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Anthony Pompliano
Founder & CEO, Professional Capital Management

How to Live an Extraordinary Life - Anthony Pompliano (#210)

📅 Oct 06, 2026 Everything But Politics 73 MIN 127 SEGMENTS · 2 SPEAKERS
Anthony Pompliano is an Entrepreneur, Investor, Podcaster, CEO of Silvia, and Author of "How to Live an Extraordinary Life" Vol. 1 & Vol. 2. Tune in, as Pomp shares what went into writing Vol. 2 of How to Live an Extraordinary Life, how he manages his time as an entrepreneur and father of 4, how to build the life you want and walk away from the one you don't, what the greatest founders all have in common, his time in the military and serving in Iraq, the emerging technologies he's most excited about, how Silvia uses AI to help you track your finances, filming a podcast with his dad, and the pu...

What Anthony Pompliano said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Anthony Pompliano discussed his approach to AI, productivity, and investing. He said he uses Grokbot for business agents, Instinct personally, and Sylvia for financial data, aiming to automate as much as possible. He advocated for 'smart dumb people' who simplify complex ideas, citing Elon Musk and Jeff Bezos. He argued that professionals aren't always better for new problems, using Steve Cohen vs. Dave Portnoy as an example. He emphasized agency, breaking inherited habits like late-night carb-heavy dinners, and learning from his near-death experience in Iraq in 2009. He advised young entrepreneurs to build undeniable products, mentioning Robo Strategy for non-accredited private market exposure. He detailed Sylvia's 18-month development, moving to proprietary models. He discussed his public company's 85% stock drop and his 'misfits' movement to turn it around.

Key takeaways

  1. Pompliano uses AI agents (Grokbot, Instinct, Sylvia) to automate professional, personal, and financial tasks, saying 'I just like replace me.'
  2. He advocates for simplicity in communication, calling Elon Musk 'the smartest dumb person in the world' for boiling SpaceX down to 'colonize Mars.'
  3. He described his company's stock dropping 85% after going public in December 2025, and his strategy to 'pull off the impossible comeback.'
  4. He recommends non-accredited investors use publicly traded funds like Robo Strategy to gain exposure to private companies.
  5. He stated his Bitcoin position is permanent: 'Bitcoin could go to $1. I'm not selling it. Bitcoin could go to a million dollars. I'm not selling it.'

Numbers and commitments

FigureWhat it refers toTypeAt
70% Stock drop in first two days of public listing metric 50:30
85% Maximum stock decline from public listing metric 50:30
18 months Time since starting Sylvia development timeline 46:10
$9,000 to $72,000 Profit from day trading foreign currencies metric 48:20
72 down to like 20 Loss in trading account value metric 48:20
500 million, then 2.5 billion, and then 10 billion Instinct's valuation increases metric 43:32
4 months Time for Instinct's valuation growth timeline 43:41
200,000 Annual income requirement for accredited investor guidance 38:25
$1 Hypothetical Bitcoin price price 36:41

Chapters

  1. 0:00Private work and productivity tools
  2. 2:46AI agents and services
  3. 4:11Generational tech adoption
  4. 8:06Meeting preparation and simplicity
  5. 12:33Professionals versus amateurs
  6. 16:11Inherited habits and breaking them
  7. 21:52Agency and intentional living
  8. 25:09Military experience and mortality
  9. 33:55Investing, buying and selling
  10. 53:54Public company comeback

