The Diary Of A CEO with Steven Bartlett - Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid!

Episode Date: June 30, 2025

Is this 1 money habit secretly keeping you poor? Shark Tank’s Kevin O’Leary reveals the brutal truth about wealth, business, and getting rich, and what you must change to build real financial free...dom.  Kevin O’Leary is a Canadian entrepreneur and investor, also known as ‘Mr Wonderful’ on Shark Tank. He is the Founder of O’Leary Financial Group, Chairman of O’Shares Investments, and bestselling author of books such as, ‘Cold Hard Truth: On Family, Kids and Money’.  He explains:  How to 10X your income without working harder.  The biggest lie about investing and what actually works.  The harsh truth about becoming rich.  The 28-rule habit that is keeping you poor.   The wealth rule that took Kevin from $100 to $100,000. 00:00 Intro 02:27 The Ice Cream Store That Changed My Life 04:56 Can Anyone Be an Entrepreneur? 07:09 What I Learned from Working with Steve Jobs 09:23 The Secret Recipe for Success from Elon Musk and Steve Jobs 13:21 The Importance of Having Balance in Your Life and Work 17:08 8 Out of 10 Businesses Will Fail 20:05 The Importance of Listening in Business 22:12 What Are the Attributes of Successful Entrepreneurs? 27:38 How to Grow a Business Aura 29:43 Hiring Women into Executive Roles 33:05 Successful Entrepreneurs from Shark Tank 35:56 No One Outcome Defines What You Are 37:32 Steve Jobs Changed My Life 41:58 The Second Most Important Step to Success 43:36 The Different Types of Leadership 46:47 How to Find Great People for Your Business 47:49 People with Balanced Lives and Diverse Interests Tend to Be More Successful 49:14 Your Personal Relationship with Money 51:53 The Power of Investing Long Term 55:52 Don’t Outspend What You Earn 56:50 Small Financial Mistakes People Make 59:34 Why Do You Wear Two Watches? 59:59 Invest in Dividend Stocks 01:01:42 Are You Bullish on Crypto? 01:04:17 Why You Shouldn’t Buy a House 01:09:21 How Much Your Relationship Impacts Your Finances 01:13:52 The Shocking Link Between Money and Divorce 01:16:40 The 5 Love Languages of Money 01:19:56 The Role of Artificial Intelligence in Your Finances 01:26:56 AI, Welfare and Wars 01:27:48 Is Apple Dying? 01:33:52 Was Steve Jobs Happy? 01:38:23 Are You Happy? 01:45:04 Turning Down Offers That Aren’t Authentic to You Follow Kevin: Instagram - https://bit.ly/4kdu3Ai  X - https://bit.ly/44kRa61  YouTube - https://bit.ly/4kfyGK5 You can purchase Kevin’s book, ‘Cold Hard Truth: On Family, Kids and Money’, here: https://bit.ly/4lryWqA  Get your hands on the Diary Of A CEO Conversation Cards here: https://bit.ly/conversationcards-mp   Get email updates: https://bit.ly/diary-of-a-ceo-yt  Follow Steven: https://g2ul0.app.link/gnGqL4IsKKb    Sponsors: Shopify - https://shopify.com/bartlett   Justworks - http://Justworks.com  Learn more about your ad choices. Visit megaphone.fm/adchoices

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Starting point is 00:00:33 thing for someone who's just trying to grow their money? So I learned this from my mother and I actually built a whole company around it. Yeah there she is. So... I haven't seen that picture in a while. I Haven't seen that picture in one Damn I mean what she did the performance was extraordinary and with that did she put my brother and I through college She took care of her family and they fell on hard times When I saw the results, I said, that's it. That's how I'm going to invest for the rest of my life. So talk me through this. I want as much detail as possible. Okay, let's start with this.
Starting point is 00:01:12 Kevin O'Leary aka Mr. Wonderful is the self-made millionaire and investor who's built and sold companies for billions. There's a lot of people don't like me for my bluntness. I don't care. Because there's people that don't think ahead and find themselves mired in debt, but then pissing away money, spending $28 for lunch. I mean, that's just stupid. What about the house?
Starting point is 00:01:32 The mistake that people make is they buy too much house. Never let the mortgage and the cost of maintaining the house be more than one third of your income. Now, how much does the person that you fall in love with have an impact? I'm kidding. It's everything. And I did some research and most marriages can survive infidelity.
Starting point is 00:01:49 They can't survive financial stress. But if everybody that's listening does this one thing, you will have over a million and a half dollars. Kevin can anybody be an entrepreneur? No, only a third of people can become successful entrepreneurs because there's a couple of things that you must achieve to be successful. First. Quick one, before we get back to this episode,
Starting point is 00:02:10 just give me 30 seconds of your time. Two things I wanted to say. The first thing is a huge thank you for listening and tuning into the show week after week. It means the world to all of us. And this really is a dream that we absolutely never had and couldn't have imagined getting to this place. But secondly, it's a dream where we feel like we're only just getting started.
Starting point is 00:02:28 And if you enjoy what we do here, please join the 24% of people that listen to this podcast regularly and follow us on this app. Here's a promise I'm going to make to you. I'm going to do everything in my power to make this show as good as I can now and into the future. We're going to deliver the guests that you want me to speak to and we're going to continue to keep doing all of the things you love about this show. Thank you. Kevin, I'm going to ask you to do something which is quite difficult because I'd find it quite hard if someone asked me to do this.
Starting point is 00:02:59 But before we get into the detail, can you give me a 30,000 foot view on your entrepreneurship and investing career? Just the three bullet points that are most pertinent before we dig into those specifics. Every entrepreneur I've ever talked to that finds himself where I am today has a defining moment where they are pushed into this path. It's something they can remember and they remember it in perpetuity. And I'll remember my moment getting fired in an ice cream store.
Starting point is 00:03:30 That simple. First day on the job, asked to serve and scoop ice cream. And I did that all day, but when people sample ice cream, they get a taster and they take their gum out and they throw it on the floor. Somebody's gotta scrape the gum off the floor at the end of the day. I only took that job because I was very interested
Starting point is 00:03:49 in a girl who was working in the shoe store and I figured I could hang out with her afterwards. And I saw her waiting for me and the woman who owned the store said, you've gotta scrape the gum off the floor. And I didn't want her to see me on my knees with a scraper. It was bad for my brand. I was in high school. And she said, no, no, you have to do it.
Starting point is 00:04:12 And I said, you hired me as a scooper, not a scraper. She said, how about you're fired? And I didn't know what that meant. And it was the defining moment for me because I realized there's two kinds of people in the world. There's people that own the store, and there's people that scrape the shit off the floor. And you have to decide who you are. And I'm not saying being an employee is a bad thing. Not at all. But for me, it hit me. It just hit me.
Starting point is 00:04:38 Kevin, there's a present for you. We give a present to all of our guests. Really? Underneath that black. Can I open it? You can open it. I just take this off? Oh, look at that. You heard the story.
Starting point is 00:04:51 That is exactly how it looked, except it was black gum. And that was exactly the tile. It was just like that Mexican tile. That's really freaking me out. So you were asked to scrape gum off a Mexican tile. Yes, just like that. In order to do that, you gotta get down on your knees and do it. And I just couldn't do it. And then you know the rest of the story.
Starting point is 00:05:12 I eventually could afford to bulldoze the whole mall if I went to. And we went back to meet her and thank her for her pushing me off the treadmill into that direction. And she was gone. There was a bodega there instead. You said there that you realize that there's kind of two people in life. There's the entrepreneurs, the person that owns the ice cream parlor and there's the person that scrapes it off the floor. That provoked a question in me, which is, do you think anybody can own the ice cream parlor? I do think anybody can be an entrepreneur. No, I've tried to teach it. and I mentor it all the time to the
Starting point is 00:05:47 CEOs that I work with. There are some attributes of people that can do this. A certain element of risk tolerance, a certain element of focus, and then the other element which I've really started to believe in late is karma. Luck. You need to be lucky. It's like Napoleon was once asked, who are your favorite generals? And he said, my favorite generals are lucky generals, my lucky generals. And I'm starting to think that in life,
Starting point is 00:06:18 particularly entrepreneurship, you look at the difference, the path of success and failure, and nobody's exposed to it more than I am in terms of how many investments I've made over the decades. I think if you want a percentage, I teach these cohorts at Harvard. I'm an executive fellow there, I'm very proud of that work. You get a class of 120 people in a room.
Starting point is 00:06:45 Two thirds of them want to become consultants. That's why they're there. And lead a life of mediocrity. And never make a decision of consequence in their lives. And after 24 months, they are tainted with that disease forever. They'll always be good consultants, but they will never achieve greatness in any way.
Starting point is 00:07:02 In life, only a third of people can become successful entrepreneurs, that's it. And the rest can be very successful employees and there's nothing wrong with that. You can have a fantastic life. You won't be shackled to the ups and downs of entrepreneurship, the challenge of it, how hard it is, but you'll never be free. And that's the debate. That's it right there.
Starting point is 00:07:24 Do you want personal freedom? It's the only path. That's it. It's the only path. It that's the debate. That's it right there. Do you want personal freedom? It's the only path. That's it. It's the only path. It is the only path. I mean, you can't, I've always said it's not about the pursuit of money. It's not about the pursuit of greed. You will fail if you do that. It's the undying love of freedom. So that one third of people that you say will be successful, they'll pursue their dreams, they'll build a business, whatever it might be. Do you think it's possible for us in this conversation
Starting point is 00:07:48 to increase the probability of their success? You said you don't think you can make someone an entrepreneur, but is there things you can do to increase their probability of success? Yes, there are a couple of things that you must achieve to be successful, and let me explain what they would be. And this is not some academic study. This is real data from real situations of real CEOs I've worked with and learned from because I used to work for guys like Steve Jobs and others in my career.
Starting point is 00:08:18 Let me give you one that I think is very important. We'll start with this one. I used to work for Steve Jobs in the early 90s, making all of his educational software. I mean, it was just, now there they are. My goodness, you guys do good research. Those are the kind of things that we did for him. You know?
Starting point is 00:08:37 Yeah, yeah, all of that. It's hard to find, those are CD-ROMs. But you know, in developing that software, we used to go quarterly. Heidi Rosen was there in the room. She's still a very famous venture capitalist. And I would say, Steve, we gotta do some market research on Oregon Trail. I mean, it's a huge title.
Starting point is 00:09:01 It's in 110,000 school buildings. We gotta do an update. It's gonna cost you 12, 15 million bucks. We've got to do an update. It's going to cost you $12 million, $15 million. We want to find out what the students want. We want to find out what the teachers want. We want to find out what the parents want. Steve would say, by the way, not a nice guy. Not a nice guy.
Starting point is 00:09:18 He would say to a room full of people, Kevin, I don't give a shit what the students want, or the parents think, or anybody thinks. It's what I want. They don't know what shit what the students want or the parents think or anybody thinks. It's what I want. They don't know what they want till I tell them what they want. And I said, Steve, you sound like such an asshole. You have no idea what that sounds like. He says, no, no. That's how it is, Kevin.
Starting point is 00:09:40 Now, are you making money with me? Am I your fastest growing OEM? Have we not been wildly successful and continue to be? I said, yes Steve, that's true. He said, then fucking shut up and do what I say. That's how he would talk to you? 100%. And here's what I learned.
