The Exchanges

Q That is very, very kind of you. Now, I always love to start with a little bit of Context. And I'm an armchair psychologist, if you can believe it. And so I want to start with your great grandparents coming over from Germany. And I always believe that our past shape us in many ways. If our past did shape us, what do you think you're running from, Nick?

A The part that people don't understand about wealth, success, just living a better life, having the life that you and I both live, which I think is pretty wonderful. It's a, it's a multi-generational journey. People don't realize that. And my great-great-grandfather came over from Germany with his wife, with nothing, and they worked basically their entire lives at jobs that sucked, so that their kids could have a little bit more of an advantage, which in their case was to, like, go to the public schools in a, in a decent area, and then have a chance to go to college. My grandparents then didn't go to college. They didn't do that, but they joined unions. They went into the military, joined unions, worked their whole life to send my parents to a little bit of a better school and have a little bit, you know, better upbringing, more stability, air conditioner, a TV. And my parents, um, are working their entire lives to make things just a little bit better for me. So we live in a day and age where everybody wants it all right now. We all want to get rich in 12 months, three years, five years, and when we look at very successful immigrant families, they play a different game. They play a, they play a multi-generational game, and they're willing to sacrifice and delay gratification to the point where they themselves may never actually get that gratification. They're just going to watch…

AI assessment note: “when you ask what I'm running from, I'm, I'm, I'm running from taking a step backwards”

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 of it”

Q What do you do when trust is lost? When things are not going well, and you've lost trust in someone? Is it possible to rebuild it? And how do you manage that situation?

A I think all stress and problems and, you know, losses of trust are a result of one of two things. One, they're not good enough at their job. They're not working hard enough. It's a competence issue. They're just not good enough. Number two is a moral issue where they don't have your best interest in heart and they are, uh, making decisions that are gonna benefit them and actually hurt you, lying, stealing, cheating, and so on. Both of those, you have to make the decision right then and like, okay, do I keep investing in this person? Do I keep giving them more, more things? Or do I take things off their plate or get this person out of my company altogether? It's, it's tough. That's why this is so hard. Everything in business is a people problem. You're managing people, you're managing their emotions, you're managing them lying, stealing, cheating, not working hard, doing whatever. It's not easy. It's not easy. That's, that's why managers get paid the big bucks.

AI assessment note: “you have to make the decision right then and like, okay, do I keep investing”

Q you've been stress testing your mind across many different disciplines, and respectfully, they've been bringing up children, but it's not intellectually always as stimulating and challenging, and for the person who's been working, it creates this chasm where it's like, what did you do? Oh, I looked after the kids. It's the same. Is that ever a challenge? Do you worry about it kind of not being intellectually stimulating enough?

A Yeah, I'm exhausted when I get home. Like, I'm, I'm gonna get off this interview, and I got three more meetings today, and then I gotta work out, and then I'm gonna get to dinner with her, and yes, I'll, I'll have to turn it on to pull up some more energy to have a conversation with her. But look, we have a lot of childcare. We have a nanny. We have, the kids are in school. My wife has a lot of friends. She has a packed social schedule. She has workouts that she does and does. She has more girlfriends That she goes and spends time with. And I think it's really, the sad part is, is that women are so isolated. They're so isolated. There's no community. Uh, 50 years ago in small town America, all the sisters and siblings and friends lived on one block, and they were popping in each other's houses, and they were having dinner constantly, and it was, it was a community. They were raising kids as a community. The women were together. And today men build businesses in lonely environments and women raise kids in lonely environments. And it can be really hard if you have that traditional structure. Now, obviously not everybody does what my family does, but.

AI assessment note: “I'll have to turn it on to pull up some more energy to have a conversation”

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”

Q finding the advantage. I didn't disagree with you. I do want to ask, you know, a lot of what we've said today actually centers around advice and a lot of people gain comfort and security and advice. Meta question. How do you advise people on Advice. Advice to take versus the advice not to take and how to action it in the right ways. How do you think about that?

