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New book from NYT bestselling author Lewis Howes is now available!


Kevin O’Leary

The Keys to Financial Freedom (Do THIS Today!)

How's your financial future looking?

Everyone wants to make money, right?

However, the reality is: not all of us can reach financial freedom. There are many reasons why this isn’t possible. Some of us lack the drive to work hard on it, some think that it’s important but have negative feelings about money, and others are just clueless on what they need to do to get it. The good thing is that more and more people are willing to share their knowledge and expertise to help us achieve the financial freedom we desire .

My guest for today is an expert when it comes to achieving this kind of freedom. I’m glad to have Kevin O’Leary here with us!

You probably know Kevin as an investor on the Emmy award-winning show Shark Tank. In this episode, Kevin shared his wisdom and expertise on how everyone can achieve financial freedom. We also got up close and personal talking about relationships and money. Lastly, we went deep into Kevin’s conviction on the importance of telling the truth, particularly in building businesses.

Kevin O’Leary is truly an expert in money matters. With years of working with CEOs and other investors, he’s earned a massive wealth of knowledge on how to reach financial freedom. If you’re ready to jumpstart your financial journey right now, let’s get started!  

Who Is Kevin O’Leary?

Kevin O’Leary was born to a middle-class family in 1954. The combination of Kevin’s mother’s family heritage as merchants and his father’s Irish charisma truly meant that O’Leary was born for business. Kevin learned most of his business intuition from his mother. She taught him key business and financial insights from an early age. These became Kevin’s core philosophies and the pillars upon which he would one day build his empire.

As a university student, Kevin’s innate business sense led him along several different paths – including some very unusual, very entrepreneurial ways of making a profit. Not long after he finished his MBA, Kevin had a meeting that changed his life forever. He met a man who had a strange idea for a software product – an idea with huge, high-profit potential that Kevin immediately recognized.

After years of ups, downs, sacrifices, challenges, and lessons learned — not to mention a critical phone call that nearly cost him everything — the opportunity that Kevin saw eventually turned into a computer software giant that was acquired for more than 4 billion dollars.

After his extraordinary success at the software company he founded — and a difficult period of obstacles and legal disputes — Kevin eventually found himself on television, quickly becoming a sought-after host and personality on a range of shows — including Discovery’s Project Earth, CBC’s Dragons’ Den, and ABC’s Shark Tank — earning the name, “Mr. Wonderful.”

Today, I have the pleasure of speaking with Kevin O’Leary — Mr. Wonderful himself. You’ll be amazed to hear his personal experiences and inspired by the values that made him what he is today, so let’s dive in!

The Keys to Financial Freedom

Most of us think that financial freedom is all about making money. But for Kevin, it goes beyond that. For him, the essence of financial freedom lies in having enough financial resources that you can do the things you love and you’re passionate about. 

Throughout our conversation, he mentioned many valuable tips on how one can reach financial freedom. Though there are many, I would like to highlight the things below.

#1: Build Powerful Habits

As an investor, Kevin has learned so many things from working with CEOs and other like-minded people. From these encounters, he learned that there are three important habits crucial to achieving financial freedom.

The first one is writing down the three things you need to get finished and putting them in the mirror. Sounds simple right? Here’s why Kevin thinks that this habit works:

“Once I’ve stuck it on my mirror, I am myopically focused to get those three things done. Before I check my email, before I do anything else, I nail those three things. You cannot believe how productive you get when that happens. You don’t let yourself get distracted with what’s happening around you.” – Kevin O’Leary

I think that what Kevin is emphasizing here is the power of concentration. When you concentrate single-mindedly on something, you can achieve whatever you can think of. So if you’re thinking of having enough money to take that trip and go around the world, then you need to have an eagle-eye focus on the top three things you need to accomplish to get this goal done. 

Another powerful habit that you need to develop is listening to your gut. Now, this might take a little bit more of your courage because you can only train your gut by letting yourself undergo many experiences, and not all experiences are great. But Kevin explains why you need to undergo both the good and the bad.

“Experiences make you who you are. Even if you’re an entrepreneur, a parent, a person, a brand, whatever you are, it’s your experiences and how you deal with them that gives you that equity eventually.” – Kevin O’Leary

I agree with what Kevin said — 100%. You might have your business plan mapped out, and you might have a great team behind you, but sometimes, life happens. So this is the perfect time for you to train yourself to listen to your gut. It’s your radar and your DNA speaking to you, figuring out what the next move is going to be. 

The last habit that Kevin thinks is crucial to your financial journey is making time for your loved ones. 

“People equate financial freedom to being an entrepreneur. But they should know that entrepreneurship isn’t a destination, it’s a journey. The challenges of that are very difficult, particularly when you’re starting.” – Kevin O’Leary

There might be points in our lives where we feel like we need to choose between our career and our significant other. But just like what Kevin said, building the habit of spending time with them can be significant in reaching your goal to be financially free.

The good news about this is that anyone can build and have these habits eventually. If Kevin can do it, so can you!