Starting point is 00:10:01 Look how wildly successful he was. But here's why. There's a concept that he understood And look how wildly successful he was. But here's why. There's a concept that he understood that very few people focused on back then in the early 90s of signal to noise ratio. What was so brilliant about jobs that I tell every CEO now,
Starting point is 00:10:22 and I don't care if you're an SAP 500 CEO or you're just starting a business. His vision of Signal was the top three to five things you have to get done in the next 18 hours. Not your vision for the business next week or next month or next year, just the next 18 hours you're awake. You're going to get those three things
Starting point is 00:10:42 or those five things done that you have deemed critical for your mission. They must get done today. Anything that stops you from doing that is the noise. So the signal to noise ratio to be successful for Steve Jobs was 80-20. 80 signal, 20 noise. And I knew that to be true with him because he would email me at 2 30 in the morning Expect me to get back to him because back then we didn't have texts. It was all email
Starting point is 00:11:10 He was right he was right and the only other person that I've seen that has a higher ratio than that Is Elon Musk he has no noise. He does not deal with noise He is 100% signal 24 seconds seconds, you know, every cycle. I mean, the guy is just 60 seconds of every minute, 60 minutes of every hour. The 18 hours he's awake, it's all signal. And look what he's achieved. Now, it's very awkward for him socially,
Starting point is 00:11:39 because noise is dealing with your family sometimes, or noise is saying hi to a friend, or noise is listening to some doom scrolling on some social media app that just takes your mind, or maybe playing your guitar. But very few people on earth, if you go back in history, you're going to find out that the geniuses of their time were close to 100% signal. And so I can really sort of summarize this for my audience. Signal is the most urgent thing you should be focused on right now and noise is basically everything else. No, the goals you set for that the way that you were awake, if you're going to be awake 18 hours and you've determined that there's three things you have to get done, you're
Starting point is 00:12:18 going to get those done. No matter what it takes, you're going to get those done and you're not going to let anything distract you from the three to five things. If you're a CEO and you achieve that and you can get those done with 80% of your time based on that, you're extraordinarily successful. You are absolutely, and you're Steve Jobs or you're an Elon Musk or you're somebody. If you even talk to Bezos, I don't know him personally, but I've heard in many interviews, like I knew, you know, I've met Elon Bezos, I don't know him personally, but I've heard in many interviews, like I knew, I've met Elon just a few times,
Starting point is 00:12:47 I spend a lot of time with Jobs, but they say the same thing. Bezos will not make a decision after one o'clock in the afternoon because he felt that the noise was too high, the signal for him was in the morning hours. This is a crucial aspect of success that I now understand to be the ability of... it defines an entrepreneur. A man or woman that understands a
Starting point is 00:13:13 signal noise ratio that focuses on that, they'll be successful. The ones that can't that get down to a 50-50 signal noise, they'll fail. It's that simple. And it's a very simple concept. You know, you made one of your things today, this interview, you're going to get it done. You're going to, all these people around and everything else, this is one of the three to five things you're going to get done. I have five things today, I'm going to get them done. I'll do the same thing tomorrow and the day after that. And you have to decide how much signal you need to get those three to five things done. And for jobs, it was 80%.
Starting point is 00:13:51 What's the opposite of that? Sometimes looking at the opposite helps us to understand some things. So the opposite of having... I hire managers and CEOs that have a balance in life between the discipline, the binary aspect of business, which is I make money, I lose money, and the chaos of the arts or some other pursuit. Dance, painting, photography, collecting crystals, whatever it is that they have that balance. You need the yin and yang in your mind to make correct decisions. It doesn't mean it takes you off the signal. The signal is you've got to get stuff done. But how do you live your life? And so I spend a fair amount of my time practicing my guitar
Starting point is 00:14:29 or working with my photography or my watch. You know, tonight, very late tonight, I will meet a master watchmaker and we will deal with the design of a new piece unique he's going to make for me. And I'm going to love that moment. That's going to be something completely different to what I did all day long. And we'll start our journey together over the next two years to make this piece unique is gonna make for me, and I'm gonna love that moment. That's gonna be something completely different to what I did all day long.
Starting point is 00:14:46 And we'll start our journey together over the next two years to make this piece unique. And that's something that just takes me away from all the shit I'm gonna be dealing with today. And I also tell successful entrepreneurs, in the same day, you will get a, and this happened to me today, it happens every day. You're gonna get a call from some aspect of your,
Starting point is 00:15:06 what you call it, your empire, whatever you want, where this company's going bankrupt. It's just gonna go bankrupt, and you're gonna lose, I don't know, 10 million bucks on that deal. And that's a piece of information you're dealing with. Half an hour later, this actually happened to me today. One of my companies is going public. It's a 450X for me. The stock will get unlocked sometime in the fall.
Starting point is 00:15:34 But how do you fit that together? Utter catastrophe, destruction, woe, loss, utter euphoria, half an hour later. That's what my life is like. That's entrepreneurship, obviously on a different scale for most founders. Well, the founders deal with the same thing. They get disastrous news, they lose an account like a Costco or something if it's consumer goods or service, and they get something else. The ebb and flow is the management of expectations and your ability emotionally to navigate those
Starting point is 00:16:12 ups and downs is part of what entrepreneurship is. But it goes back to the signal. It can't take you off the signal. This is what Steve taught me. Yes it's great news. Yes it's bad news. But focus on the signal, O'Leary. Focus on the signal. That's it.
Starting point is 00:16:30 Where does this analogy come from of signal and noise? It was his genius of making it so simple. What are the three things you've got to get done today? What are they? What are they? How do you know what they are? They will make themselves apparent. They will definitely make themselves apparent. They will make themselves apparent. They will definitely make themselves apparent. They will make themselves apparent and you will realize I have to deal with that.
Starting point is 00:16:51 You may have them set up from the day before. I actually still use sticky notes on my mirror. Got to get these three things done and or five things, whatever it is, but then something else will hit. That's the skill of understanding. Is that noise hitting me or is that signal? There is the essence of the great entrepreneur, the great manager, the great leader. Is that signal or is that noise?
Starting point is 00:17:14 What is it? That's what you're looking for. You're hiring somebody that can actually distinguish signal and noise. Because it could be noise, it could be irrelevant. You have to determine. only you makes that decision. That's the key right there. This is what I teach entrepreneurs and engineers, and this is the most important thing.
Starting point is 00:17:38 It's that judgment of prioritization, but then the sort of force of execution to get it done. Can you interpret signal and noise? And can you keep the noise away from the things you've got to get done? That's one. The other, which is something that I've learned over the last five years, and this is, you might find this interesting, but most of my, particularly the nascent startups, and you're involved in the same format I am,
Starting point is 00:18:04 you're at Dragon's Den in England, I'm Shark Tank in the US. I, you know, you put up 500,000 or a million bucks into somebody's business, eight out of 10 is gonna fail, maybe six out of 10 depends, you just don't know. And I love it when people tell me, oh, I know when I make an investment it's going to work.
Starting point is 00:18:26 They are so full of shit. I'm talking about startups. They have no idea what's going to work. And you won't know for five to seven years, which is why you need diversification in the portfolio. But I would go as far to say now, you know, when I meet venture capital firms and young analysts that work there, and they think they're so damn smart, they've never operated a business, they know nothing. They have no idea what they're doing. They're going to hope that
Starting point is 00:18:54 one or two of their portfolio is going to work out in seven years and pay for all the other mistakes. But the serendipitous nature of success in entrepreneurship is brutal. It is. So does that mean though that it's, I guess, I was going to say, does that not mean that it's highly luck? Investing is highly luck, entrepreneurship must be. I said karma, you know, I call it karma, but you need executional skills. But here's another skill that I think we should talk about. When you look at at least my experience over decades of making these naïcent, these early stage investments, these A-round investments, remarkably,
Starting point is 00:19:34 and I've done them in all 11 sectors of the economy, the majority of the successes five to seven years later are companies run by women. Why is that? Why is that? And so they don't know each other, they're in different sectors, they never meet each other. Why is that? And I have come to the conclusion, two things. They set goals that they can achieve so that in the early stage of their businesses, they put growth rate targets like 15, 16%
Starting point is 00:20:04 versus men at 30% very often. Men hit their targets 65% of their businesses, they put growth rate targets like 15%, 16% versus men at 30% very often. Men hit their target 65% of the time, at least my portfolio, and women 90% plus of the time. And that keeps the team very sticky. They want to be part of it so they don't have a lot of attrition when they're small. They don't lose the head of finance, the head of marketing. That works. But they have another attribute, and this was pointed out to me by one of my female CEOs a few years ago to me. She said, you know, Kevin, you talk too much.
Starting point is 00:20:30 You talk too much. You talk two thirds, you listen one third. Why don't you try reversing the ratio? She said that to you. Yeah. Yeah. I'm very thankful, actually, because I tried it. And she's right.
Starting point is 00:20:47 If you don't talk and you listen, you become far more effective as a manager or an investor in my case by getting information that you weren't going to get by talking. And so if you go into a room, I just did this a few minutes ago before I came here. I'm involved in a litigation and we decided to attempt settlement talks, which is why I was a few minutes late. And you know, we knew we were going in there to settle and it's long-patrooted, you know, it's a long, long, long litigation. And I remembered her as we sat at the table like this. There were other people in the room, but the two, you know, were across from each other. I just looked at him, understand, for a long time. A long time. And it gets uncomfortable and no one else is talking.
Starting point is 00:21:47 You know, just looking. And maybe after 90 seconds, he blurted out something he shouldn't have said. And I knew exactly what the price was right there. That was the end of it. You learned that as a podcaster. You learned that there's actually something going on in the silence. There is something going on in silence and it's the number that he was going to settle at.
Starting point is 00:22:15 He showed his hand. So we saved ourselves two hours, you know. It's an attribute that many people can't do because they can't stand the social uncomfort of it. I have no problem with it. I could sit here and look at you for 10 minutes, it wouldn't matter to me. And I've actually found it to be a very useful piece of information. It's not just in negotiating, but to listen to employees,
Starting point is 00:22:33 listen to investors, listen to financiers, listen to alternative ideas to yours, and become more powerful from it. You're in the very business of people selling to you and pitching to you. We both sit on a similar very business of people selling to you and pitching to you. We both sit on a similar show and where people come in and pitch to us. You're seeing at times 10 to 12 pitches a day.
Starting point is 00:22:52 So you've developed this muscle over the last couple of decades now, almost this instinctive, spidey sense of when an entrepreneur will be successful, at least in the context of securing investment. What have you come to learn about the attributes of the ones that are successful? Is there anything one can take from that? In the moment when that entrepreneur comes out onto the carpet in the context of Shark
Starting point is 00:23:15 Tank or Dragon's Den even, they need the set up shot of the product with the entrepreneur and they have, in our case, a Steadicam, or a jib that comes down and shoots it. So the stage director, Eric, is his name, I've worked with him for years, says to the entrepreneurs I've never met, usually it's a team or it's a family or it's whatever, three or four, two people, whatever, hold, hold, hold, don't speak, hold, hold.
Starting point is 00:23:45 Don't mind the camera coming into your face, hold, hold. Maybe for two minutes, and I'm right there in front of them. I'm 12 feet from them, and I just look at them. Not smiling, not blinking, not frowning, just looking at them. And before they say a single word, I know if they're winners or losers. Just like that.
Starting point is 00:24:09 And why is that? Why is that? When, and I'm right probably 99% of the time, maybe I get it wrong, one out of a hundred. I doubt it though. You walk in a room, even though you've practiced, you know, in the context of Shark Tank 20 plus cameras, a billion plus dollars in the five chairs there, you've been practicing for months your pitch, but it wasn't the real deal. Here you are.