A The problem with advice is that it's, it, it gives you a false sense of productivity. That's the problem. People are listening to this podcast and they're nodding along and they're thinking, wow, this podcast is making me better. And then they go home and get on YouTube and they listen to more advice and they get on Twitter and listen to more advice. And before they know it, they've listened to a full day of advice and they're thinking before they went to bed, wow, I'm doing a lot. This is great. If you're not doing anything in the real world, if you're not trying to advance your career, if you're not trying to get better, if you're not making yourself better by doing things that are hard and getting uncomfortable, The advice, using your words , the advice could mean fuck all to you. Like, it does not matter. Like, if you're not in the trenches building a company, you're not going to be able to listen to anything anybody says and actually apply it. Advice, unfortunately, is a lot of people's cope, and, you know, you can, you can take advice for 2030 years and get nowhere because you're not actually doing anything, and that's the hard part. And also is that everybody who gives advice is a successful person because, you know, you got to have a resume to make your advice weighted, so all the people who have the most, you know, Clout and, you know, status on Twitter, they're all su…

AI assessment note: “getting advice from successful people is very risky, because successful people look at the world totally different”

Q Talking about choosing to go about life, and sorry, I sent you a schedule, but I'm just too interested in this discussion. Ah, ah, you, I think people change a lot, and kind of self-reflect a lot. When you think about your biggest moments of change and self-reflection, what do you think your one or two biggest have been?

A I have a, a theory that there's a very dangerous thing about being successful. Especially when you're notable and you have 300,000 people on Twitter hanging on your every word, it can get very dangerous because you start to, now this is gonna sound funny, but you start to kind of be your own idol. You start to be your own god. And you start to think that, oh, maybe I am just special. Maybe I am. Like, look at all these ways that I'm winning. Look at all these people who really hang on every word that I say. And that gets very, very, very dangerous. And if you don't have an open mind, you start filtering information based on what supports your opinions, and you can lose massive amounts of money, you can turn into a complete asshole, and you can change for the worse. And it happens to a lot of successful people. I have a little sticker on my mirror above my, above my sink, because my grandfather gave me amazing advice, said, Nick, you're going to do amazing things in life, but if you don't remain humble and kind to people around you, then it'll all be for naught. And you're going to pass on things to your kids that are not great. And you're going to be, you're going to, instead of being a positive influence on a lot of people's lives, you're going to become a negative influence. I have this little sticker on my mirror that I see every morning when I brush my teeth. It says, chang…

AI assessment note: “because my grandfather gave me amazing advice, said, Nick, you're going to do”

Q but you feel something. And that's the most important thing. Uh, no great, no great brand is like, nah, nah, it wasn't really. Uh, you mentioned your team there. Um, I do want to dig into delegation. It's something that I struggle with actually as a leader to be blunt. How do you think about delegation today and what only you can do versus what you are willing to delegate?

A I think delegation is a, is a lost art for a reason. Delegation is not ingrained in human beings. It is not taught to us in school. There's no teacher in the world that is going to say, Nick, I want you to write a four page report on this book, but I want you to get somebody else to read the book, and I want you to get somebody else to write the report. It's, it's, it's non-existent in sports. Your coach is never going to be like, hey Nick, um, I want you to do, you know, three circuits of these exercises at track practice, but I want you to find some freshmen to do those exercises for you while you sit back and watch them. You go to college, and you start to study books, and science, and, and all these different things, and the answer's always a couple steps back, and it's about you doing the work. All of it is about you doing the work, and you becoming competent, and doing the work yourself, and some can argue that it's the industrial revolution of just the way the government needed to create schools, and a culture to create employees that can go to work, and follow tasks, follow, follow the rules. Like, hey, sit in a seat, and do the same job over and over again. If we build a workforce that can do that, America will thrive. A lot of arguments around that. But also just delegation is really hard. So what happens is you have a bunch of 21, 22, 23 year olds graduating college,…

AI assessment note: “Delegation is not ingrained in human beings. It is not taught to us in school.”

