73 Inspirational Kevin O’Leary Quotes on Entrepreneurship

Kevin O’Leary is a popular Canadian entrepreneur and TV personality known for Dragons’ Den and Shark Tank.

He earned a bachelor’s and an MBA from University of Waterloo and Western University, respectively.

O’Leary co-founded SoftKey Software Products in 1983, which later became The Learning Company and was sold to Mattel for $3 billion in 1999.

Kevin O'Leary

He also founded O’Leary Funds in 2008, sold in 2016. In 2017, he briefly ran for leadership of Canada’s Conservative Party, drawing comparisons to Donald Trump, before withdrawing from the race.

He has been a regular on TV programs such as Shark Tank.

Here are some of the inspirational quotes by Kevin O’Leary.

Inspirational Kevin O’Leary Quotes on Entrepreneurship

1. “You’d rather own gold; not the miner.” ~ (Kevin O’Leary).

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2. “Money equals freedom.” ~ (Kevin O’Leary).

3. “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).

4. “Don’t cry about money, it never cries for you.” ~ (Kevin O’Leary).

5. “I’m not trying to make friends, I’m trying to make money.” ~ (Kevin O’Leary).

6. “Nobody has a monopoly on good ideas.” ~ (Kevin O’Leary).

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7. “Life is hard, money doesn’t care, your tears don’t add value.” ~ (Kevin O’Leary).

8. “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).

9. “If you want a friend, buy a dog.” ~ (Kevin O’Leary).

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

11. “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).

12. “Vision is nothing without a plan to execute it.” ~ (Kevin O’Leary).

13. “Do you want to be rich or not? Let’s get focused on that, buddy.” ~ (Kevin O’Leary).

14. “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).

15. “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).

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16. “Don’t let the dark clouds of greed confuse you.” ~ (Kevin O’Leary).

Popular Kevin O’Leary Quotes

17. “I never, ever, ever let emotion get in the way of an investment.” ~ (Kevin O’Leary).

18. “Nobody forces you to work at Wal-Mart. Start your own business! Sell something to Wal-Mart!” ~ (Kevin O’Leary).

19. “The only reason to do business is to make money; that’s the only reason for doing business.” ~ (Kevin O’Leary).

20. “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).

21. “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).

22. “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).

23. “If a man could give birth it would be to a book – it’s an 18-month gestation period.” ~ (Kevin O’Leary).

24. “I think a book is your calling card, your business card.” ~ (Kevin O’Leary).

25. “I’d rather invest in an entrepreneur who has failed before than one who assumes success from day one.” ~ (Kevin O’Leary).

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26. “You can’t regulate a soul into a business.” ~ (Kevin O’Leary).

27. “Money has no grey areas. You either make it or you lose it.” ~ (Kevin O’Leary).

Top Kevin O’Leary Quotes

28. “The road to riches is never straight and narrow. It can be riddled with financial land mines.” ~ (Kevin O’Leary).

29. “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).

30. “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).

31. “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).

32. “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).

33. “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).

Famous Kevin O’Leary Quotes

34. “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).

35. “Unions are about the collective leverage, the power of numbers versus the power of capital.” ~ (Kevin O’Leary).

36. “There’s only one side with me. You get the right side. You get the correct version of the facts.” ~ (Kevin O’Leary).

37. “There are a lot of idiot fund managers out there who add no value to the process at all.” ~ (Kevin O’Leary).

38. “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).

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. “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).

41. “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).

42. “I think every entrepreneur in Canada owes the next generation a road map of how to do it again.” ~ (Kevin O’Leary).

43. “When you come to ‘Shark Tank,’ the only person you should listen to is me, because you know you’re getting the truth. I’ll decide if it’s worth it, and after I’m finished, the rest of the people can look into it.” ~ (Kevin O’Leary).

Short Kevin O’Leary Quotes

44. “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).

45. “I remember failing reading in school at a young age, and you just kinda get left behind and I felt helpless.” ~ (Kevin O’Leary).

46. “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).

