The Wolf Of All Streets - Bitcoin CRASHES To $73K As US Bombs Iran And ETFs Bleed $733M

Episode Date: May 28, 2026

Bitcoin just collapsed to a 5-week low under $74,000 as fresh U.S. airstrikes on Iran reignited Middle East tensions and U.S. spot Bitcoin ETFs hemorrhaged cash — with BlackRock's IBIT alone shedding $528 million in a single day, its 2nd-largest outflow ever, while the 2-week ETF bleed has now crossed $2 billion. Add $1 billion in long liquidations, oil ripping toward $100, the CLARITY Act stalling in Congress, and a stunning CFTC reversal admitting it weaponized crypto enforcement against Gemini — and today's setup is the most fragile crypto has looked in months. We break down what's actually driving the selloff, what could trigger the next leg down, and whether there's any catalyst left that can stop it. Learn more about your ad choices. Visit megaphone.fm/adchoices

Bitcoin has crashed to $73,000 as the U.S. is bombing Iran once again. Meanwhile, ETFs have bled $7333 million in a day, and we've seen a billion dollars once again in liquidations. Isn't it fun to be in crypto? I think so. And when we have a great day like this, I bring on Josh Frank to talk about how amazing the market is and how much fun we're having. Let's go. Good morning, everybody. Happy Thursday and welcome to the wonderful world of Minecraft. I have a special assistant in the studio today who is running the cameras and my backgrounds. Spoiler, he's seven.

And so we get chickens running around in the back and the Minecraft background. Josh, you know, you could use that. I think the thing burning is a great sign of things happening in crypto right now. Yeah, it hasn't reached the house yet. It says a fire on the outside. But yeah, I do think that. That's pretty good. The Iranian drone missed, and it missed the house and hit the ground.

I don't even know, like, where to start on these days. You know, like, well, that's not the place to start with the blank thing. Bitcoin falls to six-week low amid war jitters, ETF outflows. I mean, taking a look at the market, it's pretty ugly out there, 73,000-ish for Bitcoin. Ethereum back under 2000, even the darlings of the market, Z-cash and hyperliquid, seemingly, dropping if only somebody had said they look kind of topy. But yeah, I mean, what do you make of the market right now first? Yeah. I mean, look, I think the, I mean, I'm not surprised about Iran even one out of 10. I mean, at the end of the day, they've never been willing to negotiate ever.

So why anyone expected that to change is beyond me. And so I expected this to kind of continue. And so to me, it was more a matter of when, not if. And I don't expect them to negotiate or come to an agreement because they've said all along that they don't really have interest in doing that. And so, yeah, I mean, I'm not, I'm not particularly surprised. Surprised the market hadn't fully priced that in and was expecting, you know, the pause to last longer. But we'll see. One thing that's actually relatively interesting to me today and is very reminiscent of

2021 or 2022, Stellar is up 26 percent on some DTCC news this morning, which I have not seen any token pump on Tradfine news pretty much at all. I mean, you know, Canton partnered with the DTCC. There are tons of other chains that have and that are working with them. And to move 26.5% right now watching it live is pretty stellar. I see what you did there. I see what you did there. Yeah, I mean, Canton, I actually, when they made that first announcement,

which was the first time you'd heard the DTCC really talking about tokenization at the Canton announcement, I couldn't believe that the token didn't move. but to be fair, it did in the subsequent three or four weeks. Well, but they also had a hundred other announcements. Yeah, but this, you're right. I mean, Stellar, and Stellar is a dinosaur. Like, this is not a new token. There's got to be a lot of bagholders.

So there had to be some pretty impressive volume to get this thing going. Yeah. I mean, it's just, to me, it's nothing to do with Stellar specifically or the DTCC. It's just the fact that a token has reacted to news. That's a good thing. we've seen tokens react negatively to news. We haven't really seen tokens react particularly positively to news announcements recently. And so to see this one, I think, is promising. It might, it might say something about who Stellars supporters are. And I think they overlap with the

XRP army quite a bit. Yeah, always. I think it's a unique set of people and set of buyers. But I do think it's interesting to see the market reacting to something, and we need to see that again. Yeah, that was one of the old predict, like, easy to predict narratives of the past was that XRP would pump and then an XLM would pump immediately afterwards. It was like that Steller always followed XRP price action. Clearly, that's the thing now, but that was always a thing. Yeah. Yeah. Yeah. Yeah. So, no, I mean, to point on markets, though, look, I mean, I think it's, there's a lot of noise right now. The war is not going to last forever. It will come to a conclusion. I don't know what the game.