Questions asked in this interview

12
  1. 0:40So something I want to ask you is what is something you've recently been doing in private that is paying dividends in public?
  2. 5:16What are some of the similarities you've seen with that?
  3. 7:45So my question is, how did you when it comes to your preparation, how did you prepare for today yesterday?
  4. 16:11What was a bad habit in your life that was inherited and how did you break it?
  5. 21:44What is your advice to those people who dread going to work every single day and while at work stare at the clock till they go home?
  6. 25:05When and how did you adopt that mindset?
  7. 33:55Can you speak on the art of buying versus the art of selling when it comes to investing?
  8. 37:51And how could normal people find a way to invest in private companies?
  9. 38:22How does one become an accredited investor?
  10. 41:11What is the odds of three brothers in Indiana knowing two multi-billion dollar founders that they grew up with or, you know, met in the first 25 years of their life?
  11. 48:20Was it now on my phone, I'm not on my computer, I'm not as into it?
  12. 50:16Go like just how does Anthony Pompliano unlock peak productivity, dude?
Everything But Politics Podcast Host 0:00 ↗
The Everything But Politics Podcast. Welcome back to the 210th edition of the Everything But Politics Podcast. With us today is entrepreneur, investor, podcaster, CEO of Sylvia, and author of How to Live an Extraordinary Life and How to Live an Extraordinary Life Volume Two, which are both lessons on how to become wiser, healthier, happier, and wealthier. We look forward to exploring these lessons today. Anthony Pompliano, thank you for being with us.
Anthony Pompliano 0:34 ↗
Absolutely. Thanks for having me, guys. I should hire you guys as my PR department. That was pretty good. Pretty good intro there.
Everything But Politics Podcast Host 0:40 ↗
You make it easy with all the outlets on the internet. So, one of the main things in this incredible book right here, which as mentioned, we've read both of them now. So, congrats to you on releasing your second volume of How to Live an Extraordinary Life. One of the things that stuck with me is what you do in private always shows in public. So something I want to ask you is what is something you've recently been doing in private that is paying dividends in public?
Anthony Pompliano 1:05 ↗
Yeah. The whole idea of this is really people always want to capture the end result, right? It's, you know, we know that we live in a world where everyone just wants instant kind of success. But to me what actually ends up being the most important thing is think about fitness. If you're constantly working out every single day then over time you get a better physique, you're healthier, right? Same thing in business. If you're constantly toiling away, you end up with a more successful business. People don't see the work. They just see the result. But the opposite is true, too. If you're, you know, eating like, you know, really bad and you constantly are not taking care of yourself, you're not working out, then your body deteriorates over time and somebody shows up and they're like 250 lbs. Everyone's like, "Dude, what the hell happened?" Right? For me, I've been spending a lot of time building software tools. And the software tools that I've been building are not actually things that I want to release publicly. They're things that I've been using internally. And so I've got a whole bunch of these kind of like productivity tools that I custom built for myself. But I wanted to do it because one, it was going to help me in terms of my efficiency and effectiveness at our companies and at work, but two also is I knew that it would help me retrain myself for, you know, kind of the world we're headed into with all the AI stuff. And so my wife's been laughing that, you know, I basically have spent every weekend for the last month or so just sitting and building these things and it's fun and enjoyable for me. But nobody sees that, right? Everyone sees all the tweets and the work and all this kind of stuff, but they don't see me actually building this. And so then during the week when I'm talking about AI and coding and AI safety and all this stuff, like I can actually talk about it from a credible standpoint because I'm using the technology. We're building it at Sylvia, right? And so I think that's a prime example of this lesson.
Everything But Politics Podcast Host 2:40 ↗
And to this point, how have AI agents been complementary to you and your life and your work?
Anthony Pompliano 2:46 ↗
I don't want them to compliment me. I just like replace me. That's my general view, right? Is like you're telling me that I got something that's like 150 plus IQ. It works hard. It's persistent. It can coordinate with other agents. Like I want to automate as much as I possibly can and give it to it. And you know when you see where am I actually using it? I basically right now use two different products. I use Grokbot in terms of agents for business. So I've hooked it up to a bunch of our companies, a bunch of the databases and various services. And then I'm using Instinct personally for a lot of stuff there. And then obviously Sylvia today I don't think people really look at it as an AI agent. It's just an AI platform that allows me to talk to all of my financial data. We have aspirations to make it more agentic over time. I think you'll start to see that happening. But if you think of those three services, I got my professional life, I got my personal life, I got my financial life. That's pretty much all I need. And I have three different services that I use for each one of those.
Everything But Politics Podcast Host 3:46 ↗
So, I got to give a quick shout out to Matt Van Horn. This is episode 210. Matt Van Horn was 208. Just to show you how recently we are new to these AI agents. We're on the same two. Thanks to Matt, he put us on. So, we're about two weeks in the game.
Anthony Pompliano 4:00 ↗
That's amazing. And this two weeks in the game have saved us months of our lives. So, it's unbelievable. Insane. Doing things that would take us hours to complete.
Everything But Politics Podcast Host 4:10 ↗
Minutes.
Anthony Pompliano 4:11 ↗