Q So my question to you on the back of that is, I agree. I understand. The challenge you have is to delegate, especially decisions, but even tasks, you have to have trust. Do you trust people on day one and allow them to run in both tasks and decisions? Or is it built over time with achievements that they prove out?

A Absolutely. As a manager of people, your, your job is to get a look into somebody's brain and constantly be judging their ability to Delegate. When you start a company and you have a small team, imagine all the employees. This is a, uh, you know, a way to think about this. Imagine you're the boss and you're sitting in the corner office and you have five employees. They're all doing tasks. Every day they walk into your office with a problem that they need solved. That problem is a monkey that's on their back. Imagine a monkey literally just raising hell, pulling out here, pulling their hat off. Um, that's the problem. They walk into your office and they say, Hey Nick, I've got a problem. And they tell you their problem, and instantly that monkey jumps off of their back and onto your desk, and now it's your problem as a business owner. Most business owners, most business owners are just going to send the employee away and keep the monkey for themselves, the problem. And then all day employees are walking in and monkeys are getting dropped off in your office. And before you know it, your entire company is a zoo. You are the bottleneck. You're the zookeeper. You're putting away monkeys and all the problems are your problems. The way to do it is an employee walks in and they give you a problem and you're, you're not gonna, you're gonna make sure that they walk out of your office wit…

AI assessment note: “and they never start to trust their employees to actually make decisions”

Q How do you fire? It's really hard to do.

A There is no easy way to fire somebody, and you talk about what it's like as a business owner and why, you know, it's not for everybody. One of the things I've changed my mind on is that five years ago, I thought entrepreneurship was for everybody, and now today, I don't believe that anymore. The fact that you have to let somebody go in your company who was in your wedding Three weeks earlier, and they're crying in your arms, looking at your eyes, saying, how am I going to, you know, my wife's pregnant. How am I going to, like, what am I going to do, Nick? What, what do you want me to do when you got to let them go? And it does, it, it, I've done it a lot of times and it never, ever, ever gets easier.

AI assessment note: “There is no easy way to fire somebody, and you talk about what it's like”

Q Talking about choosing to go about life, and sorry, I sent you a schedule, but I'm just too interested in this discussion. Ah, ah, you, I think people change a lot, and kind of self-reflect a lot. When you think about your biggest moments of change and self-reflection, what do you think your one or two biggest have been?

A I have a, a theory that there's a very dangerous thing about being successful. Especially when you're notable and you have 300,000 people on Twitter hanging on your every word, it can get very dangerous because you start to, now this is gonna sound funny, but you start to kind of be your own idol. You start to be your own god. And you start to think that, oh, maybe I am just special. Maybe I am. Like, look at all these ways that I'm winning. Look at all these people who really hang on every word that I say. And that gets very, very, very dangerous. And if you don't have an open mind, you start filtering information based on what supports your opinions, and you can lose massive amounts of money, you can turn into a complete asshole, and you can change for the worse. And it happens to a lot of successful people. I have a little sticker on my mirror above my, above my sink, because my grandfather gave me amazing advice, said, Nick, you're going to do amazing things in life, but if you don't remain humble and kind to people around you, then it'll all be for naught. And you're going to pass on things to your kids that are not great. And you're going to be, you're going to, instead of being a positive influence on a lot of people's lives, you're going to become a negative influence. I have this little sticker on my mirror that I see every morning when I brush my teeth. It says, chang…

AI assessment note: “I have this little sticker on my mirror that I see every morning”

Q you've been stress testing your mind across many different disciplines, and respectfully, they've been bringing up children, but it's not intellectually always as stimulating and challenging, and for the person who's been working, it creates this chasm where it's like, what did you do? Oh, I looked after the kids. It's the same. Is that ever a challenge? Do you worry about it kind of not being intellectually stimulating enough?

