1076 The Keys to Financial Freedom w/Shark Tank’s “Mr. Wonderful” Kevin O’Leary (Do THIS Today!)

“Money can cause great joy or catastrophe in your life. Your CHOICE is where does it fit?”Today's guest is Kevin O’Leary who is an investor on the Emmy Award winning show, Shark Tank. Kevin has had an incredible career with multiple successful businesses ranging from production companies, to a software company that later sold for billions of dollars, and writing multiple best-sellers around financial literacy. He is the Chairman of the investment app Beanstox as well the founder O’Leary Fine Wines. Lewis and Kevin sit down and discuss the importance of always telling the truth, the 3 skills every person should develop to be successful, what conversations we should be having with our partner around money, and so much more! For more go to: www.lewishowes.com/1076Check out Kevin’s investment app Beanstox: https://beanstox.com/ Go to his website for more: https://www.kevinoleary.com/ Daymond John on How to Close any Deal and Achieve Any Outcome: https://link.chtbl.com/928-podSara Blakely on Writing Your Billion Dollar Story: https://link.chtbl.com/893-pod Get more from Lewis! Get my New York Times Bestselling book, Make Money Easy! Get The Greatness Mindset audiobook on SpotifyText Lewis AIYouTubeInstagramWebsiteTiktokFacebookX

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lewis Howes?

  This is episode number 1,076 with Shark Tank's Mr. Wonderful, Kevin O'Leary. Welcome to the School of Greatness. My name is Lewis Howes, a former pro athlete turned lifestyle entrepreneur. And each week, we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now let the class begin.

• 0:31Lewis Howes?

  Former Secretary of State Colin Powell said, "There are no secrets to success. It is the result of preparation, hard work, and learning from failure." And Seth Godin said, "There's no shortage of remarkable ideas. What's missing is the will to execute them." My guest today is Kevin O'Leary, who you probably know as an investor on the Emmy award-winning show Shark Tank. And Kevin has had an incredible career with multiple successful businesses, ranging from production companies to a software company that later sold for billions of dollars and writing multiple bestsellers around financial literacy. He is the chairman of the investment app Beanstalks, as well as the founder of O'Leary Fine Wines.

• 1:11Lewis Howes?

  And Kevin O'Leary has more to offer than just his successful business ideas, and I cannot wait for you to listen to our conversation. It left me feeling super inspired to not only work on my business, but also myself. And in this episode, we discuss the importance of always telling the truth. You're going to hear this throughout the entire time. Always telling the truth, no matter what, even if it hurts people. The three skills every person should develop to be successful. What conversations we should be having with our partner around money. We actually talk a lot about relationships and money, which I think is fascinating, some of the things he shares, because I don't hear him sharing a lot of this stuff anywhere else. We cover how the middle class can start working to achieve financial freedom. What qualities Kevin looks for when making an investment.

• 1:55Lewis Howes?

  How Kevin is able to manage so many businesses and passions. And you're going to love hearing about all the different talents he is consistently working on, a super fascinating human being beyond business. And if you're inspired, or you think someone else would be inspired with this message, then maybe- Make sure to share it with someone you think needs to hear it. You can just send them the link, lewishouse.com/1076, or copy and paste wherever you're listening to this podcast, and just share it with them. Text a few friends, post it on social media, and connect with me and Kevin over on Instagram, and let us know what you thought about it over on your Instagram stories. Okay, in just a moment, the one and only Kevin O'Leary.

• 2:35Lewis Howes?

  Welcome back everyone to the School of Greatness Podcast. Very excited about our guest, Kevin O'Leary is in the house. How you doing Kevin?

• 2:41Kevin O'Leary?

  Great to be here. Thank you very much.

• 2:43Lewis Howes?

  I'm very excited, and I have a mutual friend of ours who sent me a text message last night that I want to read to you. Damon John, who is a friend of the show and a friend of mine, and I said, "What's something I should ask to Kevin that would, that maybe he's never been asked, or something personal that he might connect with?" And he said that you guys have a big rivalry. And putting all the jokes aside, why are you both so close, and why do you love and respect each other so much? And he said, he's never been asked that personally. So, he was curious what you would think about on your relationship, and if you'd share.

• 3:20Kevin O'Leary?

  Well, you know, I've been working with Damon ever since he got out of prison. It's been great. It's been a terrific relationship. But you know, in all honesty, he's a very hardworking guy, and I consider myself to be the same. So, we share that. And years ago, we started, because we both do a lot of work, you know, obviously on television and social media, and we have businesses, and we support teams together. We have a group of people that work with us, and we want their career to be as exciting as it can for them, and to be as profitable as it can be for them. And we work together quite a bit. Our teams know each other. We are, you know, if Damon, just one of his guys called me the other day saying, "Listen Kevin, when we did the Shark Tank book a few years

• 4:03Kevin O'Leary?

  ago, there's a couple of shots of Damon that we think you might have in a database. Can you dig it up?" And I found them in two minutes. Happy to share it. We share our content. We shoot together. You know, Damon and I are actually... Pretty tech savvy when it comes to recording stuff. And we just record, when we go and shoot together for, you know, two weeks on the Shark Tank set, the only guys recording anything in the back are Damon and I. And everybody else has, you know, hired somebody else to do it and it's always shit compared to what we do. Cause we're there, we're right there. So we have multiple cameras and all kinds of stuff. I used to be a film editor years ago. And so I respect him for that and we actually have this, you know, unwritten agreement.

• 4:43Kevin O'Leary?

  We just share our content and we end up getting much richer, uh, social media for it. And so it's because the teams work together, we do speaking gigs together, we compare notes on things like doing speaking gigs in Saudi Arabia or in, we share gigs. I mean, I really like the guy and, and I, I, I respect the honesty the guy has. He's a noble guy, I like that. He's funny as hell sometimes, I mean.

• 5:08Lewis Howes?

  Yeah, the king of dad jokes, right?

• 5:10Kevin O'Leary?

  Yeah, and, and the whole Chocolate Thunder thing is just ridiculous. I don't know if he's pitched you on that, but you know, it's, and then he got me into, um, uh, you know, Clubhouse the other day and said, "Look, you gotta try this thing." I said, "Oh Damon, like I need another thing, like are you crazy?" He said, "No, no, it's really addictive. I'll get you locked in, I'll get you set up." And we did our first one together, we blew the whole room out. And, uh, so we're doing a lot of those together. I don't know, you know, you get to choose who you work with, right? You don't have to work with an asshole and he's a good guy.

• 5:40Lewis Howes?

  That's great, that's great. I'm curious, you seem like, uh, on all of your content you put out there on social media, plus on Shark Tank, plus I've seen speeches that you've done, you seem like you are fearless in business, uh, and financial literacy, in, uh, working with people and building teams. You just seem like a fearless human being in life. I'm curious, what was the thing in your life that was your biggest fear that you needed to overcome in order to become so confident and fearless that you are now?

• 6:10Kevin O'Leary?

  Well, it's a great question, and I try and teach it now to, you know, I do a lot of lecturing in engineering and business schools. But I think the core of it is, I'm half Lebanese and half Irish. And, you know, the Lebanese were Phoenicians. They sold the purple dye to all the warring tribes around the Mediterranean. They never got in a fight. They just wanted cash flow, and they liked royalties. So, there's a little bit of that in me. And then my dad was a salesman, who actually married my Lebanese mother. And he was from Dublin. And, you know, we were, we were a very middle-class family. And my mother taught me something when I was very young that's really affected me later in life. And I kind of agree with it. She's long gone, of course, but she said, "If you never lie to anybody,

• 6:55Kevin O'Leary?

  you'll never have to remember what you said, and you'll never get caught in a lie." The problem with that is, it's really hard to do. Because you want to make feel, you want to make people feel better? You say, "Oh, it's just a white lie. I know they'll feel better if I say this to them, even though it's not true." That will always come back and bite you in the heiny. Not maybe a month, but maybe five years later. And, so, you know, the rap I get for telling the truth, and Shark Tank's a good example. You know, I'm the only shark that says, "Your idea sucks. It's going to zero, you're gonna lose all your money." As opposed to, you know, Barbara saying, "Oh, kumbaya, kumbaya. You keep doing what you're doing. Don't worry that it's going to zero, but I'm not gonna invest anything with you."

• 7:39Kevin O'Leary?

  Like, that is complete BS. And so, that's what I think. You know, I'm willing to say, "Look, here's what I think. It's the truth. If you don't like it, I don't really care about your feelings. I care about your money, if we're in a business relationship." And so, that's sort of the, the idea behind it.

• 7:56Lewis Howes?

  Did you ever tell white lies? Or were you ever the opposite way, growing up as a kid? Or when did you learn that specifically? Was there something that you told white lies for a while that eventually caught up to you?

• 8:07Kevin O'Leary?

  Yeah, there was, and I will tell you, this applies to affairs of the heart. I mean, if you're in love with a significant other, it's so euphoric when you meet and you start dating. You know, I mean, I'll tell you how it works, because I also give guidance on this too. You know, I'm actually an ordained priest. I marry people. Because I have such a number of businesses in the wedding industry. I know that sounds crazy, but it's true.

• 8:33Lewis Howes?

  Wow, that's great.

• 8:33Kevin O'Leary?

  So, and everything's gone online, so I can marry you online and, you know, hope for happiness for you. But the bottom line is, years and years and years ago, remembering that voice of my mother saying, "Don't lie." Here's a dilemma that everybody faces, every man, every woman, okay? Think about it this way, and it applies to business too. You fall in love, and many people have multiple relationships in their life, because the euphoric period of love is the best part. It's so wonderful. You can't stop thinking about the significant other. It's just the joy in your day and all that. Then as things wear on, and you become more into the, you know, the mode of just being together,

• 9:14Kevin O'Leary?

  and the challenge of the world step on you, maybe you move in together, maybe you're married, maybe you're not. But the point is, there's going to come a time when you're going to cheat. And maybe it's just something that, you know, you feel you're not going to get caught. You're in another city, and, you know, I'll be honest, you sleep with somebody else. The opportunity comes along, you don't want to change your main relationship if you want something on the side. This happens all the time. What you should do is get up in the morning, realize that was a mistake, and tell your lover what you did, right there, right there.

• 9:53Kevin O'Leary?

  Why? Because in a relationship, you know, you can recover from being caught cheating. You can recover, but what you've lost forever is the equity of trust. It's gone. It's gone forever. Maybe it'll be a relationship, but it won't be the same relationship. And by the way, that's just as important in business. When you lie to a partner, or you lie to a customer, or you lie to somebody, and you get caught, you will never have the equity back. Even though the pain and misery of saying, "Look, I did something crazy last night. I met somebody, I slept with them, I wish I hadn't have done that. I really, please forgive me, I was weak," the truth?

• 10:36Kevin O'Leary?

  The truth is powerful, it would have made that equity stay and even, maybe even respected you more, as long as you don't keep doing it, obviously. It's a one-time mistake. But the point is, I made that mistake in a really important relationship way, way back.

• 10:51Lewis Howes?

  Really?

• 10:52Kevin O'Leary?

  Oh, yeah, yeah. And I realized the damage. And it came back to me, and it caused me horrific emotional damage. Because, you know, these things happen.

