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Breaking Down Kevin O’Leary’s Net Worth

Last updated on December 18, 2019 by

QUICK ANSWER: As of 2019, Kevin O’Leary’s total net worth is estimated to be $400 million.

Terrence Thomas Kevin O’Leary was born July 9, 1954. O’Leary is a Canadian businessman, politician, author and TV personality. He is also the cofounder of O’Leary Funds and SoftKey. From 2004 to 2014, O’Leary appeared on several television shows in Canada, including SqueezePlay, a business news program and The Lang and O’Leary Exchange.

He was also on reality shows like Redemption Inc. and Dragon’s Den. Kevin O’Leary also appeared on Discovery Channel’s Project Earth in 2008. Since 2009, O’Leary has appeared on the ABC show Shark Tank where has made dozens of successful investments into American businesses.

Business Accomplishments and Political Aspirations

Kevin O’Leary is the cofounder of SoftKey Software Products, a technology company that sold software for family entertainment and education. In the late 1980s and part of the 1990s, SoftKey acquired several rival companies, including Compton’s New Media, Broderbund and The Learning Company. SoftKey eventually changed its name to The Learning Company.

In 1999, The Learning Company was acquired by Mattel for $4.2 billion. This sale made Kevin O’Leary a multibillionaire. However, Mattel fired O’Leary soon after the acquisition, which led to major losses and several shareholder lawsuits.

After his early business success, O’Leary even campaigned to be the leader of the Conservative Party of Canada in 2017. During much of his campaign, he was a frontrunner in the polls. However, he dropped out of the race in April 2017 due to minimal support in Quebec.

Early Life

O’Leary was born in Montreal, Quebec, Canada and is one of two sons. His brother’s name is Shane. His mother was Georgette O’Leary (formerly Bukalam), an investor and small business owner who passed away in 2008. His father is Terry O’Leary, an Irish salesman. Kevin’s mother was Lebanese. Due to Kevin’s ethnic heritage on his father’s side, he is a citizen of Ireland and has an Irish passport.

When O’Leary was a child, his parents divorced, largely because his father was an alcoholic. O’Leary’s father passed away shortly after the divorce and his mother ran the family business in an executive position. Later, Georgette remarried an economist named George Kanawaty. Kanawaty worked with the United Nation’s International Labour Organization. Due to Kanatawy’s international assignments, Kevin’s family had to move often. O’Leary moved to several places as a child, including Tunisia, Cambodia and Cyprus. O’Leary also attended St. George’s School and Stanstead College, both in Quebec.

Georgette O’Leary was particularly adept in investments. Every week, she invested a third of her paycheck in large-cap, dividend-paying stocks and interest-bearing bonds. These practices helped her achieve high returns in her investment portfolio. O’Leary’s mother never disclosed her portfolio, so O’Leary only discovered that his mother had a skill for investing after she’d passed away and her will was executed. O’Leary learned many of his investment skills from after seeing how she’d handled money. Following his mother’s footsteps, he started saving a third of his earnings as well.

O’Leary wanted to become a photographer, but instead took his stepfather’s advice and went to university, where he cultivated his interest in investing and business. In 1977, O’Leary received an honors bachelor’s degree in environmental studies and psychology from the University of Waterloo. He received his MBA in entrepreneurship from Ivey Business School at the University of Western Ontario in 1980.

kevin oleary waterloo graduation

Success In Business

In 1979, between O’Leary’s first and second years of his MBA program, he was selected for a Nabisco internship in Toronto. After the internship, O’Leary worked as an assistant brand manager for Nabisco’s cat food brand. O’Leary states that his success at The Learning Company came from the skills he developed while working at Nabisco.

After O’Leary left Nabisco, he worked briefly as a TV producer. He cofounded Special Event Television (SET) with Dave Toms and Scott Mackenzie, two of his former MBA classmates; the men also assisted on O’Leary’s MBA documentary. SET was an independent production company and produced several original sports shows like Bobby Orr and the Hockey Legends, The Original Six and Don Cherry’s Grapevine. SET also achieved some success with sports documentaries, minor TV shows, soccer films and commercials for local professional hockey games. One of O’Leary’s business partners later bought out his share of the company for $25,000.

