The Wolf Of All Streets - Bitcoin To The Moon: Wall Street’s Bitcoin FOMO Begins

Episode Date: May 30, 2025

Friday Five is THE show about the main news in crypto. Join me and Nathaniel Whittemore as we break down the stories shaking the market. Trump Media’s $2.5B Bitcoin play, Vance’s fiery Bitcoin Conference speech, Gamestop jumping into BTC, and Circle’s blockbuster IPO are just the beginning. Don’t miss this explosive episode – the future of crypto is unfolding fast, and you need to be ahead of it. Nathaniel Whittemore: https://twitter.com/nlw ►► JOIN THE FREE WOLF DEN NEWSLETTER, DELIVERED EVERY WEEKDAY! 👉https://thewolfden.substack.com/ ►► Arch Public Unleash algorithmic trading. Discover how algorithms used by hedge-funds are now accessible to traders looking for unparalleled insights and opportunities! 👉https://archpublic.com/ ►►TRADING ALPHA READY TO TRADE LIKE THE PROS? THE BEST TRADERS IN CRYPTO ARE RELYING ON THESE INDICATORS TO MAKE TRADES. Use code '10OFF' for a 10% discount. 👉https://tradingalpha.io/?via=scottmelker Follow Scott Melker: Twitter: https://x.com/scottmelker Web: https://www.thewolfofallstreets.io/ Spotify: https://spoti.fi/30N5FDe Apple podcast: https://apple.co/3FASB2c #Bitcoin #Crypto #FridayFive The views and opinions expressed here are solely my own and should in no way be interpreted as financial advice. This video was created for entertainment. Every investment and trading move involves risk. You should conduct your own research when making a decision. I am not a financial advisor. Nothing contained in this video constitutes or shall be construed as an offering of financial instruments or as investment advice or recommendations of an investment strategy or whether or not to "Buy," "Sell," or "Hold" an investment.

According to the brothers Trump and of course, literally everybody at the Bitcoin conference, Bitcoin is going to the moon with targets of a million dollars across the board. But that is the main story of the day, the Bitcoin conference, but we've still got a lot to unpack from this week, especially because I've been off at the Bitcoin conference and haven't been able to do shows and cover everything that's been happening. Luckily, we have NLW who's always on top of the biggest stories here for the Friday Five. Let's go.

Let's go. I have a rule that I will only stay in Vegas for one night. I broke that rule. I stayed for three nights. Most people were staying for four to seven nights and they are all absolutely insane because Vegas is nuts. You could not have chosen a crazier place to have a Bitcoin conference. You weren't there, were you?

No, no, no, no, no. I've done my tours of duty at those, but it is looked good from afar. It was and it's strange. Just the irony of it. And I said this on a recording that we put out but having a Bitcoin conference where everybody's telling you never sell hold forever low time preference, think about your children 50 feet from a casino where the same people go out and start rolling dice and

playing stupid games like I did called Double Down Blackjack. I don't even know what it is. But you know, we played and the irony is just so thick. Yeah, hilarious. You know, yeah, I love it. But waste your money, go to the casino on the way out of the conference. Yeah, well, it's allocate a very specific portion of your money to to waste is a is another way to come out of this. Your your your entertainment budget for the Bitcoin conference. I guess if

you're not going to club 11 in Miami, it's that's what I was going to say is if you're if if your worst transgression in Vegas was staying at the Double Down Blackjack table just a little too long, you probably escaped. Okay. This game is absolutely absurd though, but I won't get into it. But it was, it was a good time. Anyways, let's talk about the Bitcoin conference. I think obviously the biggest story there was JD Vance speaking, right? Regardless of what he said, the fact that he spoke, I think was, was the real key. But he says the U S should use Bitcoin as an advantage and rivalry with China. Crypto finally has a champion in the White House during the Bitcoin Conference speech, you know, I'm not sure if everybody

heard it. But JD Vance spoke and people were very excited about his words. It to me, it felt a little bit like he just kind of took the best most viral parts of Trump's speech from last year and borrowed them. Like he said, we're gonna fire fire Gary Gensler people like Gary Gensler. If you remember last year, Trump said it twice because it was so popular, but very clear that JD Vance gets it. And it was, I think, a big signal that he was willing to show up and give this speech.

