E157:Anthony Pompliano: This is what happens when you go all-in on Bitcoin (you get rich?)

0:00I would rather my portfolio go to zero than make a ton of money playing some sort of insider game where it's just a circular thing where it's just a circular thing where money moves around and rich people keep making a lot of money to make a good. veteran and prominent Bitcoin advocate who in 2025 raised over$750 million to launch ProCap Financial. 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.

0:44So I have conviction. How much do you think about now is a good time to get married and have kids versus where I'm at in this kind of financial position? 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. Let's finish with a quick one that people will want to know. You still own a big chunk of people throwing Bitcoin. What's a realistic return for 2026 and beyond for someone who buys today at 70K or 80K or 120K?

1:15Well, I think that...

1:20Hi everyone, this is the little bit that I know none of you like that can help us make a huge difference for this show and we want to take it next. 71 % of the people who regularly watch When Shift Happens have not subscribed and so all I'd ask you if you want to make a huge difference is the following. If you've seen this show before and you like it, help me, help my team, hit the subscribe button and we'll continue to build this show for you. Thank you. I'll talk about first how you are doing. Doing great. Good. For a fifth podcast of the day.

1:55It's just like a meeting. Yeah, exactly. I mean, if you're the guest, to be honest, it's kind of easy, right? You just go, you just answer. Preparing for like, as a host is actually much harder. Yeah. We interviewed this guy today and I was like, oh, in the morning, I'll just spend a few minutes and I'll put together a bunch of questions by reading through his Twitter account. and then twitter was down i was like oh exactly i was like this is what i get man now why why did i wait till this morning so how did he go i got on i mean it's about like the feds things i'm like genuinely interested in says hey man we're just gonna talk about what i want to talk about is that good he's like yeah okay fair enough for those of you who didn't watch previous episode where you came on i think eight months ago can you just tell us who you are uh anthony popliano investor entrepreneur somebody likes to have fun you like to have fun and you have a favorite word relentless why 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 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 right it's true in business and your personal life uh anything that is kind of worth pursuing absolutely it's true also in markets right where markets going up down price going up down it's very easy to be optimistic when price go up markets go up when market go down sometimes for a long period of time it's much less easy but you are super optimistic all the time mr optimistic how do you keep conviction when things are bad or look bad and your portfolio is down bad who cares in the short term right like uh it's like buffett it'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.

4:11It's hard to do, but ultimately, what is Bitcoin? Bitcoin is something that I think is going to persist and grow and continue to appreciate and value as the world recognizes what it is. So what it does today, tomorrow, next week, next month, who cares? What really matters is if it's going to work over 10 or 20 years. Probably easier to say this when you generate really good income every month. What do you tell someone who maybe doesn't generate good income every month and is much more reliant on their portfolio when i started investing um i didn't really have that much money i didn't have any income actually i had 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 we've got a lot of stuff you just the risk versus the reward.

5:07When 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 that much to lose. As you actually grow, that's where you become more 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 you got nothing to lose how do you how do you do that well i think that 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 hard you got context switch back and forth but i've been doing a long time so you know you learn how to do it how much of a cowboy are you or do you wish you still wear i 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 when it comes to investing, how far out on the risk curve I'll push at certain times, concentration.

6:40It works when you're right, but also you got to have a plan when you're wrong. And so if you said to me, of a lot of people I know who seeks 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 so if it is one times downside loss versus unlimited upside capture okay tell me more about this concentration bets that you're putting because you're saying hey look i'm the most risk like the guy who takes the most risk amongst my friends. I want to know more about that. I want to know also if I'm crazy in what I'm doing.

7:21Well, I mean, look, there's different things you do at different points in your life, right? So when I was in my mid to late 20s, I was single and then I got a girlfriend. I had an apartment and that was pretty much all my responsibilities. I had to get food and kind of like normal living expenses, but that was the 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, maybe seeds I was planting in the ground. So I was building a business. I didn't take a salary, but at least I knew that, hey, if this works, there'll be equity value there.

8:08there 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'll 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 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?

8:50Where there's like, you know, full correlation.