• 11:07Lewis Howes?

  Yeah.

• 11:08Kevin O'Leary?

  And then the words of my mother came back saying, "You idiot. All you had to do was tell the truth, and all this misery you put everybody into is because you couldn't tell the truth, even though it was very hard. You let a 15-second lie destroy your relationship with something you really cared about." That's what I'm talking about.

• 11:25Lewis Howes?

  Wow. What ended up with that relationship? How did it?

• 11:29Kevin O'Leary?

  It got severed for two years and it came back. And it wasn't the same, it was different, but it's back, it was back. You know, I don't want to get into the details of it, but I'm telling you the truth about it to explain how brutal it was and what a huge mistake I realized. I went, "Why did I do that? Why didn't I listen to it?" So now I simply don't lie, ever. And it causes a shitstorm all over the place, but I don't care.

• 11:55Lewis Howes?

  You'd rather have a shitstorm now than a monsoon for years later?

• 12:01Kevin O'Leary?

  But that's my whole point. I think everybody thinking about this will realize he's right, because you destroy that relationship, you destroy equity, you destroy your business. Being caught as a liar takes you down multiple levels in many people's eyes. You just can't do it. It's the whole idea of who you are. It's a mistake.

• 12:22Lewis Howes?

  Yeah. That's powerful. I'm curious, what would you say are the three biggest habits that you've developed over time? Maybe you didn't have early on, but you develop over time, and maybe always telling the truth is one of them, that has made you so successful? The three biggest habits that you imply?

• 12:41Kevin O'Leary?

  Well, you know, I've learned a lot from the CEOs I've invested in over the years. And there was a woman a few years ago, it's more, probably 10 years ago now. And she said to me something really interesting. I asked her why she was so successful, because she was. She said, "I do something very ordinary and almost boring, but I do it every day." She takes a sticky note and she writes three things she has to get done before she texts, answers any calls, or does anything else. Just three things. And she sticks it on the mirror where she puts her makeup on. And she really, it doesn't have to be business things.

• 13:20Kevin O'Leary?

  It can be whatever it is that are deemed to be important to get done the next day. Maybe it's something that's a holdover from the day before, because I've been doing this now for years. And it's really effective. This isn't tech. You're not putting it in your phone. It's not a software program. It's a piece of paper with, and you have it, you know, right? When you're going to bed, brushing your teeth, whatever, you write those three things down. You stick it on the mirror. I do it every night. And then I am myopically focused to get those three things done.

• 13:49Lewis Howes?

  Before you text, before you check your email?

• 13:52Kevin O'Leary?

  Before I do anything else, I nail those three things. You cannot believe how productive you get when that happens. Because you don't let the distractions of all the other crap that's happening around you. I just don't do it until I get the three things done. And it's incredibly powerful. I tell people to try it. Most people try it, get stuck on it, and they stick with it. It's really, because in life, there's so much noise coming at you. And every year, more noise and all kinds of different distractions. And you always say to yourself, "Well, I can multitask." But you deemed that thing to be very important and you ignored it. Now it's 3:00 in the afternoon. You're exhausted. Or you're busy with other stuff and you say, "Oh, shit. I didn't get that done and it's..."

• 14:37Kevin O'Leary?

  Whatever the effects, the domino effects are, they're gonna hurt you. And that's why I tell people, try it out. It's a really great tool. Okay, that's number one. What's the second big habit? Okay, so this one's a little funky chicken. It comes with a story, okay? When I was, you know, I wanted to be a photographer or a musician, a rock star. When I was, you know, graduate, when I got out of high school, and my dad, my stepdad said to me, "You're not good, you're not good enough at either of those. You'll starve to death." If I were you, I would go get any kind of a degree and focus on business, which is what I did. You know, I didn't know what I wanted to do, but I learned some stuff. And I ended up going into postgraduate. I went, got an MBA, which was, at that time was a two-year program.

• 15:23Kevin O'Leary?

  Which, you know, we can talk about the merits of that or not, because I've come to realize what it was worth and what it wasn't worth. But anyways, I remember on the last week, the graduating class, and in those, it's sort of like an amphitheater with about a hundred people in it. And you've been there for two years, you've got your little nameplate in front, and they bring in guest lecturers to talk to you before you jump into the real world. And this guy comes in, and he says, "I'll never forget it." He doesn't, he walks up, the professor hands him the floor, and he just goes in the middle and just looks up at everybody. For maybe like, it felt like forever, but it was really maybe sixty seconds. Didn't say a word. And the whole room, like, you could have heard a pin drop.

• 16:08Kevin O'Leary?

  "I'll never forget it." And then he says, "You guys think you're so hot You think that you've come here and you've got an MBA, and you're gonna go out in the world and you're gonna rock, and you're gonna be incredibly successful. I've got news for you. For two-thirds of you, the world is gonna chew you up and spit you out. You have no idea what's going to happen to you. You are so irrelevant. You have proven nothing. You've done nothing. You think an MBA means something? It's worthless."

• 16:39Kevin O'Leary?

  And I remember, the guy beside me, I'd been beside me for two years. And we were up in the, one row down from the top, so we could chat all the time. Hide a little bit, yeah. Yeah, yeah, and so I said to him, Barry was his name, I said, "Barry, this guy is such a [bleep] what an [bleep]."

• 17:00Kevin O'Leary?

  What an asshole he is, what an arrogant asshole he is.

• 17:05Kevin O'Leary?

  Well, guess what, he was right. He was 100% right. And the reason he pointed that out was the idea that your experiences make you who you are over time. As an entrepreneur, as a parent, as a person, as whatever you are, as a brand, whatever you are. It's your experiences and how you deal with them that gives you that equity over time. And for many people, they can't make it. It doesn't work out for them. They don't have what it takes to take on the abuse that the world's gonna throw at you. And just to give you full circle in a kumbaya, you know, circle of life, Lion King kind of moment. I got caught saying the same thing a couple of months ago at the Harvard MBA group.

• 17:46Kevin O'Leary?

  And I realized I was saying the same thing that that guy said to me decades ago. I said to these kids, "You're all think you're Harvard MBAs. You are nothing burgers. You are nothing." And so there you have it. What he really explained was the idea of experience and how you'll have to listen to your gut to navigate the bombs of your career. And you have to trust it. You have to trust your gut. Every time I've lost dough, every time, and I've lost plenty. Luckily, I've had more successes than failures, is when I didn't listen to my gut, which is my experience. And I shouldn't, and he was right. He was absolutely right. It was great information, but I couldn't assimilate it because I couldn't put it in context.

• 18:32Kevin O'Leary?

  Now I understand it. So number two is, you need to build that experience and all the way through, listen to your gut. Even when you're young, your gut will tell you, you'll know when it's right and wrong. And don't go against your intuition. That is actually your radar. That's your DNA speaking to you, figuring out what the next move's gonna be.

• 18:50Lewis Howes?

  That's a powerful story, yeah. Did they say the same thing to you in the back of the room and say, "What an asshole this guy is" when you gave him the speech at Harvard?

• 18:59Kevin O'Leary?

  Yeah, well, it's Matt Higgins, who was a Get Sharp-

• 19:02Lewis Howes?

  Yeah, I know Matt very well, yeah.

• 19:04Kevin O'Leary?

  Yeah, so Matt, he emailed me the next day and said, "Hey Kevin, I gotta tell you, you're a sh*t disturber." I mean, you know, but, you know, much of the class really enjoyed it, but what he was really saying is he pissed a few people off.

• 19:16Lewis Howes?

  Yeah.

• 19:17Kevin O'Leary?

  But, you know, I know Higgins pretty well, we're good friends, and so, you know, he's a, you know, he's really savvy at what he does. We wanted to talk about direct-to-consumer branding, and that's what we were doing in that lesson, it was two hours, it was great. I'd work with that guy anytime, he's terrific.

• 19:33Lewis Howes?

  Yeah, great guy. And great content on LinkedIn he has, he's always sharing that content with me there. And the third habit that makes you very successful?

• 19:43Kevin O'Leary?

  Well, you know, it's, you have to make time in your life for your significant other and your family, and it's very hard to do. It's extremely hard to do because you, when you, this is really speaking more to the entrepreneurial community out there, which is basically a third of people. One-third will attempt to take the entrepreneurial journey. It's not a destination, it's a journey, and the challenges of that are very, very difficult, particularly when you're starting out, and I learned this the hard way, and again, I'm gonna go to a story of a class that I taught years ago, an evening class, this is, this really sums it up, and it tells you how important this is.

• 20:26Kevin O'Leary?

  Three-hour class, six to nine, we're almost closing, you know how, ten minutes left, this guy hadn't said a word, the whole class. And he finally puts up his hand and he says, "Listen, Mr. Wonderful, I have a question for you, it's not about the case, it's the case we're doing." I need some advice. I said, "Okay." You know, you really haven't participated at all. I was kind of a little condescending. Because I know, you kind of know who's engaged in the class. Even though it was a huge cohort. I think it was something like 300, 400. I can't remember. It was a lot of people. Anyways, he said, "I'm graduating this year. I'm an engineer and I've developed a cloud-based software enterprise system that helps hedge

• 21:11Kevin O'Leary?

  funds with less than $250 million be compliant." And you know, it's very difficult to stay compliant when you're small. He needs 220 hedge funds. And it was a subscription service. So these guys could use it on a cloud basis. And he had written this code while he was graduating in engineering. Wow. And his run rate was $5 million a year in subscriptions. I mean, that is like... And I said, "I don't hear a problem here. I hear something incredible going on. This is amazing." And he said, "Well, here's the problem. My fiancee came to me this morning and I'm really disturbed. She said, 'I have to make a choice. She can't live with me anymore. I never attend any of her family's picnics. I never see anybody on weekends.

• 21:56Kevin O'Leary?

  I'm either studying or I'm working on the code. That's all I can do. And I asked her to come over and sleep with me when she can and we'd be together. But I'm just buried in this. And I need to do both. I need to get my graduation in engineering and I need to keep my customers happy because this is my business.'" Now, he said, "What do I do?" Room's like, "This is getting interesting, right?" I mean, I said, "Okay. Which one is easier to replace? Your business or your fiancee?" And that was probably not the right thing to say at the time, but that's what I was thinking in my head.

• 22:40Kevin O'Leary?

  And I think everybody else was too. This guy's phenomenally successful. Clearly has gotten engaged to the wrong person that can't take that journey with him. Most likely outcome is divorce after they marry because he's going to work 25 hours a day, eight days a week because he's got a business. He's an entrepreneur. My point is, one of the biggest decisions you're gonna make in your life, that between success and failure as a person, is finding that right partner. That, you know, I don't care, you know, who that is, if you're going to take that route. They have to be in sync with who you are. You can't contort yourself to something else. And, and I think that a lot of people in their twenties

• 23:24Kevin O'Leary?

  really should think this through. Because, you know, now, I told you I'm in the wedding industry. I've, I've got a lot of companies and I've learned a lot about marriages. The reason marriages fail is not because of infidelity. Any marriage can survive that. I talked about it earlier. But why they fail, why the union breaks up 50% of the time within five years is financial stress. One outspends the other. They're not in sync together. They don't share each other's goals. That's the hardest time in your life, in your twenties. Maybe you start a family, whatever you're gonna do. The point is, picking that partner is the third thing you either do right or you do wrong. Divorce is incredibly stressful. Many people try it three, four times.

