let us dive deep and understand how he achieved this financial success. What is his psyche behind investing and creating wealth, and what are some of his most fruitful and controversial investments?
| Name | Kevin O’Leary |
| D.O.B. | 9th July 1954 (68 Years old) |
| Place of Birth | Montreal, Quebec, Canada |
| Citizenship | Canada, UAE, Ireland |
| Famous Nicknames |
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| Alma Mater |
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| Famous for |
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| Companies & Funds |
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| Investment Areas | ETFs, Startups, Cryptocurrencies, Gold and Luxury Items |
Terence Thomas Kevin O’Leary is a Canadian investor who came to the limelight when he appeared, in reality shows like Dragons’ Den at CBC and Shark Tank at ABC.
He is known for his straightforward and blunt demeanor in these shows. But, not investing in these startups made him a multi-millionaire. His empire of $400 million was built on strategic investment in multiple domains.
At first, he began by building his company Softkey (renamed The Learning Company) which he sold to Mattel for an astounding $400 billion.
His portfolio is, however, diversified into different areas following his principle of 5-20. He invests in ETFs of various types.
He invests in startups such as Wicked Good Cupcakes which turned from $150,000 to $10 million in sales, Basepaws, Benjilock, and many others.
His portfolio is also diversified into other asset classes like cryptocurrency and gold. His infamous association in promoting FTX has been heavily criticized after the company went bankrupt in 2022.
He also invests a lot of money in luxury collectibles like watches, NFTs, guitars, and cameras.
Kevin also founded the investment company O’Leary Funds, and then in 2014, he launched the O’Leary Financial Group based on his investment values and principles.
He started a wine brand called O’Leary Fine Wines. He also authored an immensely successful book series based on educating people about finance.
Although ups and downs are pretty common in any stock portfolio which even his portofolio witnessed, his portfolio has also seen a return of more than 100% on the investment in five years.
Kevin O’Leary was born into a middle-class immigrant family. Still, Kevin always believed that because of the Irish genes from his father, Terry O’Leary’s side and the family heritage of her Lebanese mother as a merchant, he was always destined to be a businessman.
His mother, Georgette, played an instrumental role in shaping his entrepreneurial spirit and finally becoming a successful entrepreneur. His mother was a small business owner whose sharp business acumen helped him grow his business intuition.
From a very early age, her mother would invest in large-cap stocks and Telco bonds by holding off a portion (about 20%) of her income.
She even created a bank account and kept it secret from everyone else for her investments in Chanel’s luxury jackets, which would sell for exorbitant prices nowadays.
All these tactics and strategies helped Kevin build his core investment philosophy, and he would inculcate these learnings in all his future ventures. He even formed the idea of saving one-third of his money from his mother to gain financial stability.
From his teenage years, Kevin always tried to learn from what was happening around him. An event at a local ice cream shop would change his life forever.
When his boss asked him to do something he was not expecting while working at a local ice cream shop, he refused and, as a result, was fired, and that is when Kevin realized he wanted to become an entrepreneur.
Kevin O’Leary always wanted to pursue photography and become a professional photographer. He even thought of becoming a rock star.
However, his stepfather George Kanawaty stepped in and suggested he pursue and complete his higher education. Following his suggestion, Kevin went to the University of Waterloo.
There he completed his bachelor’s in environmental studies and psychology and received an honors degree in 1977. During his university days, he developed a keen interest in finance and investing.
He then continued his studies and got an MBA i.e., Masters in Business Administration from Ivey Business School at the University of West Ontario in 1980. His area of specialization was Entrepreneurship.
From the beginning of his career, Kevin has always sought opportunities to learn and apply those in his life to succeed.
Kevin was actively seeking an internship during his MBA days and he found one at Nabisco. He was working in the branding department of the company’s cat food brand as an assistant brand manager.
Kevin attributes much of his early skill development as an entrepreneur to this job, which helped him later in his career.