Starting point is 00:24:41 Cameras are rolling, tape is running. You know you've only got so many minutes. This is your moment. And you're on national television, a hundred plus million people will see you in syndication. It's all in your mind. It's all in your mind. It's going through your head. Can you project who you are with your eyes and the way you're standing? Can you project your confidence? Are you looking at the ground? Are you looking away from me
Starting point is 00:25:11 because you can't stand me looking at you directly without saying anything to you? Or do you push back? Or do you say, I'm gonna stake my aura, I'm gonna stake my ground here. I'm gonna show you I'm ready. See what I'm getting at? And I can feel it. I can see that they're ready to do battle. They're ready to answer. They're ready to present. They're ready, ready, ready, ready, or they're not. And I've taken
Starting point is 00:25:37 that out of the Shark Tank. I see that every day in life. I see it. So you have to learn how to project yourself in front of your peers or who you want to lead or teach or if you're a general or a preacher. That is maybe an innate something you're born with or maybe you can learn that. I don't know. I don't care. But if you don't have it, you're going to fail. And you're just, that's before a word is spoken. Before the first word is spoken. And so then what has to happen, then Eric says, go, you're on. And everybody's just sitting there looking at you.
Starting point is 00:26:23 Can you articulate your idea in 90 seconds or less? Can you, whatever props you have or whatever you're gonna say, can I get the big idea right away? The ones that had that aura generally get there. 30 seconds later, I get it. I get what they're here for. I understand their product.
Starting point is 00:26:43 Okay, that's good. Unfortunately, great ideas are a dime a dozen. I mean, there's millions of them. The next phase begins. This is after 90 seconds. Can you explain why you're the right person to execute on this idea and create a business from it? Because you know something about this space.
Starting point is 00:27:03 You worked for a competitor, you've tried three times before and failed, you've figured out what you did wrong. What is it about you or your team that can take this idea and make it happen? Now we get those two things together, you can feel the aura of the room. The isotope is sizzling because you've derisked great idea. You got an operator in, but then the third thing, this is the killer. It's the killer. I've seen it so many times in real life and shark tanks, real life it is, but you got to know your numbers.
Starting point is 00:27:37 How big is the market? How fast is it growing? What's the gross margin? I mean, I've said this a million times to people. I teach this every day. How many competitors are there? When are you going to break even? What month? If you get the first two right and you don't know your numbers, you deserve to burn in hell and I'll put you there myself. I mean,
Starting point is 00:27:51 you wasted an opportunity for an entrepreneur that did know their numbers that could have been in that spot that I could have invested in. You don't know your numbers. I take you up behind the barn and shoot you. You should have brought somebody that understands the language of business because those three together are the definition of leadership right there. I've never heard someone talk about aura in entrepreneurship quite like that. And I was just trying to, for the people listening that are either trying to figure out if they have an aura or to grow that aura, what does it look and feel like?
Starting point is 00:28:23 Is it physically, Is it shoulders back? Is it, you said it's eye contact? Or is it indescribable? And do you think you could take someone who doesn't have that aura in business and teach them it? Does business give you that aura? I think you can teach it. I certainly try and teach it to my children. I try and teach it to my students. And the best way to do it is to look at yourself in the mirror sometime. What do you look like to yourself? If you're going to go make a presentation to take down a million dollar line of credit
Starting point is 00:29:00 or something, you want to dress the part, obviously. But you're going to walk in a room with a loan officer and maybe an assistant, maybe one other, depending on the size of the deal, they'll have never met you probably, and you're going to have to project yourself in those seconds as you're walking up to shake their hands. What does that take? It takes an aura of confidence, and it's in the eyes, it's in the way you're standing, it's in how the way you're dressed.
Starting point is 00:29:26 It's not a joke to be dressed for success. It's something about presenting yourself and keeping your eyes focused on who's talking to you so that they know that you're absorbing the information, that you respect the information, that you're about to get into a narrative with them of respect, even though there may be disagreements. All of this is happening in the first 60 seconds,
Starting point is 00:29:56 and it's setting up for the rest of your life with that person. It could be who you're gonna marry, it could be who you're gonna work with, it could be your partner in business, it could be your banker, it could be anybody. It could be a you're going to marry, it could be who you're going to work with, it could be your partner in business, it could be your banker, it could be anybody. It could be a soldier that's going to give up their life for you. It's sort of, who are you? That's it.
Starting point is 00:30:14 Just closing off on the point you made about women being your most successful investments and the companies that have given you the greatest returns tend to be led by women. Does that mean that you focus on hiring women into executive roles? Yeah, I'm practically all women, particularly Asian women. I am a, you know, this whole thing about DEI and all this stuff. I've always had diversity because I only hire on merit. I don't care if what sex you are or what you call yourself or where you came from or the color of your skin or what planet you were born on.
Starting point is 00:30:46 I couldn't give a shit. Can you execute? And the way I hire people, and that's why I have such a diverse staff in my operating company, I don't hire you. I say, look, you sound good and you look great on paper, but that doesn't mean anything
Starting point is 00:31:04 if you can't work within the team. So I know you want a job and you look great on paper, but that doesn't mean anything if you can't work within the team. So I know you want a job and you want benefits and all that stuff, but I'm not gonna do that. If you wanna be part of my universe, you're gonna work for four to six months as a contractor at a much higher salary because you're not gonna get any stock options, you're not gonna get any benefits.
Starting point is 00:31:22 But I just wanna see what it's like for you to work with all of the people that we deal with every day, all the lawyers, all the bankers, all of the CEOs that we have investments in, and your coworkers, because I don't do nine to five anymore. I do project-based work. I don't care where you live. We have people working in Dubai, Abu Dhabi, England, I mean everywhere, everywhere. And we meet, we try and find an hour every week
Starting point is 00:31:51 where we can see each other, but we're just constantly communicating using modern day tools today. But, can you actually be given a mandate and execute on it? That's it, I don't care when you do it. If you have to get the financials out, let's say you're running in finance,
Starting point is 00:32:10 you gotta get them out the 15th for taxes. I don't care when you do it, but if you miss the 15th, I care. So I need to find out if those people can fit into that kind of an environment. Some of them make it, some of them don't. Sometimes we know right away after 90 days, like let's hire them, bring them in the team, let's give them the whole package.
Starting point is 00:32:27 And sometimes after a month we say, no, it's not going to work. That's it. I think more companies should do that actually. It's more like the Swiss apprentice system. They bring you into a lot. My stepfather is Swiss. I've been going to Switzerland for 50 years. So if you're a giant company like a Pfizer or Nestle, you pull them out of high school at 14. You give them a job in the afternoon. They become an apprentice. They want to learn. They want to work. They want to understand what it's like. And then you find the winners while they're still in high school. Then you give them summer jobs and then you bring them into the company.
Starting point is 00:33:03 That's where I got the idea from. The Swiss are genius that way. Because you're sort of mitigating the risk, I guess. You're taking less of a risk on this. No, but you're also finding out if their DNA is going to fit with your... I mean, I want my team to make a ton of money. I just want them to be successful. I want every person to be proud to work with the other and just, we're almost invincible. We're so damn good at what we do. You have the same thing here. You don't have people that don't work for you well.
Starting point is 00:33:30 You get rid of them. You whack them. I'm more just formal about it. Boom, you're gone. With the investments that you've made, how many investments, how many offers have you done on Shark Tank now? Probably like 800? Oh, we don't even count it anymore.
Starting point is 00:33:41 We look at the portfolio rolling over five to seven year period a Lot like a lot and I know the thing is the thing what I've learned is You get out you get an exit like Base pause from five years ago or something and a sky for a remarkable woman I was the the cat DNA cat DNA thing. I mean nobody saw that coming. I thought the thing was a joke I was so wrong. I mean, nobody saw that coming. I thought that thing was a joke. I was so wrong. I mean, that's the whole point. And she, she had the highest IRR, I think in the whole format's history. Nobody's made. She was around for 36 months and taken out
Starting point is 00:34:16 at such an extreme number and all cashed that there was an NDA sign between Sony and the pharmaceutical company. I can't even tell you what it was. It was extraordinary. It was extraordinary. It was extraordinary. Was it nine figures? Believe me, it's a tough NDA. Because I understand why they did it. They didn't buy it for the cat DNA testing. They bought it for the data. AI didn't really, wasn't emerging then. It existed, but it wasn't. With the data they have now, they can develop products for animals that are extraordinary in terms of feeds and medicines. And nobody had that much data on the 110 million cats in America because she got it all during
Starting point is 00:35:01 the pandemic. Thousands and thousands and thousands of, you know, it was never about, it was a data company. It's like my son telling me when he got his internship at Tesla, hey, dad, it's not a car company, it's a data company. Buy the stock, I said, never mind the stock, it's a joke, it's so expensive. He said, you're an idiot, it's not a car company. So I bought the stock and he was right. It became my most successful investment.
Starting point is 00:35:27 I had to keep selling it down to 5%. My cost base is zero on Tesla now. Fuck it. Yeah, but before it split and he worked there for five years. One of the personas that I have that watches the show a lot are young people, not always young but that are on the sofa thinking about being an entrepreneur. And they talk about it a lot. You know, they come up to me in the street. Two thirds will never do it.
Starting point is 00:35:49 Two thirds will never do it. You might as well do it when you have less burdensome risk like a mortgage and a family. You might as well do it in your 20s. You're going to fail the first time, maybe the second, maybe the third. You only need one success. one success. I have plenty of failures and I still have failures. I mean, it's just, you know, that one I talked about this morning, I said to the largest shareholders, I was in the car and your assistant was looking at me
Starting point is 00:36:16 in the limo, I was telling the other two shareholders, listen guys, it's a binary decision. Soon as I get out of this interview, we're gonna make a decision. This company is going bankrupt. On the bankrupt company? Yeah. And so if we want to save it, everybody's going to have to pony up X million.
Starting point is 00:36:34 And we're going to own the whole thing. We're just going to own it all. We're just going to do a cram down round it, a fraction of a cent, we're going to own the whole thing. You want to do that or you want to let it go bankrupt? You guys choose. I'm one third of it, so it's gonna have to be two against one. And I'll do whatever they want because that's how I am.
Starting point is 00:36:52 But it's, you know, you wanna get yourself in a position in life, and I think most CEOs understand this, you are going to have bad outcomes. There are going to be bad outcomes. But never put yourself in a situation where one bad outcome defines who you are. I mean, for those shareholders, they're gonna be unhappy, but then I got the call on the IPO.
Starting point is 00:37:16 Those shareholders are gonna be very happy. They're gonna make 400X. So that was one of my deals. And so it's sort of like, learn to live with the idea that you're going to fail. You're going to lose money by taking risk. Will it change relationships permanently? Maybe, but if you're respected and you're honest
Starting point is 00:37:41 and you're transparent, probably not. I think there's a lot of people don't like me for my bluntness. I don't care. I think a lot of people respect me for my bluntness. They may not like me. And you know, it's sort of, it doesn't matter because the only people that really matter to me are probably my 20th closest friends and my family. Do you think if you hadn't worked with or known Steve Jobs you would be a different
Starting point is 00:38:05 person? 100%. Steve changed my life, there's no question. I didn't like him. But I feel so bad that he didn't have to die that way. He just wouldn't go with the modern medicine at the time, is my view. Guy was a friggin' genius. He was so smart in terms of keeping on track to getting stuff done, and look what he achieved. But he was difficult. Difficult, because he wasn't always right, but he was right so much that the mistakes just didn't matter. And I thought, you know, the people that
Starting point is 00:38:52 spent enough time with him know what I'm talking about. You know, it occurred to me, because I know Wozniak too, not as well as Jobs, but they really needed each other. They really needed each other. Because Woz understood, he understood what the, let me draw an analogy here for you, I think it's a good one. Take the situation going on right now with Take the situation going on right now with Nvidia, AMD, to a certain extent Intel, maybe Broadcom, where policymakers in Washington have decided that we can't sell those chips to countries like China or Russia or whatever the list is of adversaries. That's bad policy. And here's why.
