Great Entrepreneurship Quotes From Kevin O’Leary


When it comes to learning about entrepreneurship, sometimes the best sources to turn to are experts in the industry who have started their own business before. If you need some extra inspiration, the best place to turn is to quotes from successful individuals, such as the incomparable Kevin O’Leary. Here are some of the entrepreneur’s biggest and most influential quotes about entrepreneurship and insights into Kevin O’Leary’s life to inspire others looking to start their own business and find success in today’s market.

How Much is Kevin O’Leary Worth?

Kevin O’Leary is estimated to be worth more than $300 million. However, some sources have estimated that this amount is closer to $400 million. While the number can fluctuate, there is no denying that this is one mogul who has earned a great deal during his time in the industry. This is pretty impressive for a man that began his career with a $10,000 investment from his mother. What is even more impressive is how the software mogul has made his fortune and all of the different investments and charities that he is involved in.
– Some of Kevin O’Leary’s Investments:

It should come as no surprise that the Shark Tank star Kevin O’Leary has a number of successful investments to his name. In fact, O’Leary also claims that his mother has a great deal to do with his investment success as she taught him “you never spend the principal, only the interest.” O’Leary has taken this advice to heart and put a great deal of effort into making smart investments, which include selling The Learning Company to Mattel for $3 billion. He has also made a number of investments in companies that have made their way on to the show including:

  • $2,500,000 in Zipz
  • $1,000,000 in How Do You Roll?
  • $400,0000 in Honeyfund
  • $300,000 in xCraft
  • $300,000 in Lovepop
  • $300,000 in GreenBox
  • $300,000 in JumpForward
  • $250,000 in VerbalizeIt
  • $250,000 in Talbott Teas
  • $250,000 in First Defense Nasal Screen

These are just a handful of the many investments that O’Leary has made that have eventually helped him become one of the most successful business men and investors in the entire world. However, don’t expect “Mr. Wonderful” from slowing down anytime soon, the serial investor is always looking for new promising companies to invest in.
–  O’Leary Fine Wines

In addition to his investments, O’Leary also has a number of other successful ventures to his name, mainly, O’Leary Fine Wines. The business mogul has launched his own collection of affordable wines, along with his wife who he claims has a “remarkable” palate for wine. The fine wine brand currently has three different wines with plans in the future for expansion. While it is not clear on how much O’Leary invested in the company or how much it is pulling in, this relatively new venture is one that the businessman is hoping will only add to his fortune. Currently, the brand features a Cabernet Sauvignon, a Reserve Series Red Wine and a Chardonnay. All of the wines are made in California and are currently being promoted across the country. Most importantly, O’Leary is set on making these wines taste like a luxury brand, but come with a much more affordable price tag.
– Kevin O’Leary’s Cold Hard Truth Series

Besides his appearances on Shark Tank, one of the things that O’Leary is known most for, and one of his other biggest forms of income is his Cold Hard Truth series. The investor is a firm believer in the importance of educating yourself and on reading everything possible in order to be a true expert on a topic. This is why he developed his series. These books, as the title suggests, are designed to deliver the “cold, hard, truth” on a variety of subjects. They utilize O’Leary’s enticing yet no-nonsense approach to life and the author utilizes some of his past experiences in order to educate others.

The first book in the series, simply called Cold Hard Truth, was all about business, money and life. The best-seller created a number of dedicated O’Leary fans and inspired the businessman to create another book in the similar vain. The following works was called Cold Hard Truth on Men, Women and Money, and it took a surprisingly different turn, discussing personal and family finances for individuals at all phases of life, from young couples to retiring individuals.

Finally, O’Leary followed up his second book with a third titled called Cold Hard Truth On Family, Kids and Money. This one is a no-nonsense personal financial guide designed to help individual build a future for themselves and those that they love. They feature red flags to look for, a decade-by-decade guide to managing assets, tips on financial independence in a marriage and insight on how to minimize the amount that kids spend.

Here are the Best Kevin O’Leary Quotes About Entrepreneurship

In addition to all of his successful business ventures, Kevin O’Leary is hailed most perhaps for his ability to inspire others and to pass his financial insight on to those that he meets. He not only does this on Shark Tank in a way that has earned him a great deal of respect and recognition, but he does it in his books and during his public speaking ventures. Most of these quotes have to do with starting and building your own successful company, not just with finances. With this in mind, these are some of our favorite Kevin O’Leary quotes on entrepreneurship.

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

This is an important message for those who fear failure and an important reminder that everyone fails. Failure is a natural part of being an entrepreneur. You just need to be willing to pick yourself up move forward. For big names in the market such as O’Leary, this is a sign that someone has the willingness to move forward after they face obstacles. Confidence is important, but you should never assume you should never just have success.

“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.”

No matter how much you know, or how much experience you have, you should never forget the value of doing your research and putting in the work. This is an important story that anyone can learn from, no matter what industry you are looking to start your business in.

“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?”

Being able to acknowledge your failures and your flaws is an important part of coming up with the right idea for your business. Passion and work ethic are important, but you need to know where your company needs work and you need to know when you should walk away.

“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.”

Very few entrepreneurs are willing to speak so candidly about having a competitive edge. It is alright to have a competitive nature when it comes to starting a new business. Don’t be afraid to have this edge, it can be exactly what makes your business thrive.

“I have had some great successes and great failures. I think every entrepreneur has. I try to learn from all of them.”

Whether you fail or succeed, you need to take the time to really learn from your experiences. Every milestone is an opportunity to learn just as every setback is. If you aren’t learning from both the good and the bad, then you aren’t bettering yourself and your company, for the future.

“So much of life is a negotiation – so even if you’re not in business, you have opportunities to practice all around you.”

Never undervalue the importance of good negotiation skills as an entrepreneur. You always have new opportunities to practice the art of negotiation, so never be afraid to practice, it can only help in your efforts as a business owner.

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

If you enter into a new business, thinking only about money and believing that money is everything, you will never succeed. Don’t get overly invested in money, it is just money. If you are too focused on the finances, you will never be able to see past the finances and into what it takes to make your company succeed.


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