The Exchanges

Q What do you, what do you think of the biggest hiring mistakes you've made? I've made many in my time. You've mentioned the three to 400 people plus. What do you think of the biggest, like, ah, fuck, that was a big hiring mistake.

A Overestimating somebody's competence is a, a, a tremendous mistake and, and there's no backtracking from it. If you think that somebody can handle it and they can't, that's, those are the worst. I mean, because, because getting them out, hiring somebody is expensive. It's time consuming. Training them up is expensive and time-consuming, and getting to the point where you've done both of those expensive and time-consuming things and realize that the person's just not good enough to do the job, that hurts, and it's unavoidable. It literally is unavoidable. I hire fast, and I fire fast. I'm not going to go send somebody through 10 interviews. I'm going to get somebody in my company, I'm going to start giving them little things to work on, and then I'm going to Give them more and more and more trust as they prove that they can handle it. Early on, I was really serious about, you know, top grading and personality tests and doing all this crazy shit with hiring to try to figure out who's a good fit. And I'm still making bad hires. And I realized, hey, the only real way that I can figure out if somebody's good is to get them in and get them to start working. Like, I am not good enough. Some people are. Some people are good enough that in a ten-round interview, they can figure out if this person's gonna be highly effective. I am not arrogant enough to think that I could do that. I've g…

AI assessment note: “Overestimating somebody's competence is a, a, a tremendous mistake”

Q Speaking of that wealth, I do have to go back to the statement that you said earlier. Specifically about children and kind of your grandparents, your parents, you, and then, you know, you said I started on third and my kids will start one foot from home plate. Can you unpack that for me, Nick? What did you mean by that?

A A lot of entrepreneurs kind of brag about the fact that they're not going to give anything to their kids. They say it, they say it like I am going, I'm going to give all my money away and my kids will find, will, will get their own cash or opportunity or whatever it is. I think that is such a cop-out to the art of parenting. My job as a parent is not to, oh, your dad's rich. You're not rich. You go back to first base, and let's see if you can make it. That's not my job. My job is to raise kids, to build a family that can handle the wealth, that knows how to make people's lives better, can invest the money, not try to just avoid it altogether. It's like, it's like saying, my son's name is Timothy. Hey, Timothy, You are not allowed to drink a beer your entire life. I'm not going to ever give you a beer. I expect you never to drink one, and now go out into the world and handle it. The first day at college, they're going to get so obliterated, they can't, they just don't understand, and it's going to, it could potentially ruin their life. Money is the same way. Like, I'm going to teach my kids how to handle money, teach my kids how to think about money, and I'm going to set them up with all the opportunities that I possibly could. Why would I do all this work to build this network, to build these companies, to build generational wealth, If I'm not gonna pass on some of that advanta…

AI assessment note: “I'm going to set them up with all the opportunities that I possibly could”

Q How did they make you more focused and driven?

A I had a A measuring stick for time when that baby was born. It wasn't just wrinkles in the side of my eyes that became a little bit more apparent every year. I had a human being that was growing, and I know now that I'm in, in seven days, I'll be six years post the birth of my first child. I got extremely motivated when that child was born. I got more focused on the future and generational planning, and I got more focused on what I can do to be a better human being. I was less interested in wasting time on the weekends. I was less interested in friendships that weren't, you know, mutual, mutually beneficial, and I just improved. I, I improved. My entire goal in life is to be an old man sitting in a leather chair in a big ass house With kids and grandkids running everywhere. I'm saying, like, tearing the shit out of my house. I want new babies that can barely walk, bumping their head on my coffee table, and I want 12, thirteen-year-olds running around with Nerf guns, you know, busting holes in the walls. I want complete chaos, and you know, maybe it's a holiday, maybe we played golf the day before, but I want to raise family members that want to spend time with me. That's my whole goal as a parent. Number one goal. Okay, yeah, we can talk about the hardship raising strong boys. I will have succeeded as a parent if my kids want to spend time with me, even when they're no longer u…

AI assessment note: “I got more focused on the future and generational planning”

Q made me just think of something that you've tweeted before that I thought was interesting. And you said about two types of people, the ones who kind of obsessed to the end of the world about being brilliant, like truly brilliant about something. And then the second you take a more balanced approach. And you said everyone in the second was happier. Can you talk to me about that, Nick?