Starting point is 00:39:47 What I learned from jobs was that the computer, the chip, is the queen bee. It's the queen bee. But it has no value without the honeybees, which are the programmers around it that form a community that spend all of their energy writing code that works with the Queen Bee, which is the chip, that pushes out its influence. Because every coder that becomes familiar with that firmware, that Wo the app computer rights to that platform is
Starting point is 00:40:26 part of the honeybees Jobs understood that he said I've got to get every honeybee writing for the Mac writing for the OS of Apple It's the same with The Nvidia chip. We need to sell it to everybody, even adversaries, because within that country of Russia or China is some genius kid, you don't know who he is or she is, that's going to write the next piece of firmware or advance AI from the Queen Bee, the chip, the American
Starting point is 00:41:08 Queen Bee. The minute you shut down a market and your adversary sends their Queen Bee in, which is Huawei, we can't let that happen because I don't think the lawmakers understand what jobs understood. You create the hive with the queen in the middle. That's the chip. You convince every bee around to make the honey, which is the software and is the AI in this case.
Starting point is 00:41:37 You make it off that chip. And when you advance the chip again, everybody knows how to take that set and stay within the American chip that you're advancing. Maybe you keep the one generation behind, maybe, maybe that's the policy, but you don't ever let an adversary put their queen bee in the middle of the hive. You see what I'm saying? Of course. That is what jobs did. That was the war between Gates and jobs on the OS, on the operating system. Yeah, I was thinking about the App Store and the ecosystem.
Starting point is 00:42:08 It's the same thing. It's exactly the same thing. And so when I see this policy now, I go out of my mind. I mean, the first thing I do is get on a plane and go to Washington because AI is so important for all the investments I've made. I do not want to be putting Chinese honey into my companies at all. It's that simple. So for that person that's stewing over their ideas now, if they had just a couple of minutes with you and they asked you the question,
Starting point is 00:42:36 Kevin, I'm about to start this business. I'm about to go on this journey of trying to go from zero to something in my life. Is there anything else that I need to know as I set upon this sort of next 10 years of my life? I'm 21 years old. What are, because I think every entrepreneur has like their principles. You talked about one, which is the signal versus noise thing. Are there any other foundational principles that you think are conducive with success that you might have learned. Yeah, I mean, what I'm telling 21 year olds now is, look, go work for 24 months in a sector
Starting point is 00:43:10 you love that you're passionate about, even if they don't pay you. Go in there and be an apprentice. If you're that passionate, you're going to be able to convince some manager to go work for free in there. You're just, they're going to recognize your passion and they're going to bring you in. Do that first. Most young entrepreneurs say, nah, I don't want to work for anybody. I said, yeah, you do actually.
Starting point is 00:43:31 You do want to work for somebody. You want to just understand how all the cogs move. Just 24 months. And after that, launch. The first one will probably fail. You're going to start with your parents giving you 10,000 bucks, whatever it is, friends and family. But you will have the baseline knowledge of your industry. You will know who the participants are.
Starting point is 00:43:50 You will understand how it works. And you'll have a much higher probability of success. But the key is to launch sort of in your mid to early 20s, because you need to burn a few years failing. And that matters. On the point of how to lead people. because you need to burn a few years failing and that matters. On the point of how to lead people, when people hear about Jobs' approach, they sometimes assume that you also have to be an arsehole. And this is the conflicting thing because the world has changed since Jobs was in a leadership position.
Starting point is 00:44:20 Things have gone a little bit more soft, shall one say. Have you seen all types of leadership went out in that regard? The direct, signal-focused, kind of brash approach, but also the kind approach? I don't think kind works. I think respect works. The same number of assholes are out there being successful now as they were back in the 90s. It doesn't matter whether you're an asshole or whether people like you or not. I mean, people get so stuck on this stuff. It's the team you're building are not your friends.
Starting point is 00:45:00 They are the team you're building to execute on a mandate. Your customers come first. They are the team you're building to execute on a mandate. Your customers come first. They're more important. And then, of course, the employees and how are they respected or not. There are people that work for me I don't like. It doesn't matter. I respect them. I respect their ability to execute. And that, above all, is the most important thing. If you start getting into interpersonal relationships, you will fail because you may have to fire that person one day. People that hire family take huge risk.
Starting point is 00:45:31 Nepotism's a horrible disease. It's some of the greatest private companies on earth. Never let the kids run them. They just put them on the board and they hire professional management. That's how they keep wealth multi-generational. Think about Tetra Pak, for example. People may not know that name, but it's a massive successful company. IKEA. I mean, you know, it's sort of you have to learn those lessons. It's about respect in both directions. It's not about likeability or softness
Starting point is 00:46:05 or some social metric. It really isn't. And trying to redefine leadership that way because it's on trend, it's not gonna work. I started my first business at 12 years old and I started more businesses at 14, 15, 16, 17 and 18 and at that time what I didn't realize is that being a founder with no money meant that I also had to be the marketeer, the sales rep, the finance team, customer service and the recruiter.
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Starting point is 00:47:04 And if you're looking to get your business started, go to Shopify.com slash Bartlett and sign up for a $1 per month trial. That's Shopify.com slash Bartlett. What about finding the definition of the word company is group of people. So in terms of finding great people, is there anything that you can offer to entrepreneurs that are listening about how you've done that and what you've learned over time, the mistakes you've made with assembling
Starting point is 00:47:29 your group of people? Yeah, hiring them without testing them first. I've made that mistake. So you now test them first. Yeah, just because someone says they can execute doesn't mean they can. I mean, it's, of course, you're in an interview, you're not gonna say, I can't execute.
Starting point is 00:47:43 You know, you're looking at their past, you're saying, this looks terrific. Looks like you can fit in, but it's on a piece of paper. They haven't been road tested, they haven't been put in a situation where they have to make individual decisions that have consequence. The people you want are able to make decisions that have consequence. Good consequence, bad consequence, you don't know yet. But they have to be able to make that decision on their own without calling you up because you gave them that mandate. Maybe
Starting point is 00:48:10 you've put a set of parameters, you could spend a million bucks no more without calling me. But whatever it is, I don't want to hear from them. I just want the outcome. What about resilience and hard work? How much does that matter to you? Because I know you said they can work when, you know, as long as they get the job done. But are you trying to figure out if they are a bit of a psychopath in terms of hard work, if they're possessed obsessed? I don't find the ones that are psychopaths hard work
Starting point is 00:48:33 are actually the most successful. It's not the case. I find the ones that are eclectic people that have other pursuits that are nothing to do with the business they're in, that do crazy stuff. You know, maybe it's riding motorcycles in the desert. I don't know, you know, these are examples I'm just using because I'm living with them. And say, look, I've got to go and ride a bicycle across the desert.
Starting point is 00:49:00 Okay, how many days are you gonna be gone? I don't know, maybe three. Okay, is that anything that, is it immediate? That tells me that if you look at the year's outcome from that person, you're gonna find that they probably outperformed. You want the eclectic ones. You want the ones that are not just robots working. It's gonna be cheaper to get a robot if you want a robot. I'm gonna buy those too when they come available.
Starting point is 00:49:29 But I want people that have creative and unusual solutions that just think outside of the box. It's really interesting that way. The other thing that everybody wants to hear from you about is how to keep and grow your wealth. Because, you know, making wealth, I kind of understand through the lens of entrepreneurship, take a big bet, hopefully have an exit or, you know, draw a dividend or make profit from a company you've started.
Starting point is 00:50:00 But in terms of what you did and your relationship with your money, what is the most important things for someone to understand? Who's just trying to grow their money? Yeah, I learned this from my mother and I actually built a whole indexing company around it. When I was very young, I found out something that... So she was fiercely independent. She's one of three daughters of Lebanese descent. My Irish father, my father, my original father, biological father was Irish.
Starting point is 00:50:29 She didn't, yeah, there she is, Georgette. So I haven't seen that picture in a while. Okay. She was very independent and she never ever wanted a man to control her life so she started at an early age when she was working for her father. They paid the girls, the family all worked there. She worked in the accounting department and billing, but she got paid cash. And so she would take 20% of that cash each week. And she would put it into two asset classes, stocks that paid dividends, large cap stocks, and telco bonds.
Starting point is 00:51:50 Seven year telco bonds paid about 6.5 to 8% back then. She bought the long bonds. She had that portfolio for 55 years. She never spent any of the principal, only the dividends and the interest she put my brother and I through college. She took care of her family and her sisters when they fell on hard times. But her rule is very simple. No more than 5% in any one stock or bond of the portfolio and no more than 20% in any one sector, ever. So when a stock ran up past five, she'd sell it down.
Starting point is 00:52:27 This is not genius, this is just diversification. And when she passed, and I was the older brother and I saw the portfolio, because the lawyer said, listen, you got to come down here, you're the executor of will. I said, yeah, but my mother was middle class. He said, no, you got to come down here. She kept her account secret from both of her husbands. She wanted her own independent money. And back then you could do that.
Starting point is 00:52:56 And damn, I mean, what that portfolio did. The performance was extraordinary. It was beyond any hedge fund guy or anything, 55 years. When I saw the results, I said, that's it. That's how I'm going to invest for the rest of my life, exactly the way Georgia did. No more than 5% in any one stock ever, no matter what it is, and no more than 20% in any one sector with the exception of real estate, which is a very large part of what I have in net worth. And it's a third.
Starting point is 00:53:32 So that's broken the rule, but there's reasons for that, and I'm very happy with that portfolio. But that, if everybody that's listening to this does that, they will maintain and grow their wealth. But people bet, they make big bets. They think they're so damn right. They put half their net worth into one sector or one stock and they get wiped out. That's what happens. So would your mother pick the stocks herself or would she invest in an index fund?
Starting point is 00:54:01 She indexed. She used it. So okay. Even back then, they didn't have ETFs but they had mutual funds that said their own the only stock in this mutual fund is doesn't have any debt and pays dividends you know whatever they were very rudimentary back then they were just collections of stocks I think she had like 38 names or something like that in the portfolio but if you you looked at them, they're really
Starting point is 00:54:26 boring large cap names, but they were sectorally diverse. There wasn't 10 sectors back then. There was only, there wasn't 11, there was 10. So they didn't have real estate as a sector. So but you know, I looked at it saying, well, these are really boring. You learned a lot about money from your early upbringing, right? From your, that early context. Yeah, because what she said to me was, look, you know, I even do this today with wealthy people call me up all the time and say, look, you know, they get divorced. This very wealthy woman got divorced recently and she said, look, I'm divorcing and she was a billionaire. She was divorcing, she was more multi-billionaire. And so she said, look, I'm getting everybody's calling me up
Starting point is 00:55:12 to be my advisor, because I'm separating from my husband and it's all his guys that did all the management of our family wealth. Would you be my advisor? I said, no, I don't do that. But I can just give you some basic advice and you can hire people that stick on the mandate. And I gave her Georgette's strategy, but she, I had her do something else too. I said, let's get a piece
Starting point is 00:55:34 of paper. You're a billionaire. Let's put everything on this piece of paper on the last 90 days that you've spent on whatever the hell it is. I don't care. And let's put on no computer, no spreadsheet on this. Let's look at all the income that you've spent on, whatever the hell it is, I don't care. And let's put on, no computer, no spreadsheet, on this, let's look at all the income that you've made off your portfolio as it stands now, whether it's gold you have or land or stocks or bonds. Let's just do a gut check on do you outspend yourself? She said, why would I give a shit? I said, wouldn't you like to know
Starting point is 00:56:06 how much money you're burning, living your lifestyle the way you live it, just out of interest. Maybe you have enough for the rest of your life, but maybe you want to give some of it to your family one day or give it to charity. Wouldn't you like to know? Because one of my rules is never outspend yourself
Starting point is 00:56:20 on any 30 or 60 day cycle, ever. Just ever. Ever. I don't have any debt. So I'm very careful about that. And we went through this little thing. She freaked out. She was pissing away money. Just bleeding hundreds of thousands of dollars a week.
