Kevin O'Leary

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Terence Thomas O'Leary (born September 1954) is a Canadian businessman, author, politician, and television presenter.

He co-founded O'Leary Funds and SoftKey.

He appeared on numerous Canadian television shows from 2004 to 2014, including the business news programs SqueezePlay and The Lang and O'Leary Exchange, as well as the reality television shows Dragons' Den and Redemption Inc.

He appeared on Discovery Channel's Project Earth in 2008.

He has been on Shark Tank, the American equivalent of Dragons' Den, since 2009. SoftKey Software Products, a technology firm that sold applications geared to family education and entertainment, was co-founded by O'Leary.

SoftKey acquired rival firms, such as Compton's New Media, The Learning Company, and Brodybund, among others, during the late 1980s and 1990s.

SoftKey later changed its name to The Learning Company, which was purchased by Mattel in 1999, making O'Leary a multimillionaire.

After the merger resulted in significant losses and multiple shareholder lawsuits, O'Leary was fired by Mattel quickly.

During much of the year, he was a front-runner in the polls, but he fell out in April 2017, citing a lack of funding in Quebec.

Early life and education

O'Leary was born in Montreal, Canada, on July 9th, 1954, one of two sons of Georgette (née Bukalam), a small-business owner and investor of Lebanese descent, and Terry O'Leary, a salesman of Irish descent. Shane O'Leary is Kevin's brother. O'Leary also holds Irish citizenship and has an Irish passport, owing to his paternal history.

O'Leary grew up in Mount Royal, Quebec. His parents divorced as a child, largely due to his father's alcoholism. When O'Leary was only seven years old, his father died shortly after that. After his father's death, his mother took over the company as an executive. George Kanawaty, a researcher who worked with the UN's International Labour Organisation, married his mother later. His stepfather's international work caused the family to change often, and O'Leary lived in several countries during his time in Egypt, Ethiopia, Tunisia, and Cyprus. O'Leary attended Stanstead College and St. George's School, both in Quebec.

O'Leary's mother was a good investor, investing a third of her weekly income in large-cap, dividend-paying stocks, and interest-bearing bonds, ultimately reaping high returns in her investment portfolio. She kept her investment portfolio private, so O'Leary's mother's abilities as an investor were only revealed after her death, when she was executed. Many of his investing lessons came from his mother, including the warning to save one-third of his money.

O'Leary had aspired to be a photographer but on the advice of his stepfather, he enrolled in university, where he continued to develop his interest in business and investing. In 1977, he earned a bachelor's degree in environmental studies and psychology from the University of Waterloo, as well as an MBA in entrepreneurship from the University of Western Ontario's Ivey Business School.

Personal life

Since 1990, O'Leary and his partner, Linda, have been married. They married in 2011, but they remarried after two years. Linda is now the VP of Marketing for O'Leary Wines. They have two children. Trevor is a Tesla engineer, and Savannah is a multimedia producer and filmmaker in New York City. "In a growing market, it eats your time alive," O'Leary said in a 2016 interview. If you're looking for things your family members can't have later in life. However, you're now given the freedom you deserve because you sacrificed."

The O'Learys live in Miami Beach, Florida, and Toronto, Ontario. He also owns a cottage in Muskoka, as well as homes in Boston and Geneva, Switzerland. In a 2022 CNBC interview, he said he obtained a UAE citizenship in order to be able to work with Emiratis on investment.

O'Leary, a football fan of the New England Patriots, follows all of their games, even when traveling around the country and games take place during the middle of the night. He is a wine enthusiast and a member of the Confrérie des Chevaliers du Tastevin, a multinational group of Burgundy wine enthusiasts. He has worked as a lifelong photographer and has sold prints of his photography, donating the proceeds to charity. O'Leary is also a keen watcher and expert, shedding his hints on Shark Tank and social media.

O'Leary and his wife Linda were involved in a fatal crash on Lake Joseph, Ontario, on August 24, 2019. They were riding a boat owned by O'Leary and operated at the time by Linda. The boat collided with another one, and a 64-year-old man and a 48-year-old woman were killed on board. In a statement, O'Leary said he was cooperating with the police investigation and that the other boat did not have its lights on and "fled the scene." Both boats left the scene to "attend a location," according to the police, and both sides called 911." Linda O'Leary was charged with "careless operation of a vessel" under the Canada Shipping Act's small vessel legislation, a punishment that could result in maximum 18 months in prison and a $10,000 fine. Richard Ruh, the other boat's pilot, was charged with "failing to display navigation light while underway." Linda's prison term was suspended after the Public Prosecution Service of Canada suspended it on October 11th. Linda was not found not guilty of careless operation of the vessel on September 14th, 2021.

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Business career

In 1978, between the first and second years of his MBA program, O'Leary was chosen for an internship at Nabisco in Downtown Toronto and later as an assistant brand manager for Nabisco's cat food brand. O'Leary attributes his later success at The Learning Company to the marketing skills he acquired during his time at Nabisco.

O'Leary began working as a television producer after leaving Nabisco. O'Leary co-founded Special Event Television with two of his former MBA classmates, Scott Mackenzie and Dave Toms (both of whom worked on O'Leary's MBA film). The Original Six, Don Cherry's Grapevine, and Bobby Orr and the Hockey Legends were among SET's original sports production services. The company's minor television shows, soccer films, sports documentaries, and a short in-between-period commercials for local professional hockey games had little success. One of his coworkers sold his stake in the business for $25,000.

O'Leary, a business partner, and Gary Babcock began Softkey in a Toronto basement in 1986 after selling his SET shares. The firm was a publisher and distributor of Windows and Macintosh personal computer applications. On the day before signing the papers and delivering his cheque, a major financial backer committed $250,000 in development capital to the company backed out, leaving O'Leary and the fledgling company in need of funds to support the fledgling company. SoftKey Software Products was born out of a $30,000 seed fund raised by his entrepreneur from selling his SET share and persuaded his mother to loan him $10,000 in seed funds.