A I think the interesting thing about this world is that we're encouraged again by culture. We're encouraged to try to be the best in the world at something. And these folks will say it, and they'll be honest, and they'll say, in order to be the best in the world, you cannot be very good at really anything else. You're, you're obsessing. And we look at our most successful business moguls of all time, and many of them, it's, that's the case. Maybe unhealthy, broken families, not that great of parents, just singularly focused on business, entrepreneurship, health. Of their companies, not their bodies and their families. But, and I, and I would have to kind of agree with that. If you want to be the best, if you want to be the richest in the world, if you want to be the best business person in the world, you have to live an unbalanced life and that you can't actually be the best in the world at two things. So the ego, our personal egos will, will say, well, shit, if everybody else is on a journey to be the best, I want to be the best. I can be the best. I should work hard enough to where I am a legend and I am the best. That's what our egos will tell us. In my opinion, a more realistic approach is to yes, play the game of business at a high level, which we're going to talk about a lot in this conversation. Do amazing things with, you know, leverage and delegation so that you can be s…

AI assessment note: “In my opinion, a more realistic approach is to yes, play the game of business”

Q that again, I like just having an open conversation. When I hear you say that, I feel Accepting of mediocrity in myself. I would be scared to do that, because I'd be like, I could have been more. If I'd given it more, I could have been better. How would you advise me when I say that I'm fearful of accepting kind of mediocrity by not giving it my all?

A I think the, the lie that we tell ourselves is that we can't play the game at a high level, the game of business, our careers, that we can't play that game at a high level without, you know, being unbalanced. The hustle culture on Twitter and all over the internet will say, You know, it's all about work. I'm working 70 hours a week. My career is first. That's glorified. We're looking at kind of like the startup founders who have worked long hours. They're kind of like gladiators, right? They're, they're viewed in a different light. It does take a little bit of a, let's, you know, we got to swallow our ego and pride and say, hey, look, I'm, I'm going to leave a little bit of money on the table here, but my life overall, it's going to be more rewarding. In my opinion, there's nothing more rewarding than being a good parent, A good, a good spouse. Have amazing relationships with friends and family members, which I know you're also super passionate about. And then also being, like, physically fit. Be, be a physical specimen and feel strong and healthy. Nothing seems more fun than that. So, and I also, I think that we can do it. I think that you can play this game of business at a really high level working 30 hours a week. And the people who say that they can't and that they have to work 70 hours a week are kind of Working on the wrong shit.

AI assessment note: “you can play this game of business at a really high level working 30 hours”

Q school. We have every business book, all full of shit. And they all tell us that anyone can be an entrepreneur and anyone can be anything. Sadly, Dude, I'm not going to be LeBron James. You know, I ain't good at basketball and I don't have his, you know, structure and height and everything in between, no matter how much I train. Why do you think entrepreneurship isn't for everyone?

A The average competence of human beings is a lot lower than everybody would think. Or the average, we'll just talk about America for a second. The average American is 30 pounds overweight. They have less than a thousand dollars in their checking account. And they're just trying to do as little as possible to get paid next Friday so that they can go drink six beers with their buddies and watch Netflix. That's just the truth. That's like, we, we surround ourselves online with high performers, people who want to own companies, and we forget that most people, A, don't care. And if you've ever hired people, if you've ever built teams, you understand that a lot of people are not good at making these decisions that are required of entrepreneurs. We talk about delegation and decisions and, and the, and the constant nuance and uncertainty of being an entrepreneur. You're making incomplete decisions with incomplete information, and it's very high stakes. It's very uncomfortable. That is not for everybody. That is obviously not for everybody. Five years ago, I thought, you know, everybody should be an entrepreneur. This is the path to wealth, the sweaty startup mentality, you know, forget tech culture. Let's, let's build small businesses. Anybody can do this. Um, today, I think I couldn't have been more wrong. I think 95% of people are way better off going and working for a company. Earnin…

AI assessment note: “a lot of people are not good at making these decisions that are required of entrepreneurs”

Q drinking a six pack and having Netflix and You did a tweet about queuing in Walmart, and I joked with my, you know, team there. I said, I bet he's got a portfolio of precisely fuck all. Um, because you know what? They're in Portofino right now for the summer, or they're, you know, skiing in Courcheval in the winter. Are VCs rightly positioned given their distance from mass market?