Starting point is 00:56:40 I mean, I don't care how rich you are, you don't want to be stupid. And I said, does that shock you? One of the things that has to happen, I mean, you're losing millions of dollars a quarter. Like, why? Why? Like you've had nobody restrict what you do with your money
Starting point is 00:56:59 because you're going to have to sell stocks at some point or sell gold or sell land to keep this up. And are you really that happy? Like, what's all this shit you're going to have to sell stocks at some point or sell gold or sell land to keep this up. And are you really that happy? What's all this shit you're buying? What is all this crap that you don't need? It was an eye-opener for her. So my point is most people don't do that exercise. I don't care if you're only making $56,000 a year or $68,000 the average salary. So are you in the camp that you shouldn't spend money on the small things like the coffee if you don't need it, you should make the coffee at home? Is that kind of- I just, I can't stand it when I see kids that are making 70 grand a year spending $28 for
Starting point is 00:57:33 lunch. I mean, that's just stupid. It's just, think about that in the context of that being put into an index and making eight to 10% a year for the next 50 years. What's an index for someone that doesn't? So okay, I mean, you know, I even have it, I even built an app for this purpose just so I could, there's many apps out there, you don't have to use mine. Mine's called Bean Stocks, but you just allocate 15% of your salary and it automatically puts
Starting point is 00:57:59 it into two buckets, some stocks and some bonds. The stocks are ETFs, exchange traded funds that just track the S&P 500. Very simply. Mine's a little- The S&P 500 is the top 500 stocks. Yeah, so it's just, you know, people tell me, oh, I can beat the S&P, I can pick stocks.
Starting point is 00:58:14 They're so full of crap. Not over the long period they can. So it's better you might as well just own ETFs. I have a version of the S&P that I designed with other people that strips out all the crappy balance sheets, But that's just me. You can just buy the index that you want, the ETF. And then you pay low fees,
Starting point is 00:58:30 and then over time it appreciates. And then if you buy some treasury bills or fixed income, you get that. You should have less of those when you're young and more of them when you're older, just diversification. But the best test I do with my kids' friends too, go into a closet, go into your closet,
Starting point is 00:58:47 and look at how much shit you have you don't wear. Because you either bought it because you thought you were gonna wear it, and never wore it or wore it once, and you end up wearing 20% of your portfolio all of the time and 80% you pissed away. I mean, that's really stupid. And so for a young person, a young woman or man,
Starting point is 00:59:08 don't do that. Start putting, just buy the minimum stuff. And another thing I learned from my mother, this is interesting, because I saw it happen at her death, she would buy two Chanel jackets a year, really expensive Chanel jackets, handmade Chanel jackets. I do business with Chanel because of the legacy of my mother and the whole Coco Chanel thing in watches.
Starting point is 00:59:33 I love those guys. And her theory was this will never get old. And it never did. A classic vintage Chanel jacket from the 50s that's well kept is worth a fortune today. The classic. It still wears beautifully. They're so well made. So she wouldn't buy crap. She'd buy really good stuff, but a little just small amounts of it. And over the years, she built up this portfolio of amazing clothing. And when she died, the
Starting point is 00:59:59 women in our family had a cat fight over her portfolio. Unbelievable. Is that in part why you have so many watches? I've noticed you have a watch on either wrist right now. Yeah, I'm pretty big in watches. I mean, but watches to me, every piece I have marks something in my life that was important. A deal, a child, graduation,
Starting point is 01:00:22 you know, something, every piece. I've got a lot of watches. How many have you got? I don't even say anymore because of the insurance policy I have. I got a lot. Do you invest in, you're talking about your mother's investing strategy and one of the things you said is she invested in dividend stocks. Yes.
Starting point is 01:00:37 What is a dividend stock and should I be investing in dividend stocks? Yeah, I mean, you know, a company if it's profitable and it's operating, its business plan is working and it's growing market share, at some point says, I'm going to distribute some of the success of our profits to our shareholders. That's a dividend. And so they send that cash to you and you can either redeploy it in other ways or live off it or whatever. Many tech stocks until recently did not pay dividends, but now the behemoth tech stocks
Starting point is 01:01:03 do pay dividends because the demand of an aging population is I need to eat. And so I like to own the stock for growth, but I also want to get some of the profits. And so dividend paying stocks used to be utilities, but not so today. Every sector has dividend paying stocks. So I prefer to own dividend paying stocks, div payers. And then I also own fixed income products.
Starting point is 01:01:23 I also own crypto now and I own alternative assets like gold and watches. My watch collection has actually done quite well, even though it's been a correction. There's volatility, but I have some watches that have, you know, I bought for 200,000 worth over a million today. Crypto. So are you still bullish on crypto as an investment? I am actually, but people get crypto confused with its real potential. Let's talk about digital payment systems because what's about to pass first
Starting point is 01:01:54 where are days away from this happening is the Genius Act, which is actually the Stablecoin Act. It was just passed by the Senate 48 hours ago. It's going back to the house. I actually worked on that bill two years ago. So if that bill passes, it's really nothing to do with speculating on crypto. It's a new form of payment. So if I wanted to order a watch from Simon Britt, who's somebody I buy watches from, he's a master watchmaker. Right now, I have to take US dollars, I've got to get through a know
Starting point is 01:02:19 your client prerogative. I'm treated like a criminal by transferring $100,000 over, turn it into Swiss francs, takes about a week, I get screwed for about 200 basis points and the whole thing. If he accepted USDC, which is actually a stablecoin backed by the US dollar, just went public, very successful IPO, I was a shareholder in that company too, that's one of my best IPOs in the last two years, the transaction would happen in less than a second. And the fees would be a hundredth of what the costs are right now. So it's a digital payment system. The price doesn't, it's not, there's no speculation on it.
Starting point is 01:02:55 It's backed by the US dollar, treasury bills. So it's sort of a new form of digital payment. That's different than Bitcoin, which is a speculation. It's, if you believe in Bitcoin, you think it's a digital gold and you live through the volatility. I believe in both. I believe that crypto will be the 12th sector of the S&P
Starting point is 01:03:19 in some period of time, because it provides productivity to all 11 other sectors. So the way I own it is I own the exchanges. My exchange in one called WunderFi up in Canada just got acquired last week or two weeks ago by Robinhood. I'm happy because I think Vlad who runs Robinhood is great. And now he's got a million plus accounts in Canada and a market that he'd never participated in.
Starting point is 01:03:42 But the point is this is never going away. It's going to stay forever. So how do you participate? You can buy some Bitcoin, just like you can buy gold, buy it in ETF or actually own it yourself. You can buy the exchanges. You can use, you know, you can buy Circle stock now it's public. You can Circle makes USDC.
Starting point is 01:04:01 You can buy USDC in an account and make 4.1% interest on it right now. So there's a lot of ways to participate. But yes, I'm here to stay. But I've grown up, I was around during the period where the crypto cowboys lived. And I survived that all. And I even testified in front of the Senate and the House and whatever else the testimonies were during the tumultuous period. And most of those guys went to jail.
Starting point is 01:04:23 Your portfolio in terms of Bitcoin allocation or crypto allocation, what is it now? It's at about all in. We marked to market last month, it was 19.1%. 19.1%. I have to keep it under 20, it's a sector. But remember, in that is the cryptos itself, the Bitcoin, the USDC, and the shares of the infrastructure companies, like Circle and everything else. It was a very successful IPO.
Starting point is 01:04:47 One of the first things most people do when they get a bit of money, usually from their job, is they get a mortgage on a house. Because we're kind of taught as we grow up that the best way to make, or maybe the best, but the most obvious way to create wealth is to buy your first home. Yeah, there's a very basic rule for that. And I understand it and I did the same thing. But what I made sure again from my mother was never let the mortgage and the cost of maintaining the house be more than one third of your income. One third of your income. If it's more than one-third, you bought too much
Starting point is 01:05:25 house. So it's better to buy a house that's maybe it's only gonna be 1900 square feet to start in a neighborhood that you may not want to stay it for the rest of your life, but start to accrue the benefit of real estate from that point of view. Learn how to manage it, maybe you rent part of it out or whatever, but it can't be more than a third of your income. The mistake that people made and they're starting to suffer from it now is when money was so cheap, mortgage rates were under 4%, there were 3.2%, some of them,
Starting point is 01:05:51 they bought massive houses. And now they're running into having to refinance those houses at much higher rates, more than 7%, and it's becoming 60, 70, 80% of their income. They're screwed. They bought too much house. So it's about making sure that you can manage that. And also you want some diversification.
Starting point is 01:06:09 Yes, a mortgage is okay, particularly if you're having a family, because you're gonna pay rent or you're gonna pay a mortgage, one of the two. But you want some diversification and just starting to build up that investment account for when you retire, so that you have something to live off. If you only put aside 15% if you're making 70,000 a year and you put 15% aside from when
Starting point is 01:06:31 you're 25, you'll have over a million and a half dollars if you just invested it in the stock index in the S&P 500. That's what history has told you. In what time frame? Your whole career. I mean, you're going to be 65. You're 25, 65. You just stick with that protocol and you'll watch it grow.
Starting point is 01:06:49 You'll watch it grow. You go up and down as the market goes up and down. Some years it'll go flat, whatever. But it's the people that don't even think ahead and find themselves at 45 mired in debt, including a mortgage. You want to get rid of your mortgage in your 40s. Most people's primary investment asset is the house they buy. Is that smart? Yes it is, but it's also the debt they own.
Starting point is 01:07:08 It's a primary asset. How much debt does it have on it? It's only the equity value is the asset. So if you're buying a house that's too big and you've only put down 10% and it's 90% mortgage, what do you really own? You really own the 10% at whatever price it is. Sometimes housing goes flat for a while. It's okay, but it's not okay if it's too much house.
Starting point is 01:07:33 If you're a 25 year old and you're on that 70k that you talked about, and your objective was to make money, you don't have kids, you're not in a relationship, would you buy a house? No. No, I wouldn't because why do I need a house if I'm only, unless I'm renting as an income property. I'm buying a house because I'm getting married, I'm going to raise a family, I need a house. Is that the use case for buying a house you think? I think it is. But there are many people that say, I love real estate, I'm going to buy three houses, I'm going to rent them out. That's a different business. And I know people
Starting point is 01:08:03 in their 20s that do that. In fact, they them out. That's a different business. And I know people in their 20s that do that. In fact, they're successful. That's all they do. And so their job is to find houses, buy them, fix them up, rent them. And they manage that geographically tight portfolio. It happens a lot in student housing, for example. I've got a good friend who's involved in student housing.
Starting point is 01:08:19 He's very successful. He just focuses on one aspect, buildings that rent to students, and he manages it. And he, you know, raises a family, he's successful, but that's one thing he does. That's not the same as saying I'm going to buy a house because I just got married and I'm going to raise, I'm going to have a child in the next 24 months. Then you should have a house. But if you said to me, I'm single, I want to make money, I wouldn't buy a house. That's not the number one asset class, I think. I'd get a diversified portfolio and just ride the pony with that for a while until I meet that special person
Starting point is 01:08:48 I'm going to raise a family with, and then I have a little nest egg I can work with. Wealth creation comes down to one word, discipline. That's it. The ability to look at something and say, I'm not going to buy that. I'm going to keep that money working for me. Not many people have that discipline. Wealthy people have that discipline. You meet them later in life, you realize when they were young and had nothing, even the ones that were employees their whole lives that are now financially free had the discipline to say no. There's so much stuff you don't need and you should never buy a watch unless you can afford it. Ever.
