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Kevin O'Leary, widely recognized as a shrewd investor and a no-nonsense entrepreneur from CNBC's Shark Tank, has built a formidable reputation with a net worth once estimated at $400 million. Known for his blunt honesty and sharp business acumen, O'Leary's journey to wealth has been marked by successful ventures across various industries. However, his fortune took a significant hit in the aftermath of the FTX collapse, where he lost millions following the implosion of Sam Bankman-Fried's crypto empire. The FTX debacle not only tarnished O'Leary's finances but also called into question the due diligence practices of the seasoned investor, who now finds himself embroiled in a class-action lawsuit alongside other celebrity endorsers of the failed exchange. This introduction delves into O'Leary's rise to success, his involvement with FTX, and the financial and reputational fallout that ensued.
Family and Early Life
Born on July 9, 1954, in Montreal, Canada, Terence Thomas Kevin O'Leary didn't come from a family of wealth. His mother, Georgette O'Leary, was a small business owner, and his father, Terry O'Leary, was a salesperson. His parents divorced when he was a child, largely due to his father's alcoholism. O'Leary's mother then married an economist, George Kanawaty, who worked at the UN's International Labour Organization. This caused the family to move frequently, having lived in Cyprus, Ethiopia, Tunisia, and Cambodia.
Georgette, whom Kevin O'Leary credits for his money savvy, was a successful retail investor who put one-third of her weekly paycheck into dividend-paying stocks and interest-bearing bonds. She ultimately amassed a large amount of capital. Her other smart money moves included keeping her portfolio secret from both her husbands and buying classic Chanel jackets that have greatly appreciated in price over time.
Although O'Leary initially planned to follow his passion for photography, his stepfather convinced him to attend university. This is where Kevin continued to develop his interest in finance and investing. He graduated with a degree in environmental studies and psychology from the University of Waterloo in 1977 and later received an MBA in entrepreneurship from the Ivey Business School at the University of Western Ontario in 1980.
Business Career
O'Leary's entrepreneurial journey started with the creation of Special Event Television (SET), an independent production company that produced some minor television shows such as The Original Six, Don Cherry's Grapevine, and Bobby Orr and the Hockey Legends. O'Leary soon sold his share in a venture to his partner for $25,000.
His big break came in 1986 when, together with his business partners John Freeman and Gary Babcock, he co-founded SoftKey, a software company that sold CD-based programs for personal computers. SoftKey grew rapidly through a series of acquisitions and was eventually renamed The Learning Company (TLC). In 1999, Mattel acquired TLC for $4.2 billion, marking one of the most lucrative exits in the tech industry at the time.
Following his success with TLC, O'Leary became a co-investor and director at Storage Now, a Canadian developer of climate-controlled storage facilities, which was later acquired for $110 million. Around the same time, he also took the first steps to establish himself as a successful venture capitalist, co-founding O'Leary Funds, a mutual fund company focused on global yield investing, in 2008. He later founded O'Leary Ventures, a private early-stage VC firm.
The investor and entrepreneur is also a passionate wine lover — so it comes as no surprise that O'Leary also tapped into the wine and spirits market, partnering with Vintage Wine Estates. This is one of California's largest wine companies to launch O'Leary's wines. His family also invested in over 3,000 acres of vineyards in Sonoma and Napa in California and Washington state.
Shark Tank Deals
In 2009, the first episode of Shark Tank aired in the US on ABC — and the series quickly won the hearts of the American audience. The TV show, which was released as a franchise of the international format Dragons' Den, featured entrepreneurs pitching their startups to a panel of five investors or "sharks" who then decide whether to invest in the presented ventures and provide expert advice to founders.
O'Leary, who by then had already appeared in the Canadian version of Dragons' Den, was invited to appear in Shark Tank's pilot and remained with the show since its inception. He became known as a blunt and often ruthless investor, and on several occasions grilled entrepreneurs so mercilessly that they couldn't hold their tears on the show. O'Leary's abrasive persona on Shark Tank earned him the moniker "Mr. Wonderful," which he gladly embraced and famously made an integral part of his personal brand.
As a Shark Tank investor, O'Leary is known to make strategic and pragmatic allocations. He often demands royalties in his deals or prefers convertible loans to an equity stake in the company, which reflects his view on cash flow as a lifeblood of any business. Despite his tough TV persona, he has invested in numerous successful businesses on the show. His most notable investments include companies like Groovebook, a subscription service for a book of photo prints which was later sold to Shutterfly for $14.5 million, and Plated, a meal kit service that was sold to Albertsons for $300 million.
Other Ventures and Investments
The Shark Tank star is known for his strong emphasis on diversification, so it comes as no surprise that Kevin O'Leary's net worth isn't exclusively tied up in his venture investments and stocks. The Canadian businessman also allocates a portion of his funds to alternative investments, which include crypto, real estate, and collectibles.
Cryptocurrencies
Known for his conservative approach to investing, O'Leary had initially expressed skepticism towards cryptocurrencies, having said that he would not put this money in Bitcoin. “Bitcoin is a nothing-burger, a giant nothing-burger,” O'Leary said on a January 2021 podcast with Anthony "Pomp" Pompliano, adding “you don’t have every institution willing to play ball with it.”