A I think VCs are rightly positioned to do the things that VCs do best, which is the tail, the tail case of value add. Which is making a few people's life better. And then those, those things over years trickle down to the masses. Does that make sense? Like to change the world, you have to start with the elite. You have to start with how companies interact. You have to start with doing all these little things to make companies more efficient and make the world more efficient. And those things do require venture capital. And the goal of venture capital is to find those edge cases. The goal of venture capital is not to build a portfolio of companies that cashflow a hundred grand a month and then go on Uh, mountain biking trips every morning at 6:06 45 a.m. That's not the goal of a VC. A VC is to invest in a hundred companies and two of those companies are going to return 10 X on the entire portfolio. That's the goal. So yes, they're very well positioned in that regard. But I think when the VCs and the tech guys and the people who live in adventure, you know, in LA and New York City and San Francisco, when they're talking about business in general, one must understand that These folks have not been in a Walmart in 10 years. They have, they just haven't been in one. They haven't, they haven't looked at the average American. They have no idea what the average American thinks about, yo…

AI assessment note: “I think VCs are rightly positioned to do the things that VCs do best”

Q made me just think of something that you've tweeted before that I thought was interesting. And you said about two types of people, the ones who kind of obsessed to the end of the world about being brilliant, like truly brilliant about something. And then the second you take a more balanced approach. And you said everyone in the second was happier. Can you talk to me about that, Nick?

A I think the interesting thing about this world is that we're encouraged again by culture. We're encouraged to try to be the best in the world at something. And these folks will say it, and they'll be honest, and they'll say, in order to be the best in the world, you cannot be very good at really anything else. You're, you're obsessing. And we look at our most successful business moguls of all time, and many of them, it's, that's the case. Maybe unhealthy, broken families, not that great of parents, just singularly focused on business, entrepreneurship, health. Of their companies, not their bodies and their families. But, and I, and I would have to kind of agree with that. If you want to be the best, if you want to be the richest in the world, if you want to be the best business person in the world, you have to live an unbalanced life and that you can't actually be the best in the world at two things. So the ego, our personal egos will, will say, well, shit, if everybody else is on a journey to be the best, I want to be the best. I can be the best. I should work hard enough to where I am a legend and I am the best. That's what our egos will tell us. In my opinion, a more realistic approach is to yes, play the game of business at a high level, which we're going to talk about a lot in this conversation. Do amazing things with, you know, leverage and delegation so that you can be s…

AI assessment note: “If you want to be the best... you have to live an unbalanced life”

Q What do you, what do you think of the biggest hiring mistakes you've made? I've made many in my time. You've mentioned the three to 400 people plus. What do you think of the biggest, like, ah, fuck, that was a big hiring mistake.

A Overestimating somebody's competence is a, a, a tremendous mistake and, and there's no backtracking from it. If you think that somebody can handle it and they can't, that's, those are the worst. I mean, because, because getting them out, hiring somebody is expensive. It's time consuming. Training them up is expensive and time-consuming, and getting to the point where you've done both of those expensive and time-consuming things and realize that the person's just not good enough to do the job, that hurts, and it's unavoidable. It literally is unavoidable. I hire fast, and I fire fast. I'm not going to go send somebody through 10 interviews. I'm going to get somebody in my company, I'm going to start giving them little things to work on, and then I'm going to Give them more and more and more trust as they prove that they can handle it. Early on, I was really serious about, you know, top grading and personality tests and doing all this crazy shit with hiring to try to figure out who's a good fit. And I'm still making bad hires. And I realized, hey, the only real way that I can figure out if somebody's good is to get them in and get them to start working. Like, I am not good enough. Some people are. Some people are good enough that in a ten-round interview, they can figure out if this person's gonna be highly effective. I am not arrogant enough to think that I could do that. I've g…

AI assessment note: “Overestimating somebody's competence is a, a, a tremendous mistake”

Q Speaking of that wealth, I do have to go back to the statement that you said earlier. Specifically about children and kind of your grandparents, your parents, you, and then, you know, you said I started on third and my kids will start one foot from home plate. Can you unpack that for me, Nick? What did you mean by that?

A A lot of entrepreneurs kind of brag about the fact that they're not going to give anything to their kids. They say it, they say it like I am going, I'm going to give all my money away and my kids will find, will, will get their own cash or opportunity or whatever it is. I think that is such a cop-out to the art of parenting. My job as a parent is not to, oh, your dad's rich. You're not rich. You go back to first base, and let's see if you can make it. That's not my job. My job is to raise kids, to build a family that can handle the wealth, that knows how to make people's lives better, can invest the money, not try to just avoid it altogether. It's like, it's like saying, my son's name is Timothy. Hey, Timothy, You are not allowed to drink a beer your entire life. I'm not going to ever give you a beer. I expect you never to drink one, and now go out into the world and handle it. The first day at college, they're going to get so obliterated, they can't, they just don't understand, and it's going to, it could potentially ruin their life. Money is the same way. Like, I'm going to teach my kids how to handle money, teach my kids how to think about money, and I'm going to set them up with all the opportunities that I possibly could. Why would I do all this work to build this network, to build these companies, to build generational wealth, If I'm not gonna pass on some of that advanta…

AI assessment note: “My job is to raise kids, to build a family that can handle the wealth”

Q What do you know now that you wish you'd known before you had your first child? I asked you this before, and you didn't tell me because we said we'd save it for the show, but if you could cool yourself up when your wife was going into labor that first time, what would you tell yourself?

