35 Kevin O'Leary Quotes from the Erudite Businessman

There isn't anything quite like the business industry, with its constant evolution and applicability to every other sphere of work. But if there's one man who appears to know all the tricks of the trade, it's millionaire investor and entrepreneur Kevin O'Leary.

Kevin O'Leary was born in July 1954 in Montreal, Quebec, Canada. He holds two degrees, a Bachelor's in Environmental Studies from the University of Waterloo and an MBA from Western University.

One of the first companies he founded was the TV production agency Special Event Television, which aired sports programs. He branched off to software in 1983, co-founding SoftKey Software Products, Inc., which produced digital educational material.

Today, he is not only an entrepreneur and investor, but O'Leary is also a TV personality, best known as a panelist on "Dragon's Den" and "Shark Tank." When it comes to how he reached success and maintained it, O'Leary has been quite frank about his business philosophies.

However, it is worth noting that they came about due to his acknowledgment of what worked and what didn't and some introspection. So, for a snippet of his wisdom, his opinions, and observations, enjoy this collection of his quotes below.

A photo with Kevin O'Leary's quote, "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." | Source: Amodays

Kevin O'Leary Makes His Money Work For Him

"I like to take risks. That's how I make money. But they are calculated risks." — Kevin O'Leary

"I'm not trying to make friends, you want a friend? Buy a dog. I'm trying to make money." — Kevin O'Leary

"Life is hard, money doesn't care, your tears don't add value." — Kevin O'Leary

"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." — Kevin O'Leary

"Money is my military, each dollar a soldier. I never send my money into battle unprepared and undefended." — Kevin O'Leary

A photo with Kevin O'Leary's quotes, "Money equals freedom." | Source: Amodays

"Money has no grey areas. You either make it or you lose it." — Kevin O'Leary

"Don't cry about money, it never cries for you." — Kevin O'Leary

"Money equals freedom." — Kevin O'Leary

Kevin O'Leary on How He Goes about His Business

"Business is war. I go out there, I want to kill the competitors. I want to make their lives miserable. I want to steal their market share. I want them to fear me and I want everyone on my team thinking we're going to win." — Kevin O'Leary

"I'd rather invest in an entrepreneur who has failed before than one who assumes success from day one." — Kevin O'Leary

A photo with Kevin O'Leary's quote, "When I start something, I bring my A-game – I assume I'm going to win." | Source: Amodays

"I want to go to bed richer than when I woke up. The pursuit of wealth is a wonderful thing, but the thing is you have to be honest about it, you have to tell the truth." — Kevin O'Leary

"When I start something, I bring my A-game – I assume I'm going to win." — Kevin O'Leary

"I keep a constant diary of where I'm at and why I'm there." — Kevin O'Leary

Kevin O'Leary's Observations and Advice on Navigating the Corporate World

"It pains me to see good entrepreneurs chase bad opportunities." — Kevin O'Leary

"Nobody has a monopoly on good ideas." — Kevin O'Leary

A photo with Kevin O'Leary's quote, "In order to create wealth, I needed to pair up with people whose strengths compensated for my weaknesses." | Source: Amodays

"I've probably heard more than 10,000 pitches… and truth be told, most of them sucked." — Kevin O'Leary

"There is a discipline required as an entrepreneur about working to optimize the business. There is no balance in life as an entrepreneur." — Kevin O'Leary

"The definition of leadership is that you have to find great people and ask them to do extraordinary things. I've been doing that my whole life." — Kevin O'Leary

"In order to create wealth, I needed to pair up with people whose strengths compensated for my weaknesses." — Kevin O'Leary

"When you're an investor, you can look at the quantitative and qualitative elements of an investment, but there's a third aspect: What you feel in your gut." — Kevin O'Leary

A photo with Kevin O'Leary's quote, "I love feel-good moments but we have to get back to reality here." | Source: Amodays

"If you can't even acknowledge your failures, how can you cut the rope and move on?" — Kevin O'Leary

"I love feel-good moments but we have to get back to reality here." — Kevin O'Leary

"Whatever you pay attention to grows!" — Kevin O'Leary

"So much of life is a negotiation – so even if you're not in business, you have opportunities to practice all around you." — Kevin O'Leary

"We need physical exercise to prepare our brain for long periods of concentration." — Kevin O'Leary

A photo with Kevin O'Leary's quote, "Don't let the dark clouds of greed confuse you." | Source: Amodays

"Do you want to be rich or not? Let's get focused on that, buddy." — Kevin O'Leary

"Don't let the dark clouds of greed confuse you." — Kevin O'Leary

"Downturns are the best time to start businesses, because you develop discipline that's very lean and mean in terms of how to spend money. And those habits serve you very well in good times." — Kevin O'Leary

"The biggest mistake entrepreneurs can make is trying to do everything themselves. They usually blow up when they try. I did an inventory of every deal I've ever done and it turned out that every single deal I made money on was a partnership, and every colossal failure, where I lost millions, was something I tried to do by myself." — Kevin O'Leary

"Know everything about the companies and people you are going to be negotiating with. Insist on getting the names of everyone participating in the negotiations. Leave no stone unturned; find out as much as you can." — Kevin O'Leary

A photo with Kevin O'Leary's Quote, "I have had some great successes and great failures. I think every entrepreneur has. I try to learn from all of them." | Source: Amodays

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"I have met many entrepreneurs who have the passion and even the work ethic to succeed – but who are so obsessed with an idea that they don't see its obvious flaws. Think about that." — Kevin O'Leary

"What are the most important qualities that make a successful entrepreneur? The ability to communicate. The ability to express your idea with certainty. That's how you become a leader even if you are unsure, your ability to explain your vision and your direction is the attribute you need the most. Articulate your idea in 90 seconds or less." — Kevin O'Leary

"I have had some great successes and great failures. I think every entrepreneur has. I try to learn from all of them." — Kevin O'Leary

"The road to riches is never straight and narrow. It can be riddled with financial land mines." — Kevin O'Leary

"The biggest mistake entrepreneurs can make is trying to do everything themselves. They usually blow up when they try. I did an inventory of every deal I've ever done and it turned out that every single deal I made money on was a partnership, and every colossal failure, where I lost millions, was something I tried to do by myself." — Kevin O'Leary

A photo with Kevin O'Leary's quote, "The road to riches is never straight and narrow. It can be riddled with financial land mines." | Source: Amodays

O'Leary continues to make his money soldiers work for him, much like Jeremy Clarkson and former actor David Collins; however, he's only one of many millionaires to draw inspiration from. For more advice on the right business tactics, read these Bobby Axelrod quotes.