"If I want to buy a million dollars worth of bitcoin right now, I’ve got to do a fair amount of work to pull that off," he added, pointing out the challenges of converting funds between BTC and fiat.
Later, O'Leary seemingly had a change of heart about crypto, which coincided with his gig as a spokesperson and ambassador for FTX. In March 2021, he announced that he would be allocating 3% of his portfolio to Bitcoin, citing its performance as a hedge against inflation. He has also shown interest in decentralized finance, claiming that he is looking forward to the future where institutional money will flow into DeFi projects. Besides Bitcoin, O'Leary is known to personally hold some altcoins, including Ether, Polygon, Solana, and a lesser-known cat-themed meme coin Pawthereum.
Real Estate
Throughout his career, O'Leary made numerous investments in luxurious property, including a $17.6 million lavish cottage on the shores of Lake Joseph and mansions in Toronto, Boston, and Geneva.
Moreover, as a Shark Tank investor, O'Leary has made deals with several entrepreneurs in the real estate industry. This includes investments into platforms that connect renters with property owners, and services that improve the home selling and buying processes.
Collectibles
Kevin O'Leary is also known for his interest in investing in collectibles, particularly high-end watches. His jaw-dropping collection features luxury brands like Audemars Piguet, Omega, Rolex, F.P. Journe, and Patek Philippe.
Much like traditional investment assets, certain upmarket timepieces can greatly appreciate in value over time. For instance, one of the watches that O'Leary was spotted wearing in February 2019 — a discontinued Patek Philippe blue dial Nautilus — retailed for $30,000 at the time, but its current market price is over $140,000. Another gem in O'Leary's watch portfolio, the diamond-encrusted Rolex Daytona “Eye of the Tiger” sells on the secondary market for $200,000.
According to the most modest estimates, O'Leary's timepiece portfolio is worth several hundreds of thousands — and the millionaire never hesitates to show off his watch game. The television personality cycles through three different watches in one day, and even has his precious toys shipped ahead to his travel destinations!
Books
A steady stream of O'Leary's income also comes from his bestselling book series, Cold Hard Truth, in which the businessman teaches his readers valuable lessons on financial literacy, entrepreneurship, and family life. The books have been a hit among aspiring entrepreneurs and rank-and-file investors, who found O'Leary's advice to be straightforward and no-nonsense.
The Cold Hard Truth series includes several books such as Cold Hard Truth on Men, Women, and Money, where O'Leary provides insightful advice about making and managing money; Cold Hard Truth on Family, Kids and Money, where he gives tough-love advice on raising money-smart kids; and Cold Hard Truth on Business, Money & Life, where he shares his views on entrepreneurship, business, finance, money, and life.
Mr Wonderful FTX Endorsement
In 2021, O'Leary entered into a strategic partnership with FTX to serve as an ambassador and spokesperson for the platform. As a part of the compensation for this role, the investor took an ownership stake in the parent companies of both FTX.com and FTX.US. On top of that, he got paid $15 million to spread the word about FTX.
And indeed, O'Leary worked around the clock to promote the exchange on Twitter and his other social media channels, frequently flaunting his close relationship with Sam Bankman-Fried, who has been sentenced to 25 years in prison and 3 years of supervized release for his role in the exchange's collapse. Ironically, when O'Leary had just started his partnership with FTX, he claimed that what prompted him to take the deal was the crypto exchange's rigorous compliance processes.
How Much Did Kevin O’Leary Lose in FTX?
In November 2022, FTX collapsed after crypto news outlet CoinDesk leaked its financials that showed that much of its assets were tied up in FTT, the exchange's altcoin printed basically out of thin air. As the crypto exchange filed for bankruptcy in the aftermath of a devastating bank run, criminal and regulatory investigators began scrutinizing its execs for potentially violating securities law. The proceedings revealed that FTX founder Sam Bankman-Fried misappropriated billions of dollars in customers' funds to place risky bets through his exchange's trading arm, Alameda Research.
When it became clear that FTX was a years-long fraud, O'Leary attempted some PR cleanup by admitting that he fell victim to groupthink, noting “I obviously know all the institutional investors in this deal, we all look like idiots, let’s put that on the table.”
“We relied on each other’s due diligence but we also relied on another investment theme that I felt drove a lot of interest in FTX. Sam Bankman-Fried is an American, his parents are American compliance lawyers. There were no other American large exchanges to invest in if you wanted to invest in infrastructure plays,” he told CNBC.
O'Leary reiterated that there was nothing left from the $15 million FTX paid him for his spokesperson role. Speaking with CNBC’s Squawk Box on Dec. 8, 2022, the Shark Tank star stated: “I put about $9.7 million into crypto. I think that’s what I lost. It’s all at zero. I don’t know because my account got scrapped a couple of weeks ago. All the data, all the coins, everything. It was not a good investment. Then I lost the money I invested in the equity as well, those are zeros too”
According to O'Leary, the remainder of his $15 million after a $9.7 million loss was spent to cover various fees and taxes, and a further million dollars in FTX equity also went down to zero after the exchange's bankruptcy.
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