You got this is a great lesson for everybody, right? And especially young people should hear this. You have something that I don't have right now, which is that you guys have a very malleable mind and you got a lot of time on your hands compared to people who are married with a lot of kids, they got a bunch of responsibilities, etc. And the reason why those two things are really important and I would argue even more valuable than having money at the moment is because whenever we go through rapid change from a technology standpoint or corporate environment, what ultimately is going to be rewarded are the people who have the curiosity to go and learn the new things and aren't, you know, kind of codified in their old ways. And so even for somebody like me, I'm 38 years old. I'm not necessarily a 70-year-old, but there are certain things I've been doing the same way for years now. And so it's really hard for me to be like, I got to stop doing it this way. I got to learn the new way to do it. And you know, hopefully I'm better than most at figuring that out. But I think you all, especially in your mid-20s, you have the time, but also you've got enough experience where you know you should spend time on this, but you don't have so much experience that it actually works against you in moments of change. And so the more you lean into it, I think the better off you'll be.
Everything But Politics Podcast Host 5:16 ↗
Absolutely. And speaking of rapid change, this is kind of similar to, let's say, 15 years ago when the internet was happening. What are some of the similarities you've seen with that?
Anthony Pompliano 5:27 ↗
Well, you know, it's funny. I feel like an old man being like, well, back in my day, you know, when I was in high school, I was in high school in the mid-2000s and we got cell phones when I was like a sophomore in high school, I think, is when I got my first cell phone. And so going from a world without a mobile device or a supercomputer in your pocket to having one and at the time it was like revolutionary. I could text my friends, right? I could play games. I think the first one I got was probably a Razer phone or at least that was one of the first ones and I remember like the I think it was like the Sidekick or something where you slide it had the keyboard. That was like the big one everyone wanted. But those are like some of the very early ones and our parents were basically trying to slow down the adoption because there had been like T9 texting devices before and you know kind of like business people would have them or whatever and the kids all wanted them but you didn't really want your kid to start to use this technology because you were worried that like all the kids were going to go crazy or be addicted or you know whatever crazy thing the parents were worried about. It's the same arguments people are making about AI today, right? It's like they're trying to ban AI in the classroom or whatever. And what you find is like actually my parents should have given me the phone earlier because I would have gotten up to speed faster on the technology. And so if you then fast forward to today, it's like there are kids who will never know a life without AI.
Everything But Politics Podcast Host 5:54 ↗
What kind of phone was that?
Anthony Pompliano 6:50 ↗
That's crazy, right? And just going to be everything is going to be native. And so the example I always use is take a video editor. Most video editors that are of a certain age are used to we record it, we take the files, we put it into the video editor, I sit, I go through, I line up the audio, I match the video, I, you know, edit blah blah blah, whatever. I know a bunch of kids now that are like, yo, I just like tell the agents to do some stuff and all of a sudden I get like an edited video file. It's not perfect. They may still have to go in and kind of around the corners, but man, they're not going to ever know the world of sitting and editing a two, three hour video by hand, you know, by hand. It's going to be like archaic. And so, you can just go through every single industry, right? Lawyers. There's going to be a lawyer that at some point is going to be like, "Hey, I've never not used AI as a lawyer." And so, that's the future. And I think what people have to do is just race to catch up to this and use this technology as much as possible.
Everything But Politics Podcast Host 7:45 ↗
Yeah. Tom, what I admire most about you and what you've built is your time management. You're CEO, you're a father of four. Something this podcast has taught us is how to prepare being both for episodes and weeks in advance with guests joining the show and things of that nature. So my question is, how did you when it comes to your preparation, how did you prepare for today yesterday?
Anthony Pompliano 8:06 ↗
Dude, I'm a fantastic bullshitter. That's probably one of the big things is, you know, it's like in school, right? I was the kid who I could be sleeping in the back of class and the teacher would be like, you know, they used to call me AJ. AJ, what did I just say? And I'd repeat it right back to them and the teacher like, "God damn, how the hell this kid, right?" So, I think that there's some of that is just like kind of who you are as a person growing up in a family. I had five boys in my family. You guys, you know, are with your brothers. And so, I think that there's something about the dynamic of like you guys probably talk a little with each other, right? And kind of tease each other and all that stuff is like an environmental advantage. I've always thought. But at the same time, obviously, you know, I run a public company. I've got a bunch of investments. We've got a ton of companies that we own now. And the idea is how do I efficiently prepare? And what ends up happening is it's not so much about like how much information can I consume. I spend a bunch of time on what is the information I do not need to consume. And it's like almost like addition by subtraction. And so there are people I know who will get, you know, there's CEOs I know they'll get like 15-page briefings before the meeting. That's not helpful to me. Actually, you're just making it more work. And then I got to try to remember all this stuff and what's important. All I want is give me the five bullet points. What the most important stuff here is. If I go into this meeting with those five bullet points in mind, including who are we meeting with, what's the goal of this meeting? What's my role in the meeting? You want me to listen? You want me to provide feedback? Do you want me to make a decision? You want me to, you know, provide them feedback? Like, what do you want me to do in this meeting? And then just give me the one or two things that I need from a context standpoint. You know, do we have a relationship with this company? Are we trying to optimize for