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Kevin O’Leary

Kevin O’Leary: Success Story of Dyslexic Kid becoming Billionaire

Kevin O’Leary, also known as “Mr. Wonderful,” is a Canadian entrepreneur, businessman, and television personality. O’Leary was a co-founder of SoftKey Software Products, a tech business that offered software for family entertainment and education. 

Kevin O'Leary
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Early Life

In 1954, Kevin O’Leary was born into a middle-class household. His mother was a skilled investor. Most of Kevin’s business insight comes from his mother. She gave him important financial and economic lessons at a young age. These ideas were Kevin’s guiding principles and the cornerstones on which he eventually construct his empire.

Kevin O’Leary experienced additional difficulties in school when he was growing up due to dyslexia. When O’Leary was a student at St. George’s School, his dyslexia started to hinder his academic performance. He had trouble reading and doing simple addition and multiplication problems.

He had to use supplemental tools to keep up with the learning content because his teachers did not assist him as they were unaware of his dyslexia. While pursuing MBA, O’Leary interned for Nabisco. O’Leary started a short-lived stint as a TV producer after leaving Nabisco. He co-founded Special Event Television(SET) with two of his fellow MBA classmates.

SET produced original sports programs as a freelance television production firm. With small television programs, soccer movies, sports documentaries, and quick intermission ads for nearby professional hockey games, the company had only little success. Later, for $25,000, one of the partners bought out Kevin’s portion of the business.

Success Story

In 1986, O’Leary established Softkey in a Toronto basement with partners Gary Babcock and John Freeman.SoftKey made hostile takeover approaches to buy competing businesses in the late 1980s and early 1990s, including Compton’s New Media, The Learning Company, and Broderbund. Later, SoftKey changed its name to The Learning Company.

Softkey’s well-known position in the software sector finally aided “Mr. Wonderful” in becoming a millionaire. In 1999, Mattel recognized the software company’s absolute supremacy in the market and decided to acquire Softkey for an astounding $4.2 billion. 

In 2003 he joined “StorageNow Holdings,” a company that builds climate-controlled storage facilities, as a Director and co-investor. In 2007, the company was acquired by InStorage REIT for a staggering $110 million. O’Leary sold his shares in the company, which had a starting value of $500,000, for close to $4.5 million.

After experiencing incredible success at his software firm, Kevin began appearing on television. He soon established himself as a popular host and personality on a variety of programs, including CBC’s Dragons’ Den and Shark Tank.

Later he took control of his capital from his unreliable money managers and established his own mutual fund business, O’Leary Funds. Since then, Kevin has established O’Leary Fine Wines and a best-selling financial literacy book series.

In 2014, Kevin established the O’Leary Financial Group, a collection of companies and products that adhere to his core values of transparency, simplicity, convenience, and, excellent value.

Kevin O’Leary is a passionate supporter of environmental rights and makes an effort to invest in companies that share his views. He even co-hosts Project Earth on the Discovery Channel, a program dedicated to combating global warming. O’Leary also ran for the position of Canadian Conservative Party leader in 2017. Despite being in the lead, he withdrew one month prior to the election in April.

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