The Learning Leader Show With Ryan Hawk - 608: Anthony Pompliano - (How To Live an Extraordinary Life) Luck Is Not Real, Surround Yourself With Compounders, Fire Your Boring Friends, Get On The Plane, Practice Simplicity, & Taking Big Risks608: Anthony Pompliano - (How To Live an Extraordinary Li

Episode Date: November 11, 2024

Go to www.LearningLeader.com for full show notes Read our book, The Score That Matters https://amzn.to/3Yrxfj8 Notes Luck is not real – "Luck is something we conjure in our minds to grapple with the consequences of whatever life may throw our way. Luck is a physiological concept. It's determined by how we view a situation. Academic studies show that you can become luckier simply by telling yourself that you are lucky." Pessimists sound smart, but optimists change the world. Believe in yourself. Have agency. Strive to make something happen. "Luck is the flip side of risk. They are mirrored cousins, driven by the same thing: You are one person in a 7 billion player game, and the accidental impact of other people's actions can be more consequential than your own." - Morgan Housel Surround yourself with compounders and fire your boring friends– Being around other ambitious people who are willing to push you will make you better. Strike the balance between being loyal to longtime friends, and doing anything for them, but spending the bulk of your time around people who will push your edges and make you think bigger. Fire your Boring Friends - "If you are optimizing for living an extraordinary" life, you have to fire all the boring friends and find people living extraordinary lives." You don't get what you don't ask for. I love the story of Anthony meeting his future wife, Polina, for coffee and asking for the next date for that same night. The answer is NO if you don't ask. It's worth the potential rejection because the upside is so great. In this case, they got married and have two children. The people who sustain excellence are not afraid to make the ask. Get on the plane -- When in doubt, go see them in person. "Experience is a liability when it comes to setting expectations." Sometimes, ignorance is bliss. Not knowing that something is supposed to be hard can be useful. Respect other people's time - "When I was playing football in college one of our coaches used to say, "5 minutes early is on time and on time is late." By respecting other people's time they will realize you are a serious person. Childhood is not a crutch — Don't have a victim mindset to use childhood as a crutch for poor behavior. "It's easy to use your childhood as a crutch instead of seeing it as a chisel." - Cameron Hanes Simplicity signals mastery — Tim Urban is the master at this. As a writer and/or teacher, your writing should make the reader feel smarter, not dumber. Using big complicated words and sentences shows that you don't know what you're talking about. The world seems to separate itself into two groups - the people who never stop learning and everyone else. Document Good Ideas – Ideas run the world. "I created a system that works well for me. I broke everything down into four areas where I could find a good idea. Books, social media, conversations, and audio/video content. Advice: "Seek risk. What is the riskiest thing you can do? The greatest returns are on the other side of risk. Run towards the risk."

Fear is a silent killer. It can kill your dreams. It can kill your goals. It can kill your action. And it's because you're scared of taking action and not working. Anthony Palmdiano and we're on The Learning Leaders Show, how to live an extraordinary life. Leadership is actually an act of service.

It's there to help somebody else. It's really about how do I serve the people who I'm supposed to be leading? Luck is not real. If you go through life thinking that every outcome is just based on was I lucky or was I not, you have no agency. I like the idea of surrounding yourself with compounders. They're not just compounding their businesses, revenue, their income. They're also compounding their knowledge.

This idea of simplicity signals mastery. The people who have true mastery explain things so simply that you kind of are like, that was the worst thing that happened in my life. And it all is, how do you choose to think about it? Seek risk. Everything in your life has been beat into you that risk is bad, but the greatest returns are on the other side of risk. Welcome to the Learning Leaders Show, presented by Insight Global.

I am your host, Ryan Hawk. Thank you so much for being here. Tech Hawk to 666866 to become part of Mindful Monday. You, along with tens of thousands of other learning leaders from all over the world, will receive a carefully curated email from me each Monday morning to help you start your week off. Right, you'll also receive details about how our book, The Score That Matters. will help you become a more effective leader. Text Hawk to 66866.

Now, on to tonight's featured leader. Anthony Pompliano is an entrepreneur and investor. He's the founder and CEO of Professional Capital Management and Investment for Focused on Building and Funding Companies to Solve Difficult Problems in American Society. He's also the author of a great new book called How to Live an Extraordinary Life. During this conversation, we discuss the leadership lessons he learned. serving an Operation Iraqi Freedom as a sergeant in the United States Army.

Then Pomp shares why luck is not real. Then why you need to surround yourself with compounders and fire your boring friends. Then being willing to ask for what you want. He tells an amazing story there. And then we go deep on why simplicity is a signal for mastery. We talk about that and so much more. Ladies and gentlemen, please enjoy my conversation with Anthony Pompliano. Let's start with your time as a sergeant in the United States Army, 2006 to 2012.

First, thank you for your service. That's amazing. A veteran of Operation Iraqi Freedom. And you also were the distinguished leader graduate of the warrior leader course and a commandments list graduate of infantry leadership school. A lot of leadership stuff here, which is what this show is all about, Pomp. I would love to learn maybe a specific lesson or two or even an example from your time in the military where you really developed great leadership skills that have then helped you later in life. I mean, there's a laundry list of things that I learned. Some of them were specifically taught to us.

And then some of them you kind of pick up through practice. One of the most important ones is that leaders eat last. And a lot of folks who want to be a leader who want to lead an organization, They have to be somewhat egotistical, right? You kind of have to be a maniac to want to actually be the person who has all of the upside, but also all of the risk. But what you learn over time is that leadership is actually an act of service. It's there to help somebody else.