something? Whatever that is. But if I walk into a meeting with, you know, those, call it five to seven things, I can be really effective in the meeting. Now, if you gave me 15 pages of prep material, one, I'm probably not going to read the whole thing. I just don't have time. But also two is now I'm left wondering like, do you care about page six or page 12? Or do I like is the first page all the important stuff? And so I think that we're entering this world where brevity and specifics but also the ability to be very simple becomes important. And so one of the things I keep telling people is like we need more smart dumb people. And everyone's like, what do you mean we need dumb people? But smart dumb people is basically Elon Musk is the smartest dumb person in the world. And he also happens to be the richest guy in the world. Why? Because he's able to take these really complex ideas and he boils them down to something very simple. What is SpaceX? We want to colonize Mars. That dude boiled the entire company down to two words. That's like that's what a dumb person does, right? They don't know what else to say. Just like colonize Mars. Super simple, right? But then he was like, "Hey, what is the value proposition of SpaceX?" Initially, it was reusable rockets. It was two words. He didn't tell you about propulsion engines and this and that. All this just we're going to make reusable rockets. They're going to help us colonize Mars. Awesome. Let's go. Jeff Bezos, all of this crazy logistics, all whatever. And all he said was, "I'm going to help you buy things on the internet. We're going to sell you everything. It's the everything store." Again, like just one sentence, a couple of words, very simple. And so, obviously, these guys are incredibly intelligent. But what I find is the people who have a lot of power and influence in the world, frankly, are usually the people who are most wrong. And the reason is because they approach things from a very academic standpoint. What are your credentials? How can I make it as complex as possible to describe it because that's going to hopefully make everyone think that I'm smart. And then they are not very focused on what happens when this information meets reality. What they're focused on is how do I perceive others and how do they perceive me? But when you're building a company, Elon, Bezos, just you know, Zuck, just go through the whole line. All the great entrepreneurs, perception doesn't matter at all. Actually, they've been laughed at for years, decades in some cases. All that matters is did you win? And so I think that's really where society gets separated is you get some people who are very focused on the academic perception, you know, kind of approach and then you get actual doers who just say like, "Dude, the results are all that matter."
Everything But Politics Podcast Host 12:08 ↗
Listen guys, when I think of Buffalo, I think of fresh, never frozen wings.
Anthony Pompliano 12:13 ↗
Oh, you're making me hungry. And I think of the rich Indiana tradition, 40 years in the making from Bloomington, Indiana. Well, now 40 years later, Buffalo is officially franchising across the United States of America.
Everything But Politics Podcast Host 12:25 ↗
That's right.
Anthony Pompliano 12:26 ↗
You can't beat Louis Meat. buffalooies.com for more information.
Everything But Politics Podcast Host 12:33 ↗
I think in many ways that embodies the lesson in your book. I think the exact language is amateurs built Noah's ark and professionals built the Titanic. Is that correct? Can you speak can you go deeper on that one?
Anthony Pompliano 12:44 ↗
Good one. Right.
Everything But Politics Podcast Host 12:45 ↗
It is great. And by the way, every amateur loves that. Every professional hates that chapter, right? You know what the hell?
Anthony Pompliano 12:51 ↗
Now look, there's nuance, right? Is if I go to the doctor, I want a professional, right? I don't want to go to like some amateur dude who's like practicing, you know, sidewalk medicine and he's just going to make stuff up. I want somebody who's actually got the training, etc. But if I want to solve a problem that's never been solved before, I may not want a professional. I may want somebody who comes at it with fresh ideas. And so if you think of Elon going and saying, "Well, reusable rockets," he wasn't a rocket scientist. He didn't have a ton of experience. He had this new idea that everyone else thought wasn't possible. And so he was able to take his experience and, you know, frankly his dedication and persistence and go and pull it off. Same thing with a lot of these things. You know, people forget Zuck was not the first person to come up with the idea of a social network, but he won. He had never built a social network. And so this whole idea of kind of understanding what problem am I facing? Am I facing a problem that is new? Well, then I don't need to worry so much about do I have the professionals or not. I need somebody who can solve the problem. But if I'm facing a known problem that people have already solved over and over and over again then actually professional or expertise like they become much more valuable. And so I think that's really the thing in life is everyone just kind of blanket like oh you always want a professional. What I found in my life is you don't always want a professional. And I can give you concrete examples in our own businesses. We have people that we have hired over the years who let's say they come from a very large business and they come in and they know how to do what they do. It's codified, right? That is their playbook. That is their strategy. They hire the people that they know. They do what they've always done. But take us on the internet. The internet economy or the internet content world, the internet, you know, kind of society if you will, is very different than big corporate America. And so you can't take the tactics, tips, and you know, experience from the big corporate world and apply it on the internet. And I always remember you guys are young enough where you remember when Dave Portnoy bodied Steve Cohen off of Twitter. Big hedge fund manager, he owns the Mets. Yeah. You guys probably know him as the Mets owner, but he's a big hedge fund manager. Dude's rich. Like he's worth like I don't know 10, 20 billion dollars. In Steve Cohen's world, he's the alpha. Nobody messes with Steve Cohen. But on the internet, that's not Steve Cohen's domain. Everyone on the internet who's a dude under the age of 40 knows you don't mess with Dave Portnoy on the internet, right? Cuz