Read the full transcript of Canadian businessman and TV personality Kevin O’Leary’s interview on The Diary Of A CEO with Steven Bartlett podcast episode titled “This $28 Habit Is Keeping You Poor! Every Time You Get Paid, Do This!”, June 30, 2025.
The Defining Moment That Shaped Kevin O’Leary’s Entrepreneurial Journey
STEVEN BARTLETT: Kevin, I’m going to ask you to do something which is quite difficult because I’d find it quite hard if someone asked me to do this. But before we get into the detail, can you give me a 30,000 foot view on your entrepreneurship and investing career? Just the three bullet points that are most pertinent. Before we dig into those specifics.
KEVIN O’LEARY: Every entrepreneur I’ve ever talked to that finds himself where I am today has a defining moment where they are pushed into this path. It’s something they can remember and they remember it in perpetuity. And I’ll remember my moment getting fired in an ice cream store. That simple.
First day on the job, asked to serve scoop ice cream. And I did that all day. But when people sample ice cream, they get a taster and they take their gum out and they throw it on the floor. Somebody’s got to scrape the gum off the floor at the end of the day.
I only took that job because I was very interested in a girl who was working in a shoe store. And I figured I could hang out with her afterwards. And I saw her waiting for me. And woman who owned the store said, you’ve got to scrape the gum off the floor. And I didn’t want her to see me on my knees with a scraper. Bad for my brand. I was in high school.
And she said, no, no, you have to do it.
STEVEN BARTLETT: Kevin, there’s a present for you. We give a present to all of our guests.
KEVIN O’LEARY: Really?
STEVEN BARTLETT: Underneath that black.
KEVIN O’LEARY: Can I open it?
STEVEN BARTLETT: You can open it.
KEVIN O’LEARY: I just take this off. Oh, look at that. You heard the story. That is exactly how it looked, except it was black gum. And that was exactly the tile. It was just like that Mexican tile. That’s really freaking me out.
STEVEN BARTLETT: So you were asked to scrape gum off a Mexican tile?
KEVIN O’LEARY: Yes, just like that. In order to do that, you gotta get down on your knees and do it. And I just couldn’t do it. Then you know the rest of the story. I eventually could afford to bulldoze the whole mall if I went to. And we went back to meet her and thank her for her pushing me off the treadmill into that direction. And she was gone. And there was a bodega there instead.
Can Anyone Be an Entrepreneur?
STEVEN BARTLETT: You said there that you realize that there’s kind of two people in life. There’s the entrepreneurs, the person that owns the ice cream parlor, and there’s the person that scrapes it off the floor.
KEVIN O’LEARY: Yeah.
STEVEN BARTLETT: That provoked a question to me, which is, do you think anybody can own the ice cream parlor? Do you think anybody can be an entrepreneur?
KEVIN O’LEARY: No. I’ve tried to teach it, and I mentor it all the time to the CEOs that I work with. There are some attributes of people that can do this. A certain element of risk tolerance, a certain element of focus. And then the other element, which I’ve really started to believe in of late is karma, luck. You need to be lucky.
It’s like Napoleon was once asked, who are your favorite generals? And he said, my favorite generals are lucky generals. My lucky generals. And I’m starting to think that in life, particularly entrepreneurship, you look at the difference, the path of success and failure, and nobody’s exposed to it more than I am in terms of how many investments I’ve made over the decades.
I think if you want a percentage, you know, I teach these cohorts at Harvard. I’m an executive fellow there. I’m very proud of that work. You get a class of 120 people in a room, 2/3 of them want to become consultants. That’s why they’re there. And lead a life of mediocrity and never make a decision of consequence in their lives. And after 24 months, they are tainted with that disease forever. They’ll always be good consultants, but they will never achieve greatness in any way in life.
Only a third of people can become successful entrepreneurs. That’s it. And the rest can be very successful employees. And there’s nothing wrong with that. You can have a fantastic life. You won’t be shackled to the ups and downs of entrepreneurship, the challenge of it, how hard it is, but you’ll never be free. And that’s the domain. That’s it right there. Do you want personal freedom? It’s the only path. That’s it.
STEVEN BARTLETT: It’s the only path.
KEVIN O’LEARY: It is the only path. I mean, you can’t. I’ve always said it’s not about the pursuit of money. It’s not about the pursuit of greed. You will fail if you do that. It’s the undying love, freedom, so that.
Increasing the Probability of Entrepreneurial Success
STEVEN BARTLETT: One third of people that you say will be successful, they’ll pursue their dreams, they’ll build a business, whatever it might be. Do you think it’s possible for us in this conversation to increase the probability of their success? You said you don’t think you can make someone an entrepreneur. Is there things you can do to increase their probability of success?
KEVIN O’LEARY: Yes, there are a couple of things that you must achieve to be successful. And let me explain what they would be. And this is not some academic study. This is real data from real situations of real CEOs I’ve worked with and learned from because I used to work for guys like Steve Jobs and others in my career.
Let me give you one that I think is very important. We’ll start with this one. I used to work for Steve Jobs in the early 90s. Making all of his educational software. I mean, it was just. Now, there they are. My goodness, you guys do good research. Those are the kind of things that we did for him, you know. Yeah, yeah. All of that. It’s hard to find. Those are CD ROMs.
But, you know, in developing that software, we used to go quarterly. Heidi Rosen was there in the room. She’s still a very famous venture capitalist. And I would say, Steve, you know, we gotta do some market research on Argonne Trail. I mean, it’s a huge title. It’s in 110,000 school buildings. We gotta do an update. It’s going to cost you 12, 15 million bucks. We want to find out what the students want. We want to find out what the teachers want. We want to find out what the parents want.
Steve would say, by the way, not a nice guy. Not a nice guy. He would say to a room full of people, Kevin, I don’t give a shit what the students want or the parents think or anybody thinks. It’s what I want. They don’t know what they want till I tell them what they want. And I said, Steve, you sound like such an asshole. You have no idea what that sounds like. He says, no, no, that’s how it is, Kevin. Now, are you making money with me? Am I your fastest growing oem? Have we not been wildly successful and continue to be? I said, yes, Steve, that’s true. He said, then shut up and do what I say. That’s how he would talk to you, 100%.
The Signal-to-Noise Ratio: A Key to Success
And here’s what I learned. Look how wildly successful he was. But here’s why. There’s a concept that he understood that very few people focused on back then, in the early 90s of Signal to noise ratio. What was so brilliant about Jobs? That I tell every CEO now, and I don’t care if you’re an S&P 500 CEO or you’re just starting a business.
His vision of Signal was the top three to five things you have to get done in the next 18 hours. Not your vision for the business next week or next month or next year. Just the next 18 hours you’re awake, you’re going to get those three things or those five things done that you have deemed critical for your mission, they must get done today. Anything that stops you from doing that is the noise.
So the signal to noise ratio to be successful for Steve Jobs was 80, 20, 80 signal, 20 noise. And I knew that to be true with him because he would email me at 2:30 in the morning, expect me to get back to him. Because back then we didn’t have texts, it was all email. He was right. He was right.
And the only other person that I’ve seen that has a higher ratio than that is Elon Musk. He has no noise. He does not deal with noise. He is 100% signal. 24 seconds, you know, every cycle. I mean, the guy is just 60 seconds of every minute, 60 minutes of every hour. The 18 hours he’s awake, it’s all signal. And look what he’s achieved now.
It’s very awkward for him socially because noise is dealing with your family sometimes, or noise is saying hi to a friend, or noise is listening to some doom scrolling on some social media app that just takes your mind or maybe playing your guitar. But very few people on Earth, if you go back in history, you’re gonna find out that the geniuses of their time were close to 100% signal.
STEVEN BARTLETT: And so I can really sort of summarize this for my audience. Signal is the most urgent thing you should be focused on right now. And noise is basically everything else.
KEVIN O’LEARY: No, the goals you set for that you were awake. If you’re gonna be awake 18 hours and you’ve determined that there’s three things you have to get done, you’re gonna get those done. No matter what it takes, you’re gonna get those done. And you’re not gonna let anything distract you from the three to five things.
If you’re a CEO and you achieve that and you can get those done with 80% of your time based on that, you’re extraordinarily successful. You are absolutely. And you’re Steve Jobs, or you’re an Elon Musk, or you’re somebody.
If you even talk to Bezos. I don’t know him personally, but I’ve heard in many interviews, like I knew, you know, I’ve met Elon just a few times. I spent a lot of time with Jobs, but they say the same thing. Bezos will not make a decision after 1 o’clock in the afternoon because he felt that the noise was too high. The signal for him was in the morning hours.
This is a crucial aspect of success that I now understand to be the ability of it defines an entrepreneur. A man or woman that understands the signal noise ratio, that focuses on that they’ll be successful. The ones that can’t that get down to a 50, 50 signal noise, they’ll fail. It’s that simple.
And it’s a very simple concept. You know, you made one of your things today, this interview. You’re going to get it done. You’re going to all these people around and everything else. This is one of the three to five things you’re going to get done. I have five things today, I’m going to get them done and do the same thing tomorrow and the day after that. And you have to decide how much signal you need to get those three to five things done. And for Jobs, it was 80%.
Finding Balance in Entrepreneurship
STEVEN BARTLETT: What’s the opposite of that? Sometimes looking at the opposite helps us to understand something. So the opposite of having.
KEVIN O’LEARY: Well, I hire managers and CEOs that have a balance in life between the discipline, the binary aspect of business, which is I make money, I lose money, and the chaos of the arts or some other pursuit, dance, painting, photography, collecting crystals, whatever it is that they have that balance.
You need the yin and yang in your mind to make correct decisions. It doesn’t mean it takes you off the signal. The signal is, you gotta get stuff done. But how do you live your life?
And so I spend a fair amount of my time practicing my guitar or working with my photography or my watch. You know, tonight, very late tonight, I will meet a master watchmaker and we will deal with the design of a new piece, unique, he’s going to make for me. And I’m going to love that moment. That’s going to be something completely different to what I did all day long. And we’ll start our journey together over the next two years to make this piece unique. And that’s something that just takes me away from all the stuff I’m going to be dealing with today.
And I also tell successful entrepreneurs in the same day, you will get a. And this happened to me today. It happens every day. You’re going to get a call from some aspect of your, what you do, call it your empire, whatever you want, where this company’s going bankrupt, it’s just going to go bankrupt, and you’re going to lose, I don’t know, 10 million bucks on that deal. And that’s a piece of information you’re dealing with.