Starting point is 01:09:33 Go on debt for a watch because people hear this stuff say I'm going to buy watches like Leary's Red Bands. No, you're not. That's why I wear watches now that cost under $500 to show kids you want to get into horology, you don't have to spend $50,000. Here's a Timex for $265. It looks beautiful. Get that. You said don't buy the house until you meet your partner, etc. How much does the person that you fall in love with have an impact on your finances, your money, your chance
Starting point is 01:10:00 of success in your view? It's everything. Are you kidding? I mean, it's everything. If you read, I mean, think about this. You need to find somebody, if you're an entrepreneur, so that's for the, we're talking about the third now that want to go on the rocket ship ride. You better find somebody that's willing to tolerate the fact that you're never home for the first 10 years. They're going to raise a family by themselves because there's no balance in life.
Starting point is 01:10:25 That idea of balance is complete bullshit. I mean, it's just bullshit. You have to work so hard to compete globally these days in every sector. You're going to work your ass off. And it's not going to happen over, I mean, Anna Sky did it in three years, but she had worked much harder previously. It was not her first deal, but she was just lucky. I mean she was this the cat thing. I mean she's working again. She's back.
Starting point is 01:10:50 She wants to work. I mean that's what happens. You never stop working. But the thing is that partnership and this is what people don't get about marriage. Marriage is a business. I know people go nuts when I say that, but it's a business. And the first child you're going to have is money. It's going to be the first child, and it's going to sit at the table with you every day. It's there, sitting there. If you don't have money, you don't have a marriage. The reason people get married is to form a form of financial stability so that they can afford a family.
Starting point is 01:11:27 And you have to figure out, you know, I've been with my wife a long time, and we've been separated for a couple of years, but, you know, family's very important to me. So we got back together again, and, you know, our daughter got us back together, and we're very happy we did it. But it's, we make financial decisions together. We always check in. You know, anything that's material, you know, if we're going to do a renovation or something, and I respect her for that. I have a lot of respect for her because she doesn't just spend money. We didn't have any money when we started. We had nothing. And so that's why a great marriage can work
Starting point is 01:12:02 because you build it together. You really care about it. You care about your family, you also care about what you've created in wealth. And I consider my money her money, because she was the family that let me go and do this stuff. Now I don't have the same relationship with our kids that she does, because she raised them. But that's the thing, you give up, and you have to give something up, that's it.
Starting point is 01:12:21 You can be a great father, a great provider, but you're never gonna have the closest that she had reading them stories when they were young. I wasn't there. But you know, the outcome has been good. I think everybody looks at that and says, all right, that's great. But my mother never believed in entitlement. And so I don't believe in it either. I'm not gifting my kids a ton of money. You know, I want them to launch and they've done that successfully. They got to work. You know, they got to do their thing.
Starting point is 01:12:47 I've heard you say before that the most important financial decision you'll ever make is who you'll marry. Yes. Why? Because think of the geometric loss of wealth. Every time you get divorced, you pay the woman that you divorced or man and you pay the government a Third often through capital gains and liquidation because you can't separate all the assets without liquidating them Sometimes so you've got the government sitting there. You've got the other spouse sitting there
Starting point is 01:13:19 This is the stupidest thing you can ever do it took took your whole life to actually create this nest egg. Could be you're 45 or whatever, you've got a comfortable life and all of a sudden you don't like your wife or husband. Think about that for a while because you are going to wipe out up to two-thirds of your wealth. You better really like somebody else a lot. And frankly, sometimes it's not the other person that you're divorcing. It's you. really like somebody else a lot and frankly Sometimes it's not the other person that you're divorcing. It's you You're the problem if you're getting married for the third time. You're a guy or a woman. It's not them It's you there's something wrong with you, and you should probably not get into another economic union You should probably just date till you drop dead because it's stupid
Starting point is 01:14:04 get into another economic union. You should probably just date till you drop dead because it's stupid. Marriages are tough. I mean, they're tough. Anybody who's been married for more than 20 years knows exactly what I'm talking about. But they have, they accrue more benefit than, than, you know, anything. So if, as long as, if you're happy 51% of the day with your wife, stay with him or her husband or wife. That's very important. How often do you think divorces are a result of money issues? Well you may be shocked at this. I wrote a book about this and I decided, Men, Women and Money, a long time ago, ten years plus, right, there it is. And I did some research and I went to meet some of the top divorce lawyers in North America, in New York, in
Starting point is 01:14:48 Boston, and other cities. And I said, look, I want to kind of do a pie chart of the reasons for divorce that 50% seem to end a divorce within five to seven years. Every one of them, they didn't know each other, said, it's not infidelity. Nothing to do with it. Most marriages can survive infidelity. They can't survive financial stress. And so what happens invariably is you fall in love,
Starting point is 01:15:15 but you didn't do any due diligence on that person's spending habits or their financial history. Because l'amore is so wonderful in the early days. You didn't do any diligence on their family or them or their brother or bankruptcy in the past or whatever it is. And then you get married and you know the euphoria starts to wear off and you notice that the other is outspending you. Just buying a lot of stuff beyond your means.
Starting point is 01:15:49 And that starts the first friction. And then that credit card comes in with $100,000 on it at 23% interest and another purse was bought or whatever the hell it is. And you're starting to sink because you may have married somebody who can't stop spending. This is just a typical... There are people that can't have no discipline. They just can't. They got to have the boat.
Starting point is 01:16:17 They got to have this. They got to have that. And they pressure their other to say, look, I want to keep up with the Joneses next door, even though they may only each have a salary of 100 grand each. You can't do it. And they have kids and they're trying to put them through college. That's divorce. That's why almost 90% of unions break up is that classic financial pressure. And divorce gets them out of that mess because they can no longer spend on your credit
Starting point is 01:16:45 card anymore but it's a horrible way to go. So I'm an investor in a company called Hello prenup that does prenups for women and prenups force during the euphoric period diligence. It's that simple. You're going to find out if that person has a financial problem going into the marriage. They have to disclose their financial background. So you talk about these five love languages of money. The mooch, someone who won't pay for anything. Right.
Starting point is 01:17:17 Should I date someone like that? It's a warning signal. It's a problem. It's a problem signal. Or they don't really want you for companionship. They just want you for financial support. The Spendaholic, someone who always offers to pay for everything to appear popular and successful.
Starting point is 01:17:32 Bad. Morningside. Huge. I mean, that is insecurity measurable by cash outlay. The Loafer, someone who has no ambition and drive for money. A void with extreme prejudice. The thief, someone who steals. Can have no tolerance for that.
Starting point is 01:17:51 And the meanie, a balance spender who lives within their means. Love that. Marry a meanie. That's it. Those are the marriages that last an entire life. That's it. That's what you're looking for. That's great advice right there. Whatever the book costs, that's the best value right there. And then ask yourself, am I dating one of these or not? You should talk about money on the third date. Think about a date. Think about dating.
Starting point is 01:18:19 First date, oh my goodness, this is a really interesting person. Or not, then there's never a second date. Second date, I want to learn more. I'm really interested. You're going into a third date, there's something going on. There's something going on. You both want to meet again.
Starting point is 01:18:34 That's the first time you should say, look, I know this is crazy, but we're here together a third time because something's going on here. And I'm just wondering, what are your long-term goals? I mean, it's not about our marriage or anything else other than we're having together a third time because something's going on here. And I'm just wondering, what are your long-term goals? I mean, it's not about our marriage or anything else, other than we're having a great time, but what are your ambitions? I'm really interested in you. I'd like to know what you think.
Starting point is 01:18:54 Maybe the woman says, or the guy says, what are you, checking me out? You say, yeah, yeah, I'm really interested in you. It's a form of finding out if the connection, you know, I should be a marriage counselor. That's what I think. I mean, it's really dating is the dance, but it should involve exploring where we're going financially. I've built companies from scratch and backed many more. And there's a blind spot that I keep seeing
Starting point is 01:19:22 in early stage founders. They spend very little time thinking about HR. And it's not because they're reckless or they don't care. It's because they're obsessed with building their companies and I can't fault them for that. At that stage, you're thinking about the product, how to attract new customers, how to grow your team, really how to survive. And HR slips down the list because it doesn't feel urgent,
Starting point is 01:19:42 but sooner or later it is. And when things get messy, tools like our sponsor today Justworks go from being a nice to have to being a necessity. Something goes sideways and you find yourself having conversations you did not see coming. This is when you learn that HR really is the infrastructure of your company and without it things wobble and Justworks stops you learning this the hard way. It takes care of the stuff that would otherwise drain your energy and your time automating payroll, health insurance benefits, and it gives your team human support at any hour. It grows with your small business from startup through to growth,
Starting point is 01:20:14 even when you start hiring team members abroad. So if you want HR support that's there through the exciting times and the challenging times, head to JustWorks.com now. That's JustWorks.com. One of the bigger protagonists in the story of many things we've discussed, money, investing, building businesses now is this thing called artificial intelligence, which you mentioned earlier. Yes. It's like entered the room.
Starting point is 01:20:35 Yes. And it's changing lots of these equations in a really profound way. Again, for that person who is maybe at the start of their career, or even, you know, they're a lawyer right now. How are you thinking about AI? What should they be thinking about?
Starting point is 01:20:48 Because I don't think we've seen something quite like this, certainly not in my lifetime. I've not seen disruption of this scale. I wasn't around for the Doc-Con boom. I was too young, I was 10 or something. I was eight. Yeah. So how should we be thinking about this moment?
Starting point is 01:20:59 Is it a huge opportunity for wealth creation or? Yeah, it's immense. It's bigger than the internet. I'll tell you why. I want to keep it down to earth because I'm actually using it now in use cases. There's every sector of the economy, every aspect of research, every aspect of business has a huge opportunity here, but let's just take use cases that you would understand, everybody listening would understand.
Starting point is 01:21:22 In today's post pandemic world, most businesses have developed large and small direct-to-consumer strategies where they try and build relationships with customers and sell them product direct. Yeah, they still use retail. Say you're Nike or something, and you were 27% direct-to-consumer before the pandemic, you're now 50%. And direct-to-consumer gets you higher margins, but also gets you data, gets you consumer before the pandemic, you're now 50%. And direct to consumer gets you higher margins, but also gets you data. Gets you information about the preferences of your customer base. What they like, what they don't like, the flavors,
Starting point is 01:21:52 and what they buy, when they buy, where they buy it, all that stuff. And it's very interesting, that data. And let me give you an example, wine business. If you think about the wine business, the challenge of a thousand-year-old business, you don't know what the weather's going to be like. You don't know what varietals to grow, because you don't know what the preference of the customer is, because you're selling it through multiple tiers of distribution. During the pandemic, 43 states in America opened up direct
Starting point is 01:22:21 to consumer sales from the wineries in the West Coast. For the first time ever, the wineries found out what people buy, where they buy it, when they buy it, what they drink, what varietals. And I'm in the wine business. I sell three million bottles a year of wine. One of my companies, actually a Shark Tank company, and we partner with a company called QVC. We sell online and so I can tell you today This month this week the number one varietal in southern, Florida for women ages 44 to 64
Starting point is 01:22:57 Is Moscato a sweet wine. I think it tastes like shit. I don't care what I think It's the number one wine right now, and I knew that so to make that varietal available six months ago so that I would be able to ship it and put the inventory, the capex, in the right place at the right time to support that demand for the rest of this summer. A sweet, cold, Moscato wine. That means I spent a lot less money, a lot less risk. I don't have any varietals they don't want this summer. I have exactly what they want.