I'm not, you know, I'm not a fortune teller. I'm not going to be making any money on polymarket, unfortunately. But the war will come to some form of an end at some point. And markets will recover. I mean, I think the thing that's interesting here, and I'm sure you've been talking about this for weeks and months and I'm not breaking anything, you know, particularly interesting to people, but all of the banks, all of the asset managers, everyone is moving into crypto.

And obviously they're talking about tokenization. They're talking about stable coins. also all of these different banks are focused on allowing their retail clients to buy Bitcoin, to buy ETH, to buy other tokens, to get exposure to ETFs, get exposure to products. And so you have this kind of backdrop, which is just extraordinarily interesting. I mean, we've been building and selling institutions for eight years, nine years in crypto. So I've been doing this for a long time. I've talked to these firms since there were one people, you know, one people teams.

And, you know, I spoke to one of the top three biggest banks in the U.S. last night. And, you know, they have like, I'm like, oh, are you? working with this person, they're like, no, they're on like this other crypto team and this other crypto team. They're like, we have a commercial company like a consumer bank crypto team and we have a tokenization team and we have a stable point team. And you're talking about these large banks, not hiring one person for crypto, building out like 100 plus person teams. And I think, you know, once the market recovers, I think you're going to, you know, it's going to be significantly easier and more accessible, both for retail and institutional market participants to access digital

assets because of this. And so it's really interesting to me. You have all this interesting, this incredible infrastructure being built, all of these banks coming in, all these asset managers coming in, you know, real things lining up, but price is not reacting to that. And so I view this as a temporary just reaction to the Iran news and not necessarily something long term. That doesn't mean, by the way, that Bitcoin can't drop lower. That doesn't mean that it's going to, you know, it's going to pump overnight. That doesn't mean any of that. But I do think as you think long term and you think about the future of the space, I mean, there's so much investment coming into crypto right now, and it's coming in from real players that have deep pockets.

Pretty much the vision of Satoshi, right? A hundred percent. Massive adoption by the banks and institutions and the governments. The irony is not often a stable point. Banks on the brink of adoption of digital assets. Banks on the brink. of incorporating blockchain into everything they do. Oh, man.

The killer. But the cool thing is, it's not only blockchain, not Bitcoin. Like a lot of the times in the past, you've seen this like blockchain, not Bitcoin, tokenization, you know, thing. And there's a lot of that. There's a lot of tokenization going on. But there's not like this negative perception towards crypto broadly, which is really interesting to see. And it's interesting to see, obviously, everyone's talking about hyperliquid.

So I'm not trying to, you know, go into that too much. but the hype ETF, seeing a lot of inflows. Matt from BitWise was tweeting about how it's such an easy conversation with, I think, financial advisors to talk to them about, you know, hyperliquid and cash flow and stuff like that. So there are interesting things going on in the space. And I think, you know, we're a retail bit away from, you know, a huge, you know, huge positive movement here. Awesome. Their prices are the best marketing for Bitcoin, right?

100%. All we need is like $10,000. We need to hit $100,000 again, and I think we're good. So let's talk about the most fun story of the day, which is Robin Hood is allowing agentic trading. So your agent will be able to build portfolios, automate trading strategies, adjust your portfolio, analyze your portfolio, analyze market data. But this is the first time effectively that an agent will be able to trade. for you. It will be in a siloed account, which will be your agent's account. It will have basically read access of your entire account, but it'll have right access in its specific one. It will be

able to make trades on your behalf without you specifically pushing a button or permission. None of this is yet regulated, so I definitely appreciate the fact that they're willing to push the boundaries, knowing that they're going to get pushback probably from the government and certainly other exchanges and such. But, you know, I'm not generally particularly particularly. particularly cynical, but like feels like this is a way to just lose money faster? I think it's incredibly bullish for Robin Hood stock because what it means is that people, instead of trading once a day or once a week or once a month, are going to have AI bots trade for them at an incredible frequency,

and Robin Hood will be able to monetize every single one of those trades. So I think it's positive for the exchanges and venues. You know, Robin Hood, I think their crypto volume dropped about 75%. I think there was an announcement about that or some news about that a few days ago. And so you know, you get enough people to trade with their AI bots. We start to see volume picking up again. But I do think it's an incredible way for people to lose money, as you mentioned. There are some extremely sophisticated systematic trading firms that have access to way better data, way better tools than the average person is going to have access to.

