Anthony Pompliano: This is what happens when you go all-in on Bitcoin | E157

I would rather my portfolio go to zero than make a ton of money playing some sort of insider game where it's just this circular thing. Money moves around and rich people keep making each other richer, but you don't actually have the impact in the world.

I had 95% of my net worth in Bitcoin and every dollar I got, I bought more Bitcoin. And so it was just full conviction. There's a fine line between being a gambling addict and being like very concentrated. To me, it wasn't a risky bet. I have confidence in the analysis that I've done. So I have conviction.

I tell young men all the time, the single most motivating thing in the world is when your wife gets pregnant for the first time. There is something biologically that switches in your brain where you are like it is on me now to make sure that this kid can eat food. It's motivating.

Well, I think that um

Doing great. Good for fifth podcast of the day. It's just like a meeting.

Yeah. Preparing for like as a host is actually much harder.

Exactly. I was like, 'This is what I get, man. Now, why why did I wait till this morning?'

I got on I mean, it's about like the feds. So, things I'm like genuinely interested in. Says, 'Hey, man. We're just going to talk about what I want to talk about. Is that good?' He's like, 'Yeah.'

Uh, Anthony Pompliano. Um, investor, entrepreneur, uh somebody who likes to have fun.

That is one of my favorite words. Um I think that a lot of stuff in life just comes from uh continuously being persistent and just kind of relentlessly going after something. And uh most people they just uh they give up at some point. You know, things get hard, it becomes uncertain, uh there's darkness. And uh if you can just remember like just keep going, man, you'll be all right. It's true in business, in your personal life. Uh, anything that is kind of worth pursuing.

Who cares in the short term, right? Like uh it's like Buffett's got this great quote. He says, uh the market is a voting machine in the short term and a weighing machine in the long term. Just because Bitcoin's price is down doesn't mean Bitcoin's different. It just means that everyone is being dumb and they're letting you buy it on sale. Great. If it's really really high, maybe actually you shouldn't be so euphoric. Maybe you should say, 'Hey, hold on a second here.' You know, things got a little crazy. It's hard to do, but ultimately like what is Bitcoin? Bitcoin is something that I think is going to persist and grow and continue to appreciate in value as the world recognizes what it is. So what it does today, tomorrow, next week, next month, who cares?

When I started investing, um I didn't really have that much money. I didn't have any income actually. I was paying myself zero dollars and I figured it out and I knew that uh it was actually a superpower because I had nothing to lose, right? I can't take tons of risk as I've gotten older, right? We've got a lot of companies, got a lot of stuff. You just the risk versus the reward. When you have nothing, what's the risk that you make a bet and you're right back where you started six weeks later, six months later, it's not really, you know, that much uh to lose. As you actually, you know, grow, that's where you become more uh risk intolerant. And so you have to train yourself to say no, I have to continue to act in a way that is pursuing asymmetry that's looking for, you know, kind of outsized returns, which is actually more uncomfortable later in your career than it is in the beginning.

Well, I think that I I basically bifurcate my life. I know that there's things that, you know, I've got responsibilities. I got a family. I got, you know, certain things I got to do. And so I make sure that that stuff is covered. And then once I know that, okay, I've got a plan as to how I'll address that stuff. Like other side, it's cowboy time. Let's see what we can do. Right? And so you got to be able to compartmentalize, you know, like downside risk with upside capture. It's it's hard. You got to context switch back and forth, but I've been doing a long time, so you know, you learn how to do it.

Here's how I would describe it is I got a lot of friends who are uh very very successful. I probably take more risk than almost all of them. Um when it comes to uh investing, uh how far out on the risk curve I'll push at certain times, concentration. Um, you know, it works when you're right, but also you got to have a plan when you're wrong, right? And so if you said to me, you know, of a lot of the people I know who seek the most asymmetry, it's me. What that also means though is I'm looking for opportunities where it's really, really hard to lose substantially more than one times the downside.

Well, I mean, look, there's different um different things you do at different points in your life, right? So, when I was in my mid to late 20s, um I was uh single and then I got a girlfriend. I had an apartment and that was pretty much all my responsibilities. I had to, you know, get food and kind of like normal living expenses, but like that was the uh entirety of my responsibility. I had 95% or so of my net worth in Bitcoin and every dollar I got, I bought more Bitcoin. And so it was just full conviction. Now, with that said, there was a lot of other, you know, maybe seeds I was planting in the ground. So, I was building a business. I didn't take a salary, but at least I I knew that, hey, if this works, there'll be equity value there. Um there I was investing out of a fund outside of my personal capital. So I knew that hey if I make good investments in this fund down the road right there will be money here. So you know in terms of like the liquid assets I had I was all in for the most part. But I also you know again kind of this like risk uh reward. I knew that I was still making bets or still setting something up where okay if I'm good at this other thing or I'm or I'm right there will be some sort of you know upside there as well. They may have some correlation to each other, right? Early stage technology and Bitcoin are somewhat correlated, but it's not like I was, you know, buying Bitcoin and then buying Bitcoin miners in the public market, right? Where was like, you know, full correlation.

To me, like the DGEN stuff, all that that that to me is like fairly unsophisticated um speculation, right? So, that is I'm in a group chat, somebody tells me something, I don't even look into it, I just buy it cuz somebody says it's going up 20x. Oh, I find this thing, it's going to promise me 50% returns. That sounds too good to be true, but screw it. I'm right. Like like there's a um kind of an ungoverned unsophisticated, you know, pure gambling or speculation. That's not what I do.

Bitcoin's a great example, right? I don't think I've ever publicly said this, but um in 2018 um I had the opportunity to uh meet with a uh sovereign wealth fund. And you can remember in 2018 that was not a very popular thing for institutional type investors to be interested in Bitcoin. And there's this one gentleman who um had a very storied career, very successful. And in that uh conversation um I realized that we were going to have to explain to him what was Bitcoin. And I went back recently and I looked and we wrote more than a 20-page research paper. What is Bitcoin? How does it work? How do you custody it? How do you value it? You know, all the cycles, all this stuff. How many people did that amount of work and could explain it that clearly? Probably not that many, right? There's some definitely some, but when you do that, you have the utmost conviction. Now, I could have been wrong, right? Bitcoin could have not worked, whatever. But like to me, it wasn't a risky bet. It was I've done the work. I I have confidence in the analysis that I've done. So, I I have conviction.

I'm not the type of person that if you say to me, hey, uh, you know, here's a here's a stock tip, I'm not even going to go look at it, right? I I I have a very specific kind of, you know, strategy. And so I think that it is less about like high risk taking. What I really think of myself is I try to have a concentrated portfolio where I am a maximum risk mitigator. By mitigating risk it allows me to be very concentrated because the bets are so asymmetric.

Yeah, mid-30s. Perfect.

Okay, great.

Mid-30s is good. He'll take it.