• 24:07Kevin O'Leary?

  They're not in sync with their partner. I'm just, you know, this is kind of like a little Dr. Phil-ish in some ways. But I'm telling you, with the CEOs I work with and all the investors I work with, I see stress in people when their relationships are falling apart. And it's devastating. So there's a story, there's a, those are the three things I care about in giving guidance. And I think everybody knows what I'm talking about and should think about these.

• 24:35Lewis Howes?

  These are powerful stories and I'm curious. Love and money is such an interesting topic because most people disagree on it or one person's outspending and then they get divorced. One of the main reasons is money. What questions should partners be asking each other before they get married around money? How honest should they be? And what if they have a massive disconnect around money, but they have this intimacy and connection and love? Should they, you know, just break up before the wedding? Or what do you think would be the right move to make?

• 25:09Kevin O'Leary?

  So I, I have given a lot of guidance in this space. In fact, I've written three books about it called Men, Women and Money, Men, Women and Children. It's all kinds of advice about family. But here's, here's how the journey works. You meet somebody. It's a great first date. You have a second date. It's even better. Okay.

• 25:31Kevin O'Leary?

  By the time you're having your third date, the only reason you're having your third date is both of you are very interested in each other. And that is the time to start talking about the future. I know that sounds corny.

• 25:42Lewis Howes?

  A third date.

• 25:42Kevin O'Leary?

  I understand it. Third date, if you're just hooking up for hooking up, I get it. You don't have to worry about this. But if you're actually stopping seeing anybody else and you're on your third date with somebody you've met, and they've done the same thing and you're being honest with each other, something's going on, okay? Now it's time to start doing a little due diligence because this is gonna get serious. By the fourth date, and you're not seeing anybody else and you're talking about, you know, doing whatever you're gonna do together, it's a big deal. And you have to understand a little bit about where their heads are at. Number one is, you know, talk about family. Do you wanna have one? I mean, you know, it's a question. Some people don't. You gotta know that upfront if you make a decision about, or can you have one?

• 26:27Kevin O'Leary?

  It's a discussion you gotta have. Tough discussion. Again, staying honest. Number two, what are your goals? How do you see yourself in 10 years? Are you at home? Are you working? Or would you be raising kids? I know this sounds corny, but believe me, women want that question and men want it too. If you're on your fourth date, they're dying to get into this because they're starting to really invest their time in what they think they're going to be.

• 26:53Kevin O'Leary?

  Anybody in your family bankrupt? Tough question.

• 26:56Lewis Howes?

  Ooh.

• 26:57Kevin O'Leary?

  Tough question. Have you ever been bankrupt? Then you ask, how much debt do you have on your credit card?

• 27:06Kevin O'Leary?

  Tough question. Do you pay off your credit card every month?

• 27:09Lewis Howes?

  Oh my gosh.

• 27:10Kevin O'Leary?

  And if they say, "Why are you asking me this question?", you say, "Why can't you answer that?"

• 27:16Lewis Howes?

  Ooh, what makes you feel uncomfortable about this question?

• 27:18Kevin O'Leary?

  Well, I really worry that the reason, you know, you've gotta be in sync with something. The great, here's the thing about marriage, about getting together, whether you get married or not, or whoever your significant other is. If those are aligned, if you have an understanding of each other that is in sync, that union could last 50 years. Because after the euphoria is over with, you're in business with each other. You have to build a financial pillar to support growing old together, or raising a family, or buying a house, or doing whatever you're gonna do. And you need to be in sync on that stuff.

• 27:54Kevin O'Leary?

  This is a tough... But I'll tell you something. Every man and woman I've talked to about this, and when I was researching my books, all three of them, I was amazed at how forthcoming people would be and say, "I'm dying to answer that question. I'm dying to ask that question. I'm on my fourth date, I really want to know that about my potential partner, because I'm really interested in this person. And I think we could be great together, and at least I'd like to try it, but I gotta know these things." They're tough questions. And if you like the answers, then you should feel encouraged to keep going. And if you don't like them, you really have to do some soul searching, because high probability, at least 50%, it's not gonna work out.

• 28:39Lewis Howes?

  This is interesting. And what if someone doesn't share the same money mindset values as you do, but you're so in love with them that you have this incredible connection? You just laugh at everything that you guys share, you know, everything is easy except for that one thing. Do you still think there's a potential you could work on that? Or is it, "Hey, if they don't have the mindset now, they're never gonna have it?"

• 29:03Kevin O'Leary?

  If they don't have the mindset now, they're never gonna have it. You know what you gotta do? You gotta move on. Tough, really tough, because it'll only end in misery. You know, I always say this. People say to me all the time, "What a cold-hearted you are, talking about love this way." "It's not about money." And I say, "Oh yeah? It's always about the money. The reason people break up, you'll find out, is always about money. It's always about money. It's not about... At the root of every divorce, I'll show you money. It won't be because they screwed around. You know, it's really some stress that's occurred within the family because of financial... And look, I'm just telling you the truth.

• 29:47Kevin O'Leary?

  I already, I started our conversation saying I was gonna do that. And you're gonna get all kinds of people listening to say, "What a..." "What an..." I'm 100% right. And, you know, I've been around long enough watching this happen to so many people that I want to give them good advice, and I'm giving them good advice. You really have to get this bedrock nailed down. You really do. And particularly if you're into your second year with somebody, you know, and usually what happens is relationships get intense, they then become, you know, they agree that they're going to be just with each other, which is a very encouraging sign, and then they may go on for another year or so before they tie the knot, or maybe they're never going to tie the knot, but the point is, they move in together, start buying assets together, you gotta get the financial thing nailed down.

• 30:31Lewis Howes?

  And how does someone develop a rich mindset if they've always been told that, you know, people with money are bad, or money makes you evil, or whatever people have heard when they're growing up? How does someone shift out of that and start seeing money in a different light, in a positive light, in a powerful light, in their benefit, and in an abundance mindset as well? How do we shift that? If we've always been conditioned otherwise?

• 30:58Kevin O'Leary?

  Yeah, but I mean, you have to understand why, you know, why a third of the population seeks entrepreneurship. It's not out of the greed of money, it's the pursuit of personal freedom. In America, what sets you free is to have enough financial resources to spend your day doing things that you want to do. It's one of the greatest freedoms you can have. And what I learned about it, you know, when I had my first liquidity event, I was young and we sold the learning company for 4.2 billion dollars, and there were 10 of us who were founders. So what I found so amazing is everybody showed up the next day after we closed, right back at their desks, because they didn't know anything else. That's what they wanted to do, they wanted to work. And what I found in life is I work harder today than I've ever have, and I don't need

• 31:40Kevin O'Leary?

  to, but I still want to, and this is what I know. And so, the whole idea that I don't have to do something, you know, I work with Nancy Chung, who sort of manages my day, and I block it off into 30-minute things, and each week, you know, maybe on Saturday morning or something, we review the next week, and I look at all the things that are booked, and if I see something I don't want to do, I just say, "Take it off, I'm not doing it." And there's nothing anybody can do about that. That is my ability to be free, to choose the things that mean something to me, and avoid the ones that don't, because my most valuable asset at this point is my time. That's what I care about, and I wish that for everybody. That's my whole point.

• 32:24Kevin O'Leary?

  But something about money you should understand, and everybody should think about, is the danger of money in a family is entitlement. If you entitle somebody, and you de-risk their future, you have actually cursed them. You've cursed them. You have almost guaranteed that they will fail, that they will never launch. I experienced this myself when I was graduating from college, undergrad, and my mother came to that. Again, she was a big influence in my life from events like this, and she said to me, "Great news is I'm coming to the graduation, but I want you to know the dead bird under the nest never learned how to fly." And I said, "Mom, what the hell does that mean?" She said, "There's no more checks.

• 33:07Kevin O'Leary?

  I've paid from birth to last day of college, that's my deal, and you get nothing else from me." And I went, "Wow, like, I don't have a job, I can't even pay my rent," and like... She said, "You're gonna have to work it out. I mean, look, I've done my job, and now you're gonna have to learn how to fly." And I had a tough couple of years, but what she was really saying was she hated entitlement. And she didn't want to entitle me, and I had to go figure it out, it was very tough. And years later, you know, I always look at these things, these moments you learn something, and then you apply them later, because they've, you know, they've steeped, they've aged in your head, they've actually come, you know, it's like a wine. It's aged to a perfect flavor, and now you have to use it, because it's been something

• 33:52Kevin O'Leary?

  you've experienced. So when I had that big liquidity event, my kids were four and six, and I went across the river, we were in Cambridge. I went to Boston, I set up generational skipping trusts that did exactly that. They took from any child, from birth to last day of college, and any degree, they could go right to a PhD if they wanted. They could stay in school their whole lives if they wanted, and the trust would pay for them, long after I'm gone. But after they graduate, nothing, zero.

• 34:20Lewis Howes?

  Wow.

• 34:20Kevin O'Leary?

  And I said that, I said that to my kids, and they were four and six, they just laughed at me. And then later, in Boston, when my son was in high school, doing really poorly, not applying himself. One day, I guess he had, he talked to one of his friends in his class, was telling him all about his family trust and all that stuff. I don't know why I brought this up, but my bet is that's what happened. He said to me, "Dad, walk me through the trust that, that, um, my, my, my trust." I said, "Sure. Um, Mom and I going out to dinner, if we get run over by a bus, you don't have to worry, you're gonna get to finish high school, but, you know, it doesn't look like you're gonna get to college, because your marks are terrible."

• 35:00Lewis Howes?

  Wow.

• 35:00Kevin O'Leary?

  And then he said, "Well, okay, then what happens?" I said, "Well, I'm dead and you have no money."

• 35:04Lewis Howes?

  Oh, man.

• 35:05Kevin O'Leary?

  And that was the first, that's the first-

• 35:06Lewis Howes?

  Wake-up call.

• 35:07Kevin O'Leary?

  Yeah, well, that was the wake-up call, and, you know, it may sound cruel, and people may say, "That's terrible." Today, he has started his first week as a full-time engineer at Tesla, after, you know, going through the whole system and, and graduating as a, an engineer. I paid for the whole thing, but now, he's on his own. And, but I think the wake-up call motivated him. That's the whole idea of entitlement. If he thought he didn't have to do anything, maybe he wouldn't have taken that path. How many rich kids, screwed-up rich kids, do you know? Plenty. There's lots of them. They're entitled. Mine will never be, and they may not like me for doing what I did to them, but if they have children,

• 35:49Kevin O'Leary?

  the trust pays for them, and those are expensive, and I'll be gone. But that's my whole point.

• 35:53Lewis Howes?

  Wow. And I know you know a lot of wealthy individuals who've had big exits, billionaires, you know, all these different things. What advice do you give them, or what would you give them? Maybe they wouldn't ask you for the advice, but what would you give them on how to raise better kids who have all the money in the world to their, to their disposal?

• 36:14Kevin O'Leary?