And this idea of leaders eating last, if you come off of a mission and you go into the chow hall, you want every single one of the soldiers that is on your team to eat first and then you eat last because what if there's no food left at the end? what if something happens and all of a sudden you got to run out and go do something else and they didn't get to eat right it's all about taking care of them and the misnomer about leadership is that it's all about you as the leader but instead it's really about how do I serve the people who I'm supposed to be leading and I think that's a really big lesson there love that one of the other uncommon common commonalities we have or I should say one that we have we do not have a commonality of the military

you were in I did not but was that we both have played college football and you wrote about in your book, how to live an extraordinary life about the idea of being on time when what really that means is being early and you learn that playing college football. I learned the same thing for both my high school and college coaches. And by the way, publicly note you showed up early to this podcast. So it's not just something you write about in the books. You live it yourself. I think this is undervalued, but so important. Be on time. Be early. Respect other people's times. And this is one of the lessons. We're going to get into a lot of them,

but this is one of the lessons that you write about to your kids. Why is it so important to be on time and or be early? So when I first learned the lesson, many people in my life had kind of told me, hey, be on time, be on time, but it never really resonated until when I was in college, we had this coach. And frankly, he's kind of a quirky guy,

but he kept saying over and over again, five minutes early is on time. On time is late. And so I think it was actually the way he said it was just like something that was memorable. And then the military obviously is very kind of punctual and kind of schedule based. But really it comes down to not only are you respecting your time, you're respecting the other person's time, but you're showing up prepared. And I got a really busy schedule in my professional life.

I can't be on time to every single thing. Sometimes I'm on a call and somebody is just going on and on and on. I'm trying to get off, whatever. I hate being late. If there's one thing that I hate, it's that. And so it's not about are you perfect, but it's the fact that 95% of the time I am a few minutes early. I'm on time. I'm prepared.

I'm ready to go. All that kind of stuff. And what I have learned is if you take that mentality into the day, all of a sudden, you get more disciplined. And so time is almost this like proxy for everything else. You're like, okay, well, if I only got 30 minutes to do something on the calendar and I got to be on time to the next thing, then I better get it done in the 30 minutes. And so is this way to use time as like an organizational kind of hack to then make sure that you're actually being productive and getting the things done that you need to. The in season elements of football. So in the fall, you're in season and in the spring, you're out of season.

You're still working out and doing all the spring ball and all that stuff. But I actually got better grades. When I analyzed, I was in college for five years, I got better grades in the fall than I did in the spring, in season versus out when the schedule was in. Right. Early morning lifts, get your classwork in, then get straight to the facility so you could watch film, get ready for practice, then practice, then watch more film. And then you had a limited amount to do your schoolwork. Then you had to go to bed. That was basically every day. And then you played on Saturdays. What was it like for you having such a regimented schedule in the fall versus the spring? And how do that impact you as a student? Yeah, I was a horrible student in the first semester of college. Pretty much I went from pretty regimented in high school. Somebody takes you to school. Somebody picks you up from school.

Like there's all these different components to your parents are there to kind of oversee. Like, hey, did you do your homework, whatever? And so getting to college, it was like, I just, nobody's going to check. Okay, I'm not going to do anything. And so I got really bad grades. And there was kind of like a come to Jesus conversation, both with our coaches and with my parents. And after that, I never got, I think anything below like a three, five. or something, right?

Like, took it very serious. I was like, hey, I need to go and do this. And a big piece of it was getting a regimented schedule. When do I study? If I go into the day and I'm just like, I'll do it at some point today, I probably am not going to do it. But if I know, okay, from two to four o'clock, I don't have anything to do, but I know I got practice and stuff later, I got to get it done between two to four o'clock.

I get the work done. And so it became this thing of the regiment was really powerful. Now, one of the things I will say is when I was in college, I had both the blessing and the curse that I had already enrolled in the military. And so I was in the reserves. And so my kind of college experience was I went to class and did all kind of the normal school stuff. I played football. And so practices, lifts, film, travel, all that. But then also one weekend a month, I had to go do my reserve duty. And so on those reserve weekends, I would basically go to class on Friday. I usually would have Friday afternoons open. I would then go to the military,

like barracks, right, or the armory, I would check in. I would leave to go to practice. I'd practice. I'd do all the stuff, kind of pregame stuff on Friday night for the game on Saturday. I then would go and play in the game on Saturday. Afterwards, I'd have to go check in at the armory. And then on Sunday, I would be there all day for that reserve duty. And so it was like the regiment of playing football in college on steroids.

But what was great about it and was really powerful was I also saw great. grown men. I was 18, 19, 20 years old. And so my like schedule involved, you know, what's the party after the football game, right? Like what, you know, I got to do some homework. These guys have, they're coordinating their kids, picking them up from school, taking them to practices and stuff. They got mortgages, right? They got real life things. And so it was really a blessing to not only get the regiment, but also to see people who had to be even more disciplined, more organized, more serious kind of ramifications that I think really hammered at home for me. What made you sign up for the reserves going into college?

I think I really wanted to do something in the military, and part of it was service to the country. 9-11, I think probably had a more profound impact on me than I realized when I was younger. I think also a huge part of it was seeing Pat Tillman and him walk away from the NFL contract and go do it, and me knowing I was going to go play football in college, but if he can do it from the NFL, like, why can't I do this? And then I think, you know, frankly, there was another element that, you know, was a mix of like, I wanted to test myself, you know, you see the commercials, you see all this stuff.

Can I do that? But also it looks fun, right? They're going to like pay you some money and you're going to like go shoot guns and, you know, run around. It's like, okay, that sounds awesome. And so I was able to figure out a way there was this contract that they used to have back in the mid 2000s, which basically was like a four year reserve contract and then you did four years active duty afterwards. But usually those contracts are used by people going to college who enroll in ROTC. And so you can't get deployed when you're in that ROTC program. I did not do the ROTC program because I had football and school and the reserve duty. And so during my junior year, they called my unit up.

And I got deployed when I was a junior in college because I was unprotected. And so it was this kind of, you know, at the time, I didn't, I don't think I quite realize like how much of a gamble I was really taking. But it was a great experience because if you're going to get deployed, you know, going at 20 years old, it's probably the time to go. What was that first deployment like when you're still a college student? You grow up, right? You know, again, you're going with guys who, you know, I'm like calling my family. I call my parents or my brothers. You know, maybe there's a couple of friends from college or whatever.

