Kevin O'Leary

Kevin O'Leary - Quick Facts

Profile Overview of Kevin O'Leary

Terrence Thomas Kevin O'Leary (born July 9, 1954), self-styled as Mr. Wonderful, is a Canadian businessman and television personality. From 2004 to 2014, he appeared on various Canadian television shows, including the business news program The Lang and O'Leary Exchange as well as reality show Dragons' Den. O'Leary hosted Discovery Channel's Project Earth in 2008 and has appeared on Shark Tank, the American version of Dragons' Den, since 2009. He made his feature film debut as Milton Rockwell in Josh Safdie's Marty Supreme (2025).

This profile of Kevin O'Leary covers Early Life and Family Background, Business Ventures, Softkey, StorageNow Holdings and Other ventures.

O'Leary co-founded SoftKey Software Products, a technology company that sold software geared toward family education and entertainment. During the late 1980s and 1990s, SoftKey became a major consolidator in the global educational software market, having acquired rival companies via hostile takeover bids, such as Compton's New Media, the Learning Company, and Broderbund. SoftKey later changed its name to The Learning Company and was acquired by Mattel in 1999, surprising many financial observers, who viewed O'Leary's company as a house of cards. Nevertheless, the sale netted O'Leary around six million dollars. Mattel promptly fired O'Leary. The acquisition resulted in significant losses for The Learning Company and sparked multiple shareholder lawsuits targeting O'Leary's mismanagement.

In 2017, he campaigned to be the leader of the Conservative Party of Canada. He dropped out in April 2017, one month before the election, citing a lack of support in Quebec.

O'Leary holds Canadian, Irish and Emirati citizenship. He is a resident of Miami, Florida, United States of America.

Early Life and Family Background of Kevin O'Leary

O'Leary was born on 9 July 1954, in Montreal, one of two sons of Georgette (née Bookalam; Arabic: جورجيت بوكلام), a small-business owner and investor of Lebanese descent, and Terry O'Leary, a salesman of Irish descent. Kevin also has a brother, Shane O'Leary. Due to his paternal heritage, O'Leary also holds Irish citizenship and carries an Irish passport. O'Leary has dyslexia, which he argued helped him in the world of business by fostering out-of-the-box thinking.

O'Leary grew up in Mount Royal, Quebec. His parents divorced when he was a child, largely due to his father's alcoholism. His father died shortly after that, when O'Leary was only seven. After his father's death, his mother ran the family's clothing business as an executive. His mother later married an economist, George Kanawaty, who worked with the UN's International Labour Organization. His stepfather's international assignments caused the family to move frequently, and O'Leary lived in many places while growing up, including Cambodia, Ethiopia, Tunisia, and Cyprus. In his youth, he met both Haile Selassie of Ethiopia and Pol Pot of Cambodia. O'Leary attended Stanstead College and St. George's School, both in Quebec.

O'Leary's mother was a skilled investor, investing a third of her weekly paycheque in large-cap, dividend-paying stocks and interest-bearing bonds, ultimately achieving high returns in her investment portfolio. She kept her investment portfolio secret, so O'Leary only discovered his mother's skill as an investor after her death when her will was executed. Many of his investment lessons came from his mother, including the admonition to save one-third of his money.

O'Leary had aspired to become a photographer, but on the advice of his stepfather, who prompted the young Kevin to be more realistic with his future career aspirations, decided to attend university, where he continued to develop his interest in business and investing since his youth. He received an honours bachelor's degree in environmental studies and psychology from the University of Waterloo in 1977 and an MBA in entrepreneurship from Ivey Business School at the University of Western Ontario in 1980.

Business Ventures of Kevin O'Leary

In 1978, between the first and second years of his MBA program, O'Leary was selected for an internship at Nabisco in Downtown Toronto and then worked as an assistant brand manager for Nabisco's cat food brand. O'Leary attributed his future business success at The Learning Company as a result of the extensive marketing skills that he honed during his assistant brand management days at Nabisco.

After leaving Nabisco, O'Leary began a brief career as a television producer. With two of his former MBA classmates, Scott Mackenzie and Dave Toms (both of whom had assisted on O'Leary's MBA documentary), O'Leary co-founded Special Event Television (SET). SET was an independent television production company that produced original sports programming such as The Original Six, Don Cherry's Grapevine, and Bobby Orr & The Hockey Legends. The company achieved limited success with minor television shows, soccer films, sports documentaries, and short in-between-period commercials for local professional hockey games. One of his partners later bought out his share of the venture for $25,000.

Softkey

After selling his SET share, O'Leary then proceeded to move on to his next business venture. He started SoftKey in a Toronto basement in 1986, along with business partners John Freeman and Gary Babcock. The company was a publisher and distributor of CD-based personal computer software for Microsoft Windows and Macintosh computers. A major financial supporter who had committed $250,000 in investment capital to finance O'Leary's company backed out the day before signing the documents and delivering his cheque, leaving O'Leary to go elsewhere to seek the necessary funding sources that he needed to support his fledgling business. Desperate to secure funding, O'Leary turned to using the proceeds that he gained from selling his SET share while also convincing his mother to lend him $10,000 in seed capital to establish SoftKey Software Products.

As the software and personal-computer industries were proliferating throughout the course of the early 1980s, O'Leary convinced printer manufacturers to bundle Softkey's program with their hardware. With distribution assured, the company developed several educational software products focused on mathematics and reading education. Softkey products typically consisted of software for home users, especially compilation discs containing various freeware or shareware games packaged in "jewel-case" CD-ROMs.

Softkey weathered stiff competition from other software companies in the late 1980s and prospered throughout the 1990s. By 1993, Softkey had become a major consolidator in the educational software market, acquiring rivals such as WordStar and Spinnaker Software in the process. In 1995, Softkey acquired The Learning Company (TLC) for $606 million, adopting its name, and moved its headquarters to Cambridge, Massachusetts.

TLC lost $105 million (US) in 1998 on revenues of $800 million and suffered losses over the previous two years. TLC bought its former rival Broderbund in June 1998 for $416 million.

Source: adapted from Wikipedia (https://en.wikipedia.org/wiki/Kevin_O%27Leary), text available under CC BY-SA 4.0.