8:54Quick one. I want to thank our partners who help us make this show possible. I'd like to thank our friends at Jupyter, the DeFi super app. Anything you want to do on-chain, from trading to earning yield, you can just use Jupyter. Personally, I'd recommend getting the Jupyter wallet on either your laptop or your phone, 10 times faster and 10 times cheaper than the competition. You're going to love it. Thank you to the awesome team at Castcard, my go-to card to spend my stablecoins directly with my Apple Pay to buy anything, food, coffee, hotel night, or plane tickets without having to use a bank ever again how do you change that like i don't want to call it like the the there's a fine line between being a gambling addict and being like very concentrated but sometimes you might be kind of in denial right or you might be so confident in your bets that you're going like all in then you say at some point you have more responsibility to change that are you really able to change that or it's the other kind of seeds that you plant that you planted that actually became big enough so that you can still i don't want to say be a degen but like be all in uh and and fully concentrated in your bets in your liquid portfolio to me like the degen stuff all that that to me is like fairly unsophisticated um speculation right so that is I'm in a group chat.

10:19Somebody tells me something. I don't even look into it. I just buy it because 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 in. There's kind of an ungoverned, unsophisticated, pure gambling or speculation. That's not what I do. Bitcoin is a great example. I don't think I've ever publicly said this, but in 2018, I had the opportunity to meet with a 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 had a very storied career, very successful.

11:03And in that conversation, 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 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.

11:43I have confidence in the analysis that I've done. So I have conviction. I'm not the type of person that if you say to me, hey, here's a stock tip, I'm not even going to go look at it. I have a very specific kind of strategy. And so I think that it is less about 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 what does that mean concretely for you you said before me too late 20s i had a girlfriend an apartment and 95 of my net worth in bitcoin or liquid net worth in bitcoin you are now you mid 30s you have a wife mid 30s perfect uh late later than mid 30s okay right mid 30s he'll take he'll take it you're in your mid 30s i'm in my mid 20s um what does that what does that look like today in terms of a liquid net worth bitcoin wise like how did you change a lot or you still think well i i didn't um i made a concentrated effort that I need to dilute the percentage from a Bitcoin perspective by making more money and going and investing in other assets.

13:09Okay, fair enough. Right? So I didn't want to sell the Bitcoin, but I also didn't want to continue to have 95 % of my net worth in Bitcoin. So it's really hard, right? I mean, Bitcoin performs very well. Yeah. And so you have to, you got to do a lot of different things. And so I just think of it as this is a natural cycle of maturation for most young people who begin to invest. You start out hyper concentrated. And then over time, you end up either adding a couple of more concentrated bets. So you get diversification, even though you might go from one or two to five, more than doubled, right? Or almost 5x the number of bets that you had.

13:55But also, Bitcoin's a very interesting asset where I just at some point said to myself, I'm just going to give this to my grandchildren. Once I decided that, it's like an illiquid asset. So it means you don't buy Bitcoin anymore? I still have more Bitcoin today than I did then. Sometimes I've bought it. Sometimes I've gotten distributions from funds in Bitcoin. You know, look, I'm a Bitcoin believer, right? So if I have an opportunity to get more Bitcoin, I'm going to get more Bitcoin. But I think that there's certain things or certain attributes that you start to think about. So when I was very young, I was solely interested in what I would consider maximum return, right?

14:39Just total return. If I buy something, which one's going to go up the most? I don't care about volatility. I don't care about correlation. I don't care. I just want max return. Bitcoin was probably one of the best, if not the best assets to do that, right? So like check. Okay. Got that one. at least directionally correct. Now, I tend to think of things as I want to invest in certain areas that are solving problems and make a return. So - Rich people problem. It's not a rich people problem. Bitcoin does that, right? Bitcoin helps protect purchasing power for hundreds of millions of people around the world.

15:13I feel very good, right, about Bitcoin's role in the world and what it's producing. But also, take housing as an example. We started a business in residential real estate sector two and a half years ago. And if you go and you look at the announcement, it's called Resi Club. And in that announcement, I talked about home affordability is the worst that it's been. It's going to continue to get worse. You cannot solve the problem unless you understand the problem. We partnered with a guy who I think is the number one residential real estate reporter in the country, it's got Lance Lampert. We started a business to go and try to solve that from an information insights research, et cetera standpoint.