#2: Develop a Mindset of Abundance

People have different perspectives when it comes to money-related matters. Some think that money is the root of all evil, while others see it as a tool to achieve happiness. These differences make us unique, but to achieve financial freedom, a mindset shift is necessary. So how can someone shift from having a negative perception of money and start seeing it in a positive light? I think Kevin has the perfect answer.

“A third of our population seeks entrepreneurship, and you know why? It’s not out of greed for money. It’s the pursuit of personal freedom. When you have enough financial resources, you can spend your day doing things that you want to do.” – Kevin O’Leary

What Kevin is trying to say is that we should stop looking at money as an end goal of our efforts, but as a means to do our life’s passions. In this case, you can spend your time doing the things you love.

#3: Start Investing Early (But that Doesn’t Mean You Can’t Start Late)

If I were to ask you, “When did you first learn about credit cards and the stock market?” what would be your answer? Was it in college, or was it by the time you had your first paycheck? If this is your answer, then we might truly be failing our society.

“Financial literacy should be taught as early as high school. I know many people who are in their sixties who have nothing set aside for their retirement. If we keep on doing this and not teaching our kids how to invest, then we are on our way to failing an entire generation.” – Kevin O’Leary

But this doesn’t mean that you can’t invest in your 40s and 50s! For Kevin, financial education can still take place even when you’re older. 

“The truth is, changing your spending behavior can happen at any age. You can be in your forties, which is difficult, but you can do it. By that age, you should start saving 20 to 25% of what you’re taking in.” – Kevin O’Leary

The formula is simple. Savings and the right investments can turn you into a self-made millionaire. Repeat these, and soon you’ll be enjoying a life of wealth and abundance. Kevin even has a business initiative called Beanstox, a Robo that invests with your philosophy. Whatever type of investor you are — conservative, moderate, or aggressive — give it a shot, and see if you want to sign up.

#4: Invest in Yourself

The longest relationship that you’ll ever have is with yourself. It’s only fair enough that you take steps to learn and enrich your experience so you can increase your value. For Kevin, everything that he has and he can do now is attributed to his investments in himself.

“I went through some very tough times, right from when my mother cut me off through several business ventures I failed in. But I just got to keep getting up every day and stay in the race. It’s very hard. But I’m glad I did what I did. I wouldn’t change a thing. … I’m very proud to be able to offer the things I do to my family and, and to support different initiatives [and] charities and support the arts and collect watches and guitars and cook. All these things are made available to me because I’ve been able to focus on being successful in business.” – Kevin O’Leary

How about you? When was the last time you’ve listened to the podcast you liked? Or purchased an online course on something that you love? If you think that spending money to improve yourself is too expensive, then try to think of all the missed opportunities you could have had if only you had enrolled in this course or taken that class.

Invest your time, money, and efforts in improving yourself. Buy books, watch videos, and enroll in classes on how to get a growth mindset. Soon enough, you’ll be at the pinnacle of your financial success!

#5: Overcome Self Doubts

A limiting factor that stops us from achieving our financial freedom is self-doubt. It’s not only regular people who question their capabilities — even well-known celebrities and seemingly confident and seasoned businessmen like Kevin have self-doubts! What is just different, however, is the way we approach things. Kevin shares how he deals with his self-doubts, even in his daily life:

“I was dyslexic when I was young, so I had a lot of problems with that. Just learning how to read and keep up in school, but I didn’t let it get in my way. …Today, I think that the biggest mistake that we have is [that] we let what people say in social media get to us, but really, why would you care? The only people you should worry about are the people in your family and your close friends. … You can’t make everybody happy ever. And as long as everybody you know thinks you’re great, it doesn’t matter. It’s what you think about yourself that matters.” – Kevin O’Leary

I think that the way Kevin describes self-doubts and how to deal with them is excellent! You might be wondering if it’s right to stick to the business you’ve had for years. You might also be doubtful of the decision to buy certain stocks. But that’s okay. Overcoming self-doubt doesn’t happen overnight. There’s no specific pill that can make them go away. It’s a journey to financial freedom but also to self-discovery and happiness!

“Money can cause great joy or catastrophe in your life. Your CHOICE is where does it fit?” @kevinolearytv  

Why the Right Money Mindset Matters in Relationships

“Money can’t buy me love,” says one song by The Beatles. I beg to disagree. Money can’t buy you a person’s affection or adoration, but it’s a critical factor for a long-lasting relationship. Kevin thinks the same way.

“You know, people say to me that I’m cold and heartless for saying that love is about money. But I say it is. … Any marriage can survive infidelity. But why do they fail? 50% of the time within five years is due to financial stress.” – Kevin O’Leary

The numbers may be discouraging, I know. There are many factors to consider for the high divorce rates, such as the couple’s inability to manage their money or create shared values for the way they spend. Kevin gave another scenario that leads to failures of unions, such as when people don’t share each other’s goals. This is especially true when one spouse is on their way of pursuing financial freedom working as an entrepreneur. It can be difficult to be in sync with your partner. As an entrepreneur, you’re most likely to work 25 hours a day, eight days a week because you’ve got a business. Thus, Kevin gives a piece of advice he wants aspiring entrepreneurs who are looking for marriage, to follow.