After his stint at Nabisco, he followed the path of becoming a television producer. He even co-founded an independent television production company with his classmates from MBA college called Special Event Television (SET). However, O’Leary eventually sold his shares for $25,000 to one of his co-founders.
After he left SET, Kevin understood the growing technology market, and following the trend, he decided to launch an educational software company. So, O’Leary co-founded SoftKey with his business partners John Freeman and Gary Babcock in 1986.
He cemented an initial investment of $25000, but unfortunately, the investor backed out, and Kevin was committed, so he decided to use the entire proceeds of his sale from SET. His mother also invested $10,000 as a loan.
He finally launched Softkey Software Products, which published and distributed software in CDs for Windows and Mac. They focused on developing educational software and became a significant household brand by 1993.
They even acquired their rivals, such as Wordstar and Spinnaker Software. Their biggest acquisition was the TLC or The Learning Company in 1995 for $606 million. After this, they renamed their company from Softkey to The Learning Company.
Kevin sold TLC after witnessing massive success in 1999 to Mattel for $4.2 billion and became a multimillionaire for the first time. The bulk of his personal wealth was made from this deal.
However, the sales soon started dropping, and Mattel made a massive loss of $105 million after projecting a $50 million profit at the time of acquisition. It was considered one of the most catastrophic acquisitions in recent history.
Kevin was fired as a result of this. Mattel’s shareholders filed a lawsuit against Mattel’s executives, including Kevin and the then CEO, Michael Perik. Mattel paid $122 million to settle the case. Kevin disagreed with the charges and blamed the two organizations’ technology collapse and clashing culture for the downfall.
In 2003 he became the director of Storage, a company controlled by Reza Satchu and Asif Satchu. They specialize in cloud-controlled storage facilities. They became the operator of storage services in Canada with a presence in 11 cities, associated with reputed brands, such as Pfizer and Merck.
These are giants in their domain. As competition was rising and an offer was made to buy Storage Now by InStorage, O’Leary and Satchu accepted it. It was acquired for $110 million in 2007 by Storage REIT.
Some of his other career highlights include:
Kevin wrote one of the best-selling books on financial literacy called Cold Hard Truth: On Business, Money & Life in 2011 and followed it up with two other books in later years.
In 2006, he was first offered a place in CBC’s reality TV show Dragons’ Den as one of the five VCs or Venture Capitalists. He immediately grabbed attention because of his bullying nature and offered blunt remarks towards the participating startups in the show. He was encouraged by the executive producer of the show, Stuart Coxe, to be “more evil.”
Due to his success in Dragons’ Den, Keven O’Leary was invited as one of the sharks in ABC’s hit show Shark Tank, the American version of Dragons’ Den. He was part of both shows until he parted ways with Dragons’ Den in 2014.
Recently, in 2021 he appeared in CNBC’s money court with Katie Phang and Ada Pozo, adjudicating financial disputes.
He was sarcastically nicknamed Mr. Wonderful because of his blunt and mean attitude toward the startups. However, his words were a reality check for many startups and misguided entrepreneurs, as many were oblivious to how difficult it is to survive as a startup.
The startups that he invests in are managed by a holding company named Something Wonderful. He has made wildly successful investments, such as Talbott Teas and Groovebook. Both of them got acquired by Jamba Juice and Shutterfly, respectively.
Kevin shares the stage with many more famous sharks.
Some celebs who are his fellow sharks include Barbara Corcoran, Lori Greiner, Robert Herjavec, Daymond John, and Mark Cuban.
Apart from these two shows, he was part of the Discovery Project Earth in 2008. In 2009 he did a segment with Amanda Lang for CBC called The Lang and O’Leary Exchange, a show for Business News Network, and in 2012 he did a reality show called Redemption Inc., where he helped ex-convicts to start their businesses.
Kevin O’Leary has been a skeptic and has voiced his negative feelings about cryptocurrency for a long time. However, in 2021 he said that this attitude towards crypto has changed owing to FTX’s focus on compliance systems and that he received an equity stake and payment in crypto.