Yeah, I mean, I think to me, it read a little bit like, you know, certainly there's there's the administration line that he's reinforcing, and that's a read a little bit like, you know, certainly there's the administration line that he's reinforcing, and that's a part of it. But, you know, JD Vance was interested in Bitcoin before it became sort of part of the Trump administration agenda. And it felt to me like he was positioning himself as not just sort of a transactional friend,

but actually interested in this. He took a very populous tone with it. You know, it was Bitcoin as a tool against sort of, you know, the elites and power and all those sort of things. You know, he basically said it was a hedge against transgressions of power no matter who's in office, you know, which is at least lip service to the idea that it's not sort of a partisan thing. So, you know, I think that the tonality was a little bit different and less transactional perhaps than some political speeches that we've seen. And also I think sort of on a personal level, he was also calling on this community to continue to stay engaged. It was a sort of a not so subtle political rallying sort of speech as well.

Basically saying, we continue to not be able to ignore politics because politics is not gonna ignore this industry. Did you have any other huge takeaways from the conference from what you saw? Obviously, both Trump brothers spoke, as I alluded to before, Bitcoin's going to the moon. They reiterated the same points.

That was all great. But man, the lineup was absolutely insane. So there really were a lot of key moments. I think that what so I interestingly, I was at a TD securities, like conference in New York yesterday speaking, and and we were talking a little bit about crypto and crypto being back and, you know, or the game everyone's presumption was or Bitcoin, at least is back. And I think that sort of, you know,

the Bitcoin event, having such sort of big headline presence is very reminiscent and reflective of where we are, you know, this cycle really is a Bitcoin cycle so far doesn't mean that it'll stay that way forever. You know, there's there's certainly sort of themes that are emerging. stablecoins are obviously a big theme, you know, we constantly talk about what are what are the narratives there are, but, you know, the fact that there was so much energy and attention anchored at the Bitcoin conference, even though there are discussions of other things, I think is notable, right? That's where the energy is, right now is sort of the mainstreaming of this particular asset. I will say one thing that's not all that encouraging, if you're sort of in the industry, is like David Sacks gave us absolutely squat nothing

in terms of, you know, actually, you know, new ideas, new policies moving forward. I mean, you know, I think some people were hoping that we'd get some sort of, you know, interesting update on the BSR, given that we've had deadlines from those executive orders passed, and there was just stone nothing around that

other than sort of some lip service to the idea that it's still a relevant thing. We don't even have an audit on the United States government's Bitcoin holdings. Yeah, yeah. So now I think it's a little less encouraging. Yeah, my biggest takeaway is, I think, from being at the conference, obviously, anecdotally

is, you know, if you went to Bitcoin Miami in 2021, it was like the crypto trading degenerates partying at clubs. And it was like being at Coachella, you were there, it was at the Miami Convention Center, it was absolute insanity. This time, it was a lot of suits in a good way. And everyone I spoke to was like my age or older. This was not at all young people. This was family men with their kids and their wives.

And it was just, we've grown up. And to me, like regardless of what was said on stage, that was really kind of the single and the most noticeable takeaway that I had. Interesting. Yeah, no, I mean, that reflects sort of the substance of stuff that was coming out from the outside, you know? But look, I think it'll be interesting

to compare and contrast. We've got another massive event in permission lists, just by sheer numbers coming up at the end of this month. So, and my presumption would be that that will be a little more, you know, it's slanted more sort of diverse sets of crypto folks, not just Bitcoin. You know, they're pretty self consciously trying to have it be a bigger tent. So, you know, it'll be interesting to see how those themes, you know, is it that same

crowd just in a different location? Or, you know, is it does another part of the industry show up for that? I think it'll be somewhere in between. But I think because you're allowed to say things about altcoins at permissionless, it'll probably have a bit of a different audience, right? I mean, this is really kind of Bitcoin only focused. Even if you remember in 2021, as much the joke was always that you could say Bitcoin on stage, you couldn't ever say Ethereum on stage, but you could go like and look at a booth for an NFT project on the convention floor. Now it's Bitcoin miners and Bitcoin companies down there