this guy is lethal. He can just he'll just bully you. And not bully you in like a mean way. He's just good at the internet. Yes. So you got a billionaire who's the king of one domain who went under the turf of another guy, but the guy whose turf he's on literally bullied him off the internet. Steve Cohen deleted his account. Wow. And so you look at that and you say to yourself, well, hold on a second here. Steve Cohen's a professional in the finance world. He's an amateur on the internet and he was going up against a professional of the internet. We saw Dave Portnoy go and try to become a trader, but he was kind of amateur in the finance world, right? It's like that's why that's so fascinating to me is like you kind of got to know your game, know what is the problem set that I'm approaching here and do I need a professional or is it actually helpful to have someone who doesn't have a lot of experience and then try to fit the people that you're working with with the problem set that you're tackling.
Everything But Politics Podcast Host 16:09 ↗
I love that.
Anthony Pompliano 16:10 ↗
Yeah, I love that too.
Everything But Politics Podcast Host 16:11 ↗
So, in volume two here next to me, you speak on habits and how most are inherited. What was a bad habit in your life that was inherited and how did you break it?
Anthony Pompliano 16:19 ↗
Well, I don't know if all bad habits are inherited, but you inherit a lot of things. You obviously the knowledge that you learn. You inherit a lot of the family dynamics, right? And there's two things that I talk about in the book. One is there's a parable of there's two sons, their dad's an alcoholic. And one of them says, "Hey, I never drank alcohol before." When you ask him why, he says, "Because my dad's an alcoholic." The other one became an alcoholic. And you ask him why'd you become an alcoholic? He's like, "Because my dad was an alcoholic." So like one of them chose to not repeat the thing that they saw. The other one was like, "Oh, that's just all I know." Two brothers, one dad, you know, same situation, two different outcomes. The second thing is there's a chapter in the book that talks about like it ran in my family until it ran into me. And it's something my wife and I talk about a lot, right? Is like we both came together as a couple and got married. And we both bring everything from cultural, you know, kind of holidays and different family traditions and stuff like that. We come from ethnically a similar area but different. She's Bulgarian. My family came from Italy. And we actually have related but different religions, right? Christianity but different kind of applications of that. And then we have different life experiences. And she was very studious and nerdy. I was, you know, lucky to get through school. And so like you put all that together and you say to yourself, okay, well, like we inherited a bunch of these habits, traditions, etc. What are the ones that we want to continue? The ones that I did not want to continue. I come from a large Italian family and we ate pretty carb-heavy food late at night my entire life. And I always joke that, you know, I remember my mom and, you know, I love my mother to death, but my mom multiple times would make like pasta with butter on it and we'd eat it at like 9:00. No sauce. No, no, no. Just pasta with butter. It's like that's not healthy. Not that late. No way. Right. And at 9:00 at night, now there was a reason for it. All her sons played sports. We were constantly going from, you know, field to field, all this kind of whatever. But like it became important to me. I was like, I don't want to eat dinner late at night and I don't want to eat these really carb-heavy dinners. It's fun to do every once in a while, but like it's probably not the best thing for me. So, it's kind of like a stupid example, but it's something that I said, "Hey, I could easily just be like, "Oh, I've been eating this food my whole life, and it's what my family does, and by the way, so did my grandparents, my great-grandparents, and you know, all of Italy does the same thing." Yeah. Or you could say, "Hey, I want to do something different." You have to have the awareness to know what's good and bad and to kind of break the chain. So it doesn't carry on into your kids' lives and their generation. Yeah. And look, there's other stuff like, you know, when you have kids especially, right? Everyone has a different parenting style and so like all you know pretty much of how to parent is the way your parents parented you and there are some things that my parents did that were incredible. I am so glad even when they were hard on us. Like I actually am more thankful for when they were hard on me than when they just like gave me the pass and were like, you know, do whatever you want. Now, with that said, there's also a bunch of stuff that my parents probably did that I'm like, I want to do it different, including it would have been a nightmare to my parents to live in New York City with five boys, but I want my kids to grow up in that environment. And so, it's just trying to, you know, choose different situations, different decisions, and I'm not going to get it right. I'm not some like, you know, amazing dad. I shouldn't be the poster boy for that, but I'm at least trying to be intentional about the things that we're doing and the decisions we make so that we can take personal responsibility for the outcome. We didn't do anything by accident. We did it intentionally and if we're wrong, then hey, we'll live with the consequences, but at least we were intentional about it.
Everything But Politics Podcast Host 20:06 ↗
Why is it important for your kids to live in a city compared to a suburb?
Anthony Pompliano 20:11 ↗
I think that one of it is personal preference of like I always wanted to live in the city when I was growing up. Like I that really, you know, I was like man all my cousins, uncles, everybody lived in the city. So I was like, you know, I'd love to do that. And then by the way most of them were like dude you got a backyard like I want to live, you know, where you live. So a little bit like grass is greener. But I think what I've learned is there's some street smarts, right? You just pick things up. You see things differently. You know if you talk to a kid who grew up in New York City versus a kid who grew up in the suburbs different way about them, right? And I don't think either one's right or wrong. Like there's pros and cons to both of that, but I think that given, you know, my wife, my kids, and kind of the way that we want to raise them, being in the city is much more advantageous than not being.