  Don't give it to them. Don't let them think that they are de-risked. Don't let them think they're entitled. They will act differently. They will take a different path. They will focus on their own lives and try and achieve things on their own. There's no reason you can't support them and you can't help with them in emergencies like medical emergencies or, you know, whatever it is. But if you entitle them that they never have to work?

• 36:36Lewis Howes?

  Yeah.

• 36:37Kevin O'Leary?

  You've cursed them. You've cursed them. You've totally written them off in terms of people that could have achieved greatness because they were motivated to do so for reasons of that everybody in the world has. You have to find your own path. Like, that's the whole idea. If you're granted a free pass, you've wasted a whole lifetime. That's my view. Look, not everybody agrees, but, look, this is the way we run our family and so far, so good.

• 37:01Lewis Howes?

  Yeah.

• 37:01Kevin O'Leary?

  And, you know, the one thing that I think we failed as a society on, because you're getting into an area that I spend a lot of time on here, is financial literacy. We have failed an entire generation. There's 100 million people in America that have, and they're in, some of them are in their 60s, that have nothing set aside for their retirement. They never were taught how to invest. There's a big difference between saving and investing. A savings account gives you nothing now. Interest rates are basically zero. The markets give you 6% to 8% a year, but you've got to learn how to harness them. Nobody teaches those kids anything. And that's, like, it's a good segue into something I want to talk to you about called Bean Stocks, which is, you know, a big initiative for me, to build a robo that invests like

• 37:45Kevin O'Leary?

  I do and like my mother did. A really conservative robo that you can download and actually tries to help you do this without you understanding how to buy and sell stocks. So, let's talk about that for a minute.

• 37:57Lewis Howes?

  Yeah, well, what is, uh, what is it? How do we, how do we get it?

• 38:00Kevin O'Leary?

  So, you download it off any phone, on any app store, and the whole idea, here's what I learned. The first time I took a stab at this, I assumed that everybody knew how to buy a stock and sell it and how to build a diverse portfolio. I was 100% wrong.

• 38:15Kevin O'Leary?

  I brought out an incredibly sophisticated product, but 99% of people don't actually invest directly themselves. Some massive percentage of the population don't do that. They either have an advisor, or they don't have an advisor because they don't have a lot of money, and so we ignore them. If somebody only has $400 to put aside a month, generally, the financial services industry ignores them. Because they can't make any money off them. And that's 100 million people. So I helped a whole team develop Beanstocks. And there's a zillion different robo's on the market, and I think anything that helps you invest is great. But I couldn't find anything that invested with my personal philosophy. And so, you know, I really wanted something that was about value, about getting paid

• 38:59Kevin O'Leary?

  dividends, so get paid to wait, conservative in nature, and above all, diverse. And so I like to use exchange traded funds. I use that in my own family trust. And that's what we built Beanstocks around. So, the whole idea is that you put aside 100 bucks a week, and if you're in your, you know, early twenties and you do this, you find the discipline to put 100 dollars aside a week. And that's the hardest part, by the way, because there's always some piece of crap you want to buy, that you don't need. But you put it into Beanstocks, and it automatically diversifies it into a portfolio designed specifically for you when you set it up. And so you can put projects, you want to, maybe you want to buy a car or a house, it helps you do that.

• 39:39Kevin O'Leary?

  It helps you just diversify into a wide range of ETFs, and just, it's a place where you build a nest egg. That's the whole idea. Now, it doesn't mean you can't day trade, you can have a Robinhood account, you can do whatever you like. You can do an online broker, whatever. But this is for the part that you're putting aside for yourself for the future when you turn 65, which might be 10% of your paycheck, or 10% of your winnings if you're a day trader. But it's completely different. It's not day trading, it's investing. And that's why I built Beanstocks. I'm very proud of it. It's out there, it's a relatively new product, I've gotten behind. And people that use it really like it, so I urge everybody to try it. Download it, it's for free, give it a shot, see if you want to sign up.

• 40:24Lewis Howes?

  And it's Bean S T O X, is that right?

• 40:27Kevin O'Leary?

  Yeah, B E A N S T O X. Please try it.

• 40:30Lewis Howes?

  Awesome, yeah, we'll have people go there for sure. And it's just a way to automate your savings, so it turns into investing as well, by doing that. So I think that's a great product. I'm curious...

• 40:44Lewis Howes?

  What do you think are three things that rich people do differently than the poor people? Or people that aren't thinking about building wealth in that way?

• 40:54Kevin O'Leary?

  Yeah.

• 40:57Kevin O'Leary?

  Number one, and you'll be surprised to hear me say this, they don't take inordinate risk. You're gonna find that the majority of very wealthy people are extremely conservative in how they invest. They don't need to beat the market, they've already done that, they just need to preserve their capital. So what you find them doing, and I don't know what that number is for you, wealth means different things to different people. But when you are fortunate and you become wealthy, what you'll find is most of those people do not take a lot of risk. And they invest in things that are very long term, they don't use a lot of debt in most cases, they don't use leverage when they're investing.

• 41:40Kevin O'Leary?

  They don't take very speculative positions on, you know, you hear that they might buy Bitcoin or they may, you know, buy a speculative stock. But if you look at it as a percentage of what they're worth, it's nothing.

• 41:52Lewis Howes?

  Right.

• 41:52Kevin O'Leary?

  And so they're willing, when they're making that investment, they're saying, I'm willing to lose it, it's entertainment almost for me. It's not something I think that I'm gonna have to live off. And the other thing I found, because I advise a lot of wealthy people, because my companies that I invest in, you know, of which I have over 30, at any one time 10% of them are being acquired by a private equity firm or being bought by a strategic. And I've known the entrepreneur and maybe it's their first liquidity event, I try and help them on that journey. And some of them, you know, get a hundred million or eighty million dollars, we've got plenty of situations like that, and they're young. And what happens is you find out later that entrepreneurs are actually really bad investors.

• 42:38Kevin O'Leary?

  They're very good at running a business and they focus myopically on that their whole lives, but when they actually get liquidity, it's usually their husband or wife that was the person that was taking care of the family and mitigating the risk. And they're the ones that are the better investor. And that's why I say in a family you have to have a team approach. But I've learned this, that you really...

• 42:59Kevin O'Leary?

  You'll find that what's successful about families is they know what they're good at, or wealthy people, and they know what they're not good at. And they don't try and do things they don't understand. And this is, it's important because you have to say, "I have limits on my skills." "I know what I'm good at, but I've been very fortunate, and I'm not going to go risk anything now doing something I don't know." I see that characteristic a lot. And the other thing that I would say is different, and this may have a lot to do with the concept of karma. Another lesson I learned from my mother, that if you're successful and you talk to wealthy people,

• 43:41Kevin O'Leary?

  you'll always find that there's something that motivates them to be philanthropic, to give money to something that matters to them. And that's the whole idea of giving back. You've been successful and you have to find the cause that motivates you, you're willing to spend your time and money supporting. That is a big difference because if you believe in karma, and I do, when you do that, it kind of protects you against the horrific downside of something bad happening to you because you're just so greedy. You can't, when you had success and you're a wealthy person, if you show me a greedy wealthy person, just wait 10 years. Then you'll just show me a person.

• 44:26Kevin O'Leary?

  Somehow karma will separate their money from them. That's what I find.

• 44:30Lewis Howes?

  Or they'll get sick, or something will happen where, yeah.

• 44:33Kevin O'Leary?

  I really believe this, I really believe it, and you've got to find those things that you can give back on, that means something to you. But if you abuse karma, it's got a special gift coming for you.

• 44:47Lewis Howes?

  So finding ways to give back. Are you giving back in a lot of other ways, philanthropically, right now as well?

• 44:52Kevin O'Leary?

  Yeah, you know, I like to have a concentrated approach. I call it five in five. I prefer to pick five charities, or in our case, we support a dance company, we support some hospitals, some educational institutions, and, you know, give enough that it's a material gift, and that I have a say in how it's spent very often. And above all, I like to see expense ratios reported. I generally don't support charities that can't provide, just like an investment, some kind of a statement on where my money went.

• 45:28Lewis Howes?

  Right.

• 45:28Kevin O'Leary?

  And that is actually something I think Bill Gates is famous for early on, saying, "Why can't I treat my charitable investments as I do my private ones and ask for some performance metrics?" And I kind of believe that he's right.

• 45:40Lewis Howes?

  Yeah, it's a thing of smart. And what would you say is one other thing that rich people do differently that poor people don't do?

• 45:50Kevin O'Leary?

  This may have a lot to do with, you know, the access to... But in the last five years, I've realized how important food is, and how if you're, you know, you say "poor", how you should be, or even you should focus on what you put in your body. Because in our society, we do two things very badly. We eat too much sodium and we eat too much sugar, white cane sugar. And we have been trained to do that since the 40s by a whole industrial complex that wants to sell us that shit. And we eat it. And I'm guilty of it, and so is everybody else. Salt and sugar feel good. They're comfort foods, snacks and all

• 46:32Kevin O'Leary?

  that. It's the worst thing you could put in your body. And I have learned, it's kind of weird, but the older I get and the more I experience this, because I'm actually a classically trained chef in French fusion.

• 46:45Lewis Howes?

  Wow.

• 46:47Kevin O'Leary?

  I have a job on QVC as chef wonderful. I sell millions of dollars of food and wine each year there. It's because I grew up for a few years in Nampan, Cambodia. And that's at a place where it was a French colonized place. My dad was working the United Nations, and the two women that were the housekeepers and the cook used to go to the market, it was on the Mekong River in Nampan, and take me with them at four in the morning. And it's very hot there. And so they were classically trained French chefs. So in French cooking, particularly if you're a sous chef, which is really hard to get that designation, and I'm pretty proud of what I can do in that area, is you work with a lot of heavy butter and cream.

• 47:29Kevin O'Leary?

  But you can't do that in an environment where it's 110 degrees, 100% humidity every day. You can't eat like that. So what those chefs taught me was how to replace the butter and the cream with things like a mango puree, or lime and lemon juice, or guava crushed. I mean, all kinds of different flavors. So they would take a classic dish like crêpe flambe, which is one of my specialties, or escargot. And those are classic French dishes. They're very time-consuming to make, particularly escargot if it's made properly, with real shells and real snails. But you don't have to put all that butter in it.

• 48:12Kevin O'Leary?

  You can have, you know, a different flavor set based on using a fusion of citrus. Anyways, the whole idea of eating better for me is part of my DNA and growing up. So now, I look at what I eat every day. I used to, when I was young, I'd eat three steaks a week. I used to love that. I don't think I've had a piece of red meat in months. I eat fish, I eat fruit and vegetables, and it's, it really helps you feel better. So if you're asking me what's different, but I'm proud to see that many people are exploring plant-based and regardless of their financial income. Meat is actually very expensive and very inefficient. And there's ways to get protein. Now, you don't have to become a vegan. I'm just saying you have to choose to focus on the things that are better for you,

• 48:57Kevin O'Leary?

  regardless of your income. And you will get more energy, you'll feel better. That kind of thing, that's the difference as well.

• 49:05Lewis Howes?

  That's powerful. I love that. I'm curious, do you think the middle class is financially stuck? And if so, what can they do to start achieving more financial freedom?

• 49:18Kevin O'Leary?

  No, they're not stuck. And one thing that's democratized, and we've learned it since this whole pandemic started.