and much more serious. There really isn't just, you know, no mascots running around and none of the kind of hype and strange things. Really felt more like a TradFi conference to some degree in that way. Interesting, yep. Yeah, it was great. So obviously, one of the bigger things that happened during this week, while everyone was at the conference, Trump media to raise 2.5 billion to invest in Bitcoin. This

was kind of interesting because it was reported they were raising $3 billion. And then Trump came out and said, you know, they're idiots, and the people they listen to are even dumber, right? And this wasn't true. And then of course, a day later, it was 2.5 billion to invest in Bitcoin. So I guess it was just leaked a little too early. And I guess along those same lines, you know, GameStop stock price continues sinking, but they bought 512 million versus Bitcoin that was announced. There was actually quite a few

of these that went unnoticed. I think one huge one that nobody's talking about, not a company, Pakistan to have a strategic Bitcoin reserve. So I guess all of this in the frame of a lot of people, a lot of institutions, a lot of sovereigns actively buying Bitcoin, and then the focus on Trump and the Democrats obviously pushing back against his involvement in the industry, as you can see here,

how Donald Trump's crypto dealings push the balance of corruption. So I guess we can start with the Trump Organization buying Bitcoin and then talk about the implications of that and then just casually have a conversation about companies buying Bitcoin in general. Yeah, I mean, I think that the, well, one, the sailorification of everything

is sort of clearly a big dominant theme. You know, we talked about it, I think, either last week or the week before, you know, you're getting a louder set of people asking questions around, you know, how good it is. I think one of the things that's interesting is a lot of the sort of Layer 1 analysis of how it could all go wrong, especially if it looks at microstrategy, tends to sort of come up short, right, because Saylor's very smart and good at this, and he's structured his, you know, debt really well. And so it's unlikely that he's, you know, that he's going to sort of face, you know, crushing liquidity cascades and things like that. However, I've seen a number of people point out this week that while we don't know exactly the terms of

all these deals, it's almost for sure that they're not getting the type of terms that sailor is getting, right? They're not able to control this in the same way. And so you know, it is new risk being piled into this system. So that's that's a growing conversation. I don't know if there's anything to say about it other than just I have a lot to say about it. But yeah, finish. I'm gonna let you finish. No, but I think I think that's that's that is so sort of like, you know, a big part of the theme outside of the Trump. Let's pause there and talk about it for a minute. My biggest takeaway outside of what I saw at the conference, and I wanted to save it for this part, is that we now know exactly what the next bubble is and exactly how we're

going to completely fuck this up in this cycle. It is Bitcoin treasury companies, and there's 99% certainty in my mind that that's the case. It is insane. Within four hours of being at the conference floor, I was pitched literally 25 of these. And I saw the terms that people have gotten to participate in these. And this is the ICO shit coin cycle of the past repeated on public markets with tradable stocks.

And it's absolutely gonna blow up. It has to, I'm not saying micro strategy will blow up. I'm not saying Nakamoto or any of the responsible ones now will blow up. But I'm saying exactly what you are is that the terms are going to get worse and worse. They're going to push just like the voyagers and the Celsius is and the block buys in the past. Oh, you got 7% yield, we need to give our customers 8%

yield. Oh, your note has 8% yield, we need to do 10% yield. And then Bitcoin is going to drop and they're going to start having to sell this off. And it's going to cause a liquidation cascade. Tale as old as time. I had one person who I love and respect and these people are all going to cause a liquidation cascade, tail as old as time. I had one person who I love and respect and these people are all going to make a ton of money on it, pitch me six of these. Six. They were in six personally within a week. And so people who have participated in these, most of the early investors are already up 2530 X on their investments. And you got to remember, this isn't like I co's of the past, to some degree, you would get you know, you

invest and you'd get slowly over time. Like a lot of these guys, this is a reverse merger with a company that's already publicly traded, and they're sitting on the stock. And listen, for better for worse, if you had the opportunity, you would take those bets because it's great. But there's no way that this doesn't unwind horribly at some point in this cycle. Yeah. Well, it's interesting because you also have people like Adam Beck saying that we can absorb 100 trillion Bitcoin can absorb 100 trillion of this to band, you know, so

it's like even a lot of the Bitcoin champions are also, you know, sort of encouraging encouraging it as it stands. Now, that said, there's also a lot of let's call it a diversity of opinion here, right? This is not a sort of universal, everyone's cheering for it with Bitcoin, there are a lot of questions. But, you know, animal spirits take over and the questions get drowned out. Yeah, I mean, I actually we posted like a random live macro Monday yesterday on this channel. And we didn't have