Starting point is 01:23:25 That was AI. It cost me virtually nothing to get that data. Five, 10 years ago, it would have cost me a million bucks to go do all the market research. I got that for $18,000. So that's using an AI tool. Here's another example. So do I use that tool?
Starting point is 01:23:43 100%. And there's many tools. You don't have to just use chat. There's another example. So do I use that tool? 100%. And there's many tools. You don't have to just use chat. There's many different competing platforms. So we use them all. We check the assumptions by checking it all on all of them. See the little variances. Number two, I have to shoot an ad. I have to shoot a commercial. I'm gonna shoot it here in LA. I'm gonna do it in a studio like this with a green screen and I'm gonna spend, you know, $250,000 for a 30 you know 15, a 30 and a 60 out of the same shoot. And I'm then gonna go into post with the green screen and I'm gonna
Starting point is 01:24:16 spend more money in post I'm gonna add whatever I need whatever background I'm gonna need. Or I could fly to Dubai where they have a giant studio with a 6K digital wall where AI links up your script to the background. There is no post-production. You basically shoot the commercial in four hours and it's done. The background's perfect, the imagery's perfect, your script is perfect. commercial in four hours and it's done. The background's perfect. The imagery is perfect.
Starting point is 01:24:49 Your script is perfect. And I did that two weeks ago for the first time. I'd never seen that before. We did it for a fraction of the cost of what it would have cost to do it in the old way in post-production. But then I'll tell you what freaked me out. They reshot the commercial without me there using Kevin Agent. An AI view.
Starting point is 01:25:11 I wasn't even there. And just to show that they could produce a new commercial with the same background for $9,000, that would have cost $400,000 from scratch. So there's gonna be a lot of job disruption then, because as you said that- You don't say. But on the other hand, I've now got content
Starting point is 01:25:33 for that particular business I was shooting, you know, I've got content for that particular business I was gonna shoot that commercial for, and I said, guys, let's tweak it and shoot it again. He said, yeah, we'll do it in two seconds. We'll send you the 15 seconds back. I said, I don't like what I said there. Can I change what I said?
Starting point is 01:25:51 He said, yeah, well, do you want it in Spanish? You want it in Japanese? You want it in Arabic? That's the power, the productivity that we're gonna get. Our budgets for producing content are going to drop dramatically over the next few years. And software and everything else, right? Creating everything is going to get... Now full circle to your thing about the chips, that all came from Nvidia chips.
Starting point is 01:26:14 That's not from Chinese chips. Whoever controls the chip and the honey bees, the honey bees are, those guys are all Indians and Pakistanis, they're genius mathematicians. That's the team over there running off that platform. If we had let, anyways, I don't want to, I'm just freaked out that we got to control that. We need democracy to control that. Your children, what are you saying to them though about their professional ambitions in a world
Starting point is 01:26:37 where creating stuff like that and, you know, whether it's who do you want to do your taxes, an accountant or an AI, who do you want to do your legal documents, who do you want to do your taxes, an accountant or an AI, who do you want to do your legal documents, who do you want to do your any sort of like white-collar job, your make your videos, edit your videos. I tell them, you know, everybody's got a lot of angst about AI. I tell them listen, everybody chillax, it's a tool. You know, it's the same classic thing where radio was going to be displaced by television.
Starting point is 01:27:06 Radio is bigger than it ever has been. It just doesn't matter. The one thing I concern myself with AI is warfare. I think the country that has the best AI and data centers and the most advanced chip technology will win the wars of the future, which will be fought by drones and robots. I know that sounds kind of crazy. No, it doesn't sound crazy. That's where it's happening now.
Starting point is 01:27:28 That's where it's going to go. So when I solicit the ear of a senator, I try and explain to them my honeybee analogy saying this is about defense. I don't want to live under authoritarian, you know, I know we debate the whole political environment these days, but I don't want to live around Chinese honey. I just don't. And those are going to be the two superpowers. You both you're in one vertical. Either you let the Chinese make the honey on AI, or we make the honey and let the Chinese buy some honey from us. I
Starting point is 01:28:01 know where I want to live. I know what I want to do. And I think I can convince a lot of senators the same idea because you've got to understand the Wozniak Jobs analogy that you brought out earlier. That was the genius of jobs. Make the honey, but know who the Queen Bee is. The genius of jobs brings me to a question I've wanted to ask someone like you for a long, long time, which is, do you think Apple is dead? No. You don't? No, I'll tell you why think Apple is dead? No. You don't? No, I'll tell you why, I'll tell you why.
Starting point is 01:28:27 You know, it's so interesting. People don't understand the genius of Apple because this is again, came from Jobs. He used to say to my team over and over again, and I mentioned earlier, they don't know what they want until I tell them. And I always, just as close as you and I are right now, you're Steve. I say, Steve, how the fuck do you know that?
Starting point is 01:28:53 How do you know that? You don't know that. You don't know what you don't know. He said, show me where I'm wrong. Show me one instance of us working together, I'm wrong. I said, it hasn't happened yet, Steve. Doesn't mean it won't. Get back to work.
Starting point is 01:29:10 Don't worry about it. I'll worry about it. You make the software. I have the chips. Make the software. Go make the honey. I have the queen bee. Don't worry about it.
Starting point is 01:29:20 And that is pretty interesting because you got to prove it that he was wrong. Let's accelerate. He's dead now. But the philosophy of Apple, and I'll give you the way you win at it, you look at it. I can go buy a $330 laptop right here with the same processing power of this $1,800 Mac laptop. Why would I spend $1,800 when I could buy this for $300? Why? Brand. I want to be part of this universe.
Starting point is 01:30:01 This honey right over here. The AppleCare, the fact that the OS works on all the platforms and the messages are shown on all platforms simultaneously. All the OS, all the honey. That platform is the power of brand. It's, I'm not leaving this universe. And Apple is one of the world's largest companies.
Starting point is 01:30:25 And you may say, oh, an innovation is gonna make everybody leave that platform. I don't think so. They let other people sometimes bring in a new market and then they take it over. And I saw Steve do that multiple times. He did it with the phone. I was around for that.
Starting point is 01:30:40 That was crazy. I mean, he had the vision that we would someday run our software on the phone. I said, he had the vision that we would someday run our software on the phone. I said, you're out of your mind. The screen's too small. He said, no. You're gonna go vertical.
Starting point is 01:30:52 You're gonna rewrite all this crap vertically. I mean, I can't fault him on anything, although I kept telling him, you're gonna get it wrong one day. You're not gonna be right all the time. I can't find when he wasn't right. That's the frustration because I teach this to a bunch of really smart kids at Harvard, of which by the way, a third are international students. And they say, well, when did you catch him?
Starting point is 01:31:19 What was he doing? Did he ever practice or principles that allowed him to see around the corner? He spent a lot of time at night, you know, even studying fonts and looking at art and focusing on the signal. I think his wife talked about that a lot. She spent more time with him than anybody else, although Woz talks about it a lot because those guys spent countless hours together. Jobs defined, he would take instances from nature
Starting point is 01:32:02 into his head or from Japanese, you know, scripture or text or imagery and redefine it into technology in a way that no one else was doing. And that's the idea of the honey and the bee and the queen and all that stuff. It kind of comes from his view of the world. And I don't know if you can understand this, but because it was so, it came from
Starting point is 01:32:27 nature, it was easy for people to assimilate it. It wasn't foreign. When they looked at the imagery and the design, he tried to pull from pleasing images from nature, like the fonts on the first Max. I remember when we were writing the code for that saying, Steve, this is not what people are used to seeing on a computer screen. He said, no it isn't. That's what's gonna work. If you think about the very first scalable fonts, I saw that first and I said, see this is this is almost foreign. He said, well how does it make you feel? I said, makes me feel pretty good. This looks like it's on a piece of paper. I don't. You weren't even born when this
Starting point is 01:33:07 stuff was happening. But he was so far ahead. And this is the same way Elon is redefining whether it's SpaceX or whether it's what he's doing in neurosurgery or Tesla or you know all of these initiatives you know his satellite technologies they are the same those guys except you know Elon's 100% signal I said that earlier they are the same and they should be their treasures their national treasures it doesn't matter if you like them it doesn't matter what their politics are it's irrelevant the contributions they're making to society and to America, frankly, and the competitive nature of countries. That's why I thought it was so important that Trump make up with Elon.
Starting point is 01:33:52 The most powerful man on earth should have a very good relationship with the richest man on earth because he's the largest industrialist on earth. Maybe there's an inherent inability by way of them being who you just said they are. The most powerful man on earth. But they know. They're smart enough to know. It's the same way I felt about Jobs. I'm getting back on the plane this quarter. I know he's going to beat me up, but it doesn't matter. It's the greater good is that we get the software out there, advanced math and reading scores. Was he happy, Steve?
Starting point is 01:34:24 I don't know the answer to that question. Do you think he was a happy person? I don't know. I never saw him happy. He was always barking at me. I never saw him happy. I don't think I ever saw him laugh. He may not have been.
Starting point is 01:34:37 I mean, that's probably something his wife would know, but he looked like a tortured guy to me. But that may have been his curse. His wife would know, but he looked like a tortured guy to me. But, um... You know, that may have been his curse. You know, some... Do you love him? Yeah. I can see it in your face.
Starting point is 01:34:56 100%. I saw a lot of emotion in your face the first time you spoke about him, and I thought that's surprising for someone that barked at you. Well, he respected me, that's for sure. He wouldn't execute on my ideas. He expected me to execute on his, but he was never wrong. Where did the emotion stem from? You know, it brings me back into that room with Heidi Rosen
Starting point is 01:35:17 and all the crazy crap. I mean, it was just nuts. And you know, I'd have to spend a lot of time. The only meeting I really remember, the one that really sticks in my mind, when we were in Cupertino and we were just, I think, I don't know, we were going after him for 18 million or something and Heidi was there.
Starting point is 01:35:38 Who's Heidi? Heidi Rosen, she's a famous venture capitalist, but she was also kind of the muse, the person that could actually deal with jobs all day long at Apple and bring him back to Earth when he was out of his mind. I'll give you an example of how that would work. And I've seen her since, you know,
Starting point is 01:35:59 I don't even know if she remembers this particular. Anyways, we leave. He's barking at me. And he's got one of my product managers in tears because she wanted to do the market research. He said, no way. We're just going to do what I say. And she just felt like her job was useless.
Starting point is 01:36:15 And for him, it was. I mean, he just didn't give a shit what she thought. Although she ran the universe of the Oregon Trail or something. It's a massive title, like a huge multimillion dollar title on the Mac in every 110,000 schools in America. And he was so pissed that, you know, in these old buildings, they have a little window where you have a little knob and it only opens up four inches so you can't jump out of it in a hotel or something. So we were, we had a Hertz rental and we're, the whole team's going out, I'm going to drive the car back to San Francisco and I'm going to fly back to Boston. And he undoes the window and he's got his head stuck and he's yelling at me from, from
Starting point is 01:36:53 ... I'm looking up at him and saying, you know, what the fuck? Like, what more can we, you already kicked us out, you know? And then on the way, we had these old brick, the earliest cell phones, these brick phones. Heidi calls me and says, okay, he'll do it for 12 million. I said, Heidi, why do we have to go through all that shit? Like, why do we even have to get abused? She said, why is the sky blue?
Starting point is 01:37:29 Just get back on the plane and go do it. It was a huge hit. It was a huge hit. The guy was, if you looked at it, he could write the hit songs. That's what he did. He'd write the hit songs. Even if you hate the producer, you want the guy that can do the hit songs, right?