15:51Today, they are one of the most sought after places for information and data on the housing industry. Okay, great. I'm putting my time, my attention, my energy, and some of my capital towards trying to help solve that problem, right? If we're right, we'll all make money. Great. That's how economics and how capitalism should work. On top of that though, when I saw Open Door and a bunch of people start thinking about that business and looking at it and talking about it, et cetera, I said, I want to invest in this business because this could potentially help solve this problem. It's another way to get at that same problem, right?

16:27Now, if you said to me, hey, make the investment, you're going to lose all your money, I wouldn't have made the investment. If you said to me make the investment you've got a high upside potential but you're not going to do any good in the world i wouldn't have cared either because you mentioned rich people problem i don't think that's what it is right i don't think that um i've come to the conclusion that the businesses that create value over time do something positive in the world they solve a problem for somebody and when you look at it through that lens all of a sudden you can start to say to yourself what is the role of this business in society?

17:01What is the problem that it is solving? And how good of a solution does it have to that problem? As you understand that, now you know where economic returns are going to come. It's a bit similar. I mean, similar as building a company. You can't keep going at it if you don't believe in the thing, right? Of course. So the investment is the same. Like the thing will do well, not well, et cetera. You're not going to keep the thing if you don't have conviction. Absolutely. I tweeted this a while ago and I think the people, I think they kind of thought I was joking. And I forget the exact way I described it.

17:31But I basically said, I would rather my portfolio go to zero holding Bitcoin and Open Door and a bunch of these assets than make a ton of money playing some sort of like insider game where it's just this circular thing. Money moves around and rich people keep making each other richer. Yeah. But you don't actually have the impact in the world. and so you know i think that's easy to say once you start making these investments but just how i genuinely feel is the same as building a genuine business versus scamming people right if you think about the mindset is like okay i could maybe like take a shortcut and make much more money but like how would i feel probably like shit i mean depending who it is but like most people would feel like shit whereas i can build a business the right way it's very hard it's hard to make profits all that it takes much more time but i'll feel much better about myself and maybe i'll be less rich than a scammer but at least i'll feel good right i won't want to throw myself out of the window randomly when i wake up in the morning i tell um uh a couple friends and i have discussed this where we've seen people do things in the business world and we say man do you know how rich we would be if we didn't care about reputations if we didn't care about our ethics if We didn't care about, you know, could we go to sleep at night?

18:47Imagine me in 2021, if I had launched a crypto coin. I could make a billion dollars, right? Probably. And there's people who did that. It's just never, never. I've always said there was zero chance that I was ever going to do something like that, right? In the private tech world, how many founders went and they raised these massive valuations, took huge secondaries, and within six months walked away and said, hey, you know, I'm going to go work on other things. Right? Again, it's a different mentality. And so I think that, again, I'm not here to judge anyone. Right? It's just, what do I want to do with my time?

19:24What do I want to do with my energy? And focus on that. Thank you to our friends at Paradex for supporting this show. Paradex is the leading perpetual decentralized exchange with zero fees, deep liquidity, and privacy. Season 2 runs through the end of January, so you do not want to miss this one. Trade on Paradex and start earning points by using the link in the description down below. At WhenShift Happens, we're huge believers in freedom, and privacy is at the core of it. That is why we partnered with Zashi Wallet, the easiest self-custody wallet for private transactions. You can send, receive, and spend Zcash without middlemen or surveillance using Zashi, the wallet that was built by the team that launched Zcash in 2016.