Half an hour later, this actually happened to me today. One of my companies going public. It’s a 450X for me. The stock will get unlocked sometime in the fall. But how can, how do you, how do you fit that together? Utter catastrophe, destruction, woe, loss, utter euphoria. Half an hour later. That’s. That’s what my life is like.
STEVEN BARTLETT: That’s entrepreneurship, obviously, on a different scale for most founders.
The Signal and Noise Philosophy
KEVIN O’LEARY: Well, the founders deal with the same thing. They get disastrous news, they lose an account like Costco or something. If it’s consumer goods or service and they get something else. The ebb and flow is the management of expectations. And your ability emotionally to navigate those ups and downs is part of what entrepreneurship is. But it goes back to the signal. It can’t take you off the signal. This is what Steve taught me. Yes, it’s great news, yes, it’s bad news. But focus on the signal, O’Leary. Focus on the signal. That’s it.
STEVEN BARTLETT: Where does this analogy come from of signal and noise?
KEVIN O’LEARY: It was his genius of making it so simple. What are the three things you got to get done today? What are they? What are they?
STEVEN BARTLETT: How do you know what they are?
KEVIN O’LEARY: They will make themselves apparent. They will definitely make themselves apparent. They will make themselves apparent and you will realize I have to deal with that. You may have them set up from the day before. I actually still use sticky notes on my mirror. Got to get these three things done, or five things, whatever it is.
But then something else will hit. That’s the skill of understanding. Is that noise hitting me or is that signal? There is the essence of the great entrepreneur, the great manager, the great leader. Is that signal or is that noise? What is it? That’s what you’re looking for. You’re hiring somebody that can actually distinguish signal and noise because it could be noise, it could be irrelevant. You have to determine. Only you make that decision. That’s the key right there. This is what I teach entrepreneurs and engineers. And this is the most important thing.
STEVEN BARTLETT: It’s that judgment of prioritization, but then the sort of force of execution to get it done.
The Reality of Startup Success
KEVIN O’LEARY: Can you interpret signal and noise? And can you keep the noise away from the things you got to get done? That’s one.
The other, which is something that I’ve learned over the last five years. And this, you might find this interesting, but most of my, particularly the nascent startups. And you’re involved in the same format I am. You’re at Dragons Den in England, I’m Shark Tank in the US. You know, you put up $500,000 or a million bucks into somebody’s business, eight out of ten is going to fail. Maybe six out of ten. Depends. You just don’t know.
And I love it when people tell me, “Oh, I know when I make an investment, it’s going to work.” They are so full of nonsense. I’m talking about startups. They have no idea what’s going to work. And you won’t know for five to seven years, which is why you need diversification in the portfolio.
But I would go as far to say, now when I meet venture capital firms and young analysts that work there and they think they’re so damn smart, they’ve never operated a business, they know nothing, they have no idea what they’re doing. They’re going to hope that 1 or 2 of their portfolio is going to work out in 7 years and pay for all the other mistakes. But the serendipitous nature of success in entrepreneurship is brutal. It is.
STEVEN BARTLETT: So that, does that mean though, that it’s… I guess I was going to say, does that not mean that it’s highly luck? Investing is highly luck. Entrepreneurship must be.
Women Entrepreneurs and Their Success
KEVIN O’LEARY: Well, I said karma. You know, I call it karma. But you need executional skills. But here’s another skill that I think we should talk about.
When you look at at least my experience over decades of making these nascent, these early stage investments, these A round investments, remarkably, and I’ve done them in all 11 sectors of the economy, the majority of the successes five to seven years later are companies run by women. Why is that? Why is that? And so they don’t know each other, they’re in different sectors, they never meet each other. Why is that?
And I have come to the conclusion two things. They set goals that they can achieve so that in the early stage of their businesses, they put growth rate targets like 15, 16% versus men at 30%. Very often men hit their targets 65% of the time, at least in my portfolio and women, 90 plus percent of the time. And that keeps the team very sticky. They want to be part of it. So they don’t have a lot of attrition when they’re small. They don’t lose the head of financing and marketing. That works.
But they have another attribute, and this was pointed out to me by one of my female CEOs a few years ago. To me, she said, “You know, Kevin, you talk too much. You talk too much. You talk two thirds, you listen one third. Why don’t you try reversing the ratio?”
STEVEN BARTLETT: She said that to you?
The Power of Listening
KEVIN O’LEARY: Yeah, yeah. I’m very thankful actually, because I tried it. And she’s right. If you don’t talk and you listen, you become far more effective as a manager or an investor. In my case, by getting information that you weren’t going to get by talking.
And so if you go into a room, I just did this a few minutes ago before I came here, I’m involved in a litigation and we decided to attempt settlement talks, which is why I was a few minutes late. And you know, we knew we were going in there to settle. And it’s long protruded, you know, it’s a long, long, long litigation.
And I remembered her as we sat at the table like this. There were other people in the room, but the two, you know, we’re across from each other. I just looked at him. I didn’t speak for a long time. A long time. And it gets uncomfortable. And no one else is talking, you know, just looking. And maybe after 90 seconds, he blurted out something he shouldn’t have said. And I knew exactly what the price was right there. That was the end of it.
STEVEN BARTLETT: You learned that as a podcaster, you learned that there’s actually something going on in the silence.
KEVIN O’LEARY: There is something going on in silence. And it’s the number that he was going to settle at.
STEVEN BARTLETT: He showed his hand.
KEVIN O’LEARY: So we saved ourselves two hours. You know, it’s an attribute that many people can’t do because they can’t stand the social discomfort of it. I have no problem with it. I could sit here and look at you for 10 minutes, it wouldn’t matter to me.
And I’ve actually found it to be a very useful piece of information. It’s not just in negotiating, but to listen to employees, listen to investors, listen to financiers, listen to alternative ideas to yours, and become more powerful from it.
STEVEN BARTLETT: You’re in the very business of people selling to you and pitching to you. We both sit on a similar show and where people come in and pitch to us. You’re seeing at times 10 to 12 pitches a day. So you’ve developed this muscle over the last couple of decades now, almost this instinctive spidey sense of when an entrepreneur will be successful, at least in the context of securing investment. What have you come to learn about the attributes of the ones that are successful? Is there anything one can take from that?
Recognizing Winners Before They Speak
KEVIN O’LEARY: In the moment when that entrepreneur comes out onto the carpet in the context of Shark Tank or Dragons Den even, they need the setup shot of the product with the entrepreneur. And they have, in our case, a Steadicam or a Jib that comes down and shoots it.
So the stage director, Eric is his name. I’ve worked with him for years. Says to the entrepreneurs I’ve never met, usually it’s a team or it’s a family or whatever, three or four, two people, whatever. “Hold, hold, hold. Don’t speak, hold, hold. Don’t mind the camera coming into your face. Hold, hold” maybe for two minutes.
And I’m right there in front of them. I’m 12ft from them. And I just look at them. Not smiling, not blinking, not frowning, just looking at them. And before they say a single word, I know if they’re winners or losers. Just like that. And why is that? Why is that? When and I’m right probably 99% of the time, maybe I get it wrong one out of a hundred. I doubt it though.
You walk in a room, even though you practiced in the context of Shark Tank. 20 plus cameras, a billion plus dollars in the five chairs there. You’ve been practicing for months, your pitch, but it wasn’t the real deal. Here you are, cameras are rolling, tape is running. You know you’ve only got so many minutes. This is your moment and you’re on national television. 100 plus million people will see you in syndication. It’s all in your mind. It’s all in your mind.
It’s going through your… Can you project who you are with your eyes and the way you’re standing? Can you project your confidence? Are you looking at the ground? Are you looking away from me because you can’t stand me looking at you directly without saying anything to you? Or do you push back? Or do you say, I’m going to stake my aura, I’m going to stake my ground here. I’m going to show you I’m ready. See what I’m getting at?
And I can feel it. I can see that they’re ready to do battle. They’re ready to answer, they’re ready to present. They’re ready, ready, ready, ready. Or they’re not. And I’ve taken that out of the Shark Tank. I see that every day in life. I see it.
So you have to learn how to project yourself in front of your peers or who you want to lead or teach, or if you’re a general or a preacher, that is maybe an innate something you’re born with. Or maybe you can learn that. I don’t know, I don’t care. But if you don’t have it, you’re going to fail.
The Three Elements of a Successful Pitch
And that’s before a word is spoken, before the first word is spoken. And so then what has to happen? Then Eric says, “Go, you’re on.” And everybody’s just sitting there looking at you. Can you articulate your idea in 90 seconds or less? Can you… Whatever props you have or whatever you’re going to say, can I get the big idea right away? The ones that had that aura generally get there 30 seconds later. I get it. I get what they’re here for. I understand their product. Okay? That’s good.
Unfortunately, great ideas are a dime a dozen. I mean, there’s millions of them. The next phase begins. This is after 90 seconds. Can you explain why you’re the right person to execute on this idea and create a business from it? Because you know something about this space. You work for a competitor. You’ve tried three times before and failed. You figured out what you did wrong. What is it about you or your team that can take this idea and make it happen?
Now we get those two things together. You can feel the aura of the room, the isotope is sizzling because you’ve de-risked a great idea. You got an operator in. But then the third thing. This is the killer. This is the killer. I’ve seen it so many times in real life. Shark Tank’s real life. It is. But you gotta know your numbers.
How big is the market? How fast is it growing? What’s the gross margin? I mean, I’ve said this a million times to people. I teach this every day. How many competitors are there? When are you going to break even? What month?
If you get the first two right and you don’t know your numbers, you deserve to burn in hell. And I’ll put you there myself. I mean, you wasted an opportunity for an entrepreneur that did know their numbers, that could have been in that spot that I could have invested in. You don’t know your numbers. I take you up behind the barn and shoot you. You should have brought somebody that understands the language of business because those three together are the definition of leadership right there.
STEVEN BARTLETT: I’ve never heard someone talk about aura in entrepreneurship quite like that. And I was just trying to… For the people listening that are either trying to figure out if they have an aura or to grow that aura, what does it look and feel like? Is it physically, is it shoulders back, is it, you said it’s eye contact or is it indescribable? And do you think you could take someone who doesn’t have that aura in business and teach them it? Does business give you that aura?
The Power of First Impressions
KEVIN O’LEARY: I think you can teach it. I certainly try and teach it to my children. I try and teach it to my students. And the best way to do it is to look at yourself in the mirror sometime. You know, just what do you look like to yourself?
If you’re going to go make a presentation to take down a million dollar line of credit or something, you want to dress the part, obviously, but you’re going to walk in a room with a loan officer and maybe an assistant, maybe one other. Depending on the size of the deal, they’ll have never met you, probably. And you’re going to have to project yourself in those seconds as you’re walking up to shake their hands.