Everything But Politics Podcast Host 20:57 ↗
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What is your advice to those people who dread going to work every single day and while at work stare at the clock till they go home?
Anthony Pompliano 21:52 ↗
Why are you doing it?
Everything But Politics Podcast Host 21:54 ↗
There's some good reasons. There are some people who say, "Listen, I need to make the money. It's a good job. I hate it, but I'm making good money." Mhm. Some people who say it's the only job I could get. There's some people who say, you know, I like my first job, but I have to have a second job, so this one, you know, is necessary. There's some people who go to work and say, you know, I'm here because I'm picking up a skill. I want to do this for the long term, but I think it's good. I know people who have really good jobs, get paid a ton of money, specifically in finance, and they're like, I'm here because it's training me. It's training me to think analytically. It's training me to be prepared, you know. There's a founder that I invested in. He's got a fantastic business. In three or four years he went from zero to like a 12, 13 billion dollar business. He was working at Blackstone and he knew that he didn't want to be in finance but he wanted to learn how to analyze good businesses. He wanted to see good businesses. He wanted to be around really good investors. So he went and worked there for two or three years. He didn't need that job but it was great training ground. So if you're in that category, more power to you. But at least you're being intentional about why you were there. But if you're sitting at a job and you're just staring at the clock because you haven't taken the time or the personal responsibility to figure out what you want to do or what skills you want to acquire or how much money you want to make or you know any of that stuff, then dude, let's go get your act together. And I think that, you know, it's kind of tough love for a lot of people because they'll say like, "Oh, I don't know if I could get another job." And I talk to a lot of people about what their career ambitions are, what they're, you know, doing on a day-to-day basis. And I always ask him like, well, how do you know? Did you try? Did you go talk to anybody? Did you interview? Have you ever thought about what you want to be doing three, four, five years? Do you care what you do on a day-to-day basis? And so I think that those things are, you know, not necessarily easy. It's very time-consuming to go through that process, but it just goes back to do you have intentionality? And look, if you said to me what's the one theme out of the two books that I wrote, agency. The entire world is trying to program you to think that you cannot control your own life. You've got to accept whatever the conditions are that you were born into. You've got to accept the way that society is. You've got to accept all of these forces that push you into certain outcomes. And I completely reject that. I just think that individuals have way more agency than they believe. And when you show someone that they have agency, you know, I think the trope today on the internet is like you can just do things. And once somebody realizes that, they just start doing things. And if you can embrace that idea of agency, you can build an incredible life. And you know, I titled it like How to Live an Extraordinary Life because the beauty of extraordinary is it's different for everybody. Your version of an extraordinary life could be different than your brothers versus me versus your parents versus, you know, somebody who works at one of our companies, but we're all happy because we're living our own version of an extraordinary life. And so it really comes back to how intentional are you about the life you want to live, about the things that are required to live that life, and then are you doing the work that is going to be necessary to achieve it?
When and how did you adopt that mindset?
Anthony Pompliano 25:09 ↗
Well, I had an experience when I was 20 years old on February 21st of 2009 and I was in the middle of Iraq. We were driving down a street and an IED went off. There was a firefight that ensued and somebody died. And when that occurred, I was very fortunate to be in the position that I was, from the sense of I wasn't the one who was killed, but the guy who was killed was somebody I had never met before. There's a very kind of weird dynamic, right? You were there in a situation that is quite literally life or death, but the person who was killed is a gentleman named Sergeant Bomb, Mark Bomb, and he had showed up with his unit because we had called for help. So, if you kind of think about that from a perspective of we were in a situation, we called for help, a guy showed up with a bunch of other guys and he died, not us. And living through that experience at the age of 20, it really hit me that, hey man, it could have been my day. Could have been any of these guys' day. And I think that what I realized was I'm going to die at some point. And to be honest, I was probably too young, too naive, maybe a little too wild and stupid to really be able to articulate it in that way. But from that day forward, it showed up in all kinds of different ways in my life. And you know, there was stupid immature ways that showed up. I remember, you know, when I came home, I had a motorcycle and I would fly, you know, down the highway. And I did some really stupid stuff that was fun as hell. I'm glad I did it, but man, my wife and kids are they happy that I don't do that stuff anymore, right? You know, and there's probably a million versions of that stuff. And you know, it's a common story, right? You come back from being deployed overseas, you think like you're Superman. You're invincible. But a lot of it was just also like, dude, I'm going to die. How do I squeeze as much value out of this life as possible? And so once you kind of get a lot of that stuff out of your system or, you know, as the academics will say, your brain fully forms when you're like 25. Like right now, I mean, congratulations, guys. Your guys' brains just finally finished forming, you know. Yeah. Congratulations. Thank you. I appreciate it. Now it's like, all right, what do I want? Right? What am I going to do? And if I'm fortunate enough to live till I'm 70, 80, 90 years old, what do I want to do with that time? And so that one experience was very formidable for me in terms of understanding like time is definitely the most valuable resource we have. It doesn't mean that I'm some like, you know, psychopathic like efficiency guru. I always laugh that, you know, if you're on Instagram too long, all of a sudden you think that you're losing at life because you're not waking up at five o'clock, you know, spend seven minutes meditating, write in your journal backwards with your left hand, you know, go in the cold plunge three times, you know, drink some soy milk and then all of a sudden you got to go in like the red light therapy and do all of that in the first 45 minutes of you being awake, right? That's not my life. But I know exactly what I want in life. And so I just constantly keep trying to return to am I doing this thing? If I am, I'm happy. If I'm not, then how do I get back to it?