20:09Thank you to Mantle, the distribution layer that connects traditional finance and on-chain liquidity for real-world assets. To accelerate this vision, Mantle is running the Mantle Global Hackathon and is inviting developers, founders, and innovators to design, build, and deploy scalable real-world assets and decentralized products on Mantle. Check the description down below to participate in the Mantle Global Hackathon and make a difference. I just want to talk about what you said before you have this Bitcoin portfolio and then you say I'm not gonna sell that I need to force myself to create more value somewhere else so that part that is already outperforming so well becomes a lesser part of my portfolio right and so that's that's actually an amazing way to look at most people will look at I need to invest in this whatever next amazing assets to become rich no no you need to invest in that but then you need to never sell and build more value on the side to kind of dilute this part that you don't sell and you basically need to force yourself to go and kind of suffer more and one way to buy bitcoin another way is probably to get married and have kids in in terms of suffer more in terms of like how much money i need to generate right if you think about that for example like i'm thinking about these too how much you think about the now is a good time to get married and have kids versus where i'm at in this kind of financial position right oh maybe bitcoin did amazing well and maybe i made i reached my goal my number for retirement in terms of bitcoin right but actually i'm not generating that much money but hey i have a wife she wants to have kids etc like how do you think about that do you think it should be rational as a man or you're more like fuck it like i go for it and then i just need to find ways to not sell my bitcoin but generate more cash flow whatever with other businesses i think i've always uh approached it as um the money ultimately you can't take it with you so live your life and enjoy it right i was um in a weird way very fortunate to live through a very unfortunate situation early in my life um and it really hit me we're all gonna die once you understand that you say to yourself all of the business, the finance, the investing, the money, all that kind of stuff.

22:34It's important to a degree. You got to be able to afford to live. You got to be able to support your family or your children, or maybe you want a really important thing. And there's some people I know who are like, traveling gives me energy and happiness. Costs money, right? You got to be able to afford that stuff. So it's important to be able to do the things that you want in your life. but there's a lot of things that i consider some of the best things in life that are free right now people will be like oh you know marriage is free let me tell you you want to go on a date that costs money right you want to go so like that costs money right you want to have kids it costs money right so again it's this weird uh dichotomy of like even the things that people you know kind of uh pontificate about oh the you know things in life are free if you really want to enjoy it it costs money right so money is important when um i met my now wife uh i'd never thought i was going to get married ever and it wasn't for any other reason than i was just like i just i like my life i'm good right um i had friends who were really happily married i had friends who had disastrous marriages right now i'm good like i like my life um but once i met her i you know by the end of the first day i was calling her my girlfriend she was like will you stop that right like what are you doing and um then at some point it was just like it felt right like hey let's have a kid right okay let's have a second kid right okay right um and you just figure it out right but 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 right yeah and there's some people who that scares the hell out of them frankly right and they're like i don't want that switch to turn right like i'm good there's a lot of people who say look i you know i want to be in that situation neither one's right or wrong it's just you know what who are you what makes you happy and then go pursue that you said it's for your fifth show of the day right you talk to a lot of smart people i'm not one of them um what's one topic that comes the most in terms of uh our audience of reasons into investing and wealth building for 2026 amongst all the people you talk to i think that um there are three things uh people are very interested in right now humanoid robots is i think a huge investment trend i think that um there's going to be an explosion of the prediction markets i think that's a very still underestimated trend um and then i think that there is uh i'll call it ai but not ai like the model companies and stuff like that like the actual um applications and the things that people are going to use so kind of like ai enabled whether it's services products etc and you know if you think humanoid robots the biggest market in the world you're going to replace humans in a bunch of jobs okay um if you think of prediction markets it is a new source of information no different than the internet was a new source of information now you have this new source of information here and it's information meets finance so there's a monetization method really interesting and then the ai stuff i think all you're doing is you're taking superhuman intelligence and you're using it to do things those things are likely to be very valuable and so you just look at okay where are the opportunities in these different sectors and you know sometimes we might want to build companies other times we might want to invest in them week one i want to thank our partners who help us make this show possible thank you treasure my favorite cold wallet to store my crypto and make sure i sleep well at night if you want to order a treasure wallet and sleep well at night too.

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27:09What's one way to invest in each of these three? I mean, probably the first one is Tesla. I would say for someone normal, right? In the public market, Tesla, I think is probably the biggest one. I mean, look, if you really want to get very sophisticated, you can go and you can look, okay, what are all the component parts that are in the humanoid robots? What companies produce those? How do I go and actually isolate it? You also could use like a prediction market where you could say, hey, is there some way to bet on the number of humanoid robots that are in the market at a certain time or something like that?