What does that take? It takes an aura of confidence, and it’s in the eyes, it’s in the way you’re standing, it’s in how you’re dressed. It’s not a joke to be dressed for success. You know, it’s something about presenting yourself and keeping your eyes focused on who’s talking to you so that they know that you’re absorbing the information, that you respect the information that you’re about to get into a narrative with them.
Even though there may be disagreements, all of this is happening in the first 60 seconds and it’s setting up for the rest of your life with that person. It could be who you’re going to marry, it could be who you’re going to work with. It could be your partner in business. It could be your banker. It could be anybody. It could be a soldier that’s going to give up their life for you. It’s sort of, who are you? That’s it.
Women in Leadership and Merit-Based Hiring
STEVEN BARTLETT: Just closing off on the point you made about women being your most successful investments. And the companies that have given you the greatest returns tend to be led by women. Does that mean that you focus on hiring women into executive roles?
KEVIN O’LEARY: Yeah, I’m practically all women, particularly Asian women. You know, this whole thing about DEI and all this stuff, I’ve always had diversity because I only hire on merit. I don’t care what sex you are or what you call yourself or where you came from or the color of your skin or what planet you were born on. I couldn’t give a damn. Can you execute?
The way I hire people, that’s why I have such a diverse staff in my operating company. I don’t hire you. I say, look, you sound good and you look great on paper, but that doesn’t mean anything if you can’t work within the team. So I know you want a job and you want benefits and all that stuff, but I’m not going to do that.
If you want to be part of my universe, you’re going to work for four to six months as a contractor at a much higher salary because you’re not going to get any stock options, you’re not going to get any benefits. But I just want to see what it’s like for you to work with all of the people that we deal with every day. All the lawyers, all the bankers, all of the CEOs that we have investments in and your co-workers.
Because I don’t do 9 to 5 anymore. I do project-based work. I don’t care where you live. We have people working in Dubai, Abu Dhabi, England, I mean everywhere. And we try and find an hour every week where we can see each other, but we’re just constantly communicating using modern day tools today.
But can you actually be given a mandate and execute on it? That’s it. I don’t care when you do it. If you have to get the financials out, let’s say you’re running in finance, you got to get them out the 15th for taxes. I don’t care when you do it. But if you miss the 15th, I care.
So I need to find out if those people can fit into that kind of an environment. Some of them make it, some of them don’t. Sometimes we know right away, after 90 days, let’s hire them, bring them in the team, let’s give them the whole package. And sometimes after a month we say, no, it’s not going to work. That’s it.
I think more companies should do that actually. It’s more like the Swiss apprentice system. They bring you in a lot. You know, my stepfather’s Swiss, I’ve been going to Switzerland for 50 years. So if you’re a giant company like a Pfizer or Nestle, you pull them out of high school at 14, you give them a job in the afternoon, they become an apprentice. They want to learn, they want to work, they want to understand what it’s like. And then you find the winners while they’re still in high school. Then you give them summer jobs and then you bring them into the company. That’s where I got the idea from. The Swiss are genius that way.
STEVEN BARTLETT: You’re sort of mitigating the risk. I guess you’re taking less of a risk on this.
KEVIN O’LEARY: No, but you’re also finding out if their DNA is going to fit with yours. I mean, I want my team to make a ton of money. I want them to be successful. I want every person to be proud to work with the other and just we’re almost invincible. We’re so damn good at what we do. You have the same thing here. You don’t have people that don’t work for you well, you get rid of them. I’m more just formal about it. Boom, you’re gone.
Shark Tank Success Stories
STEVEN BARTLETT: With the investments that you’ve made. How many investments, how many offers have you done on Shark Tank now?
KEVIN O’LEARY: Probably like, oh, we don’t even count it anymore. We look at the portfolio rolling over a five to seven year period.
STEVEN BARTLETT: A lot.
KEVIN O’LEARY: Like, a lot. And the thing is, what I’ve learned is you get an exit, like Basepaws from five years ago or something. Anna Skaya, remarkable woman.
STEVEN BARTLETT: That was the cat DNA thing.
KEVIN O’LEARY: Cat DNA thing. I mean, nobody saw that coming. I thought the thing was a joke. I was so wrong. I mean, that’s the whole point. And she had the highest IRR, I think, in the whole format’s history. She was around for 36 months and taken out at such an extreme number in all cash that there was an NDA signed between Sony and the pharmaceutical company. I can’t even tell you what it was. It was extraordinary.
STEVEN BARTLETT: Was it nine figures?
KEVIN O’LEARY: Believe me, it’s a tough NDA because. And I understand why they did it. They didn’t buy it for the cat DNA testing, they bought it for the data. AI wasn’t really emerging then. It existed, but it wasn’t. With the data they have now, they can develop products for animals that are extraordinary in terms of feeds and medicines.
STEVEN BARTLETT: Yeah.
KEVIN O’LEARY: And nobody had that much data on the 110 million cats in America because she got it all during the pandemic. Thousands and thousands of samples. It was a data company. It’s like my son telling me when he got his internship at Tesla. “Hey, dad, it’s not a car company, it’s a data company. Buy the stock.” I said, “I’m never buying the stock. It’s a joke. It’s so expensive.” He said, “You’re an idiot. It’s not a car company.”
So I bought the stock. And he was right. It became my most successful investment. I had to keep selling it down to 5%. My cost base is zero on Tesla now. But before it split and he worked there for five years.
Entrepreneurship and Failure
STEVEN BARTLETT: Personas that I have that watches this show a lot are young people, not always young, but that are on the sofa thinking about being an entrepreneur. And they talk about it a lot. You know, they come up to me in the street.
KEVIN O’LEARY: Two thirds will never do it.
STEVEN BARTLETT: Two thirds will never do it.
KEVIN O’LEARY: You might as well do it when you have less burdensome risk like a mortgage and a family, you might as well do it in your 20s. You’re going to fail the first time. Maybe the second, maybe the third. You only need one success. You know, I had plenty of failures and I still have failures.
I mean, it’s just, you know, that one I talked about this morning, I said to the larger shareholders and your assistant was looking at me in the limo, I was telling the other two shareholders, listen, guys, it’s a binary decision. As soon as I get out of this interview, we’re going to make a decision. This company’s going bankrupt.
STEVEN BARTLETT: Oh, on the bankrupt company?
KEVIN O’LEARY: Yeah. And so if we want to save it, everybody’s going to have to pony up X million and we’re going to own the whole thing. We’re just going to own it all. We’re just going to do a crammed down round at a fraction of a cent and own the whole thing. You want to do that or you want to let it go bankrupt? You guys choose. I’m one third of it. So it’s going to have to be, you know, two against one and I’ll do whatever they want because that’s how I am.
But you want to get yourself in a position in life that I think most CEOs understand this. You are going to have bad outcomes. There are going to be bad outcomes. But never put yourself in a situation where one bad outcome defines who you are.
I mean, for those shareholders, they’re going to be unhappy. But then I got the call on the IPO. Those shareholders will be very happy. They’re going to make 400x. So that was one of my deals. And so it’s sort of like learn to live with the idea that you are going to fail. You’re going to lose money by taking risk. Will it change relationships permanently? Maybe. But if you’re respected and you’re honest and you’re transparent, probably not.
I think there’s a lot of people don’t like me for my bluntness. I don’t care. I think a lot of people respect me for my bluntness. They may not like me and you know, it doesn’t matter because the only people that really matter to me are probably my 20 closest friends and my family.
The Influence of Steve Jobs
STEVEN BARTLETT: Do you think if you hadn’t worked with or known Steve Jobs, you would be a different person?
KEVIN O’LEARY: 100%. Steve changed my life. There’s no question I didn’t like him. But I feel so bad that he didn’t have to die that way. He just wouldn’t go with the modern medicine at the time is my view. Guy was a frigging genius. He was so smart in terms of keeping on track to get stuff done, and look what he achieved.
But he was difficult, difficult because he wasn’t always right. But he was right so much that the mistakes just didn’t matter. And I thought, you know, the people that spent enough time with him know what I’m talking about. You know, it occurred to me, because I know Wozniak, too, not as well as Jobs, but they really needed each other. They really needed each other because Woz understood.
Let me draw an analogy here for you. I think it’s a good one. Take the situation going on right now with Nvidia, AMD, to a certain extent, Intel, maybe Broadcom, where policymakers in Washington have decided that we can’t sell those chips to countries like China or Russia or whatever the list is of adversaries. That’s bad policy, and here’s why.
What I learned from Jobs was the computer, the chip is the queen bee. It’s the queen bee, but it has no value without the honeybees, which are the programmers around it that form a community that spend all of their energy writing code that works with the queen bee, which is the chip that pushes out its influence. Because every coder that becomes familiar with that firmware, that Wozniak computer writes to that platform, is part of the honeybees. Jobs understood that.
He said, I’ve got to get every honeybee writing for the Mac, writing for the OS of Apple. It’s the same with the Nvidia chip. We need to sell it to everybody, even adversaries, because within that country of Russia or China is some genius kid, you don’t know who he is or she is, that’s going to write the next piece of firmware or advanced AI from the queen bee, the chip, the American queen bee.
The minute you shut down a market and your adversary sends their queen bee in, which is Huawei. We can’t let that happen because I don’t think the lawmakers understand what Jobs understood. You create the hive with the queen in the middle. That’s the chip. You convince every bee around to make the honey, which is the software and is the AI. In this case, you make it off that chip, and when you advance the chip again, everybody knows how to take that set and stay within the American chip that you’re advancing.
Maybe you keep the one generation behind. Maybe. Maybe that’s the policy. But you don’t ever let an adversary put their queen bee in the middle of the hive. You see what I’m saying?
STEVEN BARTLETT: Of course.
KEVIN O’LEARY: And that is what Jobs did. That was the war between Gates and Jobs on the OS, on the operating system.
STEVEN BARTLETT: Yeah, I was thinking about the App Store and it’s the same thing.
Kevin O’Leary on AI and Business Strategy
KEVIN O’LEARY: It’s exactly the same thing. And so when I see this policy now, I go out of my mind. I mean, the first thing I do is get on a plane, go to Washington, because AI is so important for all the investments I’ve made. I do not want to be putting Chinese honey into my companies at all. It’s that simple.
Advice for Young Entrepreneurs
STEVEN BARTLETT: So for that person that’s stewing over their ideas now, if they had just a couple of minutes with you and they asked you the question, Kevin, I’m about to start this business. I’m about to go on this journey of trying to go from zero to something in my life. Is there anything else that I need to know as I set upon this sort of next 10 years of my life? I’m 21 years old because I think every entrepreneur has their principles. You talked about one, which is the signal versus noise thing. Are there any other foundational principles that you think are conducive with success that you might have learned?
