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Money Management Center

Unforgettable Life Lessons From Shark Investor Kevin O'Leary

Calder Lamb Aug 25, 2015


While all the judges on the sixth season of Shark Tank are notable and entertaining in their own right, one character has emerged as the most memorable of them all: Kevin O’Leary, also known as Mr. Wonderful.

O’Leary has come to embody the very essence of a Shark, and when entrepreneurs come on the show to pitch their idea, it’s usually O’Leary’s valuations that make or break their deal. Several famous, educational, and humorous catchphrases have emerged from his snarky (sharky?) wit when analyzing Shark Tank contestants.


Notable O’Learyisms


  • “Money equals freedom.”
  • “Here’s how I think of my money – as soldiers – I send them out to war everyday. I want them to take prisoners and come home, so there’s more of them.”
  • “When you’re an investor, you can look a the quantitative and qualitative elements of an investment, but there’s a third aspect: what you feel in your gut.”
  • “If you want a friend, buy a dog.”

Even funnier still, check out these short compilations of a few of O’Leary’s shining moments on Shark Tank seasons one, two, and three.


O’Leary’s Shark Tank Moments


Season one of Shark Tank made a big splash because it was such a unique and personal piece of entertainment. There was drama, heartbreak, and dreams made or smashed. The show is packed with witty commentary and humorous squabbles, covered in a fine veener of entrepreneurial education.


By season two, the Sharks had a firm grip on their roles, and the crispness of the show clearly tightened. By that time, Shark Tank was clearly a national favorite and had struck entertainment gold.


In season three, the applicants actually have functioning companies instead of just ideas. The below compliation of O’Learyisms contains the quote I find most humorous:

“In life there are only a few moments that matter, and clearly this is one for you – you have a towel with a slit in it that someone is willing to offer you $75,000 for. Don’t screw it up.”


Outside the Shark Tank


Shark Tank is just one place where O’Leary hangs his hat. He also is featured on news and financial channels as an expert, and has been a keynote speaker at colleges as well as entrepreneurial education events.

O’Leary’s commentary is just provocative enough to be entertaining and thought provoking at the same time.

In the below video, O’Leary defends the capitalist system against Thomas Piketty’s popular book
Capital in the 21st Century with the CBC’s Amanda Lang. In part one of this great debate, Lang attempts to lampoon O’Leary against his right wing views, but her affronts are humorously parried by O’Leary.


In round two of this debate, O’Leary and Lang go head-to-head once again in a verbal sparring match. Both the interviewer and the interviewee are primed and ready for the hard hitting discusion that follows.


For a longer example, check out O’Leary speaking about entrepreneurial education at Notre Dame. The video is a long one, but the length illuminates O’Leary’s mindset as a Shark investor. He identifies the key metrics and stepping stones a young entrepreneur must complete in order to solicit institutional private equity investment.

Want to learn more about how O’Leary became the man he is today? Read our article From the Ice Cream Shop to the Shark Tank.

Follow O’Leary on his Twitter, Facebook, and Instagram pages, and check out his foundation.

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