Everything But Politics Podcast Host 28:26 ↗
Amazing. Well, so through this show in four plus years of it, we've come up with a lot of equations just like real like for us, success equals improving and not lasting. I would say confidence is keeping promises to yourself. So something in the book you mentioned is you had to convince yourself you were a winner before you were a winner. How did you go about that? How did you convince yourself daily that you were a winner prior to becoming one?
Anthony Pompliano 28:52 ↗
Well, look, I think that there's a number of different inputs in my life when I look back. The first is I played sports my entire life. You know, one of the key themes in my life in sports as a kid was I was usually on pretty bad teams. Like you guys, if you played sports, you know, growing up, you'll remember that like there was always like a team. They just showed up and won. And whether they were like practicing a lot or not, like they just they were always good and their kids were always good, right? I was always on the team where we kind of were like a ragtag group and we had to figure out how do we go from, you know, the inputs here might not be the thing that you would draft, but now we got to get good. And when I was in high school, it's probably the best example. I showed up and we were horrible. Like think of a bad high school football team and then there was us like below, right? I mean, it was really bad. I think that the first two years I was in high school, if I remember correctly, I think that the varsity football team won one game each year or something like that, right? I mean, it was just like atrocious. By the time I left, we had gone really deep in the state playoffs. And I write about this idea of as you're going through it, you know, like, yo, we're changing this place. We're changing the culture. We're changing the way that people do things. And you have in your mind that there's going to be this like Cinderella ending. You know, if it was a movie, like you win the state championship, didn't happen. And a huge part of it is probably on me along with other people. Who cares about high school football? I don't give two shits about high school. I don't even remember half of the guys, you know, on the team. Disrespect to them, but it's just like it wasn't an important thing in my life once I left high school. But it was a great life lesson of like, dude, just because you want something, just because you think that you've earned something doesn't mean you get it. And so then you go to business and you start to realize like you really only start to think that you're a winner once you have the confidence that you have actually done the work. And I always, you know, like the saying of the man you should fear in a chaotic situation is the man who is most calm because he knows what he's capable of. He's been there before. He understands what is likely to transpire and he's comfortable with it. And so when you have that mentality, you start to realize to yourself, you're like, okay, if I am nervous, if I am worried about losing, if I am concerned about the outcome, I just haven't prepared myself or done the work that is necessary to actually succeed in this situation. And so like what do you do then? Well, like what do I need to do to not be worried, concerned, etc. And then you just go do that stuff.
Everything But Politics Podcast Host 31:35 ↗
Well, something else going back to being a winner. I feel like a lot of it is eliminating that fear factor. What are ways you eliminate fear?
Anthony Pompliano 31:45 ↗
My favorite book probably that I've read in the last three or four years is a book called The 50th Law. And it's a book 50 Cent and Robert Greene wrote it together, which is like an unlikely pairing. Yes. But what they talk about is Robert Greene writes every other chapter and he writes it in his style kind of analyzing history and you know historical figures and all this stuff and he takes these life lessons kind of from like the philosophers and then the next chapter is how 50 Cent applied that idea in his life in the streets and what you find is there's an incredible overlap. The guys who run the streets understand every idea that Marcus Aurelius had 2,000 years ago. And so you say to yourself, "Wait a minute. These are timeless ideas." Because just as Marcus Aurelius wrote that, you know, one day I will die. The guy on the street's like, "Yo, my friends keep getting killed and I could be next tomorrow." They don't articulate it the same way. Now, why is that important? Well, it goes back to this idea of that entire book, The 50th Law, is about overcoming fear. And what you start to realize is okay, if I fail at this thing, what happens? And so, you know, if you use maybe for young men in particular, you go to the bar, you see a girl that you attracted to on the other side of the bar, what's the worst thing that happens if you go over and talk to her, she laughs at you. Okay, there's like 400 other girls in just that bar, let alone that entire street's probably got a couple thousand. You know what I mean? And so like when you're young like that's not how people think, right? But then all of a sudden it becomes this idea of like okay rather than be scared of failure or fear that outcome once you start to realize like the worst thing that could happen in this situation is not really that bad. That's really when you start to, you know, kind of get your potential unlocked. Now it doesn't apply to everything. Like if you're like some, you know, kid and you're like, "What's the worst that could happen if I take all these drugs?" Like, dude, really, really bad stuff could happen. Yes. So it kind of comes back to this idea of like you got to kind of, you know, be thoughtful and understand what is the game I'm playing, what is the outcome that I want, you know, think through it and be intentional.