KEVIN O’LEARY: What I’m telling 21 year olds now is, look, go work for 24 months in a sector you love, that you’re passionate about, even if they don’t pay you. Go in there and be an apprentice. If you’re that passionate, you’re going to be able to convince some manager to go work for free in there. They’re going to recognize your passion and they’re going to bring you in. Do that first.
Most young entrepreneurs say, “No, I don’t want to work for anybody.” I said, “Yes, you do actually. You do want to work for somebody. You want to just understand how all the cogs move.” Just 24 months. And after that launch, the first one will probably fail. You’re going to start with your parents giving you 10,000 bucks or whatever it is, friends and family, but you will have the baseline knowledge of your industry.
You will know who the participants are, you will understand how it works, and you’ll have a much higher probability of success. But the key is to launch sort of in your mid to early 20s because you need to burn a few years failing. And that matters.
Leadership Philosophy
STEVEN BARTLETT: On the point of how to lead people. When people hear about Jobs approach, they sometimes assume that you also have to be an asshole. And this is the conflicting thing, because the world has changed since Jobs was in a leadership position. Things have gone a little bit more soft, shall one say? Have you seen all types of leadership win out in that regard? The direct, signal focused, kind of brash approach, but also the kind approach.
KEVIN O’LEARY: I don’t think kind works. I think respect works. The same number of assholes are out there being successful now as they were back in the 90s. It doesn’t matter whether you’re an asshole or whether people like you or not. And people get so stuck on this stuff.
The team you’re building are not your friends. They are the team you’re building to execute on a mandate. Your customers come first, they’re more important. And then of course, the employees. And how are they respected or not? There are people that work for me I don’t like. It doesn’t matter. I respect them. I respect their ability to execute. And that above all is the most important thing.
If you start getting into interpersonal relationships, you will fail because you may have to fire that person one day. People that hire family take huge risk. Nepotism is a horrible disease. Some of the greatest private companies on earth never let the kids run them. They just put them on the board and they hire professional management. That’s how they keep wealthy, multi generational. Think of a Tetra Pack, for example. People may not know that name, but it’s a massive successful company. Ikea, I mean, you know, it’s sort of… You have to learn those lessons.
It’s about respect in both directions. It’s not about likability or softness or some social metric. It really isn’t. And trying to redefine leadership that way because it’s on trend, it’s not going to work.
Finding Great People
STEVEN BARTLETT: What about finding… The definition of the word company is group of people. So in terms of finding great people, is there anything that you can offer to entrepreneurs that are listening about how you’ve done that and what you’ve learned over time? The mistakes you’ve made with assembling your group of people?
KEVIN O’LEARY: Yeah, hiring them without testing them first. I’ve made that mistake.
STEVEN BARTLETT: So you now test them first.
KEVIN O’LEARY: Just because someone says they can execute doesn’t mean they can. Of course you’re in an interview. You’re not going to say, “I can’t execute.” You’re looking at their past. You’re saying, this looks terrific. Looks like you can fit in, but it’s on a piece of paper. They haven’t been road tested. They haven’t been put in a situation where they have to make individual decisions that have consequence.
The people you want are able to make decisions that have consequence. Good consequence, bad consequence, you don’t know yet. But they have to be able to make that decision on their own without calling you up because you gave them that mandate. Maybe you set a parameter. You could spend a million bucks. No more. Without calling me. But whatever it is, I don’t want to hear from them. I just want the outcome.
STEVEN BARTLETT: What about resilience and hard work? How much does that matter to you? Because I know you said they can work when you know as long as they get the job done. But are you trying to figure out if they are a bit of a psychopath in terms of hard work? If they’re possessed, obsessed?
KEVIN O’LEARY: I don’t find the ones that are psychopaths about hard work are actually the most successful. It’s not the case. I find the ones that are eclectic, people that have other pursuits that are nothing to do with the business they’re in, that do crazy stuff. Maybe it’s riding motorcycles in the desert. These are the examples I’m just using because I’m living with them and say, “Look, I’ve got to go and ride a bicycle across the desert.” Okay. How many days are you going to be gone? “I don’t know. Maybe three.” Okay.
If you look at the year’s outcome from that person, you’re going to find that they probably outperformed. You want the eclectic ones. You want the ones that are not just robots working. It’s going to be cheaper to get a robot. If you want a robot, I’m going to buy those, too, when they come available. But I want people that have creative and unusual solutions that, you know, just think outside of the box. It’s really interesting that way.
Growing and Keeping Wealth
STEVEN BARTLETT: The other thing that everybody wants to hear from you about is how to keep and grow your wealth. Because making wealth I kind of understand through the lens of entrepreneurship. Take a big bet, hopefully have an exit, or draw a dividend or make profit from a company you started. But in terms of what you did and your relationship with your money, what is the most important things for someone to understand who’s just trying to grow their money?
KEVIN O’LEARY: Yeah, I learned this from my mother, and I actually built a whole indexing company around it. When I was very young, I found out something that… So she was fiercely independent. She’s one of three daughters of Lebanese descent. My Irish father, my original father, biological father, was Irish. She didn’t… Yeah, there she is. George Ann. So I haven’t seen that picture in a while.
She was very independent and she never, ever wanted a man to control her life. So she started at an early age when she was working for her father. They paid the girls, the family all worked there. She worked in the accounting department and billing, but she got paid cash. And so she would take 20% of that cash each week and she would put it into two asset classes. Stocks that paid dividends, large cap stocks and telco bonds. Seven year telco bonds paid about 6.5 to 8% back then.
She bought the long bonds and she had that portfolio for 55 years. She never spent any of the principal, only the dividends and the interest. She put my brother and I through college. She took care of her family and her sisters when they fell on hard times. But her rule is very simple. No more than 5% in any one stock or bond of the portfolio, and no more than 20% in any one sector ever. Ever. So when a stock ran up past five, she’d sell it down. This is not genius. This is just diversification.
And when she passed and I was the older brother and I saw the portfolio because the lawyer said, “Listen, you gotta come down here. You’re the executor of will.” I said, “Yeah, but my mother was middle class.” He said, “No, you gotta come down here.” She kept her account secret from both of her husbands. She wanted her own independent money. And back then you could do that.
And damn, I mean, what that portfolio did, the performance was extraordinary. It was beyond any hedge fund guy or anything. 55 years. When I saw the results, I said, that’s it. That’s how I’m going to invest for the rest of my life exactly the way Georgette did. No more than 5% in any one stock ever, no matter what it is. And no more than 20% in any one sector, with the exception of real estate, which is a very large part of what I have in net worth, and it’s a third.
So that’s broken the rule, but there’s reasons for that. And I’m very happy with that portfolio. But if everybody that’s listening to this does that, they will maintain and grow their wealth. But people bet, they make big bets. They think they’re so damn right. They put half their net worth into one sector or one stock and they get wiped out. That’s what happens.
STEVEN BARTLETT: So would your mother pick the stocks herself or would she invest in an index fund?
KEVIN O’LEARY: She’d index. Even back then, you know, they didn’t have ETFs, but they had mutual funds that said, the only stock in this mutual fund is… Doesn’t have any debt and it pays dividends, you know, whatever. They were very rudimentary back then. They were just collections of stocks. I think she had like 28 names or something like that in the portfolio. But if you looked at them, they were really boring. Large cap names, but they were sectorally diverse. There wasn’t 10 sectors back then. There wasn’t 11. There was 10. So they didn’t have real estate as a sector. But, you know, I looked at it and saying, wow, these are really boring.
STEVEN BARTLETT: You learned a lot about money from your early upbringing, right? From your… That early context.
Financial Wisdom from a Billionaire’s Divorce
KEVIN O’LEARY: Yeah, because what she said to me was, look, you know, I even do this today with wealthy people. They call me up all the time. This very wealthy woman got divorced recently. She was a multi-billionaire, and she said, “Look, I’m getting divorced. Everybody’s calling me up to be my advisor because I’m separating from my husband. It’s all his guys that did all the management of our family wealth. Would you be my advisor?”
I said, “No, I don’t do that. But I can give you some basic advice and you can hire people that stick on the mandate.” I gave her Georgette’s strategy, but I had her do something else too.
I said, “Let’s get a piece of paper. You’re a billionaire. Let’s put everything on this piece of paper from the last 90 days that you’ve spent on whatever it is. And let’s look at all the income that you’ve made off your portfolio as it stands now, whether it’s gold you have or land or stocks or bonds. Let’s just do a gut check on do you outspend yourself?”
She said, “Why would I care?” I said, “Wouldn’t you like to know how much money you’re burning living your lifestyle the way you live it, just out of interest? Maybe you have enough for the rest of your life, but maybe you want to give some of it to your family one day or give it to charity. Wouldn’t you like to know?”
Because one of my rules is never outspend yourself on any 30 or 60 day cycle ever. I don’t have any debt, so I’m very careful about that. And we went through this little exercise, she freaked out. She was pissing away money, just bleeding hundreds of thousands of dollars a week.
I mean, I don’t care how rich you are, you don’t want to be stupid. And I said, “Does that shock you? You’re losing millions of dollars a quarter. Why? You’ve had nobody restrict what you do with your money because you’re going to have to sell stocks at some point or sell gold or sell land to keep this up. And are you really that happy? What’s all this stuff you’re buying? What is all this crap that you don’t need?”
It was an eye opener for her. So my point is most people don’t do that exercise. I don’t care if you’re only making $56,000 a year or $68,000, the average salary.
STEVEN BARTLETT: So are you in the camp that you shouldn’t spend money on the small things like the coffee if you don’t need it, you should make the coffee at home?
KEVIN O’LEARY: I just can’t stand it when I see kids that are making $70,000 a year spending $28 for lunch. I mean, that’s just stupid. Think about that in the context of that being put into an index and making 8 to 10% a year for the next 50 years.
STEVEN BARTLETT: What’s an index for someone that doesn’t know?
Investment Strategies for Everyone
KEVIN O’LEARY: I even built an app for this purpose. There’s many apps out there. You don’t have to use mine. Mine’s called Beanstalks. But you just allocate 15% of your salary and it automatically puts it into two buckets, some stocks and some bonds. The stocks are ETFs, exchange traded funds that just track the S&P 500.
STEVEN BARTLETT: Very simply, the S&P 500 is the top 500 stocks.
