The character arc of Kevin O'Leary

A life drawn by Character Arc from the public record

Born on 9 July 1954 in Montreal. Between then and now sit a Waterloo degree in 1977, an internship at Nabisco in 1978, an Ivey MBA in 1980, SoftKey started in a Toronto basement in 1986, consolidation from 1993, The Learning Company acquired in 1995 for 606 million dollars, a loss of 105 million in 1998, the Mattel sale in 1999 for 4.2 billion, a settlement in 2003, StorageNow sold in March 2007, O'Leary Funds in 2008 and a film debut in 2025. The line below draws the story so far, in order.

Tap the line to pluck it. Hover or tap any mark for its card. Drawn from the public record of his life; the sources are at the foot of the page.

Who is Kevin O'Leary?

It started in a basement.

He was born in Montreal in 1954, one of two sons of Georgette, a small business owner and investor of Lebanese descent, and Terry O'Leary, a salesman of Irish descent. 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 the Ivey Business School in 1980. Between the two years of the MBA, in 1978, he took an internship at Nabisco and worked as an assistant brand manager on a cat food brand.

In 1986 he started SoftKey in a Toronto basement with the business partners John Freeman and Gary Babcock. By 1993 it had become a major consolidator in educational software, buying rivals including WordStar and Spinnaker Software. In 1995 it acquired The Learning Company for 606 million dollars, took its name, and moved its headquarters to Cambridge, Massachusetts. It bought its former rival Broderbund in June 1998 for 416 million dollars.

The same year it lost 105 million dollars on revenues of 800 million, following losses over the previous two years. In 1999 Mattel acquired the company for 4.2 billion dollars, a result many financial observers had not expected from a business they had regarded sceptically. A lawsuit followed and Mattel paid 122 million dollars to settle it in 2003. He became a co-investor and corporate director at StorageNow Holdings in 2003, which became the largest storage operator in Canada and was acquired in March 2007 for 110 million dollars; joined the advisory board of Genstar Capital in March 2007; and co-founded O'Leary Funds in 2008, whose assets under management grew from 400 million dollars in 2011 to 1.2 billion in 2012. He appeared on Canadian television from 2004, on Shark Tank since 2009, and made his feature film debut in 2025.

The moments

Kevin O'Leary's timeline.

The 1970s

Jun 1977

Waterloo, with honours

Milestone, and it changed his direction. Environmental studies and psychology, which is not a business degree.

Jun 1978

A cat food brand

Milestone. Assistant brand manager, cat food, one summer.

The 1980s

Jun 1980

An MBA at Ivey

Milestone, and it changed his direction. An MBA in entrepreneurship, six years before he started anything.

1 Jun 1985

Use the MBA, or start something

Crossroads, decided.

The paths laid out: start it in the basement, taken, or take the corporate job. SoftKey acquired The Learning Company in 1995 and Mattel acquired the company in 1999 for 4.2 billion dollars.

Jun 1986

SoftKey, in a basement

Milestone, and it changed everything. A basement in Toronto, and two partners.

The 1990s

Jun 1993

It began buying rivals

Milestone, and it changed everything. Seven years from a basement to buying the competition.

Jun 1995

Six hundred million dollars

Milestone, and it changed everything. It bought a bigger name and took it.

Jun 1998

A hundred and five million lost

Setback, and it changed everything. Buying a rival for 416 million in the year it lost 105 million.

Jun 1999

Mattel buys it

Milestone, and it changed everything. Four point two billion dollars, from a toy company.

The 2000s

Jun 2003

The settlement

Setback, and it changed his direction. A hundred and twenty two million dollars, to make it end.

Mar 2007

StorageNow sold

Milestone, and it changed his direction. Climate-controlled storage, in eleven cities, sold for a hundred and ten million.

Jun 2008

O'Leary Funds

Milestone, and it changed everything. Four hundred million to one point two billion, in a year.

9 Aug 2009

Shark Tank

Milestone, and it changed his direction. The same format, in two countries, for two decades.

The 2020s

25 Dec 2025

A feature film debut

Milestone. An acting debut at seventy one.

The line reaches today still adding to itself, which is why it is drawn now rather than at the end. What it has set moving is the distance between two numbers: a basement in 1986, and four point two billion dollars in 1999, with a hundred and five million dollar loss drawn in between them.

Your turn

Every line draws a unique story.

His began in a basement with two partners and a cat food internship behind him. Yours is already further along than you think, and drawing it takes about five minutes.

Step through

Draw my own line Explore Character Arc

Kevin O'Leary: frequently asked questions

What people ask about his line.

What is Kevin O'Leary's character arc?

A degree in environmental studies and psychology, an MBA in entrepreneurship, and a software company started in a Toronto basement in 1986. It bought its rivals, took the name of one of them in 1995, and Mattel acquired it in 1999 for 4.2 billion dollars.

How did Kevin O'Leary make his money?

He started SoftKey in a Toronto basement in 1986 with John Freeman and Gary Babcock. It consolidated the educational software market, acquired The Learning Company in 1995 for 606 million dollars and took its name, and Mattel acquired it in 1999 for 4.2 billion dollars.

What went wrong at Kevin O'Leary's Learning Company?

It lost 105 million dollars in 1998 on revenues of 800 million, after losses over the previous two years, in the same year it bought its former rival Broderbund for 416 million. A lawsuit followed the Mattel sale and was settled in 2003 for 122 million dollars.

What did Kevin O'Leary study?

An honours bachelor's degree in environmental studies and psychology at the University of Waterloo in 1977, and an MBA in entrepreneurship at the Ivey Business School in 1980. Between the two MBA years he interned at Nabisco on a cat food brand.

What is O'Leary Funds?

A mutual fund management firm focused on global yield investing that Kevin O'Leary co-founded in 2008. Its assets under management grew from 400 million dollars in 2011 to 1.2 billion dollars in 2012.

How long has Kevin O'Leary been on television?

He appeared on Canadian shows including Dragons' Den from 2004 to 2014, hosted Project Earth in 2008, and has appeared on Shark Tank since 2009. He made his feature film debut as Milton Rockwell in Marty Supreme in 2025.

Did Kevin O'Leary invest in storage?

Yes. In 2003 he became a co-investor and corporate director at StorageNow Holdings, a Canadian developer of climate-controlled storage. It became the largest storage operator in Canada, in eleven cities, and was acquired in March 2007 for 110 million dollars.

Where does this timeline of Kevin O'Leary's life come from?

From the public record. Character Arc drew every moment on this line from the sources listed at the foot of the page, and the kind and weight of each moment are our editorial reading. Kevin O'Leary isn't a Member of Character Arc and has no connection with it, and no feeling is attributed to him.

More character arcs

Lives that rhyme with his.

Every Character, A to Z

Sources

Kevin O'Leary, English Wikipedia biography, filed under living people.
Mattel acquisition of The Learning Company, 1999, and the settlement of 2003.
University of Waterloo and Ivey Business School degree records, 1977 and 1980.