Softkey

Once O’Leary sold his share of SET, he started Softkey in a basement in Toronto in 1986 with business partners Gary Babcock and John Freeman. Softkey published and distributed CD-ROM-based personal computer software for Macintosh and Windows computers.

A huge financial backer who agreed to invest $250,000 in development capital in Softkey backed out the day before delivering his check and signing the documents, which left O’Leary searching for funding to support his business. So, he used the money from his sale of his SET share and convinced his mother to loan him $10,000 as seed money to establish Softkey Software Products.

In the early 1980s, the personal computer and software industries were growing fast. O’Leary persuaded printer manufacturers to bundle Softkey programming with their hardware. By securing distribution, Softkey developed several educational software products with a focus on mathematics and reading education. Softkey usually consisted of software for home users, especially compilation discs with shareware and freeware games in jewel-case CD-ROMS.

Softkey saw significant success and weathered the competition from other software companies in the late 1980s. Softkey’s success continued through the 1990s and by 1993, the company was a major consolidator in the educational software industry and acquired rival companies like Spinnaker Software and WordStar. In 1995, Softkey acquired The Learning Company (TLC) for $606 million. Softkey adopted the Learning Company name and moved the company headquarters to Cambridge, Massachusetts.

In 2003, O’Leary became a director and co-investor at StorageNow Holdings, a Canadian developer of climate-controlled storage facilities. StorageNow Holdings was controlled by Asif Satchu and Reza Satchu. StorageNow eventually became the operator of storage services in Canada with locations in 11 cities. The company was acquired by Storage REIT in March 2007 for $110 million. O’Leary sold his company shares for $4.5 million, which were originally worth $500,000.

In May 2005, Reza Satchu and O’Leary’s operating partner, Wheeler, filed a wrongful dismissal lawsuit for $10 million, charging that they had changed an agreed-upon compensation deal and unlawfully reduced Wheeler’s portion of the profits. O’Leary and Satchu claimed that Wheeler failed to reach performance objectives. The case was settled out of court.

O’Leary became part of the advisory board of Genstar Capital in March 2007. Genstar Capital is a private equity company with a focus on healthcare services, investing, business services, industrial technology and software. Genstar appointed O’Leary to be part of the Strategic Advisory Board to look for new investment opportunities for the firm’s $1.2 billion fund.

In 2008, O’Leary cofounded O’Leary Funds Inc., a mutual fund company with a concentration on global yield investing. O’Leary is the lead investor and chairman of the company; his brother Shane O’Leary is the director. In 2011, the fund’s assets under management increased from $400 million to $1.2 billion in 2012. The primary management for the fund was Stanton Asset Management. Stanton Asset Management was a firm controlled by Connor O’Brien and Louise Ann Poirier, a husband and wife team.

Research by Mark R. McQueen indicates that O’Leary Funds, Inc increased distribution yield by returning invested capital to company shareholders. This is pretty standard, but it was contrary to O’Leary’s statements. An additional analysis found that one fourth of the distributions from one of O’Leary’s funds were capital returns.

In 2014, O’Leary Funds Management agreed to pay penalties to Autorite des marches financiers for not adhering to technical provisions pertaining to the Securities Act. At the time, O’Leary Funds reported taking steps to correct these violations. In 2015, O’Leary Funds was sold to Canoe Financial, a private investment-management firm owned by W. Brett Wilson, a Canadian businessman. Wilson worked with O’Leary before as an investor for CBC’s Dragons’ Den.

Books and Media

O’Leary released his first book, Cold Hard Truth: On Business, Money & Life in September 2011.

kevin oleary cold hard truth

In the book, he shares his views and the lessons he’s learned on starting a business, running a company, managing finances and navigating through life while achieving professional success.

O’Leary wrote a sequel to the book, The Cold Hard Truth on Men, Women and Money: 50 Common Money Mistakes and How to Fix Them in 2012.