KEVIN O’LEARY: Yeah. People tell me, “Oh, I can beat the S&P. I can pick stocks.” They’re so full of crap. Not over the long period they can’t. So it’s better to just own ETFs. I have a version of the S&P that I designed with other people that strips out all the crappy balance sheets, but that’s just me. You can just buy the index that you want, the ETF, and then you pay low fees and over time it appreciates.
And then if you buy some treasury bills or fixed income, you get that. You should have less of those when you’re young and more when you’re older. Just diversification.
The best test I do with my kids’ friends too: Go into your closet and look at how much stuff you have you don’t wear. Because you either bought it thinking you were going to wear it and never wore it, or wore it once. You end up wearing 20% of your wardrobe all of the time and 80% you wasted. That’s really stupid.
For a young person, don’t do that. Just buy the minimum stuff.
Another thing I learned from my mother – she would buy two Chanel jackets a year. Really expensive, handmade Chanel jackets. I do business with Chanel because of the legacy of my mother and the whole Coco Chanel thing and watches, I love those guys.
Her theory was “this will never get old,” and it never did. A classic vintage Chanel jacket from the 50s that’s well kept is worth a fortune today. They’re so well made. So she wouldn’t buy crap, she’d buy really good stuff, but small amounts of it. Over the years she built up this portfolio of amazing clothing. And when she died, the women in our family had a cat fight over her wardrobe. Unbelievable.
STEVEN BARTLETT: Is that in part why you have so many watches? I’ve noticed you have a watch on either wrist right now.
KEVIN O’LEARY: Yeah, I’m pretty big into watches. To me, every piece I have marks something in my life that was important. A deal, a child, graduation, something. Every piece. I’ve got a lot of watches.
STEVEN BARTLETT: How many have you got?
KEVIN O’LEARY: I don’t even say anymore because of the insurance policy I have. I got a lot.
Understanding Dividend Stocks
STEVEN BARTLETT: You’re talking about your mother’s investing strategy and one of the things you said is she invested in dividend stocks.
KEVIN O’LEARY: Yes.
STEVEN BARTLETT: What is a dividend stock and should I be investing in dividend stocks?
KEVIN O’LEARY: A company, if it’s profitable and its business plan is working and it’s growing market share, at some point says “I’m going to distribute some of the success of our profits to our shareholders.” That’s the dividend. They send that cash to you and you can either redeploy it in other ways or live off it.
Many tech stocks until recently did not pay dividends. But now the behemoth tech stocks do pay dividends because the demand of an aging population is “I need to eat.” So I like to own the stock for growth, but I also want to get some of the profits.
Dividend paying stocks used to be utilities, but not so today. Every sector has dividend paying stocks. So I prefer to own dividend paying stocks. I also own fixed income products. I also own crypto now and alternative assets like gold and watches. My watch collection’s actually done quite well. Even though there’s been a correction, I have some watches that I bought for $200,000 that are worth over a million today.
Crypto as an Investment
STEVEN BARTLETT: Are you still bullish on crypto as an investment?
KEVIN O’LEARY: I am actually. But people get crypto confused with its real potential. Let’s talk about digital payment systems. We are days away from the Genius Act passing, which is actually the stablecoin act. It was just passed by the Senate 48 hours ago. It’s going back to the House. I actually worked on that bill two years ago.
If that bill passes, it’s really nothing to do with speculating on crypto. It’s a new form of payment. If I wanted to order a watch from Simon Britch, who’s somebody I buy watches from, a master watchmaker, right now I have to take US Dollars, go through a know-your-client process. I’m treated like a criminal by transferring $100,000, turn it into Swiss francs, takes about a week. I get charged about 200 basis points in the whole thing.
If he accepted USDC, which is a stablecoin backed by the US dollar, the transaction would happen in less than a second and the fees would be a hundredth of what the costs are right now. So it’s a digital payment system. There’s no speculation on it. It’s backed by the US dollar, Treasury bills.
That’s different than bitcoin, which is a speculation. If you believe in bitcoin, you think it’s a digital gold and you live through the volatility. I believe in both. I believe that crypto will be the 12th sector of the S&P at some point because it provides productivity to all 11 other sectors.
The way I own it is I own the exchanges. My exchange called Wonderfi up in Canada just got acquired two weeks ago by Robinhood. I’m happy because I think Vlad, who runs Robinhood, is great. And now he’s got a million plus accounts in Canada in a market that he’d never participated in.
This is never going away. It’s going to stay forever. So how do you participate? You can buy some bitcoin, just like you can buy gold, buy an ETF or actually own it yourself. You can buy the exchanges. You can buy Circle stock now it’s public. Circle makes USDC. You can buy USDC in an account and make 4.1% interest on it right now.
STEVEN BARTLETT: Your portfolio in terms of bitcoin allocation or crypto allocation, what is it now?
KEVIN O’LEARY: It’s at about, all in, we mark to market last month it was 19.1%.
STEVEN BARTLETT: 19.1%?
KEVIN O’LEARY: Yeah. We have to keep it under 20%. It’s a sector. But remember, in that is the cryptos itself, Bitcoin, the USDC and the shares of the infrastructure companies like Circle and everything else.
Home Ownership and Mortgages
STEVEN BARTLETT: One of the first things most people do when they get a bit of money, usually from their job, is they get a mortgage on a house. Because we’re kind of taught as we grow up that the best way, not maybe the best, but the most obvious way to create wealth is to buy your first home.
KEVIN O’LEARY: Yeah, there’s a very basic rule for that, and I understand it. I did the same thing. But what I made sure, again from my mother, was never let the mortgage and the cost of maintaining the house be more than one third of your income. If it’s more than one third, you bought too much house.
So it’s better to buy a house that’s maybe only going to be 1900 square feet to start in a neighborhood that you may not want to stay for the rest of your life, but start to accrue the benefit of real estate from that point of view. Learn how to manage it. Maybe you rent part of it out, but it can’t be more than a third of your income.
The mistake that people made, and they’re starting to suffer from it now, is when money was so cheap, mortgage rates were under 4%, they bought massive houses, and now they’re running into having to refinance those houses at much higher rates – more than 7%, and it’s becoming 60, 70, 80% of their income. They’re screwed. They bought too much house.
It’s about making sure that you can manage that. And also you want some diversification. Yes, a mortgage is okay, particularly if you’re having a family, because you’re going to pay rent or you’re going to pay a mortgage, one of the two.
But you want some diversification into starting to build up that investment account for when you retire so that you have something to live off. If you only put aside 15%, if you’re making $70,000 a year and you put 15% aside from when you’re 25, you’ll have over a million and a half dollars if you just invested it in the stock index in the S&P 500. That’s what history has told you.
STEVEN BARTLETT: In what time frame, your whole career?
The Importance of Financial Discipline
KEVIN O’LEARY: I mean, you’re going to be 65. You’re 25, 65. You just stick with that protocol and you’ll watch it grow. You’ll watch it grow. You go up and down as the market goes up and down, some years it’ll go flat, whatever, but it’s the people that don’t even think ahead and find themselves at 45 mired in debt, including a mortgage. You want to get rid of your mortgage in your 40s.
STEVEN BARTLETT: Most people’s primary investment asset is the house they buy. Is that…
KEVIN O’LEARY: Yes, it is. But it’s also the debt they own. It’s a primary asset. How much debt does it have on it? It’s only the equity values of the asset. So if you’re buying a house that’s too big and you’ve only put down 10% and it’s 90% mortgage, what do you really own? You really own the 10% at whatever price it is. Sometimes housing goes flat for a while it’s okay, but it’s not okay if it’s too much house.
STEVEN BARTLETT: If you’re a 25 year old and you’re on that 70k that you talked about and your objective was to make money, you don’t have kids, you’re not in a relationship, would you buy a house?
KEVIN O’LEARY: No, no, I wouldn’t. Because why do I need a house if I’m only… Unless I’m renting it as an income property. I’m buying a house because I’m getting married, I’m going to raise a family, I need a house.
STEVEN BARTLETT: Is that the use case for buying a house, you think?
KEVIN O’LEARY: I think it is people, but there are many people that say, I love real estate, I’m going to buy three houses, I’m going to rent them out. That’s a different business. And I know people in their 20s that do that. In fact, they’re successful, that’s all they do. And so their job is to find houses, buy them, fix them up and rent them. And they manage that geographically tight portfolio.
It happens a lot in student housing. For example, I’ve got a good friend who’s involved in student housing. He’s very successful. He just focuses on one aspect, buildings that rent to students. And he manages it and he raises a family. He’s successful, but that’s one thing he does.
That’s not the same as saying, I’m going to buy a house because I just got married and I’m going to raise, I’m going to have a child in the next 24 months, then you should have a house. But if you said to me, I’m single, I want to make money, I wouldn’t buy a house. That’s not the number one asset class. I think I’d get a diversified portfolio and just ride the pony with that for a while until I meet that special person I’m going to raise a family with. And then I have a little nest egg I can work with.
I mean, wealth creation comes down to one word. Discipline. That’s it. The ability to look at something and say, I’m not going to buy that. I’m going to keep that money working for me. Not many people have that discipline. Wealthy people have that discipline. You meet them later in life. You realize when they were young and had nothing, even the ones that were employees their whole lives that are now financially free had the discipline to say, no.
There’s so much stuff you don’t need and you should never buy a watch unless you can afford it. Ever go in debt for a watch because people hear this stuff, say, I’m going to buy watches like O’Leary with red bands. No, you’re not. That’s why I wear watches now that cost under $500 to show kids. You want to get into horology, you don’t have to spend $50,000. Here’s a Timex for $265. It looks beautiful. Get that.
The Impact of Relationships on Financial Success
STEVEN BARTLETT: You said, you know, don’t buy the house until you meet your partner, et cetera. How much does the person that you fall in love with have an impact on your finances, your money, your chance of success, in your view?
KEVIN O’LEARY: It’s everything. Are you kidding? I mean, it’s everything. If you read… I mean, think about this. You need to find somebody if you’re an entrepreneur. So that’s for the… We’re talking about the third now that want to go on a rocket ship ride. You better find somebody that’s willing to tolerate the fact that you’re never home for the first 10 years. They’re going to raise a family by themselves because there’s no balance in life.
That idea of balance is complete nonsense. I mean, it’s just nonsense. You have to work so hard to compete globally these days. In every sector. You’re going to work your ass off and it’s not going to happen over… I mean, Anna Sky did it in three. She had worked much harder previously. It was not her first deal, but she was just lucky. I mean, she was this…
STEVEN BARTLETT: The cat DNA.