27:38Prediction markets, it's pretty difficult right now unless you can invest in the private market, right? But I think that'll be a big sector. And then the AI stuff, I think it's pretty hard for people to predict which one of these is going to be successful and so there's the nvidia's and kind of like the infrastructure players right chip manufacturers whatever or use it you know one of the things that i always laugh about is um let's say that you and i both have a hundred dollars and i say okay i gotta go find somewhere where i can put a hundred dollars and i can double and i want to do that this year there's not a lot of two x's in 12 months now people coming from the crypto world like what are you talking about that happens in like five days right you know they're so used to you know kind of this different world but in the regular world most investors if they got 2x every year on an investment they would be ecstatic but could you just use the ai to make an extra hundred dollars yeah absolutely right no downside all upside yeah i talked to uh bernam strong from coinbase and uh avishal from electric capital and they both said the same thing the the the the technology is not lacking the resources are not lacking what's lacking is self-belief most people don't have self-belief and so at least they're talking at larger scale right thinking about launching the next big thing but here even the people don't think about themselves like hey like you have a hundred dollar or a thousand dollar probably you are the best person to invest into to double or 10x or 20x money but you're not thinking that way well just think let's say your living expenses is 2500 hundred bucks a month right but that's a lot of money for a lot of people right okay well if you have some way to cover that twenty five hundred dollars could you use your time and energy and talent to generate a better return than going and buying a stock probably right probably who are the best investors in the world entrepreneurs absolutely right their own businesses uh let's finish with a quick one that people will want to know you still own a big chunk of your bitcoin for your portfolio in bitcoin what's a realistic return for 2026 and beyond for someone who buys today at 70k or 80k or 120k well i think that um i don't know for the next year or two if i look out over a long time horizon i think bitcoin will continue to compound somewhere in the 20 to 30 percent a year range could be higher certain years could be lower certain years right but somewhere in that range kind of two to three times the stock market okay over 10 years it's a really attractive return right there's not many hedge funds that say hey i returned 25 or 30 percent a year every year compounded for a decade or two decades.

30:33For free. No fees. And you don't have to do any work. That's the other thing is if you work at a hedge fund, you got to work. You got to talk to people. You got to do research. You got to, you know, do it's stressful. What's the end of quarter mark? What's my bonus going to be? How do we hire? Oh, I got to manage people. I got to deal with LPs. I mean, there's a lot of work there. So again, it just comes back to, I think people who hold Bitcoin over a long time horizon, person they'll be happy maybe if they had unrealistic expectations they won't be as happy as they thought they would be if they had low expectations they'll be more happy than they thought but over time Bitcoin tends to do very well and I don't think that's going to stop anytime soon 30 a year where does that get us to in 10 years well it depends on where do we start right Bitcoin's prices all over the place yeah let's say 100k so to make it very easy could be 50 it could be 150 50 but like let's say 100k like what what people because people kind of think exponentially right it's very hard yeah how do you think i mean what does that mean 30 a year for 10 years more or less i don't know what the math is off top my head right i can't think exponentially either but um if you just think about uh every single year that compounding gets bigger and bigger and the longer it goes the more in the later years right so the beauty of compounding is it's like the buffet you know 65 years old and after that's when he made most of his money he started when he was 12 right so if you think about that for 12 to 65 he was pretty rich but most of his money came after the age of 65 it helps they lived to you know 90 something years old but still that's crazy you said i'm gonna leave my bitcoin to my grandchildren So that's probably in a long time.

32:26What do you think a Bitcoin could be worth in whatever 30, 40, 50 years when you leave your Bitcoin to children? One Bitcoin. What? One Bitcoin is going to equal one Bitcoin, right? Good answer. I mean, just think, fiat currency has been around since 1971, right? We're what, 55 years into the experiment? Yeah. so 40 years from now means that Bitcoin would be the same age that fiat currency is right now one Bitcoin one dollar is definitely not worth one dollar anymore one dollar is not worth one dollar from last year right amazing thank you so much for doing this that was awesome as usual thank you for having me as you probably know by now I host some of the biggest names in Bitcoin and crypto on my podcast but a lot of the best stuff never makes it on air The Shift newsletter is where I share that raw behind the scene alpha, the insights, stories, and lessons straight from my guests that you won't hear anywhere else.

33:29If you want the real insight take on Bitcoin and crypto, join my newsletter, The Shift, in the description down below.