These guys are like, I'm missing a year of my kid's life to be here. And you're just like, dude, I don't know if I could do that. Like that's, that's, you know, pretty profound. That's pretty, you know, kind of heavy. And then, you know, you get all the kind of normal stuff that happens. You know, guys are deployed and their wife leaves them or they find out that their wife's cheating on them or they're having trouble paying bills because they're not actually working their normal job because they're in the reserves and the military pay is less than what they

were making before. And so you just see all this and you realize, look, this is a very, I think, admirable thing to serve alongside some of these guys, but also like they got to deal with real life issues. They got to deal with the things that are going to be the life they're going to go back to, right? And so in a weird way, it made me grow up very quickly and realize that after college, hey, there's a real world out there. You got to be prepared for this thing. Speaking of kids, that is how you chose to put together this book, How to Live an extraordinary life, essentially 65 letters to your children. And it's like, it's like a lot of things when you give advice to your kids.

It's really useful for everybody. And that's what I found from reading through your 65 letters. So I appreciate you sending me a copy because it was just super insightful and fun to read and also really entertaining. And if you're cool with it, I'd love to pick out. a few of the ones that I really liked and we can just riff on it. Is that cool? Let's do it. Luck is not real. Luck is something we conjure in our minds to grapple with the consequences of whatever life may throw our way. Luck is a physiological concept. It's determined by how we view a

situation. Academic studies, in fact, show that you can become luckier simply by telling yourself that you are lucky. This seemed like an important one you wanted to get in early to your children. Why is it so important for them to know that luck is not real? If you go through life thinking that every outcome is just based on was I lucky or was I not, you have no agency. The world just happens to you. Instead,

when you realize that luck is just something that you made up in your mind, it's not a real thing. And the best example that I give is, let's say that you and I are both walking across, the street, we get hit by a bus and we both lose our leg. Somebody comes to the hospital and they come to your hospital bed and they say, you know, hey, you lost your leg. What's going on? I was so unlucky to be walking across the street. I lost my leg. And they say, wow, that is pretty unlucky. And they come over and they talk to me. And I say, I was so lucky to be standing where I was because I'm still alive.

Same situation, same outcome, two different perspectives on life. And so what that shows is that luck is just a thing that is in your brain. And the reason why it is important to understand that luck is not real is because then when you go through these scenarios, you start to look for the positive things. You start to look through the optimistic lens. You start to look for what is lucky about this. And it sounds almost trite to a degree. But when something bad happens, if you can simply say, what did I learn? I'm so fortunate to have gone through that event because look what I got to learn because of it. it reframes it and it puts you back in a position that gives you the power and the control in the situation. And again, it goes back to this idea of why does a kid need to learn that?

It's applicable to so many things in your life. It's going to be applicable to your personal life, your professional life, relationships, situations that happen to you literally walking down the street all the way to the biggest moments of your life in sports or work or whatever. And so it really is this idea of like give agency back to people by them realizing that they are in more control than they previously realized. I also think about the type of people you want to surround yourself with. So, for example, I don't find it really attractive to be around people who use the phrase like, with my luck, and then they fill in the blank with something bad.

And so much so, I will never forget this pomp, especially because I know Polina from having on the show and how good of a relationship for you guys have, but my wife, it was about a week before our wedding. And the forecast, it was showed that it was going to rain. And most people don't want it to rain under wedding day, whatever. And she, she looked to me and she said, well, with our luck, it's going to be a bright, sunny, beautiful day. And that was awesome. That is the type of person that I want to spend my life. That's the type of person I want to be around every day that, that uses phrases like that, not the one that everybody else does, but saying it's going to well, optimism, belief.

Like, that doesn't guarantee it's going to happen, obviously. But it's much more enjoyable to be around that type of energy of optimism and belief. And I think that person, the people like that, have the much greater chances of doing extraordinary things, as you would write, versus the ones who say, well, with my luck, and then fill in the blank with something bad. I think that's right. The idea that you believe you're lucky creates more luck is very similar to just like when you want good things to happen and you put kind of good vibes out into the world, somehow, some way

that's unexplainable to me, good things start to happen. And so it is kind of goes back to this conversation around leadership. Like leadership is all about service. Maybe in a weird way, you know, your relationship with the universe is if you serve the universe, if you put out good vibes, if you put out optimism, if you put out, you know, things that help other people, it just comes back to you. And again, I can't explain it, but it's one of the lessons I picked up in my life that I think is really important for my kids to learn. Well, the Morgan House will quote. I'll paraphrase, but essentially pessimists sound smart, optimist changed the world, right?

Those are the ones who actually make something happen. You have to have belief. You're doing big things in your life in a number of different areas. You can't do that if you're a pessimist or a cynic. I think the only way you accomplish the type of things you've already accomplished at a very young age is to this belief in yourself, belief that good things are going to happen. And then you compound that with a massive work ethic. And I like your chances of good things happening to you. I think that's a great way to look at it. I like the idea of surrounding yourself with compounders. And you wrote about your friend Martin. That's not a real name. But I love for you to tell the story of your friend and why it's such a good idea to surround yourself with compounders.

So my friend is upset because I didn't use his real name, although I thought that he would be. You're welcome to say it now if you want. Oh, no, no, no, no. We're going to keep it how it is. But yeah, I mean, look, it is the easiest way to understand this is think about ambition. If you're a highly ambitious person and you surround yourself with people who are not ambitious, it is unlikely that you are going to learn, grow, accomplish your goals, etc. Because what's going to happen is you're trying to be highly ambitious and grow, and they are unintentionally pulling you down.

If you have a bunch of friends that always tell you, be realistic. Stop it. Be realistic. What does that do? It naturally just eats at you and it desensitizes you. And it begins to kind of become this weight. And so instead of trying to change your friends and say, no, no, no, you should be more ambitious. You should be more interested in growth, whatever.

it's usually easier to just go find people who are highly ambitious already and kind of like sprint alongside them. And so I'm very fortunate that I meet a lot of people. I've been able to find a couple of folks who I think are one highly ambitious, two, that they've been very successful in their chosen careers. And then three is they understand the power of us working together, even if it is not kind of in a formal way, but just being friends, being supportive of each other, cheering each other on, telling each other. Like, actually, you think you're being ambitious.

is I don't think you're being ambitious enough. Right? And so I remembered early on, one of the things that I told my wife was there was situation and she was kind of, oh, I don't know, whatever. And I said, never let somebody else, in that case, me, believe in you more than you believe in yourself. But, man, is it really powerful to have people that really believe in you, right, who really push you to be more ambitious, to be more successful to do all this stuff?