KEVIN O’LEARY: I mean, but she’s, you know, she’s working again. She’s back, she wants to work. I mean, that’s what happens. You never stop working. But the thing is that partnership, and this is what people don’t get about marriage. Marriage is a business. I know, people go nuts when I say that, but it’s a business, and the first child you’re going to have is money. It’s going to be the first child, and it’s going to sit at the table with you every day. It’s there. It’s sitting there. If you don’t have money, you don’t have a marriage.
I mean, the reason people get married is to form a form of financial stability so that they can afford a family. And you have to figure out, you know, I’ve been with my wife a long time, and we’ve been separated for a couple of years. But, you know, family’s very important to me. So we got back together again, and, you know, our daughter got us back together. I’m very happy we did it.
But it’s… We make financial decisions together. We always check in, you know, anything that’s material, you know, if we’re going to do a renovation or something. And I respect her for that. I have a lot of respect for her because she doesn’t just spend money. We didn’t have any money when we started. We had nothing. And so that’s why a great marriage can work, because you build it together. You really care about it. You care about your family. You also care about what you’ve created in wealth. And I consider my money her money, because she was the family that let me go and do this stuff.
Now, I don’t have the same relationship with our kids that she does because she raised them, but that’s the thing you give up, and you have to give something up. That’s it. You can be a great father, a great provider, but you’re never going to have the closeness that she had. Reading them stories when they were young, I wasn’t there. But, you know, the outcome has been good. I think everybody looks at that and says, all right, that’s great.
But my mother never believed in entitlement, and so I don’t believe in it either. I’m not gifting my kids a ton of money. You know, I want them to launch, and they’ve done that successfully. They got to… They got to work, you know, they got to do their thing.
Marriage as a Financial Decision
STEVEN BARTLETT: I’ve heard you say before that the most important financial decision you’ll ever make is who you’ll marry.
KEVIN O’LEARY: Yes. Why? Because think of the geometric loss of wealth. Every time you get divorced, you pay the woman that you divorce or man, and you pay the government a third, often through capital gains and liquidation, because you can’t separate all the assets without liquidating them sometimes.
So you’ve got the government sitting there, you’ve got the other spouse sitting there. This is the stupidest thing you can ever do. It took your whole life to actually create this nest egg. Could be, you know, you’re 45 or whatever, you’ve got a comfortable life, and all of a sudden you don’t like your wife or husband. Think about that for a while, because you are going to wipe out up to two thirds of your wealth. You better really like somebody else a lot.
And frankly, sometimes it’s not the other person that you’re divorcing. It’s you. You’re the problem. If you’re getting married for the third time, you’re a guy or a woman, it’s not them, it’s you. There’s something wrong with you. And you should probably not get into another economic union. You should probably just date till you drop dead, because it’s stupid.
Marriages are tough. I mean, they’re tough. Anybody who’s been married for more than 20 years knows exactly what I’m talking about. But they accrue more benefit than anything. So if you’re happy 51% of the day with your wife, stay with him or her husband or wife. That’s very important.
STEVEN BARTLETT: How often do you think divorces are a result of money issues?
KEVIN O’LEARY: Well, you may be shocked at this. I wrote a book about this, and I decided “Men and Women and Money” a long time ago, 10 years plus. Right. There it is. And I did some research, and I went to meet some of the top divorce lawyers in North America, in New York, in Boston and other cities.
And I said, look, I want to kind of do a pie chart of reasons for divorce that seemed… That 50% seemed to end in divorce within five to seven years. Every one of them, they didn’t know each other, said, it’s not infidelity, nothing to do with it. Most marriages can survive infidelity. They can’t survive financial stress.
And so what happens invariably is you fall in love, but you didn’t do any due diligence on that person’s spending habits or their financial history. Because love is so wonderful in the early days, you didn’t do any diligence on their family or them or their brother or bankruptcy in the past or whatever it is.
And then you get married and, you know, the euphoria starts to wear off and you notice that the other is outspending you, just buying a lot of stuff beyond your means. And that starts the first friction. And then that credit card comes in with $100,000 on it at 23% interest and another purse was bought or whatever the hell it is. And you’re starting to sink because you may have married somebody who can’t stop spending.
This is just typical. There are people that have no discipline. They just can’t. They got to have the boat. They got to have this, they got to have that. And they pressure their other to say look, I want to keep up with the Joneses next door even though they may only each have a salary of 100 grand each. Can’t do it. And they have kids and they’re trying to put them through college.
That’s divorce. That’s why almost 90% of unions break up. Is that classic financial pressure. And divorce gets them out of that mess because they can no longer spend on your credit card anymore. But it’s a horrible way to go.
So I’m an investor in a company called Hello Prenup that does prenups for women. And prenups force during the euphoric period, diligence. It’s that simple. You’re going to find out if that person has a financial problem going into the marriage. They have to disclose their financial background.
The Five Love Languages of Money
STEVEN BARTLETT: So you talk about these five love languages of money. The mooch. Someone who won’t pay for anything.
KEVIN O’LEARY: Right.
STEVEN BARTLETT: Should I date someone like that?
KEVIN O’LEARY: It’s a warning signal. It’s a problem.
STEVEN BARTLETT: It’s a problem.
KEVIN O’LEARY: Or they don’t really want you for companionship. They just want you for financial support.
STEVEN BARTLETT: The spendaholic. Someone who always offers to pay for everything to appear popular and successful.
KEVIN O’LEARY: Bad warning sign. Huge. I mean that isn’t… That is insecurity measurable by cash outlay.
STEVEN BARTLETT: The loafer. Someone who has no ambition and drive for money.
KEVIN O’LEARY: Avoid with extreme prejudice.
STEVEN BARTLETT: The thief. Someone who steals.
KEVIN O’LEARY: You can have no tolerance for that.
STEVEN BARTLETT: And the meanie, a balance spender who lives within their means.
KEVIN O’LEARY: Love that. Marry a meanie. That’s it. Those are the marriages that last an entire life. That’s it. That’s what you’re looking for. That’s great advice right there. Whatever the book costs, that’s the best value right there.
And then ask yourself, am I dating one of these or not? You know, you should talk about money on the third date. Think about a date. Think about dating. First date. Oh my goodness. This is a really interesting person. Or not. Then there’s never a second date. Second date. I want to learn more. I’m really interested. You’re going into a third date. There’s something going on. There’s something going on. You both want to meet again.
That’s the first time you should say, look, I know this is crazy, but we’re here together a third time because something’s going on here. And I’m just wondering, what are your long term goals? I mean, it’s not about our marriage or anything else other than we’re having a great time, but what are your ambitions? I’m really interested in you. I’d like to know what you think.
And maybe the woman says or the guy says, what, are you checking me out? You say, yeah, yeah, I’m really interested in you. It’s a form of finding out as the connection, you know, I should be a marriage counselor. That’s what I think. I mean, it’s really dating is the dance, but it should involve exploring where we’re going financially.
The Impact of Artificial Intelligence
STEVEN BARTLETT: One of the big protagonists in the story of many things we discussed. Money investing, building businesses. Now is this thing called artificial intelligence which you mentioned earlier.
KEVIN O’LEARY: Yes.
STEVEN BARTLETT: It’s like entered the room.
KEVIN O’LEARY: Yes.
STEVEN BARTLETT: It’s changing lots of these equations in a really profound way. Again, for that person who is maybe at the start of their career or even they’re a lawyer right now, how are you thinking about AI? What should they be thinking about? Because I don’t think we’ve seen something quite like this. Certainly not in my lifetime. I’ve not seen disruption of this scale. I wasn’t around for the dot com boom. I was too young. I was 8.
KEVIN O’LEARY: Yeah.
STEVEN BARTLETT: So how should we be thinking about this moment? Is it a huge opportunity for wealth creation or…
AI’s Business Impact and Real-World Applications
KEVIN O’LEARY: Yeah, it’s immense. It’s bigger than the Internet. I’ll tell you why. I want to keep it down to earth, because I’m actually using it now in use cases. There’s every sector of the economy, every aspect of research, every aspect of business has a huge opportunity here.
But let’s just take use cases that you would understand. Everybody listening would understand. In today’s post pandemic world, most businesses have developed large and small direct to consumer strategies where they try and build relationships with customers and sell them product direct. They still use retail, say for Nike or something. And you were 27% direct to consumer before the pandemic. You’re now 50%.
Direct to consumer gets you higher margins, but also gets you data, gets you information about the preferences of your customer base, what they like, what they don’t like, the flavors and what they buy, when they buy, where they buy it, all that stuff. It’s very interesting data.
Let me give you an example. Wine business. If you think about the wine business, the challenge of a thousand year old business, you don’t know what the weather’s going to be like, you don’t know what varietals to grow because you don’t know what the preference of the customer is because you’re selling it through multiple tiers of distribution.
During the pandemic, 43 states in America opened up direct to consumer sales from the wineries. In the west coast, for the first time ever, the wineries found out what people buy, where they buy it, when they buy it, what they drink, what varietals.
I’m in the wine business. I sell with 3 million bottles a year of wine. One of my companies, actually a Shark Tank company, and we partner with a company called QVC, we sell online. And so I can tell you today, this month, this week, the number one varietal in southern Florida for women ages 44 to 64 is Moscato, a sweet wine. I think it tastes terrible. I don’t care what I think. It’s the number one wine right now.
And I knew that to make that varietal available six months ago so that I would be able to ship it and put the inventory, the capex, in the right place at the right time to support that demand for the rest of this summer, a sweet, cold Moscato wine. That means I spent a lot less money and took a lot less risk. I don’t have any varietals they don’t want this summer. I have exactly what they want. That was AI. It cost me virtually nothing to get that data. Five, ten years ago it would have cost me a million bucks to go do all the market research. I got that for $18,000.
So that’s using an AI tool. Do I use that tool? 100%. And there’s many tools you don’t have to just use Chat. There’s many different competing platforms, so we use them all. We check the assumptions by checking it all on all of them. See the little variances.
AI in Content Production
Number two, I have to shoot an ad. I have to shoot a commercial. I’m going to shoot it here in LA. I’m going to do it in a studio like this with a green screen, and I’m going to spend $250,000 for a 15, a 30 and a 60 second ad out of the same shoot. And I’m then going to go into post with the green screen and I’m going to spend more money in post. I’m going to add whatever background I’m going to need.
Or I could fly to Dubai, where they have a giant studio with a 6K digital wall where AI links up your script to the background. There is no post production. You basically shoot the commercial in four hours and it’s done. The background’s perfect, the imagery’s perfect, your script is perfect. And I did that two weeks ago for the first time. I’d never seen that before. We did it for a fraction of the cost of what it would have cost to do it in the old way in post production.