McGlone, but we had James Lavish and Dave Weisberger and I asked them flat to their face like what do you think of this? Because I know James runs is a partner in the Bitcoin Opportunity Fund and I knew for a fact that they're participating in a lot of this. Right? And he said, listen, we're going to leave a ton of money on the table like the minute that they're too overvalued, we're selling them. But this is the opportunity right now.

We have a fiduciary duty to take advantage of it. We have access, but shared the same concerns long-term. So even the people who are participating to some degree very responsibly know that there's gonna be a time when the music stops with these things. My biggest concern, you're gonna get 100 of these at the top, right? Like if Bitcoin's gonna be at 150 or 175,

I want to make it clear. I don't think that like this bubble pops today at 105. But you know, as the FOMO goes up and people realize there's not the same kind of money to be made in altcoins and VC and that narrative is kind of passing, this is going to be the new version of that. I definitely learned that a lot of people who purport themselves to be Bitcoin maximalists all made their money in those ICOs and shitcoins quietly. And this is a new way to do that. But there will be a time when, you know, 100 hedge funds come in at the top and try to do this.

Or you know, they'll say they're Treasury companies, but really LARPing and will be like hedge funds and they're going to structurally do it wrong. They're going to have some idiot running it and they're going to have to sell a ton of Bitcoin. I asked Jack Mullers about it too, actually, and he was like, good. He was like, because we'll be the responsible ones who are buying Bitcoin at a 50% discount. So even those who are bullish on these, there'll be a big drawdown to buy and it'll be yet another weak hands to strong hands transfer.

But I'm concerned. Jim Collison Yeah, yeah. I put that firmly in the category of things that we are now actively watching and checking in on week over week, I think, at this point. I mean, we have officially hit the point where there's too many of these announced or sort of, you know, who have made buys to really capture them all. Even with the Daily Show, I'm finding it like they're I'm watching them roll off the list of things that I actually cover, you know. Yeah, well, I'm definitely here for any company that would rather be holding Bitcoin than cash.

Beyond that, if you're financially engineering a way to get more Bitcoin, it's somewhat a replication of stock buybacks and all the issues that we've seen in the traditional financial system. But you know what, if they can secure the bag and not kill the market somehow, I'm here for it. Yeah, I mean, one of the things that our function is with the financial system is to push the boundaries

far enough to figure out where the fault lines are. So, you know, here we go again. Well, let's quickly before we move on to the next topic, I don't want to miss the Trump Organization's participation here raising 2.5 billion to buy Bitcoin. And then, of course, the criticism from the Democrat side and others. Yeah, I mean, look, I think that the, you know, the the challenge here is there's a lot of things that are, you know, I think that I absolutely take them at face value when they say they're true believers. That was a big part of the sort of Don Jr. and and Eric's, you know, speech this week was just confirming that this is not, you know, they're they're all in on this.

They have been for a while, but it's very clear. This is sort of a natural thing for them to do. This isn't surprising at all. In fact, it's, you know, this is exactly the type of kind of financial engineering that, that, you know, these organizations tend to like. So that, that doesn't surprise me at all. They're in a position to do it, you know. I think it does add fuel to the to the fire, obviously, for Dems as everything will. But I think that the meme coin is where a lot of the focus is right now from Democrats. You know, you're seeing, I'm noticing a lot more connecting the dots between meme coin purchases and pardons. And you know, maybe it's just the occasion of this dinner that they had, you know, a week ago or whatever it was. But I'm seeing that start to pop up on, you know, Instagram stories from normie friends

who aren't, you know, connected to crypto at all. And it feels like that's where sort of like the story is hitting the mainstream a little bit. Yeah, we talked about sailor obviously, I think consensus is that sailors safe, but that doesn't secure keep him safe from criticism because he had a big one this week. Michael sailor calls on chain proof of reserves a bad idea rules it out for strategy over security concerns.

