YouSaid · the spoken record

Kevin O'Leary

lines on the record: 150
first: 2025-06-30
most recent: 2025-06-30
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Believe me, it's a tough NDA. And I understand why they did it. They didn't buy it for the cat DNA testing. They bought it for the data. With AI didn't really wasn't 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. Nobody had that much data on the one hundred ten million cats in America because she got it all during the pandemic. Thousands and thousands and thousands of, you know, It was never 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. The stock is 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“I mean, nobody saw that coming. I thought that thing was a joke. I was so wrong. I mean, that's the whole point. And she had the highest IR, I think, in the whole formats history. Nobody's made. She was around for 36 months and taken out at such an extreme number in all cash that there was an NDA sign between Sony and the pharmaceutical company. I can't even tell you what it was. It was extraordinary. It was extraordinary.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“We don't even count it anymore. We look at the portfolio rolling over five to seven year period. I like a lot. The thing is, what I've learned is You get an exit like bass pause from five years ago or something. Anaskaya, a remarkable woman.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“No, but you're also finding out if their DNA is going to fit with your I mean, I want my teen 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. You whack them. I'm more just formal about it. Boom, you're gone.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“You give them a job in the afternoon. They become an apprentice. They want to learn 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“Care when you do it, but if you miss the fifteenth, 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. I go, let's hire them, bring them in the team. And, you know, let's give them the whole package. And sometimes after a month, we say, no, it's not going to work. Here's like, you know, that's it. I think more companies should do that, actually. It's more like the Swiss apprentice system. They bring you into a lot. My stepfather, 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“England, I mean everywhere, everywhere. And we meet, 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. You know, 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 about the 15th for taxes”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“The way I hire people, and 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, you know, the CEOs that we have investments in, and your co-workers, because I don't do nine to five anymore. I do project-based work. I don't care where you live. We have people working in Dubai, Abu Dhabi.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, and practically all women, particularly Asian women, I am this whole thing about DEI and all this stuff. I've always had diversity because I only hire on merit. I don't care if 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 shit. Can you execute?”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“But 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 of respect, even though there may be disagreements. All of this is happening in the first sixty seconds. And it's setting up for the rest of the life with that person. It could be 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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 address 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 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 the way you're dressed. It's not a joke to be dressed for success.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“How many competitors are there? When are you going to break even? What month? If you get the first to write and you don't know your numbers, you deserve to burn in hell, and I'll put you there myself. 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 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“The next phase begins this is after ninety 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 competitor. You've tried three times before and failed. You've figured out what you did wrong. What is it about you or your team that can take 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 growing? What's the gross margin? I mean, I've said this a million times to people. I teach this every day.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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. And you're just, that's before a word is spoken. Before the first word is spoken. And so then what has to happen? Then Eric says Go And everybody's just sitting there looking at you. Can you articulate your idea ninety 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. Thirty seconds later, I get it. I get what they're here for. I understand their product. Okay, that's good. Unfortunately, great ideas are diamond dozen. I mean, there's millions of them.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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 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 take. 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 a”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“When and I'm right probably ninety nine percent 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've practiced in the context of Shark Tank twenty 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 a hundred 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 head. Can you project?”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“In the moment when that entrepreneur comes out onto the carpet, in the context of shark tank or dragon stand even. They need the setup shot of the product with the entrepreneur, and they have, in our case, a steady cam or a jib that comes down and shoots it. So the stage director... Eric is his name. Says to the entrepreneurs I've never met, usually it's a team or it's a family or it's 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. For two minutes And I'm right there in front of them. I'm 12 feet from them, and I just look at them. Not smiling, not blinking, not frowning, just looking at him. 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”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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 uncomfort 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 a negotiating, but to listen to employees, listen to investors, listen to financiers, listen to alternative ideas to yours. and become more powerful from it.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“Maybe after ninety seconds he blurted out something he shouldn't have said I knew exactly what the price was, right there. That was the end of it.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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 and you're 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. Is why I was a few minutes late and um You know, we knew we were going in there to settle. It's long protruded. It's a long, long, long. Litigation. Then I remembered her as we sat at the table like this. There were other people in the room, but the two, you know. Are crossing from each other I just looked at him For a long time. Gets uncomfortable and no one else is talking. Just”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“They set goals that they can achieve so that in the early stage of their businesses they put growth rate targets like fifteen, sixteen percent versus men at thirty percent very often. Men hit their target sixty five percent of the time, at least my portfolio and women ninety plus percent of the time. And that keeps the team very sticky. They want to be part of a, so they don't have a lot of attrition when they're small. They don't lose the head of finance 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've talked two-thirds. You listen one-third. Why don't you try reversing the ratio?”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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 Nacenth's early stage investments, these A round investments. Remarkably, and I've done them in all eleven 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“I would go as far to say now, you know, 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 one or two of their portfolio is going to work out in seven years and pay for all the other mistakes. But the serendipitous nature of success in entrepreneurship is brutal. It is”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“And can you interpret Singland 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. 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 Dragonsten in England, I'm Shark Tank in the U.S. You know, you put up 500,000 or a million bucks into somebody's business, eight out of ten are 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 shit. 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.”