But then, I’ll tell you what freaked me out. They reshot the commercial without me there, using Kevin agent.
STEVEN BARTLETT: An AI you.
KEVIN O’LEARY: I wasn’t even there. And just to show that they could produce a new commercial with the same background for $9,000. That would have cost 400,000 from scratch.
STEVEN BARTLETT: So there’s going to be a lot of job disruption then, because as you said, you don’t say…
KEVIN O’LEARY: But on the other hand, I’ve now got content for that particular business I was shooting. And I said, guys, let’s tweak it and shoot it again. He said, yeah, we’ll do it in two seconds. We’ll send you the 15 seconds back. I said, I don’t like what I said there. Can I change what I said? He said, yeah, well, do you want it in Spanish? Do you want it in Japanese? You want it in Arabic?
That’s the power, the productivity that we’re going to get. Our budgets for producing content are going to drop dramatically over the next year.
The Strategic Importance of AI Technology
STEVEN BARTLETT: And software and everything else, right, creating everything is going to get now full.
KEVIN O’LEARY: Circle to your thing about the chips that all came from Nvidia chips, that’s not from Chinese chips. Whoever controls the chip and the honeybees that the honeybees are, those guys are all Indians and Pakistanis. They’re genius mathematicians. That’s the team over there running off that platform. If we had let… Anyways, I don’t want to… I’m just freaked out that we got to control that. We need democracy to control that.
STEVEN BARTLETT: Your children, what are you saying to them, though, about their professional ambitions in a world where creating stuff like that and, you know, whether it’s who do you want to do your taxes, an accountant or an AI? Who do you want to do your legal documents? Who do you want to do any sort of like white collar job, make your videos, edit your videos.
KEVIN O’LEARY: I tell them, you know, everybody’s got a lot of angst about AI. I tell them, listen, everybody chillax. It’s a tool. You know, it’s the same classic thing where radio was going to be displaced by television. Radio is bigger than it ever has been. It doesn’t matter.
The one thing I concern myself with, with AI is warfare. And I think the country that has the best AI and data centers and the most advanced chip technology will win the wars of the future, which will be fought by drones and robots. I know that sounds kind of crazy.
STEVEN BARTLETT: No, it doesn’t sound crazy. It’s happening now.
KEVIN O’LEARY: That’s where it’s going to go. So when I solicit the ear of a senator, I try and explain to them my honeybee analogy, saying, this is about defense. I don’t want to live under authoritarian. I know we debate the whole political environment these days, but I don’t want to live around Chinese honey. I just don’t.
And those are going to be the two superpowers. You’re in one vertical. Either you let the Chinese make the honey on AI, or we make the honey and let the Chinese buy some honey from us. I know where I want to live, I know what I want to do. And I think I can convince a lot of senators the same idea. Because you got to understand the Wozniak Jobs analogy that we, that you brought out earlier, that was the genius of Jobs. Make the honey, but know who the queen bee is.
STEVEN BARTLETT: The genius of Jobs. Brings me to a question I’ve wanted to ask someone like you for a long, long time, which is, do you think Apple is dead?
KEVIN O’LEARY: No.
STEVEN BARTLETT: You don’t?
The Genius of Apple and Steve Jobs
KEVIN O’LEARY: No. I’ll tell you why. I’ll tell you why. You know, it’s so interesting. People don’t understand the genius of Apple because this, again, came from Jobs. He used to say to my team, over and over again. And I mentioned earlier, they don’t know what they want until I tell them.
And I always, just as close as you and I are right now. “Steve. How do you know that? How do you know that? You don’t know that. You don’t know what you don’t know.”
He said, “Show me where I’m wrong. Show me one instance of us working together where I’m wrong.”
I said, “It hasn’t happened yet, Steve. Doesn’t mean it won’t.”
“Get back to work. Don’t worry about it. I’ll worry about it. You make the software. I have the chips. Make the software. Go make the honey. I have the clean bee. Don’t worry about it.”
And that is pretty interesting because you got to prove that he was wrong. Let’s accelerate. He’s dead now, but the philosophy of Apple, and I’ll give you the way you win at it. You look at it, I can go buy a $330 laptop right here with the same processing power of this $1800 Mac laptop. Why would I spend 1800 when I could buy this for 300? Why? Brand? I want to be part of this universe.
This honey right over here, the Apple Care. The fact that the OS works on all the platforms and the messages are shown on all platforms simultaneously. All the OS, all the honey. That platform is the power of brand. I’m not leaving this universe. And Apple is one of the world’s largest companies.
And you may say, “Oh, innovation is going to make everybody leave that platform?” I don’t think so. They let other people sometimes bring in a new market, and then they take it over. And I saw Steve do that multiple times. He did it with the phone. I was around for that. That was crazy.
I mean, he had the vision that we would someday run our software on the phone. I said, “You’re out of your mind. The screen’s too small.” He said, “No, you’re going to go vertical. You’re going to rewrite all this crap vertically.”
I mean, I can’t fault him on anything. Although I kept telling him, “You’re going to get it wrong one day. You’re not going to be right all the time.” I can’t find when he wasn’t right. That’s the frustration. Because I teach this to a bunch of really smart kids at Harvard, of which, by the way, a third are international students, and they say, “Well, when did you catch him?” I said, “I didn’t.”
STEVEN BARTLETT: What was he doing? Did he ever practice or principles that allowed him to see around the corner?
Steve Jobs’ Creative Process
KEVIN O’LEARY: He spent a lot of time at night, you know, even studying fonts and looking at art and focusing on the signal. I think his wife talked about that a lot. She spent more time with him than anybody else, although Woz talks about it a lot because those guys spent countless hours together.
Jobs would take instances from nature into his head or from Japanese scripture or text or imagery and redefine it into technology in a way that no one else was doing. And that’s the idea of the honey and the bee and the queen and all that stuff. It kind of comes from his view of the world.
And I don’t know if you can understand this, but because it was so… it came from nature, it was easy for people to assimilate it. It wasn’t foreign when they looked at the imagery and the design. He tried to pull from pleasing images from nature, like the fonts on the first Macs.
I remember when we were writing the code for that saying, “Steve, this is not what people are used to seeing on a computer screen.” He said, “No, it isn’t. That’s why it’s going to work.”
If you think about the very first scalable fonts, I saw that first and I said, “See, this is almost foreign.” He said, “Well, how does it make you feel?” I said, “It makes me feel pretty good. This looks like it’s on a piece of paper.” You weren’t even born when this stuff was happening, but he was so far ahead.
And this is the same way Elon is redefining. Whether it’s SpaceX or whether it’s what he’s doing in neurosurgery or Tesla or all of these initiatives, satellite technologies, they are the same, those guys, except Elon’s 100% signal. I said that earlier. They are the same, and they should be. They’re treasures. They’re national treasures.
It doesn’t matter if you like them. It doesn’t matter what their politics are. It’s irrelevant. The contributions they’re making to society and to America, frankly, and the competitive nature of countries. That’s why I thought it was so important that Trump make up with Elon. The most powerful man on Earth should have a very good relationship with the richest man on Earth because he’s the largest industrialist on Earth.
STEVEN BARTLETT: Maybe there’s like an inherent inability by way of them being who you just said they are.
KEVIN O’LEARY: It’s the most powerful man but they know. They’re smart enough to know. It’s the same way I felt about Jobs. I’m getting back on the plane this quarter. I know he’s going to beat me up, but it doesn’t matter. The greater good is that we get this software out there. Advanced math and reading scores.
Was Steve Jobs Happy?
STEVEN BARTLETT: Was he happy, Steve?
KEVIN O’LEARY: I don’t know the answer to that question.
STEVEN BARTLETT: Do you think he was a happy person?
KEVIN O’LEARY: I don’t know. I never saw him happy. He was always barking at me. I never saw him happy. I don’t think I ever saw him laugh. He may not have been, you know, I mean, that’s probably something his wife would know, but he looked like a tortured guy to me. But, you know, that may have been his curse.
STEVEN BARTLETT: Do you love him?
KEVIN O’LEARY: Yeah.
STEVEN BARTLETT: I can see it in your face.
KEVIN O’LEARY: 100%.
STEVEN BARTLETT: I saw a lot of emotion in your face the first time you spoke about him. And I thought, that’s surprising for someone that barked at you.
KEVIN O’LEARY: Well, he respected me, that’s for sure. He wouldn’t execute on my ideas. He expected me to execute on his. But he was never wrong.
STEVEN BARTLETT: Where did the emotion stem from?
KEVIN O’LEARY: You know, it brings me back into that room with Heidi Rosen and all the crazy crap. I mean, it was just nuts. And, you know, I’d have to spend a lot of time. The only meeting I really remember, the one that really sticks in my mind, when we were in Cupertino and we were, I think, I don’t know, we were going after him for 18 million or something, and Heidi was there.
STEVEN BARTLETT: She’s Heidi.
Working with Jobs and Heidi Rosen
KEVIN O’LEARY: Heidi Rosen. She’s a famous venture capitalist. But she was also kind of the muse, the person that could actually deal with Jobs all day long at Apple and bring him back to earth when he was out of his mind.
I’ll give you an example how that would work. And I’ve seen her since, I don’t even know if she remembers this particular… Anyways, we leave, he’s barking at me, and he’s got one of my product managers in tears because she wanted to do the market research. And he said, no way. We’re just going to do what I say. And she just felt like her job was useless. And for him it was. I mean, he just didn’t care what she thought. Although she ran the Universe of Oregon trailer or something. It’s a massive title, like a huge multi-million dollar title on the Mac in every 110,000 schools in America.
And he was so pissed that, you know, in these old buildings, they have a little window where you have a little knob, and it only opens up 4 inches, so you can’t jump out of it in a hotel or something. So we had a Hertz rental and the whole team’s going out. I’m going to drive the car back to San Francisco. I’m going to fly back to Boston.
And he undoes the window and he’s got his head stuck and he’s yelling at me. I’m looking up at him and saying, “What? What more can we… You already kicked us out,” and then on the way, we had these old brick phones. Heidi calls me and says, “Okay, he’ll do it for 12 million.”
I said, “Heidi, why do we have to go through all that? Like, why do we even have to get abused?”
She said, “Why is the sky blue? You know, just get back on the plane and go.”
It was a huge hit. The guy could write the hit songs. That’s what he did. He’d write the hit songs. So, you know, even if you hate the producer, you want the guy that can do the hit songs, right? If you’re an artist, you put up with a crazy producer.
STEVEN BARTLETT: Could he not have been nice, do you think?