A I wish we would have started a little bit earlier. I look at it as now that I'm having these kids and we're on the way up, and I have one that's about to turn six years old, and I can have mentally stimulating conversations with him, and I'm really starting to be able to teach him. In the early years, it's, it's They want their mom and their mom is the number one influence in them. And this kid is finally starting to find interest in dad. Dad, I want to go on a hike. Dad, I want to go camping. Dad, I want to go play golf with you. That is so much fun and rewarding that I just wish that we would have got started earlier. I think it's a duty. It is my duty as a, a person who I think at least that I have my shit together when it comes to parenting and that I'm going to raise decent kids. It's my duty to create as many as I possibly can. I would, I wish that we had started a little bit earlier so we could have six, seven, eight kids. Kids are the most amazing thing about life. Why would you delay that? Kids make, kids made me stronger. They made me more focused. They made me more motivated. They made me more driven. They made me more protective of my time.

AI assessment note: “I wish we would have started a little bit earlier.”

Q on. I knew nothing about venture when I started, but people like Go with me on the journey. And everyone likes to see development in themselves, in someone else. And so, I find it the best way to learn, but bring people with you. Final one, I always get told, never meet your mentors, uh, or never meet your idols. They'll always disappoint you. Do you agree with that statement?

A I think that that's a, that's a very encouraging, beautiful thing about life. And yes, I would agree with it. I think people could meet me And I would let them down in so many ways with my competence, with my ability, with the way my businesses are run. And I think it's a beautiful thing about life in that you don't have to be spectacular. You don't have to be perfect to do, to do amazing things. Like that should be inspiring. It should be inspiring that the men that are at the top of the, you know, the echelon of the most wealthy people in the world are, are broken in some areas of life. That's inspiring to me. It makes me not feel that bad that I am broken in so many areas of my own life.

AI assessment note: “And yes, I would agree with it. I think people could meet me”

Q that again, I like just having an open conversation. When I hear you say that, I feel Accepting of mediocrity in myself. I would be scared to do that, because I'd be like, I could have been more. If I'd given it more, I could have been better. How would you advise me when I say that I'm fearful of accepting kind of mediocrity by not giving it my all?

A I think the, the lie that we tell ourselves is that we can't play the game at a high level, the game of business, our careers, that we can't play that game at a high level without, you know, being unbalanced. The hustle culture on Twitter and all over the internet will say, You know, it's all about work. I'm working 70 hours a week. My career is first. That's glorified. We're looking at kind of like the startup founders who have worked long hours. They're kind of like gladiators, right? They're, they're viewed in a different light. It does take a little bit of a, let's, you know, we got to swallow our ego and pride and say, hey, look, I'm, I'm going to leave a little bit of money on the table here, but my life overall, it's going to be more rewarding. In my opinion, there's nothing more rewarding than being a good parent, A good, a good spouse. Have amazing relationships with friends and family members, which I know you're also super passionate about. And then also being, like, physically fit. Be, be a physical specimen and feel strong and healthy. Nothing seems more fun than that. So, and I also, I think that we can do it. I think that you can play this game of business at a really high level working 30 hours a week. And the people who say that they can't and that they have to work 70 hours a week are kind of Working on the wrong shit.

AI assessment note: “the lie that we tell ourselves is that we can't play the game at a high level”

Q I love it. Where are you insecure, Nick? And what I mean by that is everyone who I think proclaims that, me included, who will proclaim that openly and actively, a lot of it's based out of insecurity. Uh, I'm insecure in many ways. How do you think about where you're insecure?

A It takes a unique person to do what I do, which is write thoughts of my own and ideas and stories from my past on the internet. And compete for likes and follows. That game is a game that I'm not proud that I play because it just shows that I am very, I, I do care a lot about what people think. And we got on this call and immediately you said, you know, Nick, I really respect that reading your stuff. I can tell that you just don't care what people think. And that would be, that would be a lie. Like I'm putting on a front that I don't care, but we all care. Like we all care. I care deeply about what the people closest to me think of me. But it's hard not to care what people think, and that's why I tweet and get followers and trying to build a personal brand. So the, the insecurity and fear of failure is evident, and the people who don't talk about it, the entrepreneurs who just say, all this is easy for me, are lying because business is really hard. Putting yourself out there is really, really hard. I think the interesting thing about being a notable person, whether it be an influencer, a leader of any kind, is that you cannot please everybody. Number one, I can't please everybody. It's impossible. I'm going to do what I can do to, you know, please the most amount of people, but I can't possibly ever please them all. The second one is that you're going to get a lot of hate that …

AI assessment note: “I do care a lot about what people think.”