And they're going to pick off trades and they're going to make a lot of money. Yeah, I mean, I understand. Everyone's not going to be successful, but, you know, there's also this idea of alpha decay, right? The more people that have access to the same signal or the same data and the more people that trade on that signal and trade on that data, the more that there's a decay in the alpha and the opportunity to make money. And so I'm not particularly bullish on people's ability on average to make money using AI agents to trade. Yeah, I mean, so basically you'll be able to plug in Claude or ChatGBT, Qatcer, Codex. those are the four that I'm seeing, and then using a natural language prompts, you'll be able to automate strategies and build portfolios like build a portfolio of little-known

tickers across the AI supply chain, right? And it will build you a portfolio and go access that. My favorite thing is the risk disclosure in that article that I just showed you. Here's how they wrote it out. You are ultimately responsible for the trades your AI agent places in your account. You're in charge of your trades. When you use an AI agent to place orders, all investment decisions are yours. Before your agent takes action, you can review what it's about. to do. Be aware that if you ask your agent to take action without asking your approval,

it can place trades without your confirmation. Review disclosures from more details about the risks. I mean, obviously, this is just like legal. I think the other opportunity, by the way, is if you're a token or an equity and you can do a really good job training these AI that you're an undervalued asset, you're going to get a big bit. So I definitely recommend hiring marketers who are good at, you know, AI placement. Because that's, I mean, that's, I mean, you know, You know, used to be SEO, you know, was the focus for a lot of marketers and, and, and, and, and, and, and, and, and, and, and, and, and, and, and, and, and, and, and, and, I think ranking an AI agents is, you know, maybe going to create a bit for some tokens.

I mean, now, if we're going to be, I guess, honest, this is the direction things are moving, whether we like it or not, right? I mean, this is where the, the puck is headed. All exchanges are going to have AI integrations with crypto and prediction markets on stable coin rails, you know, that, that's where we're headed. Yeah, 100%. 100%. I just think that, you know,

there are, just thinking about all of the times that you've been given misinformation from AI, and then you're going to give it your money. I don't, AI is incredible. I use it in my workflow every single day.

I spend hours on AI every day. But am I ready to let it trade for me against sophisticated, you know, systematic trading firm? Here's what I've found. AI talks to me like it's my, mom, not like it's my wife. Like, whatever I tell AI, it tells me it's a great idea and I'm doing wonderfully. Your mom likes you a lot more than my mom. It agrees, you know, and it's like, you know,

really support. And if I told my wife that thing, she'd be like, that's dumb, you know, like, should be brutally honest. We need AI that's more wife than mom. Yeah, I mean, I've been, especially if it's going to trade for us. Like, I don't want me to be like, you know, is it really a good idea for me to trade esoteric, you know, crypto on Robin Hood for my AI agent, like, go find find the coins between 100 to 200 market capital. No, I want to tell me that's a stupid strategy. Focus on hyperliquinsie cash and Bitcoin. Yeah, like is FTT going to make a comeback?

Am I? Is this a great idea here? Should I put all my money in FTT? So good. Undervalued token in the market. Real powerful narrative because of name brand. Yeah. It's also going to give you, you know, like I wouldn't be surprised if it's trading off of like

old information too, like some partnership announcement from six months ago than gets incorporated. Look, and I'm sure these things are going to get better. I'm just not putting my money in it. No, I'm not going to let them trade for me yet. Like, I, you know, unless I'm a very big strategy and I've developed myself. Yeah. So, I mean, we're talking about kind of the institutional adoption and plumbing. I mean, there was actually three stories, I think, in a line that kind of for stable coin adoption. One was, I don't even have all pulled up, but SOFI is basically launching their

own stable coin, I believe, for 15, their 15 million users. So it's basically a bank issued stable coin, which is a little different than what we've been seeing. Then you had MasterCard getting their bit license in New York, which is like the most difficult thing you can ever do, which is obviously to build stable coin rails. But then this one,

which really caught my eye, Block kicks off cash apps phase stablecoin rollout to its nearly 60 million users. So this is Jack Dorsey. I mean, Jack Dorsey was like our last Yeah, it was our last like Bitcoin for payments maximalists, I think, that we had. And so, you know, this, when he throws in the towel and says, we're going to use stable coins and he said it reluctantly. I'm now looking for the exact quote.

