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

“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. I want them to launch and they've done that successfully. They got to work. They got to do their 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
“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 closest 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.”
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've been with my wife a long time and we've been separated for a couple of years. But family is very important to me. So we got back together again and our daughter got us back together and we're very happy we did it. But it's... We make financial decisions together. We always check in. Know anything that's material.”
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, but 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, 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 what”
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
“Everything. Are you kidding? I mean, it's everything. 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 the rocket ship ride. You better find somebody that's willing to tolerate the fact that you're never home for the first ten years. They're going to raise a family by themselves because there's no balance in life. That idea of balance is complete bullshit. I mean, it's just bullshit. 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 Skye did it in three years, but she had worked much harder previously. It was not her first deal. She was just lucky. I mean,”
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
“Wealthy people have that discipline. You meet them later in life, you realize when they are 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 on debt for a watch because people hear this stuff say, I'm going to buy watches like Lyriet Red Bands. No, you're not. That's why I wear watches now that cost under five hundred dollars to show kids you want to get into horology, you don't have to spend fifty thousand dollars. Here's a Timex for $265. It looks beautiful. Get 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
“Wealth creation Comes down to one word discipline. 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.”
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 it is people, but it's not there are many people that say I love real estate. And I know people in their 20s that do that. In fact, they're successful. That's all they do. And so that their job is to find houses, buy them, fix them up, 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.”
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 wouldn't, because why do I need a house if I'm only unless I'm renting 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.”
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, 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 value is 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.”
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
“Your whole career. 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.”
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, 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 she wants some diversification into starting to build up that investment account for when you retire so that you have something to live up. If you only put aside 15%, 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.”
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, there's a very basic rule for that, and I understand it, and I did the same thing. But what I made sure again for my mother was never let. The Mortgage and the Cost of Maintaining the House be more than one third of your income, 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 it's only going to be nineteen hundred square feet to start in a neighborhood that you may not want to stay there 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 or whatever, 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 four percent, there were three point two percent some of them. They bought massive houses. And now they're running into having to refinance those houses at much higher rates, more than seven percent, and it's becoming sixty, seven, eighty percent of their income. They're screwed. They bought too much house. So it's about making sure that you can manage that. And also you want some diversification.”
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 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. I've got, you know, it was a very successful IPO.”
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 the point is. 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 it an ETF or actually own it yourself. You can buy the exchanges. You can use, you know, can buy circle stock. Now it's public. You can circle makes USDC. You can buy USDC in an account and make 4.1% interest on it right now. So there's a lot of ways to participate. But yes, I'm here to stay. But I've grown up. I was around during the period where the crypto cowboys lived and I survived that all. And I even testified in front of the Senate and the House and whatever else the testimonies were during the tumultuous period. And most of those guys went to jail.”
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 fees would be at hundredth of what the costs are right now. So it's a digital payment system. The price doesn't have no speculation on it. It's backed by the US dollar treasury bills. So it's sort of a new form of digital payment. 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 in some period of time because it provides productivity to all 11 other sectors. The way I own it is I own the exchanges. My exchange in one called WonderFi up in Canada just got acquired last week or two weeks ago by Robin Hood. I'm happy because I think Vlad who runs Robin Hood is great. And now he's got a million plus accounts in Canada and market that he'd never participated in.”
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 am actually, but people get crypto confused with its real potential. Let's talk about digital payment systems because what's about to pass first? We are days away from this happening is the Genius Act, 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. So if that bill passes, it's really nothing to do with speculating on crypto. It's a new form of payment. So if I wanted to order a watch from Simone Britch, who's somebody I buy watches from, he's a master watchmaker, right now I have to take US dollars. I've got to get through and know your client prerogative. I'm treated like a criminal by transferring $100,000 over turning into Swiss francs. Takes about a week. I get screwed for about $200 basis points in the whole thing. If he accepted USDC, which is actually a stablecoin back of the US dollar, it just went public, very successful IPO. I was a shareholder in that company too. That's one of my best IPOs in the last two years. The transaction would happen in less than...”
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, I mean, you know, a company, if it's profitable and it's operating 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 a dividend. And so they send that cash to you and you can either redeploy it in other ways or live off it or whatever. 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. And so I like to own the stock for growth, but I also want to get some of the profits. And so 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, div payers. And then I also own fixed income products. I also own crypto now and I own alternative assets like gold and watches. My watch collections has actually done quite well, even though it's been a correction. There's volatility, but I have some watches that have, you know, I bought for...”
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, I'm pretty big in watches. I mean, but watches to me, every piece I have marks something in my life that was important, a deal, a child, graduation, you know, something, every piece I've got a lot of work.”
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
“is worth a fortune today. The classic it still wears beautifully. They're so well made, so she wouldn't buy crap, she'd buy really good stuff, but just small amounts of it. And over the years, she'd built up this portfolio of amazing clothing. And when she died, the women in our family had a cat fight over her portfolio. Unbelievable.”
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, that's really stupid. And so for a young person, a young woman or man, don't do that. Start putting just By the minimum stuff, and another thing I learned from my mother this is interesting because I saw it happen at her death, she You know, would buy two Chanel jackets a year, really expensive Chanel jackets, handmade Chanel jackets. I do business with Chanel because of the legacy of my mother and the whole Cocoa Chanel thing in watches. I love those guys. Her theory was this will never get old, and it never did. A classic vintage Chanel jacket from the fifties that's well kept.”
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, so it's just, you know, people tell me, oh, I can beat the SP, I can pick stocks. They're so full of crap, not over the long period they can. So it's better you might as well just own ETS. 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 then over time it appreciates. And then if you buy some treasury bills or a fixed income, you get that. You should have less of those when you're young and more than when you're older. That's just diversification. But the best test I do with my kids' friends to go into a closet. Go into your closet and look at how much shit you have you don't wear because you either bought it because you thought you were going to wear it and never wore it or wore it once, and you end up wearing 20% of your portfolio all of the time and eighty percent you pissed away.”