Early 1980s and 1990s applications and personal computers were thriving, and O'Leary's printers were perplexed with printer manufacturers' attempts to bundle Softkey's services with their hardware. With distribution promised, the company produced several educational software suites focusing on mathematics and reading instruction. Softkey CD-ROMs were typically composed of games for home users, particularly compilation discs containing various freeware or shareware games packed in "jewel-case" CD-ROMs.

Softkey faced fierce competition from other software firms in the late 1980s and 1990s, and the 1990s thrived. Softkey had established itself as a key player in the educational software market by 1993, acquiring rivals such as WordStar and Spinnaker Software. Softkey bought The Learning Company (TLC) for $606 million, adopting the company's name, and relocating its headquarters to Cambridge, Massachusetts, in 1995.

TLC lost $105 million (US) in 1998 on $800 million (US) and suffered losses in the intervening two years. Brody, TLC's former adversary, was purchased by the TLC in June 1998 for $416 million.

Mattel bought TLC in 1999 for $4.2 billion. Mattel's sales and profits have declined quickly, and O'Leary has left. Mattel's acquisition was later identified as one of the most costly acquisitions in recent history. Mattel had expected a loss of US$105 million as a result of merger control, but not so much. Mattel's shares plummeted, wiping out US$3 billion of shareholder value in a single day. Mattel's shareholders commenced a class-action lawsuit against Mattel executives O'Leary and former TLC CEO Michael Perik for misleading customers about the health of the TLC and the benefits of its merger. TLC was charged with using accounting tricks to conceal losses and raise quarterly revenue. Both O'Leary and his lawyers denied any of the charges. In 2003, Mattel paid $122 million to settle the case. The acquisition's demise was attributed to the technology meltdown and a culture clash of the two companies' leadership.

The video game business Atari was unsuccessfully pursued by O'Leary and the Citigroup's backers. O'Leary's ambitious bid to start a video-gaming television channel that never came to fruition.

O'Leary joined StorageNow Holdings, a Canadian designer of climate-controlled storage facilities, which is owned by Reza Satchu and Asif Satchu in 2003. StorageNow became Canada's storage provider, with facilities in 11 towns, and was purchased by Storage REIT in March 2007 for $110 million. He sold his shares, which had originally valued $500,000, for more than $4.5 million.

Reza Satchu and O'Leary's operating partner, Wheeler, filed a $10-million wrongful dismissal lawsuit in May 2005, alleging that they modified an agreed-upon compensation contract and unlawfully reduced Wheeler's share of the gains. Wheeler's results were not met, according to O'Leary and Satchu. The lawsuit was decided out of court.

O'Leary joined Genstar Capital, a private equity company that focuses on investing in healthcare, industrial technology, company services, and software in March 2007. O'Leary has been appointed to the Strategic Advisory Board of Genstar Capital to look at new investment opportunities for its $1.2 billion fund.

O'Leary co-founded O'Leary Funds Inc., a mutual fund company that focuses on international yield investing, in 2008. He is the company's chairman and lead investor, while his brother Shane O'Leary serves as the director. The fund's assets under management increased from $400 million in 2011 to $1.2-billion in 2012. Stanton Asset Management, a company owned by Connor O'Brien and Louise Ann Poirier's husband-and-wife team, was the fund's primary administrator.

According to Mark R. McQueen's study, the fund increased distribution yield from his accounts by returning invested capital to shareholders. Although this is not unusual, it is nevertheless contrary to O'Leary's remarks. According to another report, one-quarter of the distributions from one of O'Leary's funds was return of capital.

O'Leary Funds Management decided to pay fines to the Autorité des marchés financiers for breaching certain technical terms of the Securities Act in November 2014. O'Leary Funds reported that correcting the wrongdoings had been underway at the time of the deal. O'Leary Funds was sold to Canoe Financial, a private investment-management firm owned by Canadian businessman W. Brett Wilson, on October 15, 2015. On CBC's Dragons' Den, he was once an investor with O'Leary.

O'Leary Ventures, a private early-stage venture capital investment firm, O'Leary Mortgages, O'Leary books, and O'Leary Fine Wines, founded O'Leary Ventures, O'Leary Ventures, O'Leary Wines. O'Leary Mortgages closed in April 2014. O'Leary's funds have a turbulent past and are expected to have dropped over 20% in a year, which is often a major blow to fund managers. O'Leary no longer manages outside funds.

O'Leary Investments, a division of his investment fund, O'Leary Funds Management LP, where O'Leary is chairman, launched an ETF on July 14, 2015. He has worked on personal finance, and he has been a value investor. He advocates portfolio diversification and claims that investors should have their age as the percentage of bonds in their portfolios rises, with an increasing number of bonds and decreasing percentage of stocks decreasing as the investor ages. On several occasions, O'Leary has also stated that he would not invest in publicly traded stock unless it pays him a dividend."

With five percent of his financial portfolio invested in physical gold, O'Leary also ventured into gold investing. However, he does not invest in gold-mining stocks because, according to him, cash balance is a primary investment factor. O'Leary also recommends diversification in several industry sectors to ensure that no more than 20% of one's financial account is held in one sector.

O'Leary has been a fan of cryptocurrency investing and personally owns coins in Ether, Polygon, SOL, Bitcoin, and Pawthereum. He became a strategic investor in Defi Ventures, a Vancouver-based decentralized finance platform; the firm later rebranded itself WonderFi Technologies in honor of O'Leary's nickname, "Mr." "Wonderful" is the word that came to mind.

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