And so in that relationship, what you're looking for is the exact opposite of the friend who says be realistic. Instead having people who say, you know what, you think that you're being ambitious. I actually believe you can do something even greater than that. And if you really think about most people's kind of circle of friends, almost none of them are those type of people. And so what you have to do is you have to work at it. You have to be intentional. You have to go find those people because they're so rare. and then you have to figure out

how do I spend as much time with this person as possible and usually one of the ways that you can get them to spend time with you is you offer that service to them. Again, this idea of service being, okay, well, am I the type of person that will say to my friends, you think that this is good? I think this is only 50% of what you can accomplish. Why are you not trying to do, you know, A, B, and C thing that's, you know,

10 times bigger? And then what you find is all of a sudden that permeate, through your friend group and all of you start to think and act that way and you all start to kind of reinforce it and it becomes this really really powerful kind of collaboration. And then you almost normalize exceptional performance. Your level of normalcy just gets higher and higher and higher. And before you know, you look around like, oh my God, look what we're doing here. You know, where five years ago you would have thought that would be crazy or that was insane.

But now it's just normal. It's just the way you are. Do you have an example or a story of a person maybe who has done that for you? And then the result of that is maybe one of the things that you're doing today? I am very fortunate that I've got a number of friends who we've known each other for a long time. And we weren't friends like in high school. We all met kind of in our professional life. But I'll give you three quick examples.

Martin, who I allude to in the book, runs a business that's worth about $500 million. And whenever him and I talk, it's just like, who can go bigger? Who can, you know, kind of even dream bigger, let alone actually do things that are bigger. And so it's very invigorating and very motivating. I was at dinner with a friend last night who over the last year he had built a company and he sold it to a public company. He's now done his year there. He's going to leave.

And we start talking about what's he going to do next? But like you're sitting down with a friend who's a very dear friend of mine, somebody that I'm very close with and I really respect. And now he is walking out of this company as a founder who built a company, sold it to this public business, got a track record of success and the world's at his feet. And so he's talking about, I want to design my life in a certain way that checks off, you know, A, B, and C boxes. It's pretty hard to not walk out of a dinner like that and say, damn, am I doing what I'm telling

him to do, right? Am I fulfilling it? Am I living up to the same standard? And then I've got a third friend who runs a very large asset management firm manages, you know, over $3 billion. It's in his 30s. It was very rare for somebody that young to be able to build such a big firm that quickly. And every time I talk to him, he will sit there and he'll sit there and he'll say,

say, well, this happened, this happened, this happened. And I'll leave and I'll say, I got to get going, man. I got like, you know, he's rocking. And, you know, I hope he walks away from the same conversation. He's like, damn, I got to get going. And we probably both could kind of nitpick. What are the things I like about his business that I wish I had in mind and vice versa? But it's done from this supportive standpoint of if I ever meet someone that I think can be helpful to him, I want to be as helpful as possible. And so we're cheering for each other kind of in this like implicit, you know, way that again goes back to if there's ever an issue, damn, I got a great group of people that I can call and say, I'm confused.

I don't know what to do. And they may not have the right answers, but they can help me get to the right person. They can help me figure out maybe some examples in history or kind of think through it with me. And so that's the whole idea of surrounding yourself with these compounders is they're not just compounding their businesses, their revenue, their income. They're also compounding their knowledge. They're compounding their networks. They're compounding their experience.

And so you just want to be around people who are doing things. and then you can use them as resources as you continue doing things as well. It reminds me of Scott Belsky. He's probably one of your friends or I would assume you guys have met because he said he looks for people who are much more interesting each time he sees them. He looks to hire people like that. When I asked them for some of the things he looks for and people, I was like, I've never heard that. I'm like, what do you mean?

He's like, well, they're the ones who are moving, meeting people, doing interesting things, traveling, reading cool stuff. they're more interesting each time I see them because they're an active participant in life. And I thought, ah, yeah, that's a big part of it. Think big. Be an active participant, right? You write about you, you're not going to make anything happen on the couch. Like, you got to get out there. You got to do it. And I like that kind of as a proxy for a compounder is every time I talk to them, they're learning something new. They're implementing something. They're trying something. It doesn't always work, but they're moving. They have action. I think having that bias for action.

again, gives you a better odds of something going well versus sitting on the couch. I could not agree more. And it really comes back to this idea. I think it was John Rockefeller was famous for finding smart people, not even having a role for them, but just saying, come work with me. Like, we'll figure something out. And when I read that, I said, I'm going to start doing the same thing. Rob, I'm just going to steal that idea.

And there are multiple people who work with us who we just met them. We really liked them. We thought that they had huge asymmetry to their career. and we said, you know, we want to work together. Like, let's figure out a role for you. And they are probably some of our most productive, valuable, you know, kind of teammates. And so the more that we can do that, obviously we want to. A collector of amazing people.

On the flip side of that, you got to fire your boring friends. If you are optimizing for living an extraordinary life, you have to fire all the boring friends and find people living extraordinary lives. Some people might not like this. Oh, Pomp, aren't you loyal to your elementary school friends? they're boring. I'm not. I'm curious, like, how do you juxtapose loyalty with long-term friends if they're boring? You can be loyal and still fire them. And so if you think about, you know, I have a lot of friends that I've known for 20 plus years. And if they called me, I would do

anything for them. I literally give them the shirt off my back. The loyalty runs so deep because it's not about money or any degree of success or anything. It's just like I genuinely care about these people. But I also understand I can't hang out with them every day. I can't see them six times a week. I can't talk to them because the things I want to accomplish require me to be surrounded by people who are the compounders. And maybe some of these people aren't.

And so what I need is I need to strike the balance between having a lifetime of loyalty for people, even if I don't talk to them frequently. And so I have friends who I didn't talk to for five or ten years. And then they called me and they needed help with something. Done. Easy as ask of the day. But I don't talk to them every single day because they're not the type of person that's going to help me get where I need to go.

And so having that balance is very hard. But if you can figure out how to do it, it's very powerful. because it allows you to continue to serve the people you've met throughout your life, but also understand who are the people I need around me right now to help me grow to where I need to be. And maybe the best example of this is like, think of a company. We have people who have worked with us over the years. They don't work with us anymore. They wanted to go work somewhere else.