Q school. We have every business book, all full of shit. And they all tell us that anyone can be an entrepreneur and anyone can be anything. Sadly, Dude, I'm not going to be LeBron James. You know, I ain't good at basketball and I don't have his, you know, structure and height and everything in between, no matter how much I train. Why do you think entrepreneurship isn't for everyone?

A The average competence of human beings is a lot lower than everybody would think. Or the average, we'll just talk about America for a second. The average American is 30 pounds overweight. They have less than a thousand dollars in their checking account. And they're just trying to do as little as possible to get paid next Friday so that they can go drink six beers with their buddies and watch Netflix. That's just the truth. That's like, we, we surround ourselves online with high performers, people who want to own companies, and we forget that most people, A, don't care. And if you've ever hired people, if you've ever built teams, you understand that a lot of people are not good at making these decisions that are required of entrepreneurs. We talk about delegation and decisions and, and the, and the constant nuance and uncertainty of being an entrepreneur. You're making incomplete decisions with incomplete information, and it's very high stakes. It's very uncomfortable. That is not for everybody. That is obviously not for everybody. Five years ago, I thought, you know, everybody should be an entrepreneur. This is the path to wealth, the sweaty startup mentality, you know, forget tech culture. Let's, let's build small businesses. Anybody can do this. Um, today, I think I couldn't have been more wrong. I think 95% of people are way better off going and working for a company. Earnin…

AI assessment note: “a lot of people are not good at making these decisions that are required”

Q drinking a six pack and having Netflix and You did a tweet about queuing in Walmart, and I joked with my, you know, team there. I said, I bet he's got a portfolio of precisely fuck all. Um, because you know what? They're in Portofino right now for the summer, or they're, you know, skiing in Courcheval in the winter. Are VCs rightly positioned given their distance from mass market?

A I think VCs are rightly positioned to do the things that VCs do best, which is the tail, the tail case of value add. Which is making a few people's life better. And then those, those things over years trickle down to the masses. Does that make sense? Like to change the world, you have to start with the elite. You have to start with how companies interact. You have to start with doing all these little things to make companies more efficient and make the world more efficient. And those things do require venture capital. And the goal of venture capital is to find those edge cases. The goal of venture capital is not to build a portfolio of companies that cashflow a hundred grand a month and then go on Uh, mountain biking trips every morning at 6:06 45 a.m. That's not the goal of a VC. A VC is to invest in a hundred companies and two of those companies are going to return 10 X on the entire portfolio. That's the goal. So yes, they're very well positioned in that regard. But I think when the VCs and the tech guys and the people who live in adventure, you know, in LA and New York City and San Francisco, when they're talking about business in general, one must understand that These folks have not been in a Walmart in 10 years. They have, they just haven't been in one. They haven't, they haven't looked at the average American. They have no idea what the average American thinks about, yo…

AI assessment note: “I think VCs are rightly positioned to do the things that VCs do best”

Q in on? Say child is cycling too fast on bike. Chance of falling off and hurting themselves. Well, good. You should learn that you shouldn't cycle too fast on a slippery surface or close to other people, but also could hurt themselves. You don't want to see Timothy crying. He's going to have a cut on his leg. You're going to have to clean that up. What is too much?

A It's, that's the ultimate question of life. How much do you protect your kids? How much do you coddle them? And how much do you let them figure out and solve their own problems? A wealthy person has a high school kid who gets a DUI. They get a DUI. They have two options. They call their friend who they play golf with, who is the judge and get them off the hook. Or they make their kids spend two nights in jail and live with the consequences of that DUI. I'd like to think that I'm going to make my kids live with those, the consequences of their decisions. They're going to live that if they make a poor decision, if they drive their car too fast and crash it, if they don't put a case on their iPhone and it shatters, they're going to live with the consequences of that poor decision. If they ride their bike too fast and they fall, they're going to live with it. I just hope that I can teach them to not make those big mistakes that can screw up your life.

AI assessment note: “I'd like to think that I'm going to make my kids live with those”

Q like the separation. I, I think to Warren Buffett's statement on, many people have said this, but the most important decision you'll ever make is the partner that you choose in life. Can I ask you, but it sounds academic in how I'm asking it, quite a romantic question. When you were thinking about the partner selection process, what did you want in the partner that you chose for life?