This was all while we were at the conference. I didn't get to dig too deeply into it. I did see I believe that Arkham actually went ahead and found and docs the addresses anyways, but big head scratcher for a lot that sailor was not willing to be transparent about their proof of reserves and their wallet addresses. Look, I like sailor but every six months or so he reminds you that he is doesn't give a fuck about like the you know, the

community can talk the game all he wants he is here for a specific purpose. He's an absolute mercenary. And he's not going to play by crypto community rules just because their norms like he's going to do exactly what is good for him. And again, this literally every six months, there's some new thing where he says something that's completely out of sync with, with what sort of Bitcoiners believe and they have to sort of pause and reevaluate. And then

where they always get is like, you know, what, whatever, we don't, we don't require, usually what has happened is that people realize that they don't require 100%, you know, alignment with, with someone to sort of still consider them on the same team. But, you know, for a lot of people, this is a big one. And the logic, I don't think think is super resonating with people, you know, especially when you have like, you know, Bitwise who's ETF, they've been able to sort of, you know, share this type of information without it being a big concern and stuff. There's just enough counter examples that it just doesn't super hold muster.

But, you know, I can't imagine that this won't blow over, you know, Sailor's gonna do exactly what he's't blow over, you know, sailors going to do exactly what they do. And I get that everybody's upset about it. And like I said, I didn't really pay much attention. This was one of those less less signal than noise situations. But do people really believe that because he's not sharing them, that there's some sort of fraud and they don't hold the Bitcoin like what? What are they? What's the real concern?

What are they worried about? That he's not being transparent? Yeah, I think the concern is that the industry has spent a lot of time trying to sort of normalize proof of reserves as just a thing that you do for exchanges, for other big players. And so to have the person who's sort of arguably the most influential in the field right now, just crap all over that and not only say that he's not going to do it, but that it's genuinely a bad idea, it creates cloud cover for everyone else not to do it. You know, he basically like if you dig in, like some of the more offensive parts of the, of the comments are like, you know, basically saying that the problem with, you know, things like FTX wasn't proof of reserves, It was like, I don't know what I said, like something like, you know, don't work with little offshore tweakers or something like that, you know, like a clever catchphrase, but a complete deflection from like transparency norms that the industry has started to, you know, rally around.

So it does do damage to the normalization of proof of reserves as a sort of standard thing for a leading actor to just sort of, again, not only not do it, but to publicly crap all over it. Yeah, that all makes perfect sense. Let's move on to stable coins, because that was another huge thing on the docket throughout the week, generally. But I think the biggest story in that space, obviously, is that Circle seeking $624 million in their IPO.

Obviously, that's not the value of the IPO, that's how much they're looking to raise. And of course, to follow that up, BlackRock maybe gonna be buying about 10% of that. Some other big names obviously looking to participate. And all of this, while stories are still circulating, that Coinbase and Ripple are trying to buy Circle. Yeah, man. This is just... I have no idea at this point what's likely to happen with Circle.

Every couple of days we turn around and where it's pointed is headed in a different direction, which makes me think that they're playing all kind of angles right now and seeing where it lands. Yeah. We obviously don't know what's going to happen here. But I think that this is indicative of how much incredible demand there is for companies like this. I mean, generally for companies in crypto to go public, but also I think to grab a piece of the stable coin market as legislation heats up. Maybe we should talk just very briefly

about where Genius is at and what the odds are of that passing. Yeah, I mean, look, I think that Circle has been right at the center of two sometimes conflicting forces. Force one is political machinations, right? Like when the political fortunes of the Genius Act and some of the specifics around the Genius Act have been more in question, circles, you know, the appeal of the IPO has been sort of lower. But then you have sort of this countervailing force of, you know, the interest in the IPO market feels like it changes, is incredibly quick

shifting, right? ETORoro was a surprise, but then everyone sort of is like, now geared up. And I think people are prepared or trying to seize extremely small IPO windows, right? I think that like people feel like there may be a window right now, but that it could be a very, very short one. And so you have sort of this extra concentration of demand. I mean, look, you know, side long this news, we also got news that the big banks in the US were like planning a stablecoin consortium, right? So that was our next story. Yeah, Circle's gonna have ridiculous competition. You know, so they got to, they got to either they got