It wasn't a fit. Whatever. Every single one of them knows they can call me and I will do whatever I can to help them. Reference calls, give them advice, whatever. but they're not on the team today. And so your friends are similar. Who's on the team today? Isn't necessarily every person you've ever met.

But you can still be loyal to the former players. Right? Like you can still look out for them. You can still make sure that everything's good. You just know, like, they're not at practice today. They're not playing in the game on Saturday. And so that difference of kind of what is the role or what is the relationship can evolve, but it doesn't mean that you get rid of them.

It just means that they just mean. shift to a different kind of position and that's okay that it's actually a good thing it means you're growing there's a Naval tweet about this it's a signal and a marker for growth right that there are some friends who just are at growing at a different trajectory or even going in the opposite direction doesn't mean you're not you still wouldn't do anything for them if they called but you're probably not going to see them as much probably not going to talk to them as much because you're choosing to surround yourself with compounders and that's a signal and a marker for growth that that's just part of life Again, it doesn't mean you're not a loyal friend or a little person.

You're just not going to spend as much time with them. I think that's part of an audit you can do for yourself is thinking about that. Am I surrounding myself with compounders or not? Are these people pushing me? They're lifting me up. I remember I just had a one-on-one six months ago with the CEO of Insight Globe one named Bert Bean. Bert's an amazing dude.

And I had this like big report written up. This is all the things I've done. I'm really, you know, it's really impressive. And here's what I'm doing in the future, all this stuff. And I was expecting him to be impressed. when I met with them. Wow, dude, this is really good. Big growth, good stuff happening. This is great. And he looked at it and he goes, he kind of put it down and he goes, dude, you're not thinking nearly big enough. I was expecting you to ask me for a few million dollars to make a Netflix show

out of your podcast. What are you doing? Why aren't you thinking bigger? And I thought, that's a CEO. That's a leader. That's what you should be doing. He was, I'm sure like he knew I need to push. I need to push. This guy has a higher capacity to do more. But almost not a lot. lot of people are willing to do that. So when you find them, they are such gold that they're willing to challenge and push you. I encourage people that same thing. That's why that struck me so much of surround yourself with the compounders and fire the boring friends because it will literally change your life. It's also, it's contagious. Yes. Right. And so literally yesterday in our office, somebody said to me, be realistic. And if there's one phrase I hate,

to that phrase. But I explained to this person, I said, you know, why do you think that it's not realistic? And they said, well, we're working with this other company. There are a partner on something. And they have a lot of experience. And they said that that's not realistic. And I said to this person, I said, you know, experience is a liability when it comes to setting expectations.

If you think about that, experience is a liability when it comes to setting expectations because what do people do? they just fall back on what are the previous results that they got. And so if you had gone to the rocket companies and said, let's build reusable rockets, they all told you, come on, be serious,

be realistic. You needed somebody who had no experience to have a different set of expectations. And so I think that a lot of that lesson can be applied to just everyday, you know, parts of your life when it comes to, you know, what is the expectation you have of yourself, of the people around you, the things that you're going to do, et cetera. Yeah.

This is why it's good to have a mix of less experience slash younger people mixed with others because I remember I was I was a sales rep in 2008. And when I was interviewing, I was selling at Lexis Nexus, like legal information tool, I remember. And as I was going for interviews to get promoted or other jobs, they were like, oh, my God, how did you handle 2008? And I was like, what do you mean? They're like, that was just, it was just such a terrible year for the economy.

Everything was brutal. I was like, honestly, I watched a sports center. I worked out all the time in the gym. And then I tried really hard to sell a ton because I wanted to make money and be first on the stack rankings. I didn't even know the economy was bad. This ignorance was bliss in the fact of there was no expectation that it should be hard. It was like, I'm just going to go and do the thing. And I think that part of it, that inexperience or a little bit of.

of ignorance, didn't say, oh, well, it's just bad economy. So let's just ride this out and wait until it gets better. It's no, you got to go. Like, we don't have the choice to not hit the goal or to not get after it, regardless of what's happening in the world. I'm going to keep at it. And I think sometimes that can be a really useful way to go about your business, as opposed to putting these self-imposed lower expectations because of something that's outside

of your control. I do think that one of the things. I'm fond of saying to people who work with us is that fear is a silent killer. It can kill your dreams. It can kill your goals. It can kill your action. And it's because you're scared of actually being rejected, of actually, you know, taking action and not working. And so if you think of it, it's like a weird self-censorship. You know, how many people have something to say? They don't want to say it online and they self-censor themselves. Yep. Well, fear does the same thing in your life, which is, I want to do this thing. What if it doesn't work? What are my first?

friends think that I'm not cool. What if my family, you know, makes fun of me? And so fear is a silent killer is this, you know, idea that just reminds you, like, if luck's not real, neither is fear. It's just something you made up in your mind. And so just go do it. You, this just came to be based on you have, there are four boys in your family. Is that right?

Five. Five. So you have four brothers? Yes. Okay. What? And they're, they're all like, from what I can see. I don't know them, but doing quite well.

What did your parents do to raise such hardworking, gritty, tough, resilient, get after it type kids? I've talked to them about it because, you know, frankly, when you're growing up in a family like that, you don't have other data points. So you don't know what's, you know, the same or different. You're just like, hey, this is how everyone's life gets lived. I think that my parents did a couple of things that probably were in hindsight valuable. one was they spent time with us and really was my mom you know she spent a lot of time with us two if you ask my father he would tell you that the single most important thing they did is they just loved us they genuinely cared they wanted us to be successful they wanted us to you know figure things

out they were mad when we did something that was dumb but they also took it through the lens of you know we learn from this and so i think that just like having good parents usually leads to having good kids which is simple but but powerful on top of the that, I think that they did a great job of really instilling in us hard work. And a huge reason why they were able to instill that is because we saw them work hard. And then on top of that, probably one of the best decisions they ever made was we lived in an area where every kid was constantly asking their parents for an allowance. Or I grew up in an age where we got cell phones in high school. All of a sudden you can drive. You got a phone. They get a little bit more freedom than maybe, you know, just 10 years before.