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47. “Building fast-growing, globally competitive companies is tough.” ~ (Kevin O’Leary).

48. “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).

49. “If you put a woman in prison for four years when she’s young and make her pay her time in a horrible place and she wants to come out and work, and become a mother and be a contributor to society and pay taxes and you never give her that chance. There is something un-Canadian about that.” ~ (Kevin O’Leary).

50. “Steve Jobs had his critics. Some saw him as an egomaniac, and others, as a control freak.” ~ (Kevin O’Leary).

51. “I could have easily gone down the wrong path and dropped out of school, but I was given a second chance.” ~ (Kevin O’Leary).

Best Kevin O’Leary Quotes

52. “In his first term, President Barack Obama played a cautious manager navigating the worst economic disaster since the Great Depression and cleaning up the messes left by President George W. Bush in Iraq and Afghanistan.” ~ (Kevin O’Leary).

53. “Once Michigan stood proud. In addition to GM, Ford and Chrysler, it was home base for the United Auto Workers, a powerful escalator transporting hundreds of thousands of blue-collar workers into America’s middle class.” ~ (Kevin O’Leary).

54. “Imagine how foolish you’d look if, like one clever salesman who once pitched to me, you tried to license your product to a big industry player without knowing they just launched a competing product. With the right background research, he could have avoided that and other landmines – and so can you.” ~ (Kevin O’Leary).

55. “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 leader.” ~ (Kevin O’Leary).

56. “As far as I’m concerned, Twitter has wiped out Facebook. I’m done with Facebook.” ~ (Kevin O’Leary).

57. “I like gold because it is a stabilizer; it is an insurance policy.” ~ (Kevin O’Leary).

58. “My worst fashion faux pas: probably orange shoes with white pants. I thought I looked spectacular.” ~ (Kevin O’Leary).

59. “Many blue-collar families struggling to pay rent would be happy to skip paying optional union dues.” ~ (Kevin O’Leary).

60. “The practical reality of managing cars in the family – I do 36-month leases. I think they’re horrible investments. And you want to give them back after their warranty is over.” ~ (Kevin O’Leary).

61. “Television is the most interesting hobby I’ve ever had.” ~ (Kevin O’Leary).

62. “When you bring an idea that has no merit to me, and you ask me to comment on it, I’m going to tell you it has no merit.” ~ (Kevin O’Leary).

63. “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).

64. “All we do is bring the debate from both sides, and let you as a viewer decide where you want to end up on the issue. That’s very important. That’s exactly what happens in ‘Redemption Inc.’” ~ (Kevin O’Leary).

65. “I keep anywhere between 5-10 percent of my net worth in venture ideas.” ~ (Kevin O’Leary).

66. “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).

67. “Filming ‘The Road to Riches’ was surprisingly difficult for me. I learned that going back to career successes and failures can be emotionally exhausting as you are forced to revisit the euphoric highs and painful lows in high speed.” ~ (Kevin O’Leary).

68. “I look at Twitter as brand building.” ~ (Kevin O’Leary).

69. “Protecting Americans from harm goes beyond police and national defense. It’s imperative that we not destroy the commons, the physical environment on which we rely.” ~ (Kevin O’Leary).

70. “People are aware of what I stand for through television. Nobody gets rich on TV but you build brand. That’s what I’m attempting to do.” ~ (Kevin O’Leary).

71. “Too many great ideas die at the feet of those afraid to pick up the phone because they don’t want to face potential rejection.” ~ (Kevin O’Leary).

72. “When you’re alone with your kids, focus on spending quality time, not quality cash.” ~ (Kevin O’Leary).

73. “The so-called conservative right that now dominates the Republican Party is, in fact, extreme, radical, and deeply at odds with the American political tradition; it poses a profound threat to the American republic. The assault on liberalism by the right targets not only the New Deal state, but the Constitution and the American political system as well.” ~ (Kevin O’Leary).

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Chandan Negi
Chandan Negi

I’m the Founder of Internet Pillar - I love sharing quotes and motivational content to inspire and motivate people - #quotes #motivation #internetpillar