A Yeah, I'm exhausted when I get home. Like, I'm, I'm gonna get off this interview, and I got three more meetings today, and then I gotta work out, and then I'm gonna get to dinner with her, and yes, I'll, I'll have to turn it on to pull up some more energy to have a conversation with her. But look, we have a lot of childcare. We have a nanny. We have, the kids are in school. My wife has a lot of friends. She has a packed social schedule. She has workouts that she does and does. She has more girlfriends That she goes and spends time with. And I think it's really, the sad part is, is that women are so isolated. They're so isolated. There's no community. Uh, 50 years ago in small town America, all the sisters and siblings and friends lived on one block, and they were popping in each other's houses, and they were having dinner constantly, and it was, it was a community. They were raising kids as a community. The women were together. And today men build businesses in lonely environments and women raise kids in lonely environments. And it can be really hard if you have that traditional structure. Now, obviously not everybody does what my family does, but.

AI assessment note: “And I think it's really, the sad part is, is that women are so isolated.”

Q but you feel something. And that's the most important thing. Uh, no great, no great brand is like, nah, nah, it wasn't really. Uh, you mentioned your team there. Um, I do want to dig into delegation. It's something that I struggle with actually as a leader to be blunt. How do you think about delegation today and what only you can do versus what you are willing to delegate?

A I think delegation is a, is a lost art for a reason. Delegation is not ingrained in human beings. It is not taught to us in school. There's no teacher in the world that is going to say, Nick, I want you to write a four page report on this book, but I want you to get somebody else to read the book, and I want you to get somebody else to write the report. It's, it's, it's non-existent in sports. Your coach is never going to be like, hey Nick, um, I want you to do, you know, three circuits of these exercises at track practice, but I want you to find some freshmen to do those exercises for you while you sit back and watch them. You go to college, and you start to study books, and science, and, and all these different things, and the answer's always a couple steps back, and it's about you doing the work. All of it is about you doing the work, and you becoming competent, and doing the work yourself, and some can argue that it's the industrial revolution of just the way the government needed to create schools, and a culture to create employees that can go to work, and follow tasks, follow, follow the rules. Like, hey, sit in a seat, and do the same job over and over again. If we build a workforce that can do that, America will thrive. A lot of arguments around that. But also just delegation is really hard. So what happens is you have a bunch of 21, 22, 23 year olds graduating college,…

AI assessment note: “Delegation is not ingrained in human beings. It is not taught to us in school.”

Q So my question to you on the back of that is, I agree. I understand. The challenge you have is to delegate, especially decisions, but even tasks, you have to have trust. Do you trust people on day one and allow them to run in both tasks and decisions? Or is it built over time with achievements that they prove out?

A Absolutely. As a manager of people, your, your job is to get a look into somebody's brain and constantly be judging their ability to Delegate. When you start a company and you have a small team, imagine all the employees. This is a, uh, you know, a way to think about this. Imagine you're the boss and you're sitting in the corner office and you have five employees. They're all doing tasks. Every day they walk into your office with a problem that they need solved. That problem is a monkey that's on their back. Imagine a monkey literally just raising hell, pulling out here, pulling their hat off. Um, that's the problem. They walk into your office and they say, Hey Nick, I've got a problem. And they tell you their problem, and instantly that monkey jumps off of their back and onto your desk, and now it's your problem as a business owner. Most business owners, most business owners are just going to send the employee away and keep the monkey for themselves, the problem. And then all day employees are walking in and monkeys are getting dropped off in your office. And before you know it, your entire company is a zoo. You are the bottleneck. You're the zookeeper. You're putting away monkeys and all the problems are your problems. The way to do it is an employee walks in and they give you a problem and you're, you're not gonna, you're gonna make sure that they walk out of your office wit…

AI assessment note: “they never start to trust their employees to actually make decisions”