The book offered advice and pointers for financial education and literacy to help people achieve long-term wealth. In 2013, O’Leary released a follow-up book where he discusses subjects pertaining to monumental life choices like marriage, family, career, retirement and education. He covers the challenges of raising a family while working to ensure the family is financially secure and provides advice for teaching family members financial literacy.

book 3

The book also provides helpful advice on investing and saving money and managing credit and debt.

Media

O’Leary appeared as one of the five venture capitalists on Dragon’s Den on CBC in 2006.

dragons den

The show was the Canadian installment of the international show Dragons’ Den. O’Leary developed a reputation for being shrewd and aggressive. His tactics were overwhelming for some contestants.

One contestant even started crying on the show, and O’Leary responded with “Money doesn’t care. Your tears don’t add any value.” Stuart Coxe, the producer of Dragon’s Den, encouraged O’Leary to be abrasive and even asked O’Leary to be “more evil” to add entertainment value to the show. Dragon’s Den became one of the most successful shows in the history of CBC – about two million people watched per episode. Coxe stated that O’Leary’s persona significantly contributed to the success of the show.

The American version of Dragon’s Den, Shark Tank, began in 2009. The executive producer of the show, Mark Burnett, invited Robert Herjavec and Kevin O’Leary, two Dragon’s Den investors to make guests appearances on Shark Tank. O’Leary and Herjavec have remained a part of Shark Tank. For years, the two men appeared on both Shark Tank and Dragon’s Den. Eventually, Herjavec left Dragon’s Den in 2012; O’Leary left Dragon’s Den in 2014. Shark Tank became a huge hit, with about 9 million people tuning in per episode during its peak 2014-15 season. Shark Tank also won the Primetime Emmy Award for Outstanding Structured Reality Program three times.

O’Leary’s appearances on Shark Tank and Dragon’s Den popularized his “Mr. Wonderful” nickname. Fans often refer to him by the nickname in public. O’Leary has stated that “Mr. Wonderful” is a tongue-in-cheek nickname because he has a reputation for being mean. The nickname also reflects the fact that his straightforward approach has helped several entrepreneurs achieve success. O’Leary stated in 2013 that he didn’t remember how he got the nickname, but he was recorded referring to himself as “Mr. Wonderful” in a casting video for Dragon’s Den in 2006.

Due to his blunt personality, O’Leary has also gained a reputation on both Dragon’s Den and Shark Tank for taking business deals that involve him loaning business owners money in exchange for a percentage of revenue instead of being a company shareholder.

O’Leary has been involved in several notable business deals, such as Talbott Teas, which was later purchased by Jamba Juice. O’Leary was also involved in GrooveBook (Groovewallet likes this name 😀 ), a company that was later acquired by Shutterfly. O’Leary participated in the GrooveBook deal with fellow Shark Tank host Mark Cuban. Kevin O’Leary has a holding company, “Something Wonderful,” reserved for managing his Dragon’s Den and Shark Tank investments.

Personal Life

Kevin O’Leary has been married to his wife, Linda since 1990.

linda oleary

In 2011, the couple separated, but they reconciled in 2013. Linda is now the VP of Marketing for O’Leary Wines. The couple has two children, Trevor and Savannah. Trevor is a DJ and music producer and Savannah is a multimedia producer for the Huffington Post. O’Leary stated in an Inc. Magazine interview with Brian D. Evans that “in a successful growing business, it eats your time alive.” O’Leary also states that when you put in hard work, you can provide things for your family that many others won’t be able to experience. He shares that “because you sacrificed, you’re then given the reward of freedom.”

kevin oleary kids

O’Leary’s primary tax residency and main home is in Toronto, Ontario. He also has a cottage in Muskoka and homes in Geneva, Switzerland and Boston, Massachusetts. He has also maintained his passion for photography and has sold several prints of his photographs to donate the proceeds to charity.

Kevin O’Leary Net Worth

As of 2019, Kevin O’Leary’s total net worth is estimated to be $400 million.