KEVIN O’LEARY: Not in his DNA, no.
STEVEN BARTLETT: Do you think if he was a nice person, he wouldn’t, you know what.
KEVIN O’LEARY: He would say about that? That’s noise.
STEVEN BARTLETT: He gives a fuck.
KEVIN O’LEARY: Yeah, he doesn’t give a shit. No, being nice is noise. That for him. I mean, we spend a lot of time talking about him. But I think there’s a lot of lessons learned from him that I think managers today, parents today, certainly CEOs today, you know, this show’s about CEOs.
I wish every CEO had spent the time, the minimal time that I spent with Jobs had such an impact on me. I owe a lot of my success to him because I think… I always think, what would Steve have done? And I make decisions like that. It’s amazing the guy’s still around.
I bet you if you talk to any of the management at Apple, they have that ghost in those rooms, for sure. Including the current CEO, I think was doing a phenomenal job. He spent so many hours with Jobs. He knows exactly what I’m talking about. Nobody spent more time in business than that guy, for sure.
On Personal Happiness
STEVEN BARTLETT: I asked you a second ago if Steve Jobs was happy, but are you happy?
KEVIN O’LEARY: I get happier the older I get because I’m very comfortable. I found a place, you know, and this may be just what aging does. When I was in my 30s, I had a lot of trauma and turmoil and just hard time trying to figure out who I was. And I also suffered from dyslexia, which I’ve come to think of as a superpower now. But it was kind of like, it’s hard to know what journey you’re going to be on until you find it.
And then I found it, and then I started on a new journey. And it’s something where you ask yourself every day, this noise and signal thing, how much of this day was I happy doing the things that I wanted to do? And I am very happy.
If I measure it by, is there anything that I spend my time doing that I don’t want to do today? The answer is no, because I don’t have to. And so I don’t waste my time. Even coming here to spend two hours with you. When I first heard about it, I went online and said, “Oh, yeah, this guy’s great. I’d love to work with him.” You allocate your time. I’m happy to do this. I want to be here. And I think we had a very interesting couple hours together, but that’s the definition of happiness.
What concerns me, and my wife often says to me, “We don’t need any more money. Why are you flying 300 hours a year on an airplane? What are you doing?” I said, “I’m happy. I’m happy doing this. I want to do this stuff.”
You know, sometimes I do five cities in a day. It’s crazy. And it’s the wonderful thing about air travel, you can do that.
STEVEN BARTLETT: It’s sport for you.
KEVIN O’LEARY: It’s so interesting. I get so many interesting opportunities. I can’t turn them down. They’re just such, you know…
STEVEN BARTLETT: Are you driven or are you dragged? You know, you use the word trauma there. And I often ask myself that question because I came from an all white area. I was the black kid with strange hair and strange family. I was insecure. And I think that resulted in this force of will to try and correct the insecurity or to prove something to myself. Which then resulted in success.
Drive and Determination
KEVIN O’LEARY: I think there is no drag, there’s only driven. I don’t understand being dragged. Drag insinuates that you don’t care about performance. You don’t care whether you succeed or not. You’re just being sucked into the void of success. You might be able to say that for a rock star that gets a hit song, but most of them don’t last. You need massive amounts of drive.
And I love… The most exciting thing I like to do is when someone tells me, you can’t do that. Like watch insurance. You will never launch a watch insurance company. You will never do that. You will never get around the compliance state by state. You will never launch in the Middle East, you’ll never launch in England. Bullshit. That’s exactly what I did. I found the right team, I found the right partners. I figured it out. I was passionate about it, and I think I’m going to kick ass. I think in two, three years from now, you won’t be able to catch up with me. That’s what I think.
STEVEN BARTLETT: I’m 32 years old. What is the advice that you wish you got at 32 years old, Kevin?
The Value of Authenticity
KEVIN O’LEARY: What I have learned, and this is something that you should really think about for yourself. Your real value, your real brand, are your followers. This army of people that have decided to invest their time in you. You’ve cut across a vast swath of people. So you influence very successful managers, CEOs, and a lot of young entrepreneurs want to hear what you have to say because they’re expecting you to deliver valuable information across multiple sectors. And you also have your own data, both men and women.
And so where do you take that? Because, you know, do you want to launch a clothing line? Do you want to sell burgers? Do you want to do consulting? You have all those opportunities, but what fits your brand?
You’ll get to do this. You’ll be approached by a lot of people that want to ride that network you’ve built. And my advice to you is, because this has really worked for me: Is this a product or service that I personally would use, that I would actually use? Because you’ll get offered a lot of money to talk about one brand or another brand. They will. And you may be weak and take it. But the minute anybody in your network, in your community thinks you’re not authentic, you’re finished. And you know that.
So you better be authentic. You better be transparent, you better be honest. Even when turmoil hits, whatever it’s going to be, I found that saved me so many times by just saying, here’s what I know, here’s what happened. And that actually bonds them even closer to you.
That’s the difficulty you’re going to have, is how much do you want to take, because you’re going to have that opportunity. But if you stay authentic and say, I’m going to support this brand because I use it, every single brand or commission I have in supporting a business, I use myself, I’m a shareholder in it and I believe in it, and I use the product. Like the wines I make myself with my wife, we drink them in our family and everybody knows that. I wouldn’t drink it if it’s bad wine.
So that’s my advice to you, because I meet a lot of people, but you’re very rare. What you’ve built, maybe by happenstance that it occurred, whatever alchemy occurred, you have it. Now it’s yours to lose. Don’t mess it up.
STEVEN BARTLETT: Everything you said is so true. And obviously, the things that I… The things that we talk about in the show, in terms of brands that I promote, pretty much all of them I’ve invested my money into.
KEVIN O’LEARY: Yeah.
STEVEN BARTLETT: And this is like, super important. So I talked about my Whoop. If you look at the investments I have and the things I talk about, there’s a really clear through line through them. And it’s actually reflective of just where I am in my life.
There’s actually a sponsor I used to have on the show that I was very big on, and I just stopped. I stopped consuming the product. They offered me 6 million pounds, which is about, what, $8 million, to continue for another year and a half.
KEVIN O’LEARY: Yeah.
STEVEN BARTLETT: And I said, it just wouldn’t… I’m about to basically start talking about and investing in the antithesis of what you do. So I had to turn down that $7 million, which is a lot of money for anybody. But it’s because my life shifted and I shifted in a different direction.
People don’t see those things. They don’t see that this foreign government comes along and offers you $4 million to go and talk about their country or to go do the Diary of a CEO in their country. They don’t see those decisions that you make. But I think hopefully, if you listen to me long enough, you’ll see a through line between the things that are authentic to me.
Focus on Longevity
KEVIN O’LEARY: Yeah, I think that… So you’ve already figured it out. And the other thing that I would do and say to anybody your age, because I wish I’d done it, is start focusing on longevity in your 30s, start thinking about what you eat and what you drink and how much sleep you get and how much exercise you have. You could live to 120 years old.
I mean, you’re wearing a Whoop, you know what I’m talking about. I’m very, very, very focused on what I do and exercise and what I eat and all that. But that makes you feel healthier and just better about your day as you go through it.
But the fact that you figured that out at your age, because most people at your age would have taken $7 million or whatever it was, that would have been a huge mistake. Because now the next product that you do endorse, I will know with certainty that you use it, because you told me that.
STEVEN BARTLETT: We have a closing tradition on this podcast where the last guest leaves a question for the next guest, not knowing who they’re leaving it for. And the question that was left for you, funnily enough, I feel like I might have asked it, is where do you believe happiness really comes from?
The Journey of Happiness
KEVIN O’LEARY: You know, I think the answer is very simple. Consistently achieving your goals. Because happiness is not a destination, it’s a journey. That’s what it is. So you have to set those goals. Whether it’s noise to signal, going full circle, what we talked about, or long term, whatever it is, it’s consistently achieving those goals, you will be happy. Consistently not achieving them, you will be unhappy. Because it is not a destination. Happiness is not a destination ever. It’s a mistake that’s so elusive. I mean, it’s just not a destination, it’s a journey.
STEVEN BARTLETT: This is one of the great things you’ve taught me today, reaffirmed for me today is this idea of like signal and noise and radical prioritization because kind of dovetailing into what we were just talking about. When you have a lot of opportunity, it gets even harder, I think to know which ones should be taking you 18 hours a day. This is something I struggle with.
Trust Your Intuition
KEVIN O’LEARY: You should feel it. You know, you’re kind of a weird dude because you’re like a 70-year-old man in a 30-year-old body. You’ve got the intellect of experience, which most people don’t have at your age, but deals… There’s a certain feeling that you should feel that it’s a good deal. It should be in your gut.
And I’ve learned this. There’s many deals that sound great, that when I just do the gut check, I don’t participate in. They just don’t give me that. It came from experience. But you seem to have that in some weird way to avoid that one we just talked about. It’s an intuitive feeling that you generally get by having a lot of winners and losers over time, but you seem to have accelerated that somehow.
It’s an intuitive nature of where you want to get to and what it’s going to take to get there. And there’s going to be sacrifice along the way. It’s never about the money. Never. It’s not about the money. It’s, do I want to achieve that goal?
I’m having a… It’s just a weird thing because I had a similar situation just a couple of days ago, when somebody approached me and said, look, can you get behind this and back it and I’ll pay you a ton, like just a crazy amount of money. And I thought, do I actually want to spend one hour pursuing that? And I went back to him, said, look, no, it’s just not interesting. I can’t see myself getting involved in that narrative, which was a complicated situation. And then he said, look, how about I give you two and a half percent of it? I said, no, I just don’t want to be associated. It’s the same idea intuitively.
STEVEN BARTLETT: It was noise.
KEVIN O’LEARY: Yeah. And what that would do is some opportunity you don’t know about down the future that you pursued some goal that somehow tainted your brand. And that opportunity never comes to you. You’re the captain of your brand. You have to define yourself right through the journey. It’s hard. It’s really hard.
And if there’s going to be a downfall for you, you will have chosen unwisely somewhere. But it better not be for money. There should never be an amount that you would take because if your gut says no, it doesn’t matter what the money is, not after what you’ve achieved. I mean, you don’t need to buy a guarantee anymore. You got it. I’m assuming you’ve put some away.
I mean, it’s very simple. If you’ve got 5 million bucks in the bank, you can do whatever you want. Now, it may sound like I want more, but that is enough. Under catastrophe. Always have. Always. I have an account that just sits there with 5 million bucks in it in T-bills. I never touch it. That’s my nest egg.
STEVEN BARTLETT: Kevin. Thank you.
KEVIN O’LEARY: You got it.
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