However, 2022 was one of the worst years of crypto, where some of the biggest crypto companies collapsed, including FTX. As Kevin was one of the primary endorsers of the brand, his image was at stake. He was heavily criticized and received a lot of flak for his endorsement.
He tried to run a PR campaign in December 2022 to clear his name and even claimed that he lost the entire $15 million he received as part of the partnership deal.
Although we know that Kevin O’Leary’s Net Worth is $400 million, we don’t know how he has diversified his portfolio. He has publicly discussed his investing strategy of 5-20 and diversification, where 60% is invested in stocks via ETFs and 40% in startups, NFTs, Gold, and other collectibles such as watches, guitars, and cameras.
Kevin O’Leary net worth was built on taking calculated risks. He never lets go of an investment opportunity that aligns with his ideology. So he invested in a lot of startups, but his current portfolio of Shark Tank Startups is as follows:
1. Basepaws
It is a DNA testing company for cats that can help the cat’s owner identify the breed, health, and habit details of anyone’s cat
2. BenjiLock
It is a company that develops rechargeable padlocks with fingerprint tech
3. Bottle Breacher
This company produces 50-caliber bottle openers that Active Duty service members and Veterans handcraft.
4. Certifikid
It is a website with mobile deals for parents and is extremely popular. CertifiKID helps parents provide unique experiences like camps, getaways, gifts, or different classes on an affordable budget
5. DrainWig
DrainWig, with its innovative product built with stainless chain and rubber whiskers, helps people prevent clogs in drains by catching hair.
6. Geek My Tree
Geek My Tree offers the state of the art full-color LED Light Show Systems.
7. Honeyfund
Honeyfund is the number one registry for cash wedding gif and offers free honeymoon registry
8. Illumibowl
It is a company that provides an innovative product that will help illuminate the toilet’s inner bowl. As a result, there will be a soft glow in the dark every time someone enters the bathroom.
9. Le-Glue
Le-GLue is the glue that makes your blocks stick together almost 12 times stronger than the normal ones. They will ensure that the blocks stay on so that creativity is preserved.
10. LovePop
Lovepop offers greeting cards that are 3d pop-ups for various occasions.
11. Monti Kids
Monti Kids delivers toys and an online curriculum for children to improve their potential based on proven methods of Montessori
12. Potato Parcel
It’s a greeting card but on potatoes. Now anyone sends their loved ones a message they want to convey on a potato instead of greeting cards or flowers
13. Pop it Pal
Pop it Pal is a simulation toy where people can satisfy their urge to pop a huge pimple made of skin-safe silicone and all-natural pus.
14. PRx
If anyone wants to build their own garage or home gym, an easy way to start is to use PRx’s patented wall-mounted Profile Folding Squat Rack.
15. Rareform
By repurposing billboards, they built durable and unique bags and accessories, such as surf bags, backpacks, wallets, totes, etc.
16. Rounderbum
They produce undergarments using the latest tech that helps people to enhance their physique.
17. SnarkyTea
They provide the best tea to boost energy and enhance wellness and a jolly mood.
18. Surprise Ride
Surprise Ride aims to tap into kids’ creative potential and guide them to achieve the best results with the help of their curated activities.
19. Waivecar
They have revolutionized the transportation system. They connect users anywhere in their city with the help of ad-displaying electric cars for free.
20. Wicked Good Cupcakes
They produce some of the best freshly baked products and can be shipped nationwide. They can also be bought as gifts for different occasions.
21. Wine and Design
Their unique selling point is to offer fun and memorable parties at a low cost. One can paint and sip wine at the same time and have a wonderful experience.
22. Deskview
It offers a one-of-a-kind window-mounted and adjustable standing desk that can be easily used anywhere, such as the office, home, or co-working space.
23. Boost Oxygen
Boost Oxygen provides 95% pure supplemental Oxygen in a canister that can be used in different situations or conditions where there is a lack of Oxygen.