He said, I don't like that we're going to support stable coins, but our customers want to use them. I don't think it's wise to go from one gatekeeper to another. So, I mean, listen, there's the irony that like our killer app is obviously the thing Bitcoin. was created as a hedge against. We've like hyper-dollarize the world and made fiat faster and cheaper and more plentiful, but he's got to do what he's got to do for his business.

But this really does just to support your, everybody has a stable coin plan or a crypto plan and it's all happening. Every single, every single firm does. Every single firm does. I mean, Jack is really like that. He was, I think he was truly our last holdout. I mean, Jeremy Aller said it too.

He was like, everybody has a plan. And you just have to wonder, though, how that accrues value to anything we might be holding. Do you think that their stable coin mass adoption will make Salon on Ethereum go up? I think it depends on where the stable coins are issued, where they're used, if they accrue fees to the network, if there's a lot of transactions. But I think ultimately, the way that a lot of these institutions are building, they don't care about, like an institution isn't going to brag about using. using AWS over Google Cloud. I don't think they really care. And I think that's also why this L1, like L1s and L2s have really sold off quite hard

is because this idea of like owning this kind of platform for users is not, is not, you know, I think maybe from a retail perspective, you can own that more. But I think from an institutional perspective, it's really plug in play where a lot of these banks, institutions are going to plug into six or seven or eight or nine or ten different networks and they're going to choose whoever is cheapest and route trades or route orders or route flow to wherever is least expensive because why would you pay more money to do something if you don't have to pay more money to do something? So I think, you know, I think it's I think what is a net positive about all the staple coin adoption is if it can bring people on chain and then it

can be a way to enter into additional things. But I think in terms of like if there's another billion dollars in stable coin issued on a chain, it's positive. It's positive. It's positive, but, you know, does it justify the token going up by $5 billion? Probably not. I mean, then what about, I guess, in that context, the private blockchains that are being purpose built for stable coins, you know, tempo with stripe and arc with circle and those? They're launching specifically for that purpose. Do you think if we can get access to those tokens after BlackRock and everybody else's

has gotten? I'm not, I'm not, I, transparently, I haven't looked into that space enough. But I think you can see it with, you know, a lot of the chains that exist today, you know, people aren't really watching stable coin minting and redemption on particular chains and making investment decisions based off of that, to my knowledge. This is a hilarious tweet that I just got sense. I just got to say this one. Crypto, the only asset class to go down on a Trump tweet.

Micron is good. It's to 20% up. I'll never let crypto down 3%. It's pretty funny. I mean, like you were kind of talking about how with the. Iran war, you're surprised that the market hadn't priced things in. What I'm surprised about is that people still believe anything about the Iran war based on a tweet or a statement or anything in that markets actually continue to react at all. Like we all know that it's theater, right? I'm not

speaking specifically about Trump. Iran makes a comment. Trump makes a comment. Somebody else makes a comment. Israel makes their comment. And like, markets actually react as if anybody is telling you the truth. Yeah. And I just, I just, yeah, yeah, I know, look, I agree. I agree. And Trump, if you're listening to this, and I'm sure you are not, but if you're listening, please, please mention specific tickers in your tweets. Don't say crypto broadly. We want some tickers. Yeah, we have too many. We have millions of coins. It's yeah, we need a couple of things. And I'll leave the tickers up to you. Maybe, maybe leave World Liberty Financial and Trump and Melania coin out, but, but, you know, some other tickers would be great. That's reading about those hasn't worked.

I mean, yeah, it's crazy. I mean, my thesis around the market has been that sort of the launch and an evolution of prediction markets has been actually kind of the silent killer of all points. I mean, you take a look at a hyperliquid, not to, it keeps coming up all the time. But even what Robin Hood's doing and all the others, it seems like they're just building more massive casinos. And we used to be the only casino in town. Right. I mean, it's like you could basically view it as like, you know, the early days of Vegas and there was just like one or two casinos. that was all coins on a weekend 24-7-365 and meme coins and now they've built all of Vegas

around it with prediction markets. I think the other thing too is when's the last time one of your friends told you they made money on a coin, right? Like that's what started, you know, starts a lot of these bull markets, right? Is somebody say, oh, I got into this thing and I 50x my money, I 20x my money, I 10x my money, I 5x my money. Even I went up 20% at this point, I think we'd take. You know, we're not hearing any of those conversations. And I think once those conversation start to happen and your Uber drivers starts telling you about how much money he made trading a coin you never heard of before. I think that's really what starts the, you know, what's what starts the movement. And I think ultimately at the end of the day, there were

