Kevin O’Leary // O’Leary Funds, O’Leary Financial Group, Shark Tank panelist and more

When Kevin O’Leary talks, people listen. And for good reason. An entrepreneur who grew his own software company to a successful exit and a serial investor in dozens of successful companies, Mr. O’Leary has a unique perspective on what it takes to succeed in business.

Kevin O’Leary is one of the most well-known entrepreneurs and investors in the world. He rose to prominence after selling his software company, The Learning Company, to Mattel for $4.2 billion in 1999. Since then, he has invested in a wide range of companies and launched his own mutual fund company focused on global yield investing, O’Leary Funds. He has several companies under the O’Leary brand, including O’Leary Books and O’Leary Fine Wines.

He is known internationally as an investor on the business shows Dragons’ Den and Shark Tank, on which entrepreneurs come before a panel of “sharks” to pitch their business ideas with the aim of securing an investment. He has written several books on business, including his bestseller Cold Hard Truth.

Despite his business success, Mr. O’Leary shared about his difficult years, when he had to borrow money to make ends meet and keep his company afloat; as we spoke, he even teared up a few times. Though he normally does not grant print interviews (or any of this length), he happily agreed to speak to Ami readers.

At the beginning of our conversation, I told Mr. O’Leary that I have a different agenda than most of the other interviews he has had with mainstream media. As one of the most sought-after guests across national media, he is often consulted for his opinions on everything financial, from the stock market and crypto (yes, we discussed FTX) to investments and more. But most of his interviews are only a few minutes long. The host asks a few rapid-fire questions covering a small range of topics, often with the aim of catching Mr. O’Leary in a gotcha moment.

As I told Mr. O’Leary, my goal was different: I want to educate and motivate. In addition to his business advice, I was curious about how an entrepreneur in the big leagues manages to balance it all. Over the course of multiple conversations, we covered that and many other topics. It was real, raw and honest. There is much to learn here.



“I was born in Montreal, Canada, to immigrants from Ireland and Lebanon. My father was a Lebanese entrepreneur who came to Canada seeking an opportunity, and he took a job as a salesman in a company that made winter clothing for children. My mother was the owner’s daughter, so that worked out.

“Unfortunately, my father died when he was very young. He was only 37 years old; I was seven.

“Montreal has a huge Jewish community. I lived in TMR (Town of Mount Royal), which is more than half Jewish. I was, in a sense, raised by the family of my friend Andrew Tany, who lived across the street with his bubby. I went to school with Howard Dover, who is a rabbi today. Having grown up enmeshed in a Jewish environment, I consider myself to be an honorary Jew, and I appreciate the Jewish values that haven’t changed over the course of thousands of years. Particularly, in the Jewish faith, an elderly person is honored, and that’s how it should be everywhere. The knowledge that you accumulate over the course of your life becomes your equity. I even went to Temple many times.

“After my mother remarried, our family moved to Champaign-Urbana, Illinois, but then my stepfather got a job with the ILO (International Labour Organization), the United Nations agency, out of Geneva. We moved every two years. His first assignment was in Cambodia. After that, we went to Tunisia, Ethiopia, Italy, France and Germany. I thought everybody lived like that, moving around. I learned a lot during that period; it opened my eyes to how the rest of the world lives. This was a huge advantage for me when I became a global investor later on in life. I am not afraid to invest money in these foreign places because I know how they work.

“Because we moved every few years, school was generally online or with tutors. In some places, like Tunisia and Ethiopia, there weren’t even any high schools. I started to learn French in Cambodia because, at the time, they were just leaving French colonization. My stepfather can speak six languages, but I can barely speak French. I am dyslexic, so learning languages was hard for me.

“From the time I was a child, I had a business mindset. I had a huge hobby with stereos, and I wanted to buy equipment, but we were a middle-class family and my mother wasn’t going to give me $1,000 for an amplifier. So I went and earned it. I did every side job I could. I shoveled snow, trying to sell my services up and down the street. I also ran a paper route and sold magazines. School finished at 4:00 p.m. I would do homework until 6, and then go to the call center from 7 to 11 p.m., just sitting on the phone, trying to sell. It was good training, learning how tough the business world is and how to work long hours. I took this work ethic with me into my adult life. Whether it was at The Learning Company (the software company that I started) or any of the other ventures that I became involved in later, I have always worked hard and approached my work with total honesty.

“That honesty is on display when I speak to an aspiring entrepreneur on Shark Tank. If I think someone’s idea is a waste of time, I tell them. This might be a cultural thing, but don’t you think you need to be honest with people? On Shark Tank, I get into fights with [fellow sharks] Lori [Greiner] and Barbara [Corcoran] about this all the time. They will tell someone, ‘Keep doing what you’re doing, go ahead, mortgage your house. I am not going to invest with you, but I will still give you encouragement.’ Not me. I’ll say, ‘This is a stupid idea. You’re wasting your money. You’re going to go to zero, and that’s your family you’re putting at risk with this stupid idea.’ Maybe this comes across as tough and hurts their feelings because they’ve been working on this piece of garbage for two years, but if it’s a bad idea, someone has to tell them the truth. And for that, I get named the bad shark? Are you kidding? I am their best friend, the only one who is telling the truth!

“Why lie to people? This is business. It’s black and white, not gray. You either make money or you lose money. There are a lot of things in life that are not that way, but business is very binary. You have to ask yourself: Am I making money or not? If I’m not making money after three years, it’s a hobby, not a business. And remember that when you start hiring people, you have the responsibility to take care of them. That’s why I’m careful with how I choose my investments.”

It was clear how emotional it was for you to relive the times when you struggled. Now that you’re a celebrity, do you still feel that you can relate to the average person’s day-to-day struggles?

It is tough to go back to those memories. It was a difficult time. Looking back, I understand that what doesn’t kill you makes you stronger. Although of course my circumstances have changed since I was a child, I do feel I can relate to people and their struggles. Your past becomes a part of who you are as a person.

My mother was a special person. When I started The Learning Company, I had to borrow $10,000 from my mother. Later, when I sold the company for $4.2 billion, I said to her, “Mom, you made a fortune on that $10,000.” She said, “Great! Just give me my $10,000 back.”

I’m curious to hear how you manage to balance all of your business commitments and investments.

I have an amazing, cohesive team of people around me. My personal assistant chops my day up into 30-minute increments.

I often tell people that you don’t work as an entrepreneur for the greed of money. It has nothing to do with that. You’re pursuing personal freedom. If you’re successful as an entrepreneur, you set yourself and your family free. The most important freedom is doing what you want with your time. For example, if I didn’t want to do this interview, I wouldn’t do it, because I don’t have to. I chose to do this because I feel a real connection here and I want to inspire people.

How did you learn to delegate, especially in the beginning of your career?

I figured that out very early on by hiring great people. We were able to grow in geometric leaps and bounds by having a very powerful group that knew exactly what their lanes were. These were people who could build the business. If you can’t do that, you’re going to fail anyway.

Do you find that being able to delegate is a skill that separates successful entrepreneurs from those who fail?

Yes, and that’s the jump you need to make when you hit $5 million in sales. Up to that point, you can generate revenue pretty well with a very small team. But if you want to play in the big leagues and you want to get to $50 million, and then $500 million, and then $1 billion in sales, you’re going to have to delegate. You’re going to have to find people who are good at things that you’re not good at and make them part of your core team.


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