Kevin’s O’Shares Investments, where he is the chairman, focuses on generating sustainable growth with the help of a balanced portfolio. O’Shares’ popular index, OUSAX or O’Shares U.S. Quality Dividend Index, has more than 100 companies in its portfolio.
The index has been built with two of his core principles, not more than 5% in any stock and 20% in one sector and diversification. There are only two anomalies here: the Home Depot stock, where the holdings are slightly over 5% at 5.19%, and the healthcare sector, which is more than 20%.
They also offer other indices, including one index for small cap known as OUSMX, an index focused on the top 50 European leading stocks called OEURX, and an index called OGIGX focused on technology-driven and digital companies.
All the details provided are as of 12/31/2022.
Index Ticker | OUSAX |
Index Inception Date | 5/22/2020 |
Rebalance | Quarterly |
Reconstitution | Annually |
Weighting | Factor-Based |
AVG Market Cap | $158.8 Billion |
Weighted AVG Market Cap | $321.7 Billion |
| Ticker | Name | Sector | Weight |
|---|---|---|---|
| HD | Home Depot Inc | Consumer Discretionary | 5.19% |
| MSFT | Microsoft Corporation | Information Technology | 4.58% |
| JNJ | Johnson & Johnson | Health Care | 4.40% |
| PFE | Pfizer Inc. | Health Care | 4.30% |
| MRK | Merck & Co. Inc | Health Care | 4.02% |
| SPGI | S&P Global Inc | Financials | 3.87% |
| MMC | Marsh & McLennan Companies Inc. | Financials | 3.79% |
| TROW | Price T Rowe Group | Financials | 3.40% |
| MCD | McDonald’s Corporation | Consumer Discretionary | 3.18% |
| AAPL | Apple Inc. | Information Technology | 3.10% |
Sector | Weight |
Health Care | 21.77% |
Information Technology | 20.70% |
Consumer Discretionary | 16.67% |
Financials | 14.79% |
Industrials | 11.16% |
Consumer Staples | 9.91% |
Communication Services | 5.00% |
Source: OUSAX
Index Ticker | OUSMX |
Index Inception Date | 5/22/2020 |
Rebalance | Quarterly |
Reconstitution | Annually |
Weighting | Factor-Based |
AVG Market Cap | $5.5 Billion |
Weighted AVG Market Cap | $6.6 Billion |
| Ticker | Name | Sector | Weight |
|---|---|---|---|
| EHC | Encompass Health Corporation | Health Care | 2.34% |
| HLI | Houlihan Lokey Incorporation | Financials | 2.25% |
| JNPR | Juniper Networks Inc. | Information Technology | 2.24% |
| ERIE | Erie Indemnity Co | Financials | 2.22% |
| IPG | The Interpublic Group of Companies Inc. | Communication Services | 2.22% |
| DCI | Donaldson Co Inc | Industrials | 2.20% |
| ORI | Old Republic International Corporation | Financials | 2.19% |
| DOX | Amdocs Limited | Information Technology | 2.18% |
| LECO | Lincoln Electric Holdings Inc. | Industrials | 2.10% |
| SEIC | SEI Investments Co | Financials | 2.09% |
Sector | Weight |
Industrials | 22.61% |
Financials | 20.81% |
Information Technology | 20.29% |
Consumer Discretionary | 13.08% |
Health Care | 8.68% |
Consumer Staples | 5.73% |
Utilities | 4.48% |
Communication Services | 4.31% |
Index Ticker | OEURX |
Index Inception Date | 5/22/2020 |
Rebalance | Quarterly |
Reconstitution | Annually |
Weighting | Factor-Based |
AVG Market Cap | USD 75.8 Billion |
Weighted AVG Market Cap | USD 118.5 Billion |
| Ticker | Name | Sector | Weight |
|---|---|---|---|
| SAP | SAP SE | Information Technology | 5.50% |
| MC | LVMH Moet Hennessy Vuitton SE | Consumer Discretionary | 5.22% |
| ASML | ASML Holding N.V. | Information Technology | 5.18% |
| NOVOB | Novo Nordisk A/S | Health Care | 5.15% |
| NOVN | Novartis AG | Health Care | 5.14% |
| NESN | Nestle SA | Consumer Staples | 4.71% |
| ROG | Roche Holdings AG | Health Care | 3.88% |
| SU | Schneider Electric SE | Industrials | 3.36% |
| III | 3i Group PLC | Financials | 2.77% |