Starting point is 01:37:42 If you're an artist, you put up with a crazy producer. Could he not have been nice do you think not in his DNA no do you think if he was a nice person he wouldn't know what he would say about that that's noise he gives a fuck no it being nice is noise that for him I mean we spent a lot of time talking about him but I think there's a lot of lessons learned from him that I think managers today, parents today, certainly CEOs today, you know, you're about, this show's about CEOs.
Starting point is 01:38:14 I wish every CEO had spent the time, the minimal time that I spent with jobs had such an impact on me. I mean, I owe a lot of my success to him because I always think, what would Steve have done? And I make decisions like that. It's amazing. The guy's still around. I bet you if you talk to any of the management at Apple, they have that ghost in those rooms for sure, including the current CEO who I think was doing a phenomenal job. He spent so many hours with Jobs, he knows exactly what I'm talking about.
Starting point is 01:38:50 Nobody spent more time in business than that guy for sure. I asked you a second ago if Steve Jobs was happy, but are you happy? I get happier the older I get because I'm very comfortable. I found a place, you know, that I'm... This may be just what aging does. I mean, it's just, you know... And when I was in my 30s, I had a lot of trauma and turmoil and just, you know, hard time trying to figure out who I was. And I also suffered from dyslexia,
Starting point is 01:39:25 which I've come to think of as a superpower now, not an affliction. But it was kind of like, it's hard to know what journey you're gonna be on until you find it. And then I found it, and then I started on a new journey. And, you know, it's something where, You know, it's something where, you know, you ask yourself every day goes by, and you know, the noise and signal thing,
Starting point is 01:39:53 how much of this day was I happy doing the things that I wanted to do? And I am very happy if I measure it by, is there anything that I spend my time doing that I don't want to do today? The answer is no, because I don't have to. And so I don't waste my time. Even coming here to spend two hours with you,
Starting point is 01:40:15 when I first heard about it, I went online and said, oh yeah, this guy, this guy's great. I'd love to work with him. That kind of thing, you allocate your time. This is, I'm happy to do this, I want to be here. And I think, you know, we had a very interesting couple hours together. But that's the definition of happiness.
Starting point is 01:40:33 What concerns me, and my wife often says to me, we don't need any more money. Why are you flying 300 hours a year on an airplane? What are you doing? I said, I'm happy. Like, you know, I'm happy doing this. I want to do this stuff. You know, sometimes I do five cities in a day. It's frigging crazy.
Starting point is 01:40:55 And it's the wonderful thing about, you know, air travel today. You can do that. But it's- It's sport for you. It's so interesting. I get so many interesting opportunities. I can't turn them down. They're just such You know, are you driven or you dragged you used the word trauma there? And I often ask myself that question because I came from a all-white area
Starting point is 01:41:15 I was the black kid with the strange hair and a strange family I was insecure and I think that resulted in this this force of will to try and crack the insecurity or to prove something to myself which then resulted in success? I think there is no drag. There's only driven. I don't understand being dragged. Drag insinuates that you don't care about performance, you don't care whether you succeed or not, you're just being sucked into the void of success. You might be able to say that for a rock star that gets a hit song, but most of them doesn't last. You need massive amounts of drive. And I love the most exciting thing I like to do is when someone tells me, you can't do that, like watch insurance,
Starting point is 01:41:59 you will never launch a watch insurance company. You will never do that. You will never get around the compliance state by state. You will never launch in watch insurance company. You will never do that. You will never get around the compliance state by state. You will never launch in the Middle East. You will never launch in England. Bullshit. That's exactly what I did. I found the right team. I found the right partners.
Starting point is 01:42:14 I figured it out. I was passionate about it. And I think I'm going to kick ass. I think in two or three years from now, you won't be able to catch up with me. That's what I think. I or three years from now, you won't be able to catch up with me. That's what I think. I'm 32 years old. What is the advice that you wish you got at 32 years old, Kevin? What I have learned, and this is something that you should really think about for yourself,
Starting point is 01:42:38 your real value, your real brand, are your followers. This army of people that have decided to invest their time in you, your real brand, are your followers. This army of people that have decided to invest their time in you, you know, you've cut across a vast swath of people. So you influence very successful managers, CEOs, and a lot of young entrepreneurs want to hear what you have to say because they're expecting to deliver valuable information across multiple sectors. And you also have your own data, but men and women. And so where do you take that? Because you know, do you want to launch a clothing line?
Starting point is 01:43:23 Do you want to sell burgers? Do you want to sell burgers? Do you want to do consulting? You know, you have all those opportunities, but what fits your brand? And so, I have, and you'll get to do this, you'll get to do this. You'll be approached by a lot of people that want to ride that network you've built.
Starting point is 01:43:43 And my advice to you is, because this has really worked for me, is this a product or service that I personally would use, that I would actually use? Because you'll get offered a lot of money to talk about one brand or another brand. They will. And you may be weak and take it, but the minute anybody in your network, in your community thinks you're not authentic, you're fucked. And you know that. And so you better be authentic,
Starting point is 01:44:25 you better be transparent, you better be honest, even when turmoil hits, whatever it's gonna be. I found that saved my ass so many times by just saying, here's what I know, here's what happened, and that actually bonds them even closer to you. And that's the difficulty you're gonna have is how much do you wanna take,
Starting point is 01:44:44 because you're gonna have that opportunity. But if you wanna take net? Because you're gonna have that opportunity. But if you stay authentic and say, I'm gonna support this brand because I use it, every single brand or commission I have in supporting a business, I use myself. I'm a shareholder in it and I believe in it and I use the product or whatever. Like the wines I make myself with my wife,
Starting point is 01:45:07 we drink them in our family and everybody knows that. So I wouldn't drink if it's shit wine. So it's sort of like, that's my advice to you because I meet a lot of people but you're very rare. What you've built, maybe by happen chance that it occurred. Whatever alchemy occurred, you have it now. It's yours to lose. Don't fuck it up.
Starting point is 01:45:34 Everything you said is so true. And obviously the things that we talk about in the show in terms of brands that I promote, pretty much all of them I've invested my own money into. And this is like super important. so I talked about my whoop. If you look at the investments I have and the things I talk about, there's a really clear through line through them. So there's a really clear through line,
Starting point is 01:45:53 and it's actually reflective of just where I am in my life. There's actually a sponsor I used to have on the show that I was very big on, and I just stopped consuming the product. They offered me six million pounds, which is about what, eight million dollars to continue for another year and a half. And I said like, it just wouldn't, I'm about to basically start talking about and investing
Starting point is 01:46:11 in the antithesis of what you do. So I had to turn down that seven million dollars, which is a lot of money for anybody. But it's because my life shifted and I shifted in a different direction. People don't see those things. They don't see that the, this foreign government comes along and offers you four million dollars to go and talk about their country or to go do the Dyer of a CEO in their country. They don't see those decisions that you make. But I think, hopefully, if you listen to me long enough, you'll see a through line between the things that are authentic to me.
Starting point is 01:46:38 Yeah. I think that, so you've already figured it out. And the other thing that I would do and say anybody your age, because I wish I'd done it, is start focusing on longevity in your 30s. Start thinking about what you eat and what you drink and how much sleep you do and how much exercise you have. You could live to 120 years old. I mean, it's sort of, if you understand, if you're wearing a whoop, you know what I'm talking about. It's sort of, I am very, very focused on what I do
Starting point is 01:47:02 and exercise and what I eat and all that. But that makes you feel healthier and more and just better about your day as you go through it. But the fact that you figured that out at your age, because most people your age would have taken the seven million pounds or whatever it was, that would have been a huge mistake. Because now the next product that you do endorse, I will know with certainty that you use it, because you told me this. We have a closing tradition on this podcast where the last guest leaves a question for the next product that you do endorse, I will know with certainty that you use it, because you told me this. We have a closing tradition on this podcast where the last guest leaves a question for the next guest not knowing who they're leaving it for. And the question that was left for you, funnily enough I feel like I might have asked it,
Starting point is 01:47:33 is where do you believe happiness really comes from? You know, I think the answer is very simple. Consistently achieving your goals. Because happiness is not a destination, it's a journey. It's what it is. So you have to set those goals, whether it's noise to signal going full circle, what we talked about, or long term, whatever it is, it's consistently achieving those goals, you will be happy. Consistently not achieving them, you will be unhappy. Because it is not a destination. Happiness is not a destination. Ever. It's a mistake that's
Starting point is 01:48:19 so elusive. I mean, it's just not a destination. It's a journey. This is one of the great things you've taught me today, reaffirmed for me today, is this idea of like signal and noise, but radical prioritization because kind of dovetailing into what we were just talking about. When you have a lot of opportunity, it gets even harder I think to know which ones should be taking you 18 hours a day. This is something I struggle with. You should feel it. You're kind of a weird dude, because you're like a 70 year old man in a 30 year old body.
Starting point is 01:48:49 You've got the intellect of experience, which most people don't have at your age, but deals, there's a certain feeling that you should feel that it's a good deal. It should be in your gut. And I've learned this. There's many deals that sound great that when I just do the gut check, I don't participate in.
Starting point is 01:49:11 They just don't give me, and that came from experience, but you seem to have that in some weird way to avoid that one we just talked about. It's intuitive feeling that you generally get by having a lot of winners and losers over time. But you seem to have accelerated that somehow. It's an intuitive nature of where you wanna get to and what it's gonna take to get there
Starting point is 01:49:36 and there's going to be sacrifice along the way. It's never about the money, never. It's not about the money. never about the money, never. It's not about the money. It's do I want to achieve that goal? You know, I'm having a, it's just a weird thing because I had a similar situation just a couple of days ago. You know, when somebody approached me and said,
Starting point is 01:50:01 look, can you get behind this and back it and I'll pay you a ton, like just a crazy amount of money. And I thought, do I actually want to spend one hour pursuing that? And I went back and said, look, no, it's just not interesting. I can't see myself getting involved in that narrative, which it was a complicated situation. But, and then he said, look,
Starting point is 01:50:32 how about I give you 2 1 1 2% of the company? I said, no. I just don't want to be associated. I, you know, it's the same idea. It would intuitively. It was noise. Yeah, and what that would do is some opportunity you don't know about down the future,
Starting point is 01:50:50 that you pursued some goal that somehow tainted your brand, and that opportunity never comes to you. You're the captain of your brand. You have to define yourself right through the journey. It's hard. It's really hard. You know, it's really hard. And if there's gonna be a downfall for you,
Starting point is 01:51:14 you will have chosen unwisely somewhere. But it better not be for money. There should never be an amount that you would take because if your gut says no, it doesn't matter what the money is. Not after what you've achieved. I mean, you don't need to buy a guarantee anymore. You got it. I'm assuming you've put some away. I mean, it's very simple.
Starting point is 01:51:39 If you've got five million bucks in the bank, you can do whatever you want now. I mean, it's may sound I want more, but that is enough under contact. Always have always I have an account that just sits there with five million bucks in it in T bills. I never touch it. That's my nest egg. Kevin, thank you. You got it. Two things I wanted to say. The first thing is a huge thank you for listening and tuning into the show week after week. Means the world to all of us.
Starting point is 01:52:13 And this really is a dream that we absolutely never had and couldn't have imagined getting to this place. But secondly, it's a dream where we feel like we're only just getting started. And if you enjoy what we do here, please join the 24% of people that listen to this podcast regularly and follow us on this app. Here's a promise I'm going to make to you. I'm going to do everything in my power to make this show as good as I can now and into the future. We're going to deliver the guests that you want me to speak to and we're going to continue to keep doing all of the things you love about this show. Thank you.

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