The internet had just like hit. And now all of some people had, Facebook came to high school when I was a senior. Like that was big deal. You know, all that kind of stuff. And my parents always took the approach of if you want $20 to go to the movies, like you have to do something. And we're not talking like Herculean tasks, right?

You know, rake the leaves, do this, do that, whatever small thing around the house. But it tied the idea of if you want X, you got to do Y to get it. And it was an implicit lesson, right? It wasn't something that they like harped on it. They didn't rub it into us. Like you don't have any money or anything like that. But it was very much this belief that like kind of capitalism works.

Maybe it was the lesson. And then probably the single greatest thing that my father really, I think, used to explicitly say is he would say to every single one of us in some form or fashion, you know, I genuinely believe you can do anything that you want in the world. No matter what you pick. I think that growing up in this house, the way that you guys are, how you guys act, you can accomplish anything. And I think some parents say that to their kids. And maybe they almost say it

because they feel like they're obligated to say that. For whatever reason, when my dad said that, I believed it. And so that's really empowering for a young, especially young man, right? Where you're like, oh, you know what? Dude, this guy that we look up to, he really believes that we can do anything.

what can we do right and i think that those types of things are it's not what do you buy your kids what school do you send them to or like like you know all that kind of stuff is probably more so like just don't make a mistake right but if you raise good kids you can pretty much send them to any school and they should be able to navigate it now sure some schools are better than others or whatever but i do think that there's something about the way that you teach them to think has probably the most asymmetric payoff in terms of how your kid

actually ends up performing in the world. It's an ultimate act of leadership too. That last one, especially we were talking about with your dad. And do you think about that both as a dad, but as a leader of a business, when you genuinely let somebody know

that you believe in them and you tell them explicitly and you give some specific sense to why, God is that powerful. Like I think of my parents. I think of two of my high school football coaches. The people who you could tell had that genuine belief in you.

They raised the level of expectations that maybe you even had for yourself. That is leadership. That's an active leadership. And I think that's what all of us in leadership roles, whether it's as a parent or as a business leader, that's what we should be striving to do is to raise the level of expectations and belief in people. Okay, one that you learned from a sales professional that I really wanted to hit on. And it's simple. It seems obvious, but people don't do it.

And that is get on the plane. Get on the plane. Go see them. Can you tell a story about how you learned that when in doubt, get on the plane? Yeah, this was a hard lesson to learn. Part of growing up as like a digital native is you got the internet. Why would we ever spend all day to go to the airport, sit there, get on the plane, get off the plane, get the rental car on Uber, drives a little place, do all that.

Come back. It's crazy. It's just, let's do it, you know, a 30 minute Zoom. And I learned it when I was fundraising for the first, like, large fund from an investment standpoint that we're fundraising for. There's nothing that replaces the in-person conversation. But more importantly is getting on the plane signals a seriousness to the person that you're going to meet. I've been fortunate to meet some very, very successful, you know, multi-billionaire type investors.

And I've literally seen it. They will talk to someone over the phone and they'll say, I'm going to come see you tomorrow. How serious do you think they are if they're going to get on a plane and literally come see you tomorrow? Now, it helps that they have private jet, right? It helps that they, you know, like, you know, they got a lot of money and the cost isn't a problem. But there's an element of, I just talked to. to somebody on the phone yesterday and now they're going to fly here tomorrow to see me, they catch your attention, right?

And so again, it doesn't mean that you got to do that for every single person, but remembering that sometimes it is worth getting on the plane. Sometimes it's an advantage to do that is pretty important. Have that bias for action. Do you think because I've met with companies, specifically their sales organizations where they learn to sell in COVID via Zoom and teams. they're like, dude, I can crush it that way. I learned how to do it. People are fine, not meeting in person. In fact, some of them prefer Zoom and teams just because they don't have to,

whatever, they can be at home. What do you say to those people who maybe crushed it during COVID and they're still doing well, having those types of meetings and they don't want, they never had to get on the plane because they started earlier in their career not doing it. What about for that person? I think that if you're good over Zoom, imagine what you can do in person. Right? It's like, imagine you're in a boxing ring

and you learned a box with one hand tied behind your back. Imagine if they gave you a second one. Right? Like, you probably be better. And so a similar idea here is if you learn to sell and you're good at it in the impersonal kind of virtual world, imagine how good you're going to be.

in person. And so I do think that it's just an element of the last couple of years made it harder. And so just take what you learned and then go apply it and, you know, play the game on easy mode. Go meet people in person is much easier, especially in sales. You don't get what you don't ask for. I love the story about, I believe, was this your first date with Polina? Yes. I wasn't even a date really, but yeah. Okay. So you met Polina in the morning this is your now wife for coffee. Is that right? Can you tell the story of how that went and then what happened next? Well, I can tell you my version, which obviously is the truth. But no, we met, she was a reporter at Fortune magazine. I'd made a number of investments in

private tech companies. And we met because she was looking at some of them. And I'd sent her a list beforehand of, hey, you know, here's all the companies. And during the conversation, I think it became pretty clear to both of us that, hey, this is either going to be a work relationship or, you know, something else. It's a little weird when you're like, am I thinking what she's thinking? I don't know what she's thinking, you know, like it's kind of like this like awkward thing, whatever. And after we left, I messaged her. And I just said, hey, you know, this may be a little weird, but she had told me she was leaving. It was on a Thursday. And she was leaving, I think, on Saturday morning. And so I just had to her. I said, hey, do you want to go to dinner tonight?

You want to go to dinner or can I see you tomorrow or whatever? And she said yes, thankfully. Maybe the story turns out differently if she's been like, no, you weirdo, right? You know, or something like that. But it was just like, I wanted to see her. I genuinely was like, hey, I enjoyed that conversation. I thought she did as well. And if I don't ask her, we don't get dinner that night.

Who knows? Maybe we don't actually end up getting married. Maybe I don't have, you know, two kids. Maybe I never write the book. Like that, you know, one thing had a huge impact on my life. but at the time it was just like, hey, I want to go to dinner with her. Let me ask. And what's the worst is she going to say?