a tremendous amount of tokens that launched that raised a ton of money, but there are not that many buyers of those tokens. And I think you need one of two things. Either you need retail to come back or you need institutions, especially liquid funds to raise capital, especially those that are more like discretionary long bias that are going to actually be the ones that are buying the tokens. And right now we're seeing redemptions and a lot of those funds. So you need like the question that I always have is it doesn't matter what these people, you know, what people do and what they announce. At the end of the day, someone needs to buy the thing, right? If you're only thinking about how I sell my coins and not what do I buy, then you have to imagine other people are

thinking very similarly. Yeah. I mean, what's really sad in that vein is that now like when the biggest mover is like it's pulled like a 3x this year which is amazing by the way but crypto people want to hear 3,000 x this year it's may already right when you have 10 assets in your portfolio one three X is the other is drop 90% the portfolio is still down yeah yeah the 3x is not not getting there it's kind of wild man kind of wild yeah look we'll see I'm not I'm not I'm not long-term bearish. I'm still long-term bullish on the space, especially with everything I see behind the scenes and everyone coming in. You know, the fact that, you know, one day you'll be able to, you know, log into your, you know, brokerage account, whatever bank you work with and,

you know, buy, you know, insert token name. I mean, that's pretty cool. The fact that you can work with your financial advisor and they can, you know, help you with the crypto allocation, all of these things are going to, are going to help, right? And it's, you know, it seems. It seems, like it's a matter of time. It's a matter of, you know, when, not if. And I think even in DeFi, a lot of people are extremely negative about Defi, especially with AI and, you know, the ability to hack things much more easily, right? You know, when you think about, you know, building a, you know, a smart condo or anything else for that matter, right? When you're an engineer, you need to prevent a rat against thousands of different attack vectors, but to be a hacker, you just need to find one entry point.

And I think that scares a lot of people in Defi, but I go and I speak to financial institutions. And I mean, you saw Apollo with Morpho and you saw BlackRock with Uniswap. Like there's real things happening behind the scenes. There's institutions coming into the space that are interested in the space that are going to build in Defi that are going to think about offering their customers products with Defi, you know, potentially using these different lending, borrowing marketplaces to offer yield to customers. Like that's really happening. It's really coming. And so I think it's just a matter of when that happens, not if it happens. And I think you'll start seeing a lot of announcements in the next few months into the next year.

Yeah, I agree. I mean, listen. Whether they'll move the market, though, is a different story. That's the thing. I think that that remains the narrative that we could keep pounding the pavement on is that adoption is absolutely real. Every institution. I will say, though, a lot of it is still pilots.

And so I think what we also have to see is a large number of actual transactions happening on chains. A lot of it is pilots. A lot of it is very, very early. And so I think what we need to see is like, okay, X bank announces the tokenization initiative on Y chain. I want to see 500,000 transactions a day that that bank is doing, right? And it can be on a privacy chain and I can, maybe I can't see what the transactions are, but I can just see that it's the bank or maybe it's on a public chain, whatever it is. I think it's just a matter of seeing some of these things hit production. I think once that does, the narrative shifts very quickly. Yeah, I agree. I'm trying to bring up a really funny meme, but I can't get it to go into

the window because I wanted to just show it to you because it's funny. It can't get it to go. It won't work. It's, it's, uh, it's not a JPEG, but it's Michael Saylor with a huge green candle coming out of his pants. The doctor's measuring it. And it says, this man will single handily drive the price of Bitcoin up so much. Learn about these stocks of his STRC and MSTR. We had the point where Sailor is like the only thing that's doing this for us anymore. Yeah, I mean, he is, but I think also people view him as an existential risk, too. So I wonder how much, you know, people see a buy. And partially it's like, okay, great, he bought the token.

But on the other side, it's like, all right, he's continuing to own more and more of this token. You know, you know, how much of a risk is that? Yeah. I just really want to be able to show this meme. It's not working. Okay, I think I got it. Wait. Yep, won't go.

It's coming as the wrong kind of file. I blew it. All right, man, well, that's actually everything that I wanted to discuss today. So we get to get you out of your empty room earlier today. So I congratulate you. Next time I'm on, the candles are going to be green. And if they're not, Blaine Scott. We'll live.

We'll live. And everybody else, I'll see you for The Daily Wolf. And then, of course, show tomorrow. Thank you, Josh. There again.