A People get way too serious about trying to, to find that person. I think if you find somebody who you're physically attracted to, You're emotionally stimulated, mentally and emotionally stimulated by, and you can trust them, and you can, that's number one. If you can trust them, um, odds are you can make a marriage work. That sounds brash, but many people are way too picky today about who they marry. They should have gotten married a long time ago to one of those girls that they thought wasn't perfect in some way. But me and my wife have very similar moral views, and how we think about Household responsibilities, and jobs, and who does what, and she thinks, and I think as well, that her raising kids is miraculously and 10 times more important than a career. The child that you create is more, is, is way more important than her having a career, and she is also in that camp. Many people aren't, and that's okay, but in my, in our house, my, my job is to Take care of the finances and be a good dad and be around and do all the things I'm supposed to do. And her job is to take care of these kids and, and grow human beings, which I think is a little bit more important than growing a business for somebody who you don't even have equity in that business.

AI assessment note: “me and my wife have very similar moral views, and how we think about Household responsibilities”

Q How did they make you more focused and driven?

A I had a A measuring stick for time when that baby was born. It wasn't just wrinkles in the side of my eyes that became a little bit more apparent every year. I had a human being that was growing, and I know now that I'm in, in seven days, I'll be six years post the birth of my first child. I got extremely motivated when that child was born. I got more focused on the future and generational planning, and I got more focused on what I can do to be a better human being. I was less interested in wasting time on the weekends. I was less interested in friendships that weren't, you know, mutual, mutually beneficial, and I just improved. I, I improved. My entire goal in life is to be an old man sitting in a leather chair in a big ass house With kids and grandkids running everywhere. I'm saying, like, tearing the shit out of my house. I want new babies that can barely walk, bumping their head on my coffee table, and I want 12, thirteen-year-olds running around with Nerf guns, you know, busting holes in the walls. I want complete chaos, and you know, maybe it's a holiday, maybe we played golf the day before, but I want to raise family members that want to spend time with me. That's my whole goal as a parent. Number one goal. Okay, yeah, we can talk about the hardship raising strong boys. I will have succeeded as a parent if my kids want to spend time with me, even when they're no longer u…

AI assessment note: “I got more focused on the future and generational planning”

Q in on? Say child is cycling too fast on bike. Chance of falling off and hurting themselves. Well, good. You should learn that you shouldn't cycle too fast on a slippery surface or close to other people, but also could hurt themselves. You don't want to see Timothy crying. He's going to have a cut on his leg. You're going to have to clean that up. What is too much?

A It's, that's the ultimate question of life. How much do you protect your kids? How much do you coddle them? And how much do you let them figure out and solve their own problems? A wealthy person has a high school kid who gets a DUI. They get a DUI. They have two options. They call their friend who they play golf with, who is the judge and get them off the hook. Or they make their kids spend two nights in jail and live with the consequences of that DUI. I'd like to think that I'm going to make my kids live with those, the consequences of their decisions. They're going to live that if they make a poor decision, if they drive their car too fast and crash it, if they don't put a case on their iPhone and it shatters, they're going to live with the consequences of that poor decision. If they ride their bike too fast and they fall, they're going to live with it. I just hope that I can teach them to not make those big mistakes that can screw up your life.

AI assessment note: “teach them to not make those big mistakes that can screw up your life”

Q Are you in wealth protection mode or in wealth creation mode? And can you be in both?

A I'm in both now. Yes. I went from, I went from wealth creation mode early in my career and, and look, this, this is just the perfect example. If somebody came to me and they were 25 years old and they were me and they had my first storage deal that I built from the ground up that changed my entire life and made me millions of dollars. If they had that sitting on a desk in front of me right now, I would tell them not to do it because I wouldn't do it because it was too risky. Does that make sense? Like the deal that we built for 2.9 million, it's worth eleven million. Now I've made over two million dollars personally on that deal. It changed my life. I would tell somebody probably not to do looking back at what decisions we made at the very beginning of building that building. How, how messed up is that?

AI assessment note: “I'm in both now. Yes. I went from wealth creation mode early in my career”

Q You said network. Final one there, because I could talk to you all day. How do you think about networking? I hate the word network. It feels transactional, dehuman. I've loved this because we've already opened up. I hate networking where it's like, here's my business card. Let's do deals.

