30 Inspirational Kevin O’Leary Quotes About Business & Success

Kevin O’Leary is a Canadian businessman, author, and television personality. He co-founded O’Leary Funds and SoftKey.  

O’Leary has appeared on business news programs ‘SqueezePlay and The Lang’ and ‘O’Leary Exchange’, as well as the reality television show ‘Dragons’ Den and Redemption Inc’.In 2008, he appeared on Discovery Channel’s ‘Project Earth’, and since 2009 he has appeared on’ Shark Tank’.

Here’s a collection of the most inspirational Kevin O’Leary quotes about business and success:


30 Inspirational Kevin O’Leary Quotes

1. “Here’s how I think of my money, as soldiers, I send them out to war every day. I want them to take prisoners and come home, so there’s more of them.” – Kevin O’Leary

2. “I like to take risks. That’s how I make money. But they are calculated risks.” – Kevin O’Leary

3. “I’m not planning on giving my kids any of my wealth. They know when their education is over, I’m pushing them out of the nest. The bird you see dead under the nest is the one who didn’t think about the future.” – Kevin O’Leary

4. “Money equals freedom.” – Kevin O’Leary

5. “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

6. “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

7. “I keep anywhere between 5 to 10 percent of my net worth in venture ideas.” – Kevin O’Leary

8. “I’m not a tough guy. I’m just delivering the truth and only the truth and if you can’t deal with it, too bad.” – Kevin O’Leary

9. “It pains me to see good entrepreneurs chase bad opportunities.” – Kevin O’Leary

10. “We need physical exercise to prepare our brain for long periods of concentration.” – Kevin O’Leary


11th of 30 Kevin O’Leary Quotes 

11. “You’d rather own gold; not the miner.” – Kevin O’Leary


12. “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

13. “I keep a constant diary of where I’m at and why I’m there.” – Kevin O’Leary

14. “I’d rather invest in an entrepreneur who has failed before, than one who assumes success from day one.” – Kevin O’Leary

15. “If you can’t even acknowledge your failures, how can you cut the rope and move on?” – Kevin O’Leary

16. “Nobody forces you to work at Wal-Mart. Start your own business! Sell something to Wal-Mart!” – Kevin O’Leary

17. “There’s only one side with me You get the right side. You get the correct version of the facts.” – Kevin O’Leary

18. “Working 24 hours a day isn’t enough anymore. You have to be willing to sacrifice everything to be successful, including your personal life, your family life, maybe more. If people think it’s any less, they’re wrong, and they will fail.” – Kevin O’Leary


19th of 30 Kevin O’Leary Quotes 

19. “Building fast-growing globally competitive companies is tough.” – Kevin O’Leary


20. “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

21. “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 you have to be honest about it, you have to tell the truth.” – Kevin O’Leary

22. “I’m starting to think about things that I want to do, things that are fun.” – Kevin O’Leary

23. “Money is my military, each dollar a soldier. I never send my money into battle unprepared and undefended. I send it to conquer and take currency prisoner and bring it back to me.” – Kevin O’Leary

24. “There is a discipline required as an entrepreneur about working to optimize the business. There is no balance in life as an entrepreneur. You can’t expect to work 9 to 5 that’s never going to happen. You have to expect that it is going to consume your life for a period of time. That’s the downside, but the upside is that you buy yourself freedom in perpetuity.” – Kevin O’Leary

25. “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

26. “Being an employee is a bad outcome. You want to avoid that. Being an employee is never a good outcome. That’s just an opinion.” – Kevin O’Leary

27. “I don’t mind rude people. I want people that I can make money with, so if their executional abilities are good, and they’re arrogant and rude, I don’t care.” – Kevin O’Leary 


28th of 30 Kevin O’Leary Quotes 

28. “I think a book is your calling car, your business card.” – Kevin O’Leary


29. “I’m not trying to make friends, you want a friend? Buy a dog. I’m trying to make money.” – Kevin O’Leary

30. “Money has no grey areas. You either make it or you lose it.” – Kevin O’Leary



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