• 49:26Kevin O'Leary?

  You can create a new opportunity for yourself online with virtually no barrier to entry. Many, many people did it as a side hustle, and it's now producing more income than their first job. The whole idea of trying to solve for customer acquisition using creativity, using video, using music, using photography, using storytelling, animatics, graphics, to actually sell a service or product, starting locally and then expanding. There's millions of new businesses that have been started during the pandemic. We see them every day on Shark Tank, but they are basically taking middle-class people out of middle-class. There, and I'd say, if you look at Shark Tank, we have plenty of people that have, you know,

• 50:08Kevin O'Leary?

  been working in the middle class for years and all of a sudden exploded to the upside with a great service or idea that they did online. And that, that's why I, I really think people should empower themselves. You can try things online. You can see what works. You don't have to get the first one right. But those tools are there for you.

• 50:26Lewis Howes?

  Yeah.

• 50:27Kevin O'Leary?

  And most of this is done on Facebook in geo-locked advertising. Eighty cents on the dollar of what my company spends is on Facebook. So I always find it very funny to see people, you know, bashing Facebook, saying how evil it is, when really it's running small business in America because they have that unique geo-locking advertising feature. So, you know, we shouldn't shut it down till we find something better.

• 50:48Lewis Howes?

  Yeah. And what would you say are a couple of qualities that you really look for when you're, when you're looking to invest in someone or when someone has an idea and you, whether you invest them or not, you're like, this person's going to be successful, whether it's in this thing or something else. What are those two or three qualities that all of them seem to have in your mind, whether it be a leadership skill or? Clarity, what would that be?

• 51:12Kevin O'Leary?

  I prefer to invest in entrepreneurs that have failed once or twice before, that have felt the sting of failure and have gone down the road and not had success the first time because their motivations are completely different than a more arrogant first-timer that thinks everything they do is going to make a hundred million dollars. It's just not, doesn't work that way. And so, that's one thing. I love, there's three things you have to have, the ability to do and know if you're going to be successful in business. Number one is, you have to be able to articulate your idea 90 seconds or less, explaining to me why anybody would want that product or service. And if you take more than a minute and a half, you're never going to be successful. You're just not.

• 51:53Kevin O'Leary?

  And number two is, you have to be able to explain why you're the right person to execute on that idea. In other words, what is it about you that knows how to take this idea, which good ideas are dime a dozen? Executional skills are really hard to find. So what is it about you that can execute on this business and make it work? I mean, those two together start to be really interesting because then as an investor looks at it and says, "Well, I'm going to mitigate my risk. I've got a great executional expert here and I've got a great idea." And then lastly, the one that I think you have to have, a good command of, you have to know your numbers. You have to be able to explain gross margins, market share, break-even analysis, how many competitors, how fast can you grow?

• 52:37Kevin O'Leary?

  If you don't know your numbers, you deserve to burn in hell and I'll put you there myself. Because you really, those are the three things that define success. And I think, you know, that's who I want to invest in, someone who has the command of all three of those. That's probably got more than a 50% chance of being successful if they can do that right.

• 53:01Lewis Howes?

  I love your take on things. I wanted to know, for those that are in their late teens, early twenties, what conversations should they be having with friends or mentors around money? I feel like a lot of people are afraid to talk about it. Or they don't, they don't share how much they make, or how much a home costs, or whatever. It's just like this hush, hush mentality. What should we be talking about in our late teens, early twenties, or even thirties? But what types of conversations should we be having to shift the narrative around money? So we can start attracting it in our favor as opposed to rejecting it?

• 53:37Kevin O'Leary?

  Well, first of all, we need to teach it in high school. Luckily, here in Florida, it's been put into the curriculum. And I'm very proud of that. You know, I used to be in the educational software business. There's 110,000 school buildings in America. Majority of them in New York, and Florida, Texas, and California. And abysmally, most of them don't teach even debt. They don't even teach how to use a credit card, which is ridiculous. We've got to change that, and luckily, we are. We're starting to see it creep into the curriculums in all the major states, which is good. But I, I think parents have a responsibility to talk about money, which is always sitting at the table every day. It always is. And, you know, getting their kids to understand how a credit card works is very important. And again, I talked about not entitling, that's important too. But within, within your friends, I mean, don't be embarrassed to talk about money.

• 54:21Kevin O'Leary?

  You're going to be talking about money for the rest of your life. It's always going to be part. You can't live without it. You have to deal with it. It can cause great joy and give you personal freedom, or can be catastrophic in your life. Destroy your happiness completely. Your choice is where does it fit? Do you want it to destroy your life? Or would you prefer that you understand how it works and respect it for what it is? And deal with it? That's a personal choice people have to make. And I would say the best way to do that is learn more, talk more about it, and don't be afraid to discuss it. I don't care what age you're at, but certainly at the age of 16, you should be discussing that. And above all, taking 10% of whatever anybody gives you, your grandmother, your birthday gift, whatever it is, and set it aside and start investing it.

• 55:06Kevin O'Leary?

  The earlier you start, the less pressure you have when you're in your 60s. Because you've got to have at least a million and a half bucks in the bank. And you can, if you just save a hundred dollars a week. That's what Beanstalks is all about. That's why, that's why I got involved in Beanstalks. That's the whole idea.

• 55:21Lewis Howes?

  And do you think someone in their late 40s and 50s, do you think it's too late for them to start learning about financial literacy if they've struggled in their 20s and 30s and 40s? Do you think it's too late to start investing and saving? What should people do in their 40s and early 50s?

• 55:36Kevin O'Leary?

  No, they should at any age. I mean, the truth is, changing your spending behavior in your 40s is difficult, but you can do it. And at that age, you should start saving 20 to 25% of what you're taking in, which sounds hard to do, but it isn't. You just stop buying those $5 coffees and you stop buying stuff you don't use. Anybody can go look in their closet and see all the crap they bought that they never used. And basically, you killed that money when you did that. You bought something that you could have had invested, and it could have grown 6% to 8% a year for you, but instead you bought some piece of junk that you're throwing out now. Everybody's guilty of that. I actually think my mother was right. She's always said that people can save 20%, they just don't have the backbone to do it.

• 56:21Kevin O'Leary?

  And she did, and she died a very wealthy woman. She had a secret account she kept from both of her husbands, and I was the older brother and was the executor for the state. And I remember the lawyers calling me up saying, "You gotta come down here. Your mother, your mother had a lot of money." And I always wondered how she did it. She basically bought dividend-paying stocks in her 20s and a whole bunch of telco bonds, 50/50 portfolio. She loved telco bonds, they used to yield 6% in those days, and she loved dividend-paying stocks, S&P stocks. And over the 50 years that she had this account, it just provided massive appreciation.

• 56:54Lewis Howes?

  Wow. Should people die wealthy, or should they die broke because they spent their wealth on charity, or giving back, or whatever, living their life and going on trips and adventures? What's your philosophy there?

• 57:09Kevin O'Leary?

  You know, the trouble these days is you don't know when you're going to die. You make certain assumptions, and then you live an extra 10 years or 20 years. And you live at a time in your life when you really needed that money for your comfort. You know, it's probably better to not make an assumption, "Oh, I think I'm gonna die when I'm 88," because you don't know what technology's gonna provide, or what your genes really have in store for you. I would prefer to die with a good chunk of dough in the bank, and then gift it to a cat.

• 57:39Lewis Howes?

  A cat?

• 57:40Kevin O'Leary?

  Yeah, you know, cats only last 14 years, be a great 14 years for them. I'm just kidding. I'd probably give it to a combination of, you know, in my case, I feel safe because I can roll it into a trust that doesn't provide for you after, you know, you finish college. So I don't feel I'm entitling anybody or cursing anybody's future. So I'll just probably roll it into one of my family trusts and say, I don't need it anymore. The only thing I'm taking with me to the afterlife is my watch collection, all of them. I'm going to eternity, I got a lot. I don't even say anymore how many I've got. I haven't, you know, really, I'm very proud of my watch collection and it's incredibly, it's got some amazing pieces and it's taken me years to build this collection.

• 58:24Kevin O'Leary?

  And I'm going to need it to tell time in eternity, so I'm taking it all with me.

• 58:29Lewis Howes?

  What do you think is the best investment you've ever made in yourself?

• 58:34Kevin O'Leary?

  Well, the best investment I ever made in myself was myself. You know, you often doubt yourself, but you know, it was, it was, you know, I went through some very tough times, right from when my mother cut me off, through several business ventures I failed in, and then you just don't know, serendipity knocks on the door. The thing is, as an entrepreneur, you've just got to keep getting up every day. You have to stay in the game, you have to stay in the race. It's very, very hard. It's like that story of the guy with his fiance, you know, you just have to focus. And you have to find somebody that's willing to focus with you. But I'm glad I did what I did. I wouldn't change a thing. I've made plenty of mistakes. But I, it is who I am today and I'm very, you know, proud to be able to offer the things I do to my family

• 59:20Kevin O'Leary?

  and to support different initiatives and charities and support the arts and collect watches and guitars and cook and all these things are made available because, you know, I've been able to focus on being successful in business. And that is the great American dream. It's going to remain that way forever. It's the essence of why Shark Tank works. It's, I'm very proud to be part of the platform. I can guarantee you 13 years ago when we started this thing, we had no idea what was going to happen. I mean, it's just... Who knew? But now, nine-year-old girls to 99-year-old men come up to me saying, "Look, let's talk about that deal last week on Shark Tank." And I'm happy to do it.

• 1:00:03Kevin O'Leary?

  I mean, I think it's a wonderful outcome, and we're proud of it. And as we start to work on season 13, I mean, it's, you know, no television show lasts 13 years, practically none, less than 5% of them.

• 1:00:14Lewis Howes?

  It's amazing.

• 1:00:15Kevin O'Leary?

  So, it's great, and we're proud to do it. And, I don't know, that's the whole idea that I encourage people, don't pursue entrepreneurship out of greed of money, you will fail for sure. Because every time I talk to anybody that's had a big liquidity event, I say, "You know, did you see it coming? And how did it happen?" They said, "We never saw it coming. We were just working one day, and then boom, I was poor, now I'm rich." That's always the way it is. It's not that you're saying, you're counting, you know, your dollars. You don't have any until one day, boom, something happens. And then, the funny thing is, you find yourself right back to work.

• 1:00:49Lewis Howes?

  Yeah. You're not gonna just sit around all day and do nothing, you wanna get back to...

• 1:00:53Kevin O'Leary?

  I tried it. I went all around the world for three years. I wanted to see every beach in the world. And I did. And it was boring as hell. It's just, and so I finally said, "I gotta get back in the game. I gotta, you know, I gotta get into something, I gotta do something." And, you know, I got back in the game, did other deals, had success, had failure, you know, worked on television, did other things, started cooking again. I mean, there's a lot of, there's a lot of things. You know, one of my first jobs was to be a film editor. When film, there was no video then, it was in the 70s, late 70s, and I was a film editor on an eight-plate steenbeck. And I learned how to cut film, make, you know, sound effects, and sync up sound and everything.

• 1:01:35Kevin O'Leary?

  And to this day, I still spend a few hours every weekend editing to keep my chops up.