“One of the biggest decisions you’re going to make in your life is finding that right partner. They have to be in sync with who you are.” – Kevin O’Leary

So to know if the person that you’re currently dating is the person you can be with for the rest of your lives, Kevin suggests asking them tough questions.

“Number one is, talk about family. Do you want to have one? … If you’re on your fourth date, talk about bankruptcy. Have you ever been bankrupt? Then, ask how much debt you have on your credit card.” – Kevin O’Leary

Another relationship affected by the presence of money is the one you have with your family. He warns that the danger of money in a family is entitlement.

“If you entitle somebody and you de-risk their future, you have cursed them. You’ve almost guaranteed that they will fail, and they’ll never launch.” – Kevin O’Leary

This is the advice that Kevin gives parents of kids who have all the money in the world at their disposal. He believes that once kids feel that they’re entitled, they act differently. They’ll be afraid to take a different path. 

By entitling them with all the money in the world, you’ve removed one source of motivation from them. Allow them to work and achieve things on their own.

The Importance of Honesty in Reaching Financial Freedom

Kevin’s wisdom is truly helpful for those people who are aiming to achieve financial freedom eventually. His knowledge on the subject matter is expansive and composed of practical tips that everyone can follow. But what lies underneath this wealth of wisdom that he’s sharing with us is his strong belief in the importance of honesty. Just as people in romantic relationships emphasize its value, Kevin sees that it’s also a building block in doing business with other people.

“When you lie, what you’ve lost forever is the equity of trust. It’s gone forever. That’s just as important in business. When you lie to a partner or a customer … and you get caught, you will never have the equity back.” – Kevin O’Leary

Trust is gained, not given. For some entrepreneurs, this could mean years and decades of hard work and persistence. By lying, you can destroy within 15 seconds what some have been building their entire lifetime. For Kevin, being caught as a liar takes you down multiple levels in many people’s eyes. He even thinks that as hurtful as it might be, everyone’s priority should always be to speak the truth, particularly when it comes to matters of finance.

“You can try to sugarcoat lies so that it leaves hope where there is none, but that’s a huge mistake, particularly when it comes to matters of finance. Be honest when you think that an investment is not going to work out. That it’s a horrible idea. … When people look back at you, they’ll only remember that you’re the guy who never lied to them.” – Kevin O’Leary

Aside from this, what I ultimately love about the truth and being honest is that it allows you to build confidence in yourself. When you’re lying, even if it’s a white lie, you’re out of integrity with yourself. Kevin would always use the teaching he learned as a kid from his mother:

“Understand that there are some things out of your control and you have to deal with them. If you tell the truth, you don’t have to remember what you said. “ – Kevin O’Leary

This is because lying would require you to make up things, which you can sometimes forget. It doesn’t make you consistent, and consistency is important in your business. It builds trust with your customers which makes them want to do business with you every time!

Why You Should Listen to This Kevin O’Leary Podcast Episode Right Now…

Ready to live the life you’ve always wanted?

Whatever dreams or plans you want to pursue in life, Kevin O’Leary’s advice will definitely help you achieve the financial freedom you’ve always wanted. It’s a combination of many practical steps that even you can start right now!

If you want to learn more valuable and brutally honest tips from Shark Tank’s King of Truth, you can follow Kevin on Facebook, Twitter, and Instagram. You can also check out his website here.  If you are thinking about investing or trying to find a way to make it painless for yourself, you have to checkout Beanstox. It’s awesome, it’s free to download, and it can help start your journey to financial freedom.

Before I go, I want to leave you with Kevin O’Leary’s definition of greatness:

Greatness is in anybody that can actually tell the truth their whole life.” – Kevin O’Leary

I hope you enjoyed this, guys. I know that Kevin’s wisdom on gaining financial freedom and staying truthful in business dealings has been meaningful to everyone. Make sure to check this full episode with Kevin O’Leary for some big takeaways that you can use to apply in your life today and beyond! 


To Greatness,

Lewis Howes - Signature

Some Questions I Ask:

  • What was the biggest fear you overcame to become successful?
  • Have you ever been bankrupt?
  • How much debt do you have and do you pay off your credit card debt?
  • What should you do if you don’t agree with your partner about money?
  • What qualities do you look for in order to invest in something?

In this episode, you will learn:

  • The importance of always telling the truth.
  • The 3 skills every person should develop to be successful.
  • What conversations we should be having with our partner around money.
  • How the middle class can start working to achieve financial freedom.
  • What qualities Kevin looks for when making an investment.
  • How Kevin is able to manage so many businesses and passions.
  • Plus much more…

Show Notes:

Connect with
Kevin O’Leary

Transcript of this Episode

Music Credits:

Music Credit:

Kaibu by Killercats

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