A I think the average person networks all wrong. They just have the wrong mindset when it comes to networking. They have a mindset of, when it comes to networking, how can you help me? And they walk around, they go to coffee, they go to meetups, they go to events, and they walk around with their handout saying, me, me, me, me, help me, help me, help me. And what you have, if you've ever been to a college networking event, you have a bunch of people with absolutely nothing to offer anybody else walking around shaking hands saying, help me, help me, help me, help me, help me, help me. It's, It's, it's ignorant. It's crazy. The way to build a network is to get really fucking good at something. Period. And end of story. As soon as you become an expert at something, and you prove to people that you know what you're doing, whether it's through making money that way, or doing something in this regard, or having something on your resume, when you prove to people that you are an expert in some field, then all of a sudden they can get something from you. They can gain, they can benefit from you, and that's when your network explodes. My network has exploded because I am a card in other people's Rolodex. Think about it that way. As soon as you become a high value card in somebody else's Rolodex, your network will explode. Until then, yes, you'll have, and look, there's nuance. Yes, you're g…

AI assessment note: “The way to build a network is to get really fucking good at something.”

Q What do you think are the rules to the game?

A The rules to the game is that if you don't have anything unique, if you don't bring a new perspective to the conversation, Nobody's going to give a shit about following you. They don't want to hear. People don't want to hear the same ideas echoed back and forth. There's already enough echo chambers in our life. We're surrounded by our family, which are all in the same world that we are in and begin to believe the same things that we believe. And then in our companies, we're all rowing the ship the same way. We're echoing ideas right off each other. It's a big echo chamber. Online communities are no different. The people who hang out in anti-work Reddit, they all feel the same way about companies and capitalism, and they're echoing ideas and just Making each other more and more and more radical. Twitter is, is no different. So when you can be open-minded and, you know, be nuanced on Twitter, it's not interesting. If you're just gonna echo the same things back and forth from everybody else and just share the same ideas that everybody else is sharing, you're not gonna be interesting.

AI assessment note: “The rules to the game is that if you don't have anything unique”

Q I love that. Are you worried about income inequality? I think one of the biggest problems we see is the massive divergence between the A bigger and bigger problem with AI actually. Are you as concerned as I am about income inequality over the next decade?

A I'm not concerned with it. I think it's a very natural phenomenon. And if you try to fight it, you're fighting a battle that has stood the test of, uh, you know, 2000 years of civilization as it has advanced. You could take all the money in the United States right now. You take all the money and you could divide it equally among everybody. Take all the money and divide it equally. And in five, 10, 15 years, you could argue about the timeframe. In five years, at least 80% of cash would be in the hands of 20% of people. 80% of power would be in the hands of 20% of people, and in 10 or 20 years, one percent of people would control the world again, because there's people who know how to make money, and there's people who know how to buy things that make money, and invest, and build companies, and delegate, and build things of value, and there's a vast majority of people who only know how to spend money. They know how to go to work, make money, and spend it, and this This stuff's a skill. It is, it is an ability, and income inequality is natural. It always has been natural, and I'm not worried about it because today the poorest people in America have a better life than the wealthiest people in America 50 years ago. They have better access to healthcare. They have better living situations. They have more amenities. They have better food. Um, it trickles down massively, at least in de…

AI assessment note: “I'm not concerned with it. I think it's a very natural phenomenon.”

Q Question for you. Could you not do more if you did less? You said that about 10 companies. I do believe in focus. Do you not think sometimes you are great, but you could build one great company rather than 10 good companies?

A Yeah. I'm trying to figure out what company has, is the best business and, and the, and requires that level of focus. I'm, I'm a very good gatherer of, of talent. And my plan right now is to gather talented people and let them do their thing with extreme levels of delegation. Meaning I'm, I'm not that involved. So I'm, I'm trying to enable people and, and layer on the synergies around my brand and my distribution and my ability to attract talent and get good operators and just see what they can do. And some of them will win. Some of them will lose. Um, but I like my strategy so far, but yeah, long term, I think it'll, it'll be a power law for sure with what I'm doing.

AI assessment note: “my plan right now is to gather talented people and let them do their thing”

Q I'm cool with it. Um, but you, you mentioned that kind of getting comfortable almost with the criticism. I get deeply saddened when people are rude to me. I don't know them, uh, on Twitter, people will say idiot, uh, product of zero interest rate environment. You name the shit that people will throw at me. It really upsets me. How would you advise me on protecting myself against hatred?