• 1:01:40Lewis Howes?

  Really?

• 1:01:41Kevin O'Leary?

  Yeah, I use Premiere Pro, I'm pretty good at it. And the difference is obviously immense, because you can go digital now, but I have 40 terabytes of content that I work with, and most of my social media you see, or a great portion of it, I cut it myself.

• 1:01:58Lewis Howes?

  Wow.

• 1:01:59Kevin O'Leary?

  And I just wanna keep my chops up, because that's a skill that helped me out. And now I find full circle that how powerful social media is, telling a story really matters. And I usually get up quite early, today was 4 o'clock in the morning, and I cut for a couple of hours, and I, you know... I pushed some stuff out. I got millions of followers and I think people appreciate it. And I even write my own music. You know, I play guitar. I have a... That's a funny thing. I said to my dad the other day, he's still alive, he's 92. I said, "You told me I couldn't be a musician." He said, "You still can't be one. You could never make any money doing this." And I say to him, "I actually can because I don't buy music rights. I make my own." He said, "Wow, you're saving like 20 bucks. That's fantastic."

• 1:02:42Kevin O'Leary?

  I said, "And he's right." But the point is, I can make music. I can publish it on any platform. I'm proud to do it. I collaborate with other musicians because you send your stuff digitally. You know, we drum riffs, guitar riffs, bass riffs, and put it all together. And I like to do it. I think it's a lot of fun. You know, you can never stop learning guitar. You know, you hear a riff from somebody else, you try and emulate it, you know. And in social media, most of the music is sort of 30 seconds and 59 seconds, and that's what I do.

• 1:03:15Lewis Howes?

  Can you share 30 seconds of the guitar?

• 1:03:17Kevin O'Leary?

  Yeah, you know, I thought we'd get to this point, so I did have... And I always have my guitar with me. I have a lot of guitars because I was a shareholder in Fender. This is actually...

• 1:03:27Lewis Howes?

  Wasn't one of your investments a guitar on Shark Tank as well?

• 1:03:30Kevin O'Leary?

  It was. It was. I pretty well invest in every single guitar deal. That has never made me any money doing that, but I just love guitars. Even Fender was really hard because if you know Fender guitars, a 1962 Telecaster is worth 100 times more than a 2021 Telecaster. It's like wine. And so, you know, I have a lot of guitars now, but... And some become favorites for a year or two. This is a Hussin Dalton. I think it's made in either North Carolina or Virginia. One at a time handmade. And I was gonna buy a Martin, and I went in. When you buy an acoustic, you have to go into the store and play every single ax. And the reason, it's not like an electric.

• 1:04:12Kevin O'Leary?

  Each handmade wooden guitar is unique. It has its own sound, its own feel. You really... And that's why they have rooms so you can go sit. And I played probably 30 Martins, and I wanted to get a Martin. And he finally said, "Listen, you're not feeling it, are you?" I said, "No, I'm not. Not that I don't like Martin, I just..." You know, you know it. When you play a guitar, and it just feels right, you know it. And then he gave me this, which is actually a 3/4 guitar. It's not a full size.

• 1:04:44Kevin O'Leary?

  But this puppy is sweet. It is just... Anybody that plays it says, "Wow." And the key to a guitar like this is, you know, I always say this, you don't buy a guitar and store it away. You play it. You have to play it, or it loses its soul. And so you've got to keep them... You've got to set them up. You've got to change the strings from time to time, which I really enjoy doing. I work with some of the greatest guitar techs in the world. There's one here in Miami, Alex, who's amazing. I dropped my Steinberger graphic this weekend, doing social media. It's out there right now. It's on Instagram. It fell on the ground on hard marble, but it's made of solid graphite. So Alex is doing a full setup on it now. Wow. Thankfully, we didn't destroy it. But, you know, you have to take care of these guitars. And that's probably worth a fortune, because they don't make that guitar anymore.

• 1:05:29Kevin O'Leary?

  Right. It's one of the prototypes. Anyway, so the idea is you try... I know you probably can't see the guitar, because it's... But I'm working on a little riff here. You know, just for social, but I'm still working on it.

• 1:06:58Kevin O'Leary?

  You get the idea, right?

• 1:06:59Lewis Howes?

  The man of many talents, I love it.

• 1:07:02Kevin O'Leary?

  It's fun to do.

• 1:07:04Lewis Howes?

  My brother is the number one jazz violinist in the world, so I grew up-

• 1:07:08Kevin O'Leary?

  Whoa!

• 1:07:08Lewis Howes?

  I grew up in pubs and in clubs and at events and he played with Les Paul for ten years in Times Square. So I got to go watch him play with Les Paul and-

• 1:07:20Kevin O'Leary?

  That's incredible, so do you have any chops yourself to play guitar?

• 1:07:24Lewis Howes?

  I'm a, I'm a, I play campfire songs on the guitar, so not as talented as you or not like my brother. He's a machine, he can, he can play the electric violin like it's a guitar, it's unbelievable, but-

• 1:07:36Kevin O'Leary?

  That is, that's a, that's a really, you know, and playing that in jazz or in rock is not easy, that's really amazing.

• 1:07:42Lewis Howes?

  Very challenging, yeah.

• 1:07:43Kevin O'Leary?

  You know, what I find in families is that musical vibe kind of runs through generations sometimes, some get it, some don't. My son is a better guitarist than I am.

• 1:07:52Lewis Howes?

  Wow.

• 1:07:52Kevin O'Leary?

  And so, he's an engineer, but he just got into playing guitar and he's really, you know, really, really good at the ear of picking it up and then figuring out what chords are in. We had a really big debate.

• 1:08:07Kevin O'Leary?

  He loves classic rock and we were listening to Hotel California one day and-

• 1:08:13Kevin O'Leary?

  You know, I told, I told him, "Look, it's played with a capo, so you're not gonna get it. You have to capo up two frets." And he said, "BS, you don't know what you're talking about. There's no capo in this track." I said, "There's definitely a capo in the track." So we got at it, you know, and, and so luckily, I have Joe Walsh's phone number because he's a big Shark Tank fan, and I met him in, in LA at his restaurant, Craig's.

• 1:08:39Lewis Howes?

  I love Craig's. Love Craig's.

• 1:08:41Kevin O'Leary?

  Okay, so I, I didn't know if, if he would respond, but I, I said, "Look, I'm having this huge fight with my son about laying down, you know, the lead to Hotel California, because he's playing it." And he said, you know, I told him, "You've got to capo up two, two frets." And he said, I said, "Who's right? We, we're just really..." And he wrote about, wrote, wrote me back 30 seconds later and said, "You're both right." Because, you know, when Felder laid it down, and Walsh, obviously, has been playing it for decades now, he started with the capo and ended up with "Open" when the lead was actually played. So there was, it was, but, and then I said, "Trevor, Joe says I'm right."

• 1:09:24Kevin O'Leary?

  Here's his text. He said, he said, "Bullshit. You don't know Joe Walsh." I said, "Here it is, right here."

• 1:09:29Lewis Howes?

  That's funny.

• 1:09:30Kevin O'Leary?

  It was, it was very cool. It was very cool. I always thank Joe, if I see him again, for doing that. But Trevor's ear was right. It was "Open" for the lead piece, and then he, and he was able to lay that down in like two hours. And we sang it as a family, because my wife's got a pretty good voice, and we recorded Hotel California, and Trevor laid down the lead.

• 1:09:47Lewis Howes?

  That's cool. That's fun. I think, I always think that, uh, music allows us to have a diversity of range of our ideas, and we can bring them to, for me, with sports, but can bring it to relationships, to business, and I think it's always important to have music in our lives and playing.

• 1:10:02Kevin O'Leary?

  I, I, I think, I think you need the yin and yang. You're making a really good point. I think great entrepreneurs and great leaders and managers pursue some chaos in the arts somewhere. They do both. That's the whole idea, you know?

• 1:10:14Lewis Howes?

  I mean, you're a, you're more of a Renaissance man than probably any shark out there in terms of mastering music. I mean, a French chef, you know, wine, business, all these different talents that you have. How do you have time? I mean, master editor and filmmaking, how, how do you have time to manage all the businesses, uh, manage, manage relationships, do all the skills that you have?

• 1:10:41Kevin O'Leary?

  I have a great team. I hire people that are really interested in what they do and manage most of it for me, particularly in my portfolio of 30-plus companies. Alex Kenjev runs O'Leary Ventures, Nancy runs relationships with all the networks, and Kirsten runs social. I've got a great accounting team. We meet once a week virtually. We go over the portfolio, we go through all the opportunities for the week, we A&A projects, and then we communicate daily, you know, through text and whatever else. I think the whole idea is, you know, and I said this at the beginning of our conversation, you only have, my number one asset's my time. I don't want to waste it. I don't want to do

• 1:11:21Kevin O'Leary?

  things that don't mean anything to me. And you find that, you know, many successful people, I remember somebody telling me, I finally got to meet him, Elon Musk, that he won't waste time on a conversation that's meaningless. He'll just walk away, or what? He'd just say, "I'm not going to talk about that. It's a waste of time," which is rude. But because he's so efficient at focusing on things that matter, he's achieved extraordinary things. And I say that about, you know, I'm very fortunate because I get to meet these entrepreneurs. Just, you know, Shark Tank's a wonderful door opener in so many ways.

• 1:12:02Kevin O'Leary?

  I talked to the CEO of Robinhood yesterday, Vlad, and, you know, we share a lot of interests together, and I really found him interesting and just completely different than what I thought. And I think that's important, that you form these relationships. Anne, who runs 23andMe, she was a guest at Shark. We really, you know, got interested in each other's businesses. That stuff's interesting. So my job is to, when I invest in a company, my job is to open doors for that CEO. Luckily, if you're a shark, I don't care what retailer you want to be in, or what, you know, online service. I can call the CEO and they're gonna call me back. It's just because they want to support American entrepreneurs. Why wouldn't they? And, and so, you know, we often will film an update. I've got some great companies.

• 1:12:47Kevin O'Leary?

  I think the whole circle of life on Shark Tank is everybody now knows that the show supports entrepreneurs and American families. And my job is to be the conduit of that and help those people. And in the meantime, I'm serving, like, I'm a, I'm an investor. You know, I put my money down these companies. I take a chance. I give them 300, 500, whatever it is. And I want to make my money back. And, and I want to, our, our interests are aligned. We, we want to be successful. This is not a charity. This is the Shark Tank.

• 1:13:18Lewis Howes?

  Right. You're trying to make money at the end of the day.

• 1:13:20Kevin O'Leary?

  Yes. And I tell, I tell Barbara that every day. And the only, you know, the only, when we go to New York, because Damon's there too often, the three of us will get together for dinner. And the only reason Barbara ever makes it is I buy her a new broom each year so she can fly in.

• 1:13:38Kevin O'Leary?

  It's the truth.

• 1:13:40Lewis Howes?

  I've got a, this is fascinating. I've got a few more questions for you if you've got a little more time.

• 1:13:45Kevin O'Leary?

  Sure.

• 1:13:45Lewis Howes?

  One is about self doubt. And you seem to have all the confidence in the world and everything that you take on. You master the skill and you have confidence around it. How did you overcome self doubts? Or do you have doubt now? And what do you do to help yourself overcome that so that you can have confidence in your day to day life?