| BMW | Bayerische Motoren Werke AG | Consumer Discretionary | 2.74% |
Sector | Weight |
Industrials | 24.56% |
Health Care | 16.54% |
Consumer Staples | 15.32% |
Information Technology | 14.95% |
Consumer Discretionary | 14.39% |
Utilities | 6.92% |
Financials | 5.72% |
Communication Services | 1.59% |
Index Ticker | OGIGX |
Index Inception Date | 5/31/2018 |
Rebalance | Quarterly |
Reconstitution | Semi-Annually |
Weighting | Factor-Based |
AVG Market Cap | USD 80.0 Billion |
Weighted AVG Market Cap | USD 225.6 Billion |
| Ticker | Name | Sector | Weight |
|---|---|---|---|
| MSFT | Microsoft Corporation | Information Technology | 5.97% |
| AMZN | Amazon.com Inc. | Consumer Discretionary | 5.73% |
| GOOGL | Alphabet Inc. | Communication Services | 4.99% |
| 3690 | Meituan | Consumer Discretionary | 2.22% |
| SNOW | Snowflake Inc | Information Technology | 1.97% |
| NOW | Servicenow Inc | Information Technology | 1.70% |
| 700 | Tencent Holdings Limited | Communication Services | 1.59% |
| TTWO | Take-Two Interactive Software Inc. | Communication Services | 1.58% |
| DDOG | Datadog Inc | Information Technology | 1.57% |
| PDD | Pinduoduo Inc | Consumer Discretionary | 1.57% |
Sector | Weight |
Information Technology | 59.27% |
Communication Services | 23.34% |
Consumer Discretionary | 17.39% |
After Kevin’s initial tryst with crypto, he finally became an endorser of digital currencies. He was a strong advocate of FTX until the collapse ensued. He is said to have invested in at least 32 crypto tokens, including Bitcoin and Ethereum.
Although he has not publicly shared his percentage allocation of each of the assets or exactly which assets he holds, he did mention in an interview with CNBC that he has millions of dollars in cryptocurrencies, with 20% of his portfolio being in crypto.
Following this, in his interview with Crypto Banter’s Ran Neuner, he mentioned that the portfolio size has come down to 16.2% post-correction. He also says that his team constantly monitors the position of his assets in crypto as it behaves differently compared to stocks and bonds. He even said that they are continually adding to the position.
Following her mother’s footsteps, Kevin understood that the value of rare luxury items increases over time, especially when they are not readily available in the market. Following this business philosophy, Kevin collects high-end watches such as Rolex, Omega, classical guitars, and vintage cameras.
Although he buys them as investments, one can easily understand that he is passionate about them and purchases them to satiate that inherent spirit that wanted him to pursue photography or become a rock star when he was young.
Although the exact ROI of all his business ventures is unknown, it is a known fact that the indices under O’Shares Investment have given excellent returns over the years.
Although he invested millions of dollars in crypto since the market is 70% down, he has incurred losses in that sector. Moreover, as he claimed in Dec. 2022, his $15 million went to zero, which he received for his partnership with FTX after the colossal fall of the crypto exchange last year.
All his investments in luxury items and collectibles have also gained significant value, but their exact amount is unknown.
The ROI on the indices are as follows:
Never put all your eggs in one old. This age-old advice but still relevant in today’s investment scenario. It is the most common advice that Kevin almost repeats regularly.
He follows the diversification rules in all Kevin O’Leary ventures, be it the traditional and conservative markets like ETFs, stocks, and bonds or a highly volatile market like crypto. He even diversified into lucrative luxury collectibles.