A I think every, every bit of hate has to be weighed from who you're getting it from, and there's a fact about the world that's a very sad part of the world that we find out when we're kids and we're in classrooms full of 30 individuals. People are very mean to each other. A lot of people are very mean to each other. Kids are very mean to each other, high schoolers are very mean to each other, and adults are very mean to each other, and it all stems from jealousy. If I had to say that maybe 80% of the world has varying levels of Jealousy and hate, hate towards people who win. People who succeed. People who thrive. And maybe 20 or 30% of them, it's serious. Like, they are literal crabs in a bucket. Instead of, instead of helping people lift, lift other people up and try to make other people's lives better, they're literally pulling other people down to make themselves lift up. Because they think that that's how they can get better and improve. There's a saying in real estate, like, there's two ways to own the largest building in town. One way is to build the largest building in town. The second way is to tear down all the buildings that are taller than your own building. That second one, tearing other people down is way easier. It's way easier than building the largest building in town. Making yourself more successful, doing the work on yourself to thrive and succeed is way harder…

AI assessment note: “We just have to do our best to be secure enough in our own actions”

Q and to hire young, hungry, ambitious people. I mean, it's a shit tweet, let's be honest, okay? Um, yeah, okay. I got massive hatred for being massively ageist, because I said young. I mean, for fuck's sake, like, I'm not saying everyone needs to be young, but I'm intrigued. Do you agree with the woke virus being so potentially damaging, and does it make you thoughtful of what you say?

A I definitely am careful about what I say. I'm not uncancellable yet. I know that I need to be careful. I have a small window in time to build these companies to capitalize on my personal brand. And I know that if I get canceled, it will set me back in my mission to get these points of view across to a lot of people. So that being said, I think this woke mindset and virus is a tremendous advantage for me and my family. The people who buy into it, Our victims, the people who buy into it are blaming other people, the people who buy into it are focusing on things that are totally outside of their control. I don't do that, and my kids are not going to do that. So we're going to have a competitive advantage, a competitive advantage against everybody who spends time focusing on things that don't matter, and worries about things that they can't control, and blames other people for their problems. So absolutely, it's going to be a net positive for me, because people Who raise their kids to be accountable. They raise strong kids. They raise their kids to suffer with grace. They raise their kids to be good stewards of money. It's going to be playing the game on easy mode while everybody else is out pointing fingers to everybody else.

AI assessment note: “I definitely am careful about what I say. I'm not uncancellable yet.”

Q Are you in wealth protection mode or in wealth creation mode? And can you be in both?

A I'm in both now. Yes. I went from, I went from wealth creation mode early in my career and, and look, this, this is just the perfect example. If somebody came to me and they were 25 years old and they were me and they had my first storage deal that I built from the ground up that changed my entire life and made me millions of dollars. If they had that sitting on a desk in front of me right now, I would tell them not to do it because I wouldn't do it because it was too risky. Does that make sense? Like the deal that we built for 2.9 million, it's worth eleven million. Now I've made over two million dollars personally on that deal. It changed my life. I would tell somebody probably not to do looking back at what decisions we made at the very beginning of building that building. How, how messed up is that?

AI assessment note: “I'm in both now. Yes.”

Q You said I could ask you anything. What do you still do today that you wish you didn't have to do?

A It's a process, but I don't have a lot of things inside of my companies right this moment that I don't think are real, really high leverage activities. Maybe I wish that My entire Twitter was automated so I could get off of it for a year and the tweets would keep flowing. But a lot of my tweets are made by my team. They're reposts from either my newsletter or, you know, written from a interview like this or something along those lines. But I am operating in a, in a really, at an area of really high leverage, but it wasn't always that way. I mean, five years ago, I was driving a box truck around the streets of Boston, you know, during the really busy season. So, um, I've, I've made a lot of, I've made a lot of strides when it comes to delegation.

AI assessment note: “Maybe I wish that My entire Twitter was automated so I could get off”

Q Can I ask you, what do you think of today's state of parenting? We mentioned that, you know, separate roles, but also like the cycling and, you know, letting your child fall versus not. Do you think we mollycoddle our children too much today?

A Oh God. Yes. Absolutely. I think the number one thing that you can do to set your children up for failure is to protect them from the fact that life is brutal. Life is hard. Life is hard. You have hard decisions to make. It's hard dealing with people. It's hard making money. It's hard working for companies. It's hard staying in shape. It's hard building relationships. It's hard having friendships. Everything worth doing in life is hard. Anything worth doing in life is hard. Being married is hard. Being a parent is hard. Building a company is hard. Staying fit is hard. Playing golf is hard. Anything worth doing is hard in life. So why, why are, is our job as a parent to put a bubble around our kids so that they don't deal with any pain? It doesn't make any sense to me. The more well off a parent and family is, the more they coddle their kids, and the more they try to keep them from feeling pain. And like I was saying, dealing with these decisions, and living with the consequences of poor decisions. So, if you're not going to teach your kids to struggle, and have a positive attitude through the struggle, then they're not going to win at life, man. They're just not going to win at life. They're going to be soft. They're going to blame other people for their problems. They're going to have the victim mentality that we hate so much on On social media. It's, it's a, it's a parenting …

AI assessment note: “Oh God. Yes. Absolutely. I think the number one thing that you can do”