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, okay, I mean, you know I even have it, I even built an app for this purpose just so I could, 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 rated funds that just track the S&P 500. Very simply.”
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 can't stand it when I see kids that are making 70 grand a year, spending $28 for lunch. I mean, that's just stupid. It's just think about that in the context of that being put into an index and making eight to ten percent a year for the next 50 years.”
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
“Why? Why? Like you don't 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? Like what's all this shit you're buying? Like 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 the average salary.”
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 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. Ever. I don't have any debt. So I'm very careful about that And we went through this little thing. 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? One of the things has to happen. I mean, you're losing millions of dollars a quarter. 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
“Would you be my advisor? I said, no, I don't do that. But I can just give you some basic advice and you can hire people to stick on the mandate. And 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 on the last 90 days that you've spent on, whatever the hell it is. I don't care. And let's put on, no, computer, no spreadsheet. On this, 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 our gut check. Do you outspend yourself? She said, Why would I give a shit? I said, Wouldn't you like to know?”
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, because she said to me was look. You know, I even do this today with wealthy people call me up all the time and say, look, They get divorced. This very wealthy woman got divorced recently, and she said, Look, divorcing, and she was a billionaire. She was divorcing. She was multi-billionaire. And so she said, look, I'm getting 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”
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
“Even back then, they didn't have ETFs, but they had mutual funds that said the only stock in this mutual fund 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 saying, wow, these are really boring.”
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 will maintain and grow their wealth, but it's people bet they make big bets. They're just, 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.”
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
“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. Damn, I mean what that portfolio did, the performance was extraordinary. It was beyond any hedge fund guy or anything, fifty-five 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 five percent. Anyone stalk ever, no matter what it is, and no more than twenty percent 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.”
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
“Seven year telco bonds paid about six and a half to eight percent back then. But the Longbonds and she had that portfolio for fifty five years. She never spent any of the principal, only the dividends and the interests 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 five percent in any one stock or bond of the portfolio, and no more than twenty percent in any one sector. Ever. So when a stock ran up past five, she'd sell it down. This is not genius. This is just diversification. When she passed, and I was the older brother, and I saw the portfolio, because the lawyer said, listen, you got to come down here, you're the executor will. And I said, yeah, but my mother was middle class.”
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 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, Georgia. I haven't seen that picture in a while. She was very independent. 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, and she worked in the accounting department. But she got paid cash, and so she Take twenty percent That cash each week and She would put it into two asset classes stalks that pay dividends, large cap, stocks, and telco bonds.”
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 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. Unusual solutions That just think outside of the box It's really interesting 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
“I don't find the ones that are psychopaths 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. Crazy stuff. You know, maybe it's riding motorcycles in the desert. I don't know, you know, 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. Is anything that is immediate? That tells me If you look at the year's outcome from that person, you're going to find that they probably outperformed.”
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
“Just because someone says they can execute doesn't mean they can. I mean, it's, of course, in your interview, you're not going to say I can't execute. You're looking at their past, you're saying this looks terrific. It looks like you can fit in, but it's not a piece of paper. They haven't been road tested, 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 put a set of parameters 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.”
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
“Think of a tetrapack, 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... It's about respect. both directions. It's not about likability or softness or some social metric. It really isn't. Trying to redefine leadership that way because it's on trend, it's not going to work.”
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 Tamar building are not your friends. They are the Tamier 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's a horrible disease. It's 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 wealth multi generational.”
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 know they kind works, I think respect works. The same number of assholes are out there being successful now than they were back in the 90s. It doesn't matter whether you're an asshole or whether people like you or not. I mean, people get so stuck on this stuff. It's”
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 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 know how much higher probability of success. But the key is to launch sort of in your mid to early twenties because you need to burn a few years failing and that matters.”
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, I mean, what I'm telling 21 year olds now is, look, Go work for twenty four 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 young entrepreneurs say nah, nad, I don't want to work for anybody. I said, yeah, 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 or whatever it is, friends and family.”
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's the same thing. It's exactly the same thing. And so when I see this policy now, I got out of my mind. I mean, the first thing I do is get on a plane and go to Washington because AI is so important for all of the investments I've made. I do not want to be putting Chinese honey into my companies at all. That's simple.”
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 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?”
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 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 advance AI. From the Queen Bee. The American Queen Bee The minute you shut down a market and you don't 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 that 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.”
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 broadcom, where policy makers in Washington have decided that we can't sell those chips to countries like China or Russia, or whatever the list is, of adversaries. Bad policy And here's why what I learned from 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 on the 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 Bosnia 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 max. Writing for the OS of It's the same with the The NVIDIA chip.”
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
“Steve changed my life, there's no question. I didn't like him 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. I was a friggin' genius. He was so smart in terms of keeping on track to get getting stuff done and look what he achieved. But he He was 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 spend 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 it was understood, he understood what the 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”
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
“For those shareholders, they're going to be unhappy. But then I got the call on the IBO. Those shareholders will be very happy. They're going to make four hundred X. 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 risks. 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 who don't like me for my bluntness. I don't care. I think a lot of people respect me for my blindness. They may not like me. And it's sort of. Doesn't matter because the only people that really matter to me are probably my 20th closest friends in my family.”
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 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 cram down round it, a fraction of a central 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, and 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, you”
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 might as well do it when you have less burdensome risk like a mortgage in 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. and I had plenty of failures, and I still have failures. I mean, it's just one I talked about this morning, I said to the largest shareholders, I was in the car and your assistant was, you know, 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 Company's going bankrupt”
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 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. Before it split, and he worked there for five years.”
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