No. Okay. You know, I'm in the same spot I am right now, which is currently, I'm not going to dinner with her. And so, you know, maybe that's kind of a simplistic example, but it's true of, you know, everything, right? If you think in business, how many times do you read a contract? And people are just like, okay, fine. Like, I'm like, I tell our team all the time, if you review a contract and there's something in there that you want or something that's not in there that you want, or something that's not in there that you want. ask. And maybe 50% of the time they say yes. And 50% of time they say no. But so 50% of time we got

something that we wanted in the contract. And so I do think that there's an element of just like being willing to kind of put yourself at risk. Because it goes back to that idea, fear is invented. You're like nervous to ask. Why? Because you've invented something in your head. And so when you can kind of distance yourself or get rid of that, it really empowers you. I learned that early on as a sales professional that you're asking and getting rejected constantly. So you like work the rejection muscle. And I think that's useful for basically anything you're going to do in your life. And it feels like this, what you did asking for the second date, the day of the first date. And you had it that night. I guess the first one's not maybe considered

a date, but it turned into one is not as common maybe as maybe it used to be. And that could go to all different areas of your life. If you don't ask, the answer is no. And even if you do ask and you get a no, it's not that big of a deal, right? You just move on. You get to the next one. You get to the next one.

I think that's what's critical. Okay. Next one is, now, this could be a little bit sensitive, but I wanted to bring it up because it's also common. Childhood is not a crutch. Using this victim mindset as a crutch for poor behavior, I realize some people have a lot worse childhoods than I did and probably you did. And I had a great childhood.

But you quote Cameron Haynes and he says, it's easy to use your childhood as a crutch instead of seeing it as a chisel. Can you share more about not using childhood as a crutch? It's the whole idea of like luck and agency, right? Is if you look at your childhood as a crutch and you constantly say, oh, I do X because this happened to me or this situation I was born into or this person was mean to me or whatever.

That doesn't mean that you're condemned to that life forever. You can absolutely change your circumstances. And I know a lot of people who have done that. I have some friends who had horrific childhoods and there's some of the highest agency, most powerful people I know because they use that as fuel.

And so the example I always use here is that there's this great saying of there's a drunk father, like an alcoholic father. And in that conversation with his two sons, somebody says, hey, you're a drunk as well as a kid. So there's a father and two sons. One of them's an alcoholic. One's not. They go to the alcoholic son. They say, hey, why do you drink? I say, well, because my father's an alcoholic. That's where I learned it. And then they go to the son that's not an alcoholic and they say, why don't you drink? And he goes, because my dad is an alcoholic. And so it is, again, two kids grew up in the same household, with an alcoholic father,

one chose to repeat, the other chose to learn from it. And so it's this idea that one of them is basically got the mindset that they're condemned to the life that they were born into. And the other is saying, this was a chisel.

It taught me something. I am not going to allow myself to fall into the same trap. It doesn't mean that either son is right or wrong. It just means that if you want to be a high agency empowered person that gets what you want out of life,

there's only one of those two sons you can be. You have to be the one that says, my childhood is a chisel. And so again, it goes back to, it's a mindset thing, right? It's a different way to view the world. And so I'm always intentional about telling people, you can't change what already happened in your life.

What you can do, though, is you can change the way you think about it. And so if you can change the way you think about it, you can either use it as a weight that hold you down, or you can use it as fuel that propels you forward. And I think that's what Cameron's getting at there is he's saying, you know, use it as a chisel, use it as the fuel to propel yourself. Take all that thing, the anger that you have, the sadness, the, you know, whatever kind of nasty, bad things, and use it to motivate you to accomplish something good.

Turn the bad thing into a good thing. And we all have certain things that have happened in our life that we would point to. and there's a varying degree of severity. For some people, it's absolutely horrific. And other people, it's like a bad day at the country club. But every person has something that they look at on a relative basis. That was the worst thing that happened in my life. And it all is, how do you choose to think about it?

And the people that I know that are highly successful choose to look at it as fuel or use it as a chisel as Cameron talks about. Ed Lattimore said on this podcast, I vividly remember, you know, he had a brutal, brutal upbringing. And he said, if I commit a crime, the judge and the jury, they don't care about my upbringing. They're going to throw me to jail. Ed having this high agency with, yes, it happened, but it's in the past.

Now it's on me to choose how I'm going to respond, how I'm going to live my life, realizing that if I inflict harm or do bad things to other people, they do not care about how bad my upbringing was. I need to be a productive member of society, and that's a high agency thing, which I love that one. Okay, simplicity signals mastery. God, I love this one, Pomp, because the writers and the communicators that I really appreciate and respect, the Morgan Housels, the Tim Urbans, the James Clears of the world, they are so good at taking complex ideas and writing in a way that makes the reader smarter. And that to me shows they have absolute mastery over the stuff that they're writing about.

And so I love that this is a letter that you're writing to your kids saying you have to learn the stuff enough to make others feel wiser for having been in your presence or reading what you're writing because you're writing at a level that they can understand. That takes ultimate mastery. So yeah, talk more about this idea of simplicity signals mastery. What you find is I talk to a lot of people. I interview people for jobs. I interview people for content. I work with a lot of people. We have a lot of partners and clients. I have a lot of investments. I've got a lot of investors. And one of the core themes of my life is learning.

And so I, for better or worse, tend to grill people when I meet them. And if you've ever been on the other side of it, it's probably not as fun as I think it would be. But, you know, if I meet somebody, I will just start asking them, what industry? Okay, how did you learn this? What did you do with the company? What was the biggest decision that you made? What was the biggest mistake? What would you do differently?

You know, what did you learn about hiring people? I just like fire away. And certain people like it. Some people don't. But what you find is the people who have true mastery explain things so simply that you kind of are like, duh.

And a great example of this is, let's say that you own a small business and you're trying to build a chain of restaurants maybe. And you say to yourself, okay, I need to be in places where there's high foot. traffic. And so one person would say, okay, let me go do a bunch of studies. Let me go do surveys. Let me have somebody stand on the street corner and count cars. Let me look at maps. Do all this kind of really big intelligent stuff. But if you go talk to the multi-millionaire

restaurant owner who's been in business for 30 years and you ask them, hey, how do you do site selection? They'll just be like, I put my restaurants next to Walmart. Right? That's it. just if there's a Walmart, I put my restaurant there. And that's what we do. We just look for the Walmart and we put the restaurant there. And why do we do that? Because we know it's high foot traffic. They did all the work.