• 1:14:08Kevin O'Leary?

  I, I, I think everybody has doubts. And, and I, you know, I was dyslexic when I was young. So I had a lot of problems with that, just learning how to read and, and keep up in school. But I didn't let it get in my way. By the way, Damon also has dyslexia. So, you know, these are things you have to start treating a different way if you're going to overcome them. But the way I look at it now is, Okay, I talked about the lying thing, so I'm not gonna lie to anybody and that's gonna cause me a various amount of problems, but I don't care. And then, um, let's say, you know, I'm doubting an investment I'm going to make. Well, I've learned that don't bet the farm. In other words, only put up capital you can afford to lose.

• 1:14:51Kevin O'Leary?

  And, and then you know that if your assumptions are wrong, um, so I don't use debt, I don't have any debt, um, I don't want to have debt, I don't wanna think about it, I don't wanna owe anybody anything. But, you know, if you're being honest with people and you're, and you're being diverse in terms of how you invest, it's, you wanna win, of course, and you wanna be successful. But, you know, what's the worst case, I say to myself? If I can stay healthy and I can get some of these investments right and I'm enjoying what I do with the cooking and photography, the music and all that stuff, what else can I do? Like, I mean, this is the way you're supposed to spend your life and then one day they turn off the lights, you take your watches and you go away.

• 1:15:35Kevin O'Leary?

  That's what happens. And that's gonna happen to me too, but at least when, when people look back, they'll say, "Well, the guy didn't lie to me, I made money with him and, uh, he can cook some good stuff." I mean, I, you know, I look at it that way, you gotta be pragmatic. So I'm not that worried about, um, and this comes over time, I mean, somebody said to me, "Don't you worry what people think about you?" And I actually thought about that for a while and I thought, "No, I don't. I just don't."

• 1:16:00Lewis Howes?

  Did you used to?

• 1:16:02Kevin O'Leary?

  Yeah, I think I did and I think that really contorted me. I think as long as I'm telling the truth, I don't worry about it. I've said that countless times now, but why would I want to stress myself out worrying about what someone thinks about me? What benefit for either they or I is that energy? That's a complete waste of time. And I would ask people that don't have, they have a lot of anxiety, or they're, they're conscious, you know, self-conscious about what others think about them, this is one of the biggest mistakes in social media. Why do you care? The only people you should worry about are the people in your family and your close friends and maybe that's a total of 50 people. I worry about them, I don't wanna lie to them, I wanna keep in touch with them, but, you know...

• 1:16:48Kevin O'Leary?

  If some random person wants to rag on me, I don't care. Like, I don't know them. And, and, and if they want to be that way, I don't want to know them. It's sort of, you know, I love meeting new people, but I'm certainly worried about my family and my friends first, and I think everybody should treat themselves that way, and you'll be a lot happier. You can't make everybody happy, ever. You just, it doesn't matter what you do, you can't. And if you sit there stressing, and I think it's great advice for my kids, I often talk to them about this, saying, "What are you doing? Why do you care? What, what, how will it change your life if everybody you know just thinks you're great? Who cares? It's what you think about yourself that matters.

• 1:17:33Kevin O'Leary?

  That's how you can get confident.

• 1:17:34Lewis Howes?

  Hmm. How do you change the perception about yourself? How do you build that, I guess, care about how you think about yourself?

• 1:17:44Kevin O'Leary?

  Well, it's like, it's like, it's like quitting smoking. I quit smoking decades ago because I said, "This is stupid. Why am I doing this? This is a really stupid thing." And, and, and, and I have to prove it to myself that I can do it. You know, I don't take drugs. I'm not saying I never did, but I don't take them now. The only drug I'm involved with is really good red wine that I make myself. I have a huge wine business called O'Leary Fine Wines. Um, I sell 150,000 cases a year. I blend it myself. My wife blends the whites. I'm the number one purveyor of wine on QVC, direct to consumer. I drink wine, that's my drug. And sometimes I drink too much of it, which is why, not to be shameful, I have a company called Boost.

• 1:18:27Kevin O'Leary?

  Pure oxygen, I always have this beside me. Yeah, this is a great company, uh, one of my most successful ones. It's, um, 95% oxygen, 5% air, which is the aeronautic oxygen. Instead of drinking coffee in the afternoon... I take a few hits.

• 1:18:42Lewis Howes?

  What does that do for the body and the mind?

• 1:18:45Kevin O'Leary?

  Oh, it's terrific. It's really refreshing. You see athletes using it all the time. You really see it in high altitude locations like in Colorado and Denver, etc. But it's a really, and it comes in different sizes. I always have one with me wherever I go. After we finish this shoot, I have one down on the beach, shooting another session. And I'm gonna boost it up first. I'm gonna bring everybody on the crew.

• 1:19:07Lewis Howes?

  I like it. I'm gonna have to get myself some.

• 1:19:09Kevin O'Leary?

  Oh, you can't ship it by air. It's gotta come by ground. So I always get a case. And I plow through it. Everybody sees this. Can I have one? And I'm giving them out all over the place. But it's a great ambassador for Boost. What a fantastic company.

• 1:19:21Lewis Howes?

  That's great. Three skills you think every entrepreneur should develop, whether they're about to launch a business or they're in the process of building their business. What do you think are three powerful skills that we should all develop?

• 1:19:37Kevin O'Leary?

  You have to have an alternative endeavor in the arts. If you're focused on business, what is it? Do you draw? Do you play music? Do you listen to music? Do you cook? Do you paint? Do you do photography? What is it that you do that gets the yin and the yang working together? That's a concept in Korea of yin and yang, and it's very important in business. The greatest entrepreneurs are often very good artists in one discipline or another, and they spend enough time to hone that talent. So I always play guitar every night. You know, I'm not the best guitarist, but I get better all the time. And I'm good enough to record stuff that people listen to and seem to like. So I like that. Took me a long time to get there. But the same thing with whatever that discipline is. And I think that's number one. Number two, you have to get your three things on the mirror every morning. I think that really works.

• 1:20:23Kevin O'Leary?

  Otherwise, you're not disciplined. You're not organized. And number three, and I've said this a million times, you gotta tell the truth, which is very hard to do. People say they do, but they don't. Very few people, you know, very few people tell the truth.

• 1:20:38Lewis Howes?

  You're the king at this and you know, one of the things I love about telling the truth is that you build confidence with yourself, you know, when you're lying or even a white lie, you lack the confidence because you know you're out of integrity with yourself. Uh, and you're obviously the king of, of telling the truth, especially on Shark Tank. You do it in a very specific deliberate way where you always tell the facts on how you feel about the facts of things or how things will work out. How can someone, uh, do, communicate in a way where they're telling the truth and telling the facts and being honest, but also caring for someone's feelings as you might put kumbaya on it, uh, like Barbara might do, how can someone do both?

• 1:21:20Lewis Howes?

  Or is it not possible? Should you just say the facts and not care about someone's feelings?

• 1:21:25Kevin O'Leary?

  It's not possible. Um, you know, it just isn't. You can try and sugarcoat it, but if the more you do and you leave hope where there is none, that's a huge mistake, particularly when it comes to matters of finance. It's very binary. You don't, there's nothing between losing and making money. It's just the abyss. You either make money or you lose it. You have to decide which, you know, you gotta tell the truth and, and I think, you know, there's a lot of angst that goes into people trying to, you, you just can't serve both masters. You have to choose one and I prefer the truth. And you know, you can try and say, well, I'm telling the truth in a, in a sugar coated way, but you're not, you're just lying to them. That's all.

• 1:22:02Lewis Howes?

  Was there any investments you passed on that you, in your gut was like, this is not going to work out. This is a horrible idea. It won't work out, but then years later it ended up being a big success.

• 1:22:16Kevin O'Leary?

  There always are, but I don't even think about them. I mean, I see so many deals now. My deal flow is insane. I, I see so much stuff in, in, inside of Shark Tank and outside of it. That, you know, It's there, I don't, I just look forward, I don't look backwards.

• 1:22:34Lewis Howes?

  Yeah.

• 1:22:35Kevin O'Leary?

  I don't care, you know, I might have missed one, I might have, you know, I've had another successful one. My portfolio, we review it weekly, we talk to our entrepreneurs, I have winners, I have losers, but, you know, I also have some fantastic successes and catastrophic failures. It's sort of, it's a passion play. I have people calling me every day, you know, crying, saying, we're gonna go out of business, and I have other people saying, I can't believe it, somebody just offered us 20 times sales in cash. Are you a seller? I mean, I get the same call in the same day.

• 1:23:04Lewis Howes?

  Wow.

• 1:23:05Kevin O'Leary?

  So, you know, that's the nature of being diverse as an investor, but also to realize that outcomes are unknown. You don't control it, you have to just understand that there's some things out of your control, and you have to deal with them, and if you tell the truth, you don't have to remember what you said, but, and I also, and I, you know, we talked about it earlier, I can't make everybody happy, so I don't try. I really don't.

• 1:23:29Lewis Howes?

  Yeah.

• 1:23:30Kevin O'Leary?

  And I don't worry about it. I don't spend a single second, you know, worrying about that, because I can't do it. It's just, it's not possible. The most miserable people on earth are the ones trying to make everybody else happy.

• 1:23:42Lewis Howes?

  That's so true. That's a good line right there. I'm curious your ideas on Bitcoin, and they've been jumping the conversation more about this, and why you're not a fan of investing because it's so volatile. Have you shifted that idea, or what's your stance?

• 1:23:56Kevin O'Leary?

  No, I do, I do have an investment in Bitcoin, but I don't use it as a replacement for gold, for example, and for single, it doesn't mean I never will, but Bitcoin is not even yet a trillion dollar market cap, which in the context of financial services is really nothing. I'm not insulting Bitcoin, I think it's really interesting what's going on out there, but, you know, the gold market is a hundred trillion dollar market. If you're trying to find something that counterweights the moves in the market, what I've learned is Bitcoin is very correlated to the S and P, so it's not really useful for me as a counterweight. It goes down more when the market goes down, and I don't think we've figured that out yet, because maybe people have to sell it to cover their margin calls, I don't know. But the point is, it's not, it's very volatile, right now it's on, going to new highs because

• 1:24:40Kevin O'Leary?

  of the Elon Musk thing. Now, when you invest in Tesla, you have two risks, you have the executional risk of Tesla, and you have the risk of the price of Bitcoin. And many people, that's okay, and I have no problem with that, but... I would like to see Bitcoin at least get to thirty percent of the market cap of gold to be an alternative asset, so that I could buy... I have a lot of money invested in things that are protecting me against inflation, gold is one of them, and I take big positions. So if I'm gonna say I'm putting five percent of a portfolio into gold, I need it to be real, and I'm not saying Bitcoin isn't, but gold doesn't go down... when the market goes down, sometimes gold goes up, it's a counterweight.

• 1:25:23Kevin O'Leary?

