Kevin O’Leary

About Kevin O’Leary

Terence Thomas Kevin O’Leary was born on July 9, 1954, in Montreal, Quebec, Canada, to Georgette and Terry O’Leary.^[2] He is of Irish and Lebanese descent, with his father being a salesman and his mother working in a small business.^[3] After O’Leary’s father died when he was seven years old, his mother married George Kanawaty, who worked for the UN’s International Labour Organization. Because of Kanawaty’s work, the family moved around frequently, and O’Leary lived in Cambodia, Ethiopia, Tunisia, and Cyprus as a child.^[4]  

O’Leary attended Stanstead College and, later, St. George’s School.^{[5] [6]} He went on to earn a bachelor’s degree in environmental studies and psychology from the University of Waterloo in 1977 and an MBA in entrepreneurship from the Ivey Business School at Western University in 1980.^[7]

Career

O’Leary’s career began at Nabisco as an intern while he was working on obtaining an MBA. After the internship, he stayed with the company as an assistant brand manager.^[8] After leaving Nabisco, O’Leary started his first company with two former MBA classmates. The company, Special Event Television (SET), produced original sports programming. He eventually sold his share in the business for $25,000.^[9] 

O’Leary has founded several companies, including O’Leary Ventures and O’Leary Fine Wines.^{[10] [11]} He also entered the real estate industry in 2013 when he opened O’Leary Mortgages.^[12] 

Kevin O’Leary started Softkey Software Products, the company that would make him a well-known name in the business world, in the basement of his Toronto home in 1986 with John Freeman and Gary Babcock.^[13] 

Softkey specialized in producing educational and family software. While the business initially had funding from an investor, the investor backed out at the last minute. Because of this, O’Leary had to use his money from the sale of his shares in SET, plus $10,000 he borrowed from his mother.^[14]  

Softkey grew through a hostile takeover approach. The company bought multiple competitors out, including Compton’s New Media, The Learning Company, and Broderbund.^[13] Softkey eventually acquired The Learning Company (TLC) in 1995 and adopted its name.^[15]   

In 1999, Mattel purchased TLC for around $4 billion.^[16] The acquisition turned out to be disastrous for the toy company and wiped out $3 billion in shareholder value in one day.^[17]   

In 2003, O’Leary co-founded StorageNow Holdings, a Canadian developer of climate-controlled storage facilities. The company was a pioneer in using innovative technologies to optimize storage space and reduce operating costs. In 2007, StorageNow was sold to InStorage REIT for $110 million.^[18]   

In 2008, O’Leary co-founded O’Leary Funds, an investment fund company with a value-yield approach. In 2015, Canoe Financial acquired O’Leary Funds.^[19] O’Leary then shifted his focus to O’Leary Financial Group, a group of brands and services.^[20]   

O’Leary became a strategic partner in the decentralized finance platform DeFi Ventures in 2021. The company then renamed itself WonderFi Technologies, a reference to O’Leary’s nickname, “Mr. Wonderful.”^[21]   

Later in 2021, O’Leary became a spokesperson for and partial owner of the cryptocurrency platform FTX.^[22] When the company went bankrupt, O’Leary was sued in a class-action lawsuit that claimed anyone promoting fraudulent cryptocurrency was liable, whether or not they had plausible deniability.^[23]  

Media Ventures

O’Leary first gained widespread attention as a television personality on the Canadian reality show, Dragon’s Den, where entrepreneurs pitch their business ideas to a panel of investors known as “dragons.” He appeared on the show from 2006 to 2014.^[24] He became known for his blunt and abrasive personality on the show. Dragon’s Den grew in popularity, eventually reaching around two million viewers per episode.^[25]   

In 2009, O’Leary joined the U.S. version of Dragon’s Den, Shark Tank, as one of the “sharks.”^[24] Shark Tank quickly surpassed Dragon’s Den in viewership, reaching over 7 million viewers per episode by 2015.^[26] O’Leary’s nickname, Mr. Wonderful, became widely used due to his appearances in Dragon’s Den and Shark Tank.^[27]  

From 2012 to 2014, O’Leary co-hosted The Lang and O’Leary Exchange, a daily business news show on CBC.^[24] In 2012, O’Leary was the co-producer and host of the reality show Redemption Inc., a show in which ex-convicts competed for investment funding from O’Leary. The show lasted one season.^[28] He has also worked as a co-host of Discovery Channel’s Discovery Project Earth and as the co-host of Bell Media’s Squeezeplay.^{[29] [30]}  

In 2019, O’Leary started the YouTube series Chef Wonderful where he shares his insights on fine dining and food.^[31] He also is a regular contributor on ABC, CNBC, and CTV, where he shares business and personal finance tips.^[32] . 

Books by Kevin O’Leary

O’Leary has written six books, four of which belong to the Cold Hard Truth Series. In 2017, he branched out and published a mystery novel. Here’s a complete list of his published books to date. 

• Cold Hard Truth: On Business, Money & Life (2011)
• Cold Hard Truth on Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them (2012)
• Cold Hard Truth on Family, Kids and Money (2013)
• Cold Hard Truth on Marriage and Money: Part Two of Cold Hard Truth on Family, Kids and Money (2015)
• The Balboa Boys and the Mystery of the Big Gyp (2017)
• Digital Pivot or Bust In a Post COVID-19 World: Why Small Businesses Must Re-Think Everything to Survive and Thrive! (2020)

Political Campaign

In January 2017, Kevin O’Leary announced his candidacy for the leadership of the Conservative Party of Canada.^[33] His campaign focused on economic growth, job creation, and lowering taxes. However, in April 2017, he withdrew from the race, citing a lack of support in Quebec and concerns about his ability to win a general election. O’Leary eventually endorsed Maxime Bernier for leadership.^[34] 

O’Leary’s political positions include supporting lower taxes, reducing government regulations, and fostering entrepreneurship.^[35] He has also proposed a fast track to citizenship for skilled immigrants as a way to boost Canada’s economy.^[36]

Kevin O’Leary Quotes

•  “Money has no grey areas. You either make it, or you lose it.”^[37] 
• “Business is war. I go out there. I want to kill the competitors. I want to make their lives miserable.”^[37] 
• “So much of life is a negotiation—so even if you’re not in business, you have opportunities to practice all around you.”^[38] 
• “I’d rather invest in an entrepreneur who has failed before than one who assumes success from day one.”^[37] 
• I actually think being an entrepreneur is a state of mind. If you’re going to be an entrepreneur, my thesis is that you have to sacrifice everything for some period in your life to be successful. You have to be myopic and completely focused and unbalanced in every way. Once you’ve achieved success, you’re free to do whatever you like.^[24] 

Personal Life

Kevin O’Leary is married to Linda O’Leary, and they have two children. Linda is an accomplished entrepreneur and philanthropist, running the O’Leary Fine Wines business with her husband.^[39] 

Kevin O’Leary Today

Today, Kevin O’Leary continues his career as an investor and television personality, sharing his business expertise and advice with entrepreneurs and viewers. He remains actively involved in various ventures, including his wine business, O’Leary Fine Wines, and his investment company, O’Leary Ventures. He currently lives in West Palm Beach, Florida, with his wife.^[40]