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10 Brutally Honest Success Lessons from Kevin O’Leary of Shark Tank



Kevin O’Leary is a Canadian born entrepreneur and TV personality who rose to prominence in the business world after his software company sold to Mattel for $3.65 Billion in 1999. He is best known for his no-nonsense and often blunt criticism of aspiring entrepreneurs and startups on ABC’s Shark Tank.

Also known as “Mr. Wonderful”, Kevin O’Leary has since written 3 best selling books about life, entrepreneurship, and money; and what it really takes to make it in the big leagues of business.

Here are 10 success lessons you can learn from Kevin O’Leary:

1. Business is war

An entrepreneur should be in it to win it – to crush the competition. Kevin has a no nonsense approach to business which is void of emotion. Business is war, and you have to play to win. Don’t let your feelings get in the way. The market will determine who survives and who doesn’t, so play the game with everything you’ve got. Don’t be afraid to lose. Just reassemble your troops and try again with a different strategy.

“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

2. Your dollars are your soldiers

Money is the lifeblood of business. Many will espouse how money is over rated, and shouldn’t be the most important pursuit of business. Kevin disagrees. He likens your start up finances to your soldiers on the battlefield of business. “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.” If some of them die, that’s bad. If they all die, that means you’re broke.


3. Entrepreneurship = Freedom

Kevin tells a story of when he was a teenager and worked at an ice-cream store in a local mall. One day he was asked to scrape gum off the floor, and when he refused to, was fired. Reflecting on this years later he says that it taught him that being an employee is slavery and being an entrepreneur is true freedom. From that day forward he vowed that he was never going to work for anyone else again.


4. Spend the interest, never the principle

As the chairman of O’Leary funds, Kevin’s entire investment firm is based on this fundamental lesson he learned from his mother at an early age. His mother would always say “Spend only the interest, never the principle.” This means don’t let go of your nest egg. Leave the principle alone to accumulate interest, and send that interest back out into the battle field.


5. Don’t fall in love with bad ideas

Money runs from bad ideas. Entrepreneurs who are in love with bad ideas kill companies and send money running. On Shark Tank, you will often see incredibly passionate entrepreneurs who are infatuated with terrible ideas that either don’t sell or aren’t backed by viable business models. Kevin is quick to bring a dose of reality. “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?”


6. Opportunity comes fast

Known for saying “opportunity knocked, nobody was home”, Kevin shows entrepreneurs on Shark Tank that opportunity comes fast. It also leaves just as quickly. An offer from an investor can arise and expire in moments. You need to think fast, and make quick decisions under pressure.


7. Passion isn’t everything

Kevin started out wanting to be a fashion photographer until his father shot down that idea with some brutal honesty. “You’re just not that good.” his father told him. Kevin realized that to make the kind of money that he wanted to make, his passion of photography just wasn’t going to get him there. He wasn’t prepared to be a starving artist with most of his photos going unsold, so he left his passion behind to pursue business.  Don’t let your passions blind you and lead you away from success.


8. Sales are everything

Many otherwise viable business ideas and startup companies have been harshly rejected in the Shark Tank because they simply have no sales. Sales are everything. You could have the greatest idea in the world with a plan to execute, but if you approach an investor with no sales or tangible purchase orders you will be in for a tough sell. Investors want to see real market demand with real paying customers before they will back ventures. They don’t want to back speculation without actual sales which will confirm that your business model works.

“Do you have what it takes to make the sale?” – Kevin O’Leary

9. Money doesn’t care about you

Kevin once said “Don’t cry about money, it never cries for you.” The lesson here is to keep your emotions separate from your money. Never let your emotions dictate what you do with your cash, especially if you are in the early stages of a start up. If you are losing money, the market is trying to tell you something. Change your model or get out of that business – but don’t cry about it.


10. The price of success is high

“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 is not a believer in the life work balance. There is no balance. You must be willing to give everything to be successful. It is this kind of hardcore work ethic that separates those who fail from those who succeed on a big level.

What do you like most about Kevin O’Leary? Please leave your thoughts in the comment section below!

Nick James is the founder of, a Toronto based company that publishes motivational articles and interviews with entrepreneurs. Nick is passionate about entrepreneurship and believes that motivation is the cornerstone to success. He is launching the Massive Success Podcast in early 2016 to pick the brain of successful entrepreneurs from around the world.



  1. Troy

    Sep 18, 2016 at 5:56 am

    A good article, however, it must be remembered that on one’s deathbed, what is most important? Accolades, millions in the bank, a close circle of family and friends? There is a price for everythi g and in 100 years, no one will care or remember.

  2. Stephen Osoko

    Dec 28, 2015 at 4:56 pm

    Awesome article man! It’s true when you say the price of success is high! I’m truly realising that sacrifice is everything if you want to secure a better tomorrow! Once again great article

  3. Joel Brown

    Joel Brown

    Dec 20, 2015 at 2:13 pm

    Awesome article Nick. I see the the lesson of “Sales are Everything” come up often with successful entrepreneurs. Thanks for breaking down why through Kevin’s experience.

  4. Timo Fischer

    Dec 18, 2015 at 10:57 am

    “Your dollars are your soldiers” I like that analogy.

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