A conversation with How to Live an Extraordinary Life author Anthony Pompliano
It’s holiday szn on The Joint Account! Consider Heather’s newsletter last week her proof of life, as she has once again banished herself to her writing hole (and by writing hole, I mean our dark office in the basement). Don’t worry, she’s got a space heater and will be just fine. All jokes aside, we’re piecing together the final chapters of our forthcoming book, Money Together. I have goosebumps just thinking about a completed manuscript.
Speaking of books, I recently spoke with my friend Anthony Pompliano (aka Pomp) about his new book, How to Live an Extraordinary Life. Anthony is an influential entrepreneur and bitcoin advocate who has created one of the largest independent financial media platforms in the world. With more than two million followers across the internet, there’s a very good chance you’ve seen him before.
What I love most about Anthony’s book (other than being able to read it in one sitting) is how personal it is. From more than 60 letters written to his children, the book draws heavily on Anthony’s experiences as an entrepreneur, investor, and writer, offering readers practical advice on how they can navigate uncertainty, embrace risk, and design a fulfilling life. I am thrilled to share some of the best parts of our conversion (edited for brevity and clarity) with you.
D: Each chapter of the book is a letter you wrote to your kids. Parenthood has made my life extraordinary. What's been the best part of being a dad so far?
A: My wife and I are very happy when we see our kids happy. You begin to realize that a huge part of life is just doing things or living a certain way because of the impact it has on them. It makes you be a little bit more introspective. That’s probably what your parents did for you, right? The willingness to do things that maybe you otherwise wouldn't do simply because you want to see your kids smile or be happy has been very rewarding.
Then there’s the positive impact of thinking much more long term, like from an investing standpoint. I always joke with my wife that every investment I make is for our kids. Parenting forces you to think very long term. And whenever you can do that, I think that you end up being in a better position.
D: A lot of people struggle with a fear of failure. As an entrepreneur, I would love to know how you manage fear while taking calculated risks. What have you instilled in yourself to deal with that?
A: When I sign books for people, on the inside of the cover, I write the same three sentences. I write: "Fear is a silent killer. Be relentless. Be extraordinary." The reason I write "Fear is a silent killer," is because I believe that most people are limited by the fear they impose on themselves. This fear doesn't show up in your actions; it shows up in your inaction. When you're younger, you're scared to go talk to that girl at the bar. You're scared to go and apply for that job. You're scared to go after whatever it is that you want to do because your parents or friends may question you.
The single greatest mitigator to fear I've found is an understanding of your mortality. I was fortunate to learn this lesson in an unfortunate situation when I was twenty years old. In Iraq, somebody died, and I just realized, like, "Hey, we're all going to die." Thankfully, I learned this lesson at 20 and not 80. But what is there really to be fearful of, right? We're all going to end up dying, so you may as well squeeze as much juice out of this life as you can. In hindsight, that was probably the single most impactful moment in my life, because it really changed how I thought about taking risks, overcoming fear, and all these different components that may censor other people from doing what they want.
D: How does risk factor into your relationship, and how you navigate financial discussions with your wife, Polina?
We divide and conquer, in the sense that she is responsible for being the brakes, and I’m responsible for being the gas pedal. When we first started dating, I remember telling her, "Don't invest a single dollar." And she was like, "What? Everything you do on a day-to-day basis says the opposite.” And I said, “No, because the way that I invest, I could blow up.” And so, one of the two of us needs to have some money left for us to be able to live. So, you just save your money, I'll go and take all the risk. I think over time, it’s proven to be a pretty good strategy, because she’s very sober in moments of volatility—she’s not paying attention to asset prices and things like that.
D: For couples that are navigating big financial decisions together, what advice would you give them about managing risk as a team?
A: I think the biggest thing is communication. Most people really don’t communicate that well, and so the better communication you have, the better off you’re going to be. And that’s both on what you want and what you’re doing. So, what’s is the goal, and what are the actions? I think that’s a big piece of it, too. And then just explicitly stating to each other what your risk profile is. I think that my partner and I got comfortable with the fact that my risk profile is probably on the upper end of almost anyone we know. Hers is not. And so, there are times where being able to communicate, "Hey, I’m at my upper limit, which I know is beyond yours, but this is kind of my allocated risk for the year," is important.
D: It always comes back to communication. Okay, back to the book! There are 62 letters in it. If you had to pull one out and be like, "Hey, I’m giving you only one lesson. Here’s the one I’m giving you," which one would it be?
A: It’s so hard to pick just one. When Polina and I had our first kid, we sat down and had a conversation about if we can only teach our kids one thing, what do we want to teach them? And the thing we landed on was to be a good decision-maker, because we felt like that was a very specific skill, but it was applicable to everything in their life. You worried about your kid being out at midnight? Well, they’re a good decision-maker. They’ll be okay. Your kid has to make professional work decisions? Again, they’re a good decision-maker. They’ll figure it out. As far as a specific letter goes, I think that "Luck Is Not Real" is probably the single most important one, because the overall theme of the book is that you have agency. Your life is the sum of the decisions that you make. Sure, people have different starting points, but ultimately, the outcome is based on the decisions you make.
D: What makes life extraordinary?
A: I think an extraordinary life is different for every single person, right? What my version is could be different than your version. But ultimately, living an extraordinary life is just kind of getting out of life what you want. And for many people, what they want to be is happy, they want to be free, they want to be secure, and they want to be surrounded by family and friends. Based on all the different people that I've spoken to, it’s sometimes less about the accomplishments or the activities and more about how you do things and who you do them with.
D: Is there anything to add as you think about how you approach risk and money in your relationship that you would add?
A: The risk you take is the return you should get. If you want small returns, you should take small risks. If you want big returns, you should take big risks. And that’s true in relationships, that’s true in portfolios, and that’s true in creating memories. I just think that there are two types of people in the world: people who run away from risk and people who run towards it. From my perspective, being the person who runs towards risk is not only more fun, but there’s a bigger reward on the other side. It’s not easy to do but it’s a pretty big competitive advantage in life.
Thank you so much to Anthony Pompliano for this thoughtful convo (and for his continued support and friendship over the years).
What makes your life extraordinary? Let us know! But also, Pomps’s book can help you figure that out. Buy your copy today!
For the past nine years, we’ve kicked off the month of December celebrating Hazel’s birthday. All she wanted on her big day was a pancake breakfast, a trip to the movies to see Moana 2, and a steak for dinner. Mom and Dad were happy to throw in a slice of cheesecake too! Although, I am not sure who is sweeter: Hazel or the cheesecake?
TJA in the News
Last week, Doug joined CNBC’s World Wide Exchange to discuss tariffs announcements, risk management for single stock investors, and how he’s speaking with his clients about 2025.
And Heather (along with 39 other Substack writers) shared with The Purse what she likes to do over the holidays (spoiler: it’s a whole lotta nothing).
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