Like, they're big brains, whatever. And like, we just put a restaurant next to it. And so it goes back to this idea of like, who's really mastered site selection. Is it the people who are going and doing all the studies and have a whole site selection team and blah, all the stuff? Or is it just the guy who's like, you know what?

I just find Walmart and I put my restaurant next to it. So that's a good kind of exercise of, it's not just language. It's not just the way you disreesome. describe things. It's also the way that you think about things. And so this idea of like simplicity equals mastery is that guy really, really, really understands what is the thing that drives value for his restaurants. And so he has identified what's the one thing that's going to pay off 90% of the value. Find Walmart. Put my restaurant there. I'm done. I didn't spend money on surveys,

car counting. I don't have a big team. Any of that stuff. But I got 80, 90% of the same result. And so I think about that a lot because when I talk to people, the other like big side to this is what are the red flags. And it's people who use huge big words. And I always tell them, I said, look, if I don't understand what you're saying,

I just, I got questions, right? Like, I talk to so many people and people who know what they're talking about can explain it to me so simply that even I can understand it. Okay. why can't you do that? And so one of the things that you can learn from this is if you want to master a subject, be able to explain it to a five-year-old.

Yep. And if you can't explain it to a five-year-old, you probably don't understand it. And so I think that is, you know, kind of just a huge lesson, both in terms of evaluating people in situations, understanding kind of, you know, business and boiling things down, but then also kind of aspiring to have a degree of mastery yourself and topics you care about to then be able to communicate those ideas to other people. I remember my 10-year-old, she was eight at the time.

She's like, what's your book about? And it caught me off guard for a second because I realized I needed to speak in a language that was more understandable. And that response, I ended up like quickly writing it in my phone and using it as like sales copy because this is better than anything else I've done because it was just so much more simplistic. So that's actually a good exercise, whether you have kids. kids or not is whatever the thing is you're doing, what your speech about? Well, explain it to somebody

like it's like it's one of your six year old kids that is asking you. And then, oh, now you got to the through line. You got to the gist of the thing is try to explain it to them. And I think that really shows that you know what you're talking about. We're right at the end of our time, so I really appreciate you being here. One more is, let's say you're meeting with somebody. You probably do this regularly. Recent college grad, they want to make a dent in the world, right? they're willing to work hard. They don't necessarily know what they want to do yet, but they do want to do something of significance.

What is some general pieces of life slash career advice you give to that person? Seek risk. Everything in your life has been beat into you that risk is bad, volatility is bad, but the greatest returns are on the other side of risk. And so in your career, especially when you're young, what is the riskiest thing you could do?

joining that really hot startup that, you know, it's growing super fast, going and starting your own business, taking a leap into an industry that was going to be really valuable, but you're not yet quite sure are you prepared for it? Going and going to a bunch of networking events and building out your network, even though you don't have any friends that want to go with you, anywhere where you see risk run towards it. It's true in your investment portfolio as well. All of the value gets created in the things that are deemed risky. They're deemed risky because they're volatile. And as volatility comes down, it's because risk is coming down.

But the secret in investing is you get paid the return for the risk you take. And so if you're buying the S&P 500, which is pretty de-risked, you get about 8%. But if you buy the thing that's deemed more risky and you're right, then you get paid a higher return. And so I think that seeking risk is something. that you almost have to like unlearn the opposite of to be able to do and you have to get comfortable being able to identify this is risky let me run towards it and if you really think of a firefighter it's insane to run into a burning building that is dumb for 99.9% of people but for a firefighter

that's their job and so if you can think of the kind of intellectual equivalent of that is go find risk and run towards it it will set you apart because the competition of people who are willing to do that is so low compared to all the people who are running away that you probably have better odds of actually being successful. So good. By the way, what do you think of Domino's pizza? Domino's is amazing. I've been told that I should not eat it every week, but not only do I think it is pretty good. I do at times like to order Domino's living in New York City because a lot of people are not so pumped about me doing that, which makes me like to do it even more. This is so good, Pop. I really appreciate you being here. I've followed your work

for quite some time. How to live an extraordinary life. These are 65 letters that you've written your kids. I think we cover four or five of them. So there's so many more that I highly, highly encourage people to get this book and read it super useful. It's entertaining. And you could implement the stuff immediately. So well done, man. Say hi to Polina. And I would love to continue our dialogue as we both progress, man. I would love that as well. Thank you so much for doing this. It is the end of the podcast. club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learning leader.com. Let me know what you learn from this great conversation with

Anthony Pompliano. A few takeaways from my notes. Luck is not real. Luck is something we conjure in our minds to grapple with the consequences of whatever life may throw our way. Luck is a physiological concept. It's determined by how we view a situation. In fact, academic studies show that you can become luckier simply by telling yourself that you are lucky. Pessimist sounds smart, but optimists change the world. It's worth it to believe that it will go well. It's worth it to have optimism, to have agency, to strive to make something happen. And also, surround yourself with compounders and fire your boring friends.

Being around other ambitious people who are willing to push you will make you. will make you better. And we have to work to strike the balance between being loyal to longtime friends who may happen to be boring. We'll do anything for them, as Pomp said. Give the shirt off your back. But we're going to spend the bulk of our time around people who will push our edges and make us think bigger.

Surround yourself with compounders. And then you don't get what you don't ask for. I love his story when Pomp talked about meeting Paulina, his future wife. for coffee and then learning that she would be going out of town. So he said, well, let's just go to dinner tonight, right? You don't get what you don't ask for. The answer is no if you don't ask. I think it's worth the potential rejection because the upside is so great.

In this case, for him, they got married and had two children. So the people who sustain excellence I've found are not afraid to make the ask. You don't get what you don't ask for. Once good day, I want to say thank you so much for continuing to spread the message and telling her friend or two. Hey, you should listen to this episode of The Learning Leader Show with Anthony Popliano. I think he'll help you become a more effective leader because you continue to do that. And you also go to Spotify and Apple Podcast and you subscribe to the show. And you're right, a thoughtful review and rate the show.

Hopefully five stars. By doing all of that, you are giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. so, so much. Talking too, can't wait.