  And it's also a hundred trillion dollars, so it's very liquid. If I need to sell a million dollars with the gold, and then another million in a minute away from now, I can do it. I don't know that about Bitcoin yet. I'm not... look, I got no problem with it. It's just, people think, "Oh, it's eight hundred billion dollars of market cap." That is nothing. That is just nothing. And so, it's gotta find its way to get to something material, and then it's gotta become more liquid, so that if I know I can buy a Tesla with it now, that's cool, but what if I wanna buy a house in Switzerland, or I need to pay my taxes in England? Like, I can't. So I gotta turn it back into the fiat currency, what a pain in the ass that is. I don't have that... even in gold, gold is now, the assay value is stamped in the serial

• 1:26:08Kevin O'Leary?

  number on the... if you own the actual physical gold, you can turn that into liquid currency anywhere in the world with practically no fee. Right. But I think there's something in, that's really interesting about cryptocurrencies. Pomp and I debate this all the time. I would love to see a cryptocurrency, maybe it will be Bitcoin, where all the regulators in England, and Europe, and Switzerland, and China, and Japan, and North America, all agree that this is the cryptocurrency. That way, let's say I have to buy, I have to adjust, you know, I'm a chairman of O'Shares, so maybe we're gonna buy a hundred million dollars worth of Swiss stocks, Nestle, Roche, or something. We have to take the hundred million, we gotta turn it into Swiss francs, if we can buy it in the local currency.

• 1:26:52Kevin O'Leary?

  We're taking the friction on that, what a total pain in the rear end. Imagine if we had a global crypto, that I could just buy anything I wanted in any country with the same currency. Now you're talking. That would be a multi-trillion dollar asset, that would be cool. I don't know why we can't do that. Maybe it's Bitcoin, maybe it's something else, but that's the real opportunity for cryptocurrency.

• 1:27:16Lewis Howes?

  This has been powerful. I got a couple of final questions I ask everyone at the end of our interviews. I'd love to ask you these final questions. First one is, of all the accomplishments you've had in your life, what's the thing you're most proud of to date that maybe people don't know about?

• 1:27:34Kevin O'Leary?

  Well, I would say, I can't really take the credit for it, because my wife really did all the heavy lifting, but you know, our kids have been successful and that takes a big burden off me. But again, it goes back to the story of the guy in the room. I found somebody that could deal with me as I disappeared for 10 years, building up my business all around the world. And she raised the family. And so when we look at our kids now, we're very proud of that, but really, that's my biggest accomplishment, providing for them, but I certainly can't take credit for raising them. That's one. And the other is, I did an exhibit of my photography work a couple of years ago here

• 1:28:14Kevin O'Leary?

  at Art Miami, and sold the work for charity. And some pieces went for very high prices. And I was able to show my father the receipts. I gave all the money to charity, but I said, "Hey, I made it as a photographer."

• 1:28:27Lewis Howes?

  That's cool.

• 1:28:28Kevin O'Leary?

  Yeah, it was cool.

• 1:28:29Lewis Howes?

  That's great. This is a question I ask. It's called the "Three Truths" question. So I'd like you to imagine for a moment a hypothetical scenario, where it's your last day on earth, many, many years from now. And for whatever reason, you've accomplished all of your dreams from here to that last day, when you know, you can live 200 years old if you want to, but eventually you've got to turn the lights off. And for whatever reason, you've got to take everything with you. All the content you've created, your books, this interview, anything you've put out into the world, you've got to take it with you. Especially your watches, you've got to take those with you as well. And you get to leave behind three things you know to be true for the world. And this is all we would have to remember you by, because there's no other written content

• 1:29:12Lewis Howes?

  or audio or video of your words. But you get a piece of paper and a pen, you can write down three lessons that you've learned that you'd like to share with the world, or what I like to say, the three truths. I'm curious, what would be yours?

• 1:29:25Kevin O'Leary?

  Well, I would go back to always tell the truth because I think by then people will know me by that. That's number one. Number two, I would say pursue something that's diagonally opposed to what you think you're going to make money doing. So if you're pursuing a career as an entrepreneur, an engineer or something, do something that has nothing to do with that discipline to balance it, which I've learned is very powerful. And for number three, I'd go back to tell the truth. I hate to say it twice, but it's the hardest thing you can do and most people can't.

• 1:30:00Lewis Howes?

  So true. And you don't have to remember your lies or what you said, which was a lie if you always tell the truth.

• 1:30:06Kevin O'Leary?

  Yeah, they blow you up. They blow you up. They will always blow you up. They will always, always, always blow you up. 100% of the time you will get caught.

• 1:30:16Lewis Howes?

  Well, Kevin, I want to acknowledge you for a moment because you have so much range to who you are as a human being. I think people see you as one thing online and see you as this tough, honest businessman who's only thinking about money, but the Renaissance man in you really inspires me and your diversity of culture and arts and creativity is inspiring for me to watch and to see that you're constantly evolving yourself, to see that you're constantly improving is amazing to watch.

• 1:30:45Kevin O'Leary?

  Well, I enjoy doing it. I mean, that's why I do it. I think it's great and I enjoy talking to friends about these journeys and all that stuff. And I just think it's, you try and find interesting work. That's the hardest thing to do is to find something that keeps your mind focused. And I think that actually keeps you young. That's really what works. Keep yourself engaged and work with people you like and the outcomes can be very good.

• 1:31:14Lewis Howes?

  Yeah. Well, I'm not a smoker or drinker and I've never done drugs and I've never been drunk in my life. My first sip of wine was with Gary Vee about 10 years ago and I haven't had a sip since because I'm just not a fan personally. But I do know Barbara and Matt Higgins and Damon pretty well. So maybe next time when you guys are all together, I'll join you for my second sip of wine if you've got a special.

• 1:31:37Kevin O'Leary?

  Yeah, well, instead of Gary, forget Gary's wine. Let's go to O'Leary's. It's much better.

• 1:31:41Lewis Howes?

  There you go. So if you've got one that you like, then maybe I'll have my second sip with you in person.

• 1:31:46Kevin O'Leary?

  Well, I just won my sixth award for my Cabernet Sauvignon and this is now the sixth time it's won. It's hard to win six times. It's spectacular if I say so myself.

• 1:31:57Lewis Howes?

  That's great. That's great. I want people to check out Beanstocks, B-E-A-N-S-T-O-X. If you're thinking about investing, if you're trying to find a way to make it painless for yourself, where you can just start putting a hundred bucks a week away, or something like that, whatever you have, check out Beanstocks. They can download it. It's free, right, to download?

• 1:32:14Kevin O'Leary?

  Yeah, absolutely. You can try it out. Check it out. I mean, we've been very transparent about how it works. But I would say the most important thing is, if you really are scared about investing, this is the most simple app you've ever seen in terms of getting you going and helping you out. It's incredibly simple to use and it works.

• 1:32:32Lewis Howes?

  So the app is free to download, is that right?

• 1:32:34Kevin O'Leary?

  Yeah, it's free to download. And it doesn't matter how much you put into it. It's a straight five dollars a month, regardless of how much you save. We tried to make it totally transparent. I don't like it when people charge fees you don't see. I just want everything above board. And the ETFs are not my personal ETFs. They're ones that I found that are great, so I can say I'm arm's length. These things are done to be the very best they can be to help people really start to invest simply. That's what it does.

• 1:33:00Lewis Howes?

  There you go. Beanstocks. Also, you're building YouTube up in a big way, so all of our YouTube viewers, make sure to check out Kevin O'Leary TV over on social media. I think it's Kevin O'Leary TV on...

• 1:33:12Kevin O'Leary?

  Yeah, it is. It's actually my Ask Mr. Wonderful channel, so I really answer a lot of questions on that. And as it's grown, I just keep getting more and more questions, and I think it's fantastic. You know, I'm basically honest on it, and I get lots of pros and cons. People say, "I can't believe you said that." I did.

• 1:33:28Lewis Howes?

  Right, right.

• 1:33:29Kevin O'Leary?

  It is what it is. I'll play a cell with a tune if you want, because I just thought of one I want to try.

• 1:33:34Lewis Howes?

  Yeah, I've got one final question, but if you want to do that first...

• 1:33:36Kevin O'Leary?

  Sure, go ahead. Let's hear the question.

• 1:33:37Lewis Howes?

  Okay. Final question is, what's your definition of greatness?

• 1:33:42Kevin O'Leary?

  Well... Again, I go back to the core anchor that we've had all day. The greatness is anybody that can actually tell the truth their whole life. Very few. Very, very few.

• 1:33:54Lewis Howes?

  There you go.

• 1:33:55Kevin O'Leary?

  Very few. Even in history, politicians and generals, great liars.

• 1:34:01Lewis Howes?

  That's true.

• 1:34:02Kevin O'Leary?

  Often dying in misery as a result of lying so much. Being strung up by their own people, or being abandoned on an island somewhere, or being defeated by others that didn't like them because they lied to them. That's right. You've become a big student of history. You go back and look at all the catastrophes. It's always the big lie that killed them.

• 1:34:20Lewis Howes?

  Hmm.

• 1:34:21Kevin O'Leary?

  That's it.

• 1:34:23Lewis Howes?

  Kevin, I appreciate it. Let's hear it on the way out. What you got?

• 1:34:26Kevin O'Leary?

  All right, just a little ditty here that I think maybe you'll recognize. I don't know.

• 1:35:00Kevin O'Leary?

  Get the idea, right? Little wings, right?

• 1:35:22Kevin O'Leary?

  Thank you, thank you, thank you.

• 1:35:24Lewis Howes?

  Yeah.

• 1:35:29Kevin O'Leary?

  All right, that was great. Take care.

• 1:35:31Lewis Howes?

  I appreciate it. Thanks so much. My friend, thank you so much for listening to this episode. If you are a consistent listener to the School of Greatness, then welcome back. And if this is your first time here and someone sent you this link, then make sure to text them or call them and share some appreciation around what you learned from this episode. And also pay it forward. Make sure to share this with a friend. You can send the link, lewishouse.com. Slash one zero seven six or copy and paste this wherever you're listening to your podcast over on Apple Podcasts, Spotify, or anywhere else and just share this link to a couple of friends because this is a free educational resource and we're here on a mission to reach 100 million people a week and we can't do this without your support. So our mission is to keep bringing you

• 1:36:13Lewis Howes?

  the biggest guests, having them share things they never share before to help you in your life right now and beyond. And all we ask is that you pay it forward and help the friends around you. So make sure to click that subscribe button right now on Apple Podcasts. If this is your first time here, leave us a review and share with us your feedback on your biggest takeaway. We share this with a lot of our fans and our internal team. So this helps us improve the quality of this show when you leave a review and share with us your feedback. Also, if you want inspirational messages sent to your phone every single week from me, then text the word podcast to six one four three five zero three nine six zero. Again, text the word podcast to six one four three five zero three nine six zero and share this message with a friend that you think will

• 1:36:56Lewis Howes?

  be inspired by Mr. Wonderful. And I want to leave you with this quote from Helen Keller, who said, "Character cannot be developed in ease and quiet. Only through experience of trial and suffering can the soul be strengthened, ambition inspired, and success achieved." And I hope you enjoyed this. I hope this resonated with you and you got some big takeaway that you can use to apply in your life today and beyond. And I want to remind you, if no one's told you lately, that you are so loved, you are so worthy, and you matter. And I'm grateful for you and your time today. And you know what time it is. It's time to go out there and do something great.