Everything But Politics Podcast Host 33:55 ↗
So, a word you previously mentioned was preparation. So, I want to pivot to the world of investing. Can you speak on the art of buying versus the art of selling when it comes to investing?
Anthony Pompliano 34:05 ↗
Dude, buying's easy. So, if I ask you guys right now, what are three technologies that you guys are excited about for the next 10 years? What would you say?
Everything But Politics Podcast Host 34:14 ↗
I mean, AI would definitely lead. AI agents.
Anthony Pompliano 34:17 ↗
Okay.
Everything But Politics Podcast Host 34:18 ↗
I mean, social media, I think if you consider that, if you put that in that realm.
Anthony Pompliano 34:23 ↗
Okay. What's the third one?
Everything But Politics Podcast Host 34:26 ↗
Chips. Yeah. Like, yeah.
Anthony Pompliano 34:29 ↗
So, guess what? If people go and they probably buy an AI ETF, they buy a social media, you know, the social media companies like Meta. Yeah. And they buy, you know, the chips ETF, they're probably going to do pretty well over the next 10 years.
Everything But Politics Podcast Host 34:43 ↗
Great. Yeah.
Anthony Pompliano 34:44 ↗
Right. Now, could you mess it up if you're day trading or what? Of course. But like those are three key themes that you guys know, every dude on Wall Street knows. Even mom sitting in suburban America know. Mhm. Social media is big, right? You know, AI is going to be big, whatever. Like the buying is pretty simple. Selling is way harder because pretty much at any point in the last 30 years, if you sold Amazon, you're dumb. Mhm. Same with Meta. Yeah. I sold Meta, right? I worked there. I got stock. I sold it. Now, I happen to sell it and put it into something that went up a lot more. But like if I make that same decision a hundred times, am I right a hundred times? Absolutely not. And so you get into this thing of, okay, well, what if I invest in a private company and it goes public? Do I sell all of it? Do I sell none of it? Do I sell some of it? How do I do it? And so the selling is way harder. And so the best answer I've ever heard specifically in that example of you know if you invest in a private company it goes public. The best kind of mechanism is sell a third at the IPO, sell a third 18 months later and never sell a third. You kind of can't be wrong. Mhm. Right. You hold at least a third of the position and you sold a third of it up front and you sold a third kind of halfway through. Okay. But really coming up with that as the mechanism for selling just means you don't have the confidence to make the decision of when to sell.
Everything But Politics Podcast Host 36:19 ↗
That's interesting. Now when you look at your portfolio, how do you stay well aware and up to date with what's happening with all of your equities?
Anthony Pompliano 36:29 ↗
You don't look. That's an interesting answer. And why is that? I try to buy things that I don't have to look. So Bitcoin, for example, I'm aware of where the price is generally on a day-to-day basis, right? Especially if it's going up. People text me, you know, call me,
Whatever. But it doesn't matter. Like, Bitcoin could go to $1. I'm not selling it. Bitcoin could go to a million dollars. I'm not selling it. I'm giving it to my grandkids. Why? Because I know Bitcoin can go up a lot. I know it can go down a lot. I know that there's fear-mongering. I know that there's real risks. I'm just not selling.
And as long as I have that mentality, you are never going to shake me out of my Bitcoin position, which means my grandkids are either getting a lot of money or no money. And they're going to think I'm a genius or an idiot, but either way, they're getting some Bitcoin and let's see how much it's worth. But I don't know, right? Like, I think it's going up, but let's see. Same thing with a lot of the stocks that I own is I just say to myself, I want to buy this and I don't want to have to figure out when to sell it. I think that this company is going to be way more valuable over the next 20 years. Let's see.
And when you do that, then it just removes two decisions. I only need to make one decision. What am I buying? I don't need to make the second decision. I already told you I think it's hard. So, like, just don't make the decision, right? Just buy things that you're never going to have to decide to sell and you're probably going to be better off.
Everything But Politics Podcast Host 37:51 ↗
And how could normal people find a way to invest in private companies?
Anthony Pompliano 37:57 ↗
The government could stop being stupid about it.
Everything But Politics Podcast Host 38:00 ↗
Go deeper on that. So, say a 25-year-old listening. He doesn't want to put his money in the stock market, but he's bullish on an AI technology that is not mainstream yet. I mean, how does someone do you email the SEC? I mean, what's the best even for...
Anthony Pompliano 38:13 ↗
No, they're not legally allowed to. That's what I mean. The government has made it illegal for somebody who is not an accredited investor to invest in the private market.
Everything But Politics Podcast Host 38:22 ↗
How does one become an accredited investor?
Anthony Pompliano 38:25 ↗
There's specific qualifications. It's like you got to, I think you got to make $200,000 a year for two years or you got to have a million dollar net worth outside of your primary home.
Everything But Politics Podcast Host 38:35 ↗
Interesting.
Anthony Pompliano 38:36 ↗
Pretty big hurdle, right? How many kids in America in their 20s make $200,000 a year? Not a lot.
Everything But Politics Podcast Host 38:41 ↗
Very few. Yeah.

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APA

Pompliano, A. (2026, October 6). How to Live an Extraordinary Life - Anthony Pompliano (#210) [Interview transcript]. Everything But Politics. CEOInterviews.AI. https://ceointerviews.ai/interview/2992448/

MLA

Anthony Pompliano. "How to Live an Extraordinary Life - Anthony Pompliano (#210)." Everything But Politics, 6 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/2992448/.

BibTeX
@misc{pompliano2026_2992448,
  author       = {Anthony Pompliano},
  title        = {How to Live an Extraordinary Life - Anthony Pompliano (#210)},
  howpublished = {Interview transcript, Everything But Politics. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/2992448/},
  note         = {Speaker-attributed transcript with timestamps}
}