Top 70 Kevin O'Leary Quotes (2024 Update)

1. “I’m not trying to make friends, I’m trying to make money.”

— Kevin O'Leary

2. “Money equals freedom.”

— Kevin O'Leary

3. “Vision is nothing without a plan to execute it.”

— Kevin O'Leary

4. “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

5. “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

6. “Nobody has a monopoly on good ideas.”

— Kevin O'Leary

7. “Don’t cry about money, it never cries for you.”

— Kevin O'Leary

8. “Life is hard, money doesn’t care, your tears don’t add value.”

— Kevin O'Leary

9. “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

10. “If you want a friend, buy a dog.”

— Kevin O'Leary

11. “We need physical exercise to prepare our brain for long periods of concentration.”

— Kevin O'Leary

12. “You may lose your wife, you may lose your dog, your mother may hate you. None of those things matter. What matters is that you achieve success and become free. Then you can do whatever you like.”

— Kevin O'Leary

13. “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

14. “Do you want to be rich or not? Let’s get focused on that, buddy.”

— Kevin O'Leary

15. “You’d rather own gold; not the miner.”

— Kevin O'Leary

16. “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

17. “Don’t let the dark clouds of greed confuse you.”

— Kevin O'Leary

18. “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

19. “I never, ever, ever let emotion get in the way of an investment.”

— Kevin O'Leary

20. “The only reason to do business is to make money; that’s the only reason for doing business.”

— Kevin O'Leary

21. “Nobody forces you to work at Wal-Mart. Start your own business! Sell something to Wal-Mart!”

— Kevin O'Leary

22. “Money has no grey areas. You either make it or you lose it.”

— Kevin O'Leary

23. “All businesses require capital, management and labor, and business executives, wanting to grow and maintain profitable enterprises, have a strong incentive to keep costs, including labor, as low as possible.”

— Kevin O'Leary

24. “I think a book is your calling card, your business card.”

— Kevin O'Leary

25. “If I were the president of the United States, I would make unions illegal. They no longer serve a functional purpose in democracy, in my view.”

— Kevin O'Leary

26. “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

27. “If a man could give birth it would be to a book – it’s an 18-month gestation period.”

— Kevin O'Leary

28. “The road to riches is never straight and narrow. It can be riddled with financial land mines.”

— Kevin O'Leary

29. “I’d rather invest in an entrepreneur who has failed before than one who assumes success from day one.”

— Kevin O'Leary

30. “I do not own a single security anywhere that doesn’t pay a dividend, and I formed a mutual-fund company with that very simple philosophy.”

— Kevin O'Leary

31. “There are a lot of impractical things about owning a Porsche. But they’re all offset by the driving experience. It really is unique. Lamborghinis and Ferraris come close. And they are more powerful, but they don’t handle like a Porsche.”

— Kevin O'Leary

32. “You can’t regulate a soul into a business.”

— Kevin O'Leary

33. “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

34. “I’m starting to think about things that I want to do, things that are fun. One of them is driving a car like a Porsche. I’ve driven a lot of cars – sedans, trucks and big family vehicles all year long. But there’s nothing like a four-wheel-drive Porsche.”

— Kevin O'Leary

35. “Unions are about the collective leverage, the power of numbers versus the power of capital.”

— Kevin O'Leary

36. “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

37. “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

38. “There’s only one side with me. You get the right side. You get the correct version of the facts.”

— Kevin O'Leary

39. “You either make it illegal, in which case you support a huge underground economy or you tax it within the limits people can afford.”

— Kevin O'Leary

40. “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. If you can’t even acknowledge your failures, how can you cut the rope and move on?”

— Kevin O'Leary

41. “I remember failing reading in school at a young age, and you just kinda get left behind and I felt helpless.”

— Kevin O'Leary

42. “Steve Jobs had his critics. Some saw him as an egomaniac, and others, as a control freak.”

— Kevin O'Leary

43. “There are a lot of idiot fund managers out there who add no value to the process at all.”

— Kevin O'Leary

44. “When you’re travelling, your day is jam-packed. I just don’t have time to whip out a PC all the time. But I can whip out a BlackBerry and tweet. I keep a constant diary of where I’m at and why I’m there.”

— Kevin O'Leary

45. “I’m proud to be on the CBC and to see the management here represents both sides of every story. This is what’s unique about the new CBC: you get a Kevin O’Leary on it when five years ago you wouldn’t.”

— Kevin O'Leary

46. “Television is the most interesting hobby I’ve ever had.”

— Kevin O'Leary

47. “Once in a while, I see my fellow TV investors praise a business just because they like the entrepreneur behind it. That kind of thinking might make you feel warm and fuzzy inside – but let’s get back to reality.”

— Kevin O'Leary

48. “I could have easily gone down the wrong path and dropped out of school, but I was given a second chance.”

— Kevin O'Leary

49. “For whatever reason somebody can be convinced to buy a PC, it opens up a whole new market for all of us in the software business.”

— Kevin O'Leary

50. “I think every entrepreneur in Canada owes the next generation a road map of how to do it again.”

— Kevin O'Leary