Luxury watches such as Rolex and AP Watches have gained parabolic gains recently. After an investing platform opened up selling AP Royal Oak A-series watch shares with a share price of $75, Investors who bought those shares made an ROI of 46% in 3 years from 2018 to 2021. People can invest in shares of watches like Omega, Speedmaster, or Rolex, which are currently offering their shares to be bought.
Kevin O’Leary always mentions investing with the 5-20 rule. According to this rule, one should never allocate over 5% of his portfolio to one asset and over 20% to one sector.
Following this strategy would mitigate many risks and protect your investments if one sector faces a downturn. For example, Kevin’s conservative investments protected him against his crypto investment, which is going through one of its worst bear markets.
Kevin suggests not to shy away from risky ventures, but that doesn’t mean you allocate all your funds to the risky venture. Following this ideology, Kevin diversified his investments in different asset classes from his traditional investment in stocks and bonds.
But you should always take a calculated risk and thoroughly research the project and its future potential, then invest according to your risk appetite and invest only what you can lose. Investing with a calculated risk may help you beat other retail investors.
No one is perfect, so don’t be disheartened when you make mistakes. Instead, take that loss positively, learn what mistakes you made, and try to implement that learning in future investments so that the same mistakes are not repeated.
It is essential to learn and adapt to become a better investor continuously. Kevin himself has learned from his mistake in his crypto investments and FTX. He said that the key is to avoid repeating the mistake to become a successful businessman.
He mentions that one need not be a gigabrain investor but focus on smart investments; over time, the experience will help them become a skilled investor, making more good than bad ones.
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Kevin O’Leary decided to pursue the Conservative Leadership race as the leader of the Conservative Party of Canada. He announced it on 8th January 2017 after a lot of public speculation.
When campaigning, he became immensely popular for being compared to Donald Trump. The comparison was made since both of them rose to fame through reality TV and on the premise that taxes and regulations would be reduced. For example, he mentioned that if he became the Prime Minister, he would scrap the carbon tax.
However, O’Leary discouraged the comparison of the fact that he has an entirely different take on immigration than Donald Trump.
Mainly because he belongs to an immigrant family of Irish and Lebanese descent, he would not have been able to establish himself in Canada if there were strict immigration rules and a Canadian Wall proposed by Donald Trump.
However, on 6th April 2017, Kevin withdrew his name from the leadership election run as he failed to garner any support from the Quebec region because he understood that without this support, he wouldn’t be able to beat Justin Trudeau.
Kevin O’Leary married his wife Linda in 1990. Although they were separated for a couple of years in between, they got back and have stayed married since.
They have two children, Trevor and Savannah. His wife, Linda O’Leary, is the VP of marketing at O’Leary Wines. Trevor is an engineer at Tesla, and Savannah is a producer and filmmaker based out of New York.
He lives in Miami Beach, Florida, and Toronto. He also has other luxury properties across the world. He also got UAE citizenship which is extremely rare for foreigners, so that he can partner with Emiratis.
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Mark Cuban is the richest shark and has made the most deals in Shark Tank. His number of investments is almost double what other investors did. He also owns the Dallas Mavericks.
Kevin O’Leary from Shark Tank owns a lot of companies.
Arum Kang turned down an offer of $30 million for his dating app Coffee Meets Bagel. It was by far the highest offer in the history of Shark Tank.
As you can understand, Kevin O’Leary Net Worth of $400 million was not made in a day. No one thing would define his key to success; rather, years of hard work, investment strategies, mistakes, learning from those mistakes, taking risks, and protecting the portfolio helped him build so many successful companies and become the person he is today. The goal is to follow his investing principles, focus on his positives and apply them in our life so that we can also learn as we embark on our investment journey and become successful.
Disclaimer: The information provided in this article is for informational purposes only and should not be construed as financial advice. The author’s opinions are their own and should not be taken as a recommendation to invest in any particular product or service. It is strongly advised that you consult a financial advisor before making investment decisions. Investing always carries risk, and it is up to each individual to consider their options and make informed choices carefully.
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