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“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. Gotta 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 who can actually distinguish signal and noise. Because it could be noise. It could be irrelevant. You have to determine only you makes that decision. That's the key right there. This is what I teach.”
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“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?”
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“The founder still with the same thing. They get disastrous news. They lose an account. 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.”
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“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 what you do, you call it your empire or 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. Of my company is going public. It's a 450x for me. The stock will get unlocked sometime in the fall. How do you how do you fit that together? Utter catastrophe, destruction, woe, loss utter euphoria. Half That's what my life is like”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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. 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've got to 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 tonight, very late tonight, I will meet a master watchmaker, and we will deal with the design of a new piece unique is 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 shit I'm going to be dealing with today. And I also tell successful entrepreneurs.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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. I'll 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. For jobs it was 80%.”
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“will not make a decision after one 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 fifty fifty signal noise, they'll fail. It's that simple. And it's a very simple concept”
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“No, the goals you set for that you were awake. If you're going to be awake 18 hours. And you've determined that there's three things you have to get done, you're going to get those done. No matter what it takes, you're going to get those done. And you're not going to 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 absolute, 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 many interviews like I knew I've met Elon just a few times. I spent a lot of time with Jobs, but they say the same thing.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“Elon Musk, he has no noise. He does not deal with noise. He is one hundred percent signal twenty four seconds 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, and if you go back in history, you're going to find out that the geniuses of their time were close to 100% signal.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“So this signal to noise ratio to be successful for Steve Jobs was eighty twenty. eighty signal twenty noise. And I knew that to be true with him because he would email me at two thirty 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?”
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“One hundred percent and here's what I learned. Look how wildly successful he was. But here's There's a concept that he understood that very few people focused on back then in the early 90s of signal to noise ratio. but was so brilliant about jobs That I tell every CEO now, and I don't care if you're an SP 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 eighteen hours, not your vision for the business next week or next month or next year, just the next eighteen 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“Have we not been wildly successful and continue to be? I said yes, Steve, that's true. He said, then fucking shut up and do what I say.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“And I would say, Steve, you know. We got to do some market research on Argonne Trail. I mean, it's a huge title. It's in $110,000 school buildings. We got to do an update. It's going to cost you $12,000, $15 million. We want to find out what the students want. We want to find out if the teachers want to find out what the parents want. Steve would say, by the way, not a nice guy. Not a nice 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. 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?”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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 nineties making all of his educational software. I mean, it was just, there they are. My goodness, you guys do good research. Those are the kind of things that we did for him. Yeah, yeah, all of that. It's hard to find those are CD realms. 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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 of freedom.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“I'm an executive fellow there. I'm very proud of that work. You get a class of $120 people in a room. Two thirds of them want to become consultants. That's whether they're, and lead a life of mediocrity and never make a decision of consequence in their lives. And after twenty four months, they are tainted with that disease forever. There'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 debate. That's it right there. Do you want personal freedom? It's the only path. That's it.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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 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. Need to be lucky. It's like Napoleon was once asked. Where 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, particular 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 have made over the decades. I think if you want a percentage, and I teach these cohorts at Harvard,”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“Yes, just like that. In order to do that, you got to get down on your knees and do it. And I just couldn't do it. And 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. There was a bodega there instead.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“I just take this off Oh look at that. You've 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.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“I could hang out with her afterwards. And I saw her waiting for me. And the woman who owned the store said, you've got to script to 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. And I said, you know, you hired me as a scooper, not a scraper. She said, how about your fired? And I didn't know what that meant. And it was the defining moment for me because I realized there's two kinds of people in the world. There's people. And there's people that scrape the shit off the floor. And you have to decide who you are. And I'm not saying being an employee is a bad thing, not at all. But for me, it hit me. It just hit me.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“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's simple. First day on the job asked to serve and 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 script their 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 the shoe store and I figured”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“No, only a third of people can become successful entrepreneurs because there's a couple of things that you must achieve to be successful. First,”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“Kidding, it's everything, and I did some research, and most marriages can survive infidelity. They can't survive financial stress. But if everybody that's listening does this one thing, you will have over a million and a half dollars to do.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“The mistake that people make is they buy too much house. Never let the mortgage and the cost of maintaining the house be more than one third of your income.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“Billions. There's a lot of people who don't like me for my bluntness. I don't care because there's people that don't think ahead and find themselves mired in debt, but then pissing away money. Spending $28 for lunch. I mean, that's just stupid.”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT
“So I learned this from my mother, and I actually built a whole company around it. Yeah, there she is. So I haven't seen that picture. Damn, I mean what she did. The performance was extraordinary. And with that she put my brother and I through college. She took care of her family when they fell on hard times. When I saw the results, I said, that's it. That's how I'm going to invest for the rest of my life”
2025-06-30 · The Diary of a CEO · Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! · IDENTIFIED FROM THE TRANSCRIPT