Kevin O'Leary
Kevin O'Leary's success story starts where most entrepreneurs begin: with a big idea and zero cash. From his basement, he launched SoftKey Software Products. As sales took off, Kevin moved to headquarters in Cambridge, Massachusetts and went on an industry consolidating acquisition binge.

In 1999 Kevin sold his company to the Mattel Toy Company for a staggering 3.7 billion dollars, one of the largest deals ever done in the consumer software industry. To keep his money working hard, he took control of his wealth from his lackluster money managers and founded his own mutual fund company, O'Leary Funds. He raised hundreds of millions of dollars from investors who share his "get paid while you wait" yield oriented, value investing philosophy. As a star on Shark Tank and a regular contributor to ABC and CNBC, he shares his tips and tribulations with a national television audience and turns The Street upside down in the process.

He recently launched O’Leary Financial Group, a group of brands and products that share Kevin O’Leary’s guiding principles for business, including honesty, directness, and, above all, great value.

Kevin is also a bestselling author, photographer, guitarist, and wine expert!

You can follow Kevin on Twitter (@kevinolearytv), on Facebook ( or at

Entries by Kevin O'Leary

Dear Premier Wynne: I Would Have Fired You Long Ago

(162) Comments | Posted January 23, 2017 | 10:01 AM

Dear Premier Wynne,

Thank you for your letter. I have been writing you for a while now and was getting worried you were never going to write back.

I'm getting involved in the Conservative leadership race because I can't stand watching incompetent...

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Open letter to Ontario Premier Kathleen Wynne, Part 2

(566) Comments | Posted August 29, 2016 | 9:01 AM

Hi Premier Wynne,

I'm worried.

I asked you to keep me informed about the $1.9 billion you are extracting out of the Ontario economy in new carbon taxes. I was excited when you promised lots of new jobs and reductions in carbon emissions. Then I saw the July jobs report....

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An Open Letter from Kevin O'Leary to Premier Rachel Notley

(783) Comments | Posted March 4, 2016 | 11:52 AM

Hi Premier Notley,

How's it going? I don't think this is an unreasonable question given the situation we all find ourselves in Canada today.

First some facts:

Energy is the #1 export in Canada by miles; nothing even comes close. The second largest export is car and car...

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This Tax Tip Will Make You a Philanthropist and Stone-Cold Capitalist

(0) Comments | Posted December 7, 2014 | 8:54 PM

Everybody's heard the old saying, "It's better to give than to receive." I'd argue that it's even better to give and receive, and now it's possible by using a little-known tip that can help Canadians get back up to 78 cents for every dollar you donate to charity.

A lot...

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How to Win in Business Negotiations: Never Forget, it's All About the Money

(8) Comments | Posted December 6, 2011 | 8:55 AM

A lot of people have asked me for help on how to negotiate more effectively. Whether you're applying for a job, pitching to investors, or buying or selling anything, you need to know what you're doing. Thank goodness I'm here!

Know What You Want
Anything can happen in...

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Five Business Lessons From Steve Jobs

(21) Comments | Posted October 10, 2011 | 12:36 AM

A lot of people have said a lot of great things about Steve Jobs. And for good reason: he built the world's second-most valuable company, with billions in profits and products that have improved every aspect of our lives. But Steve didn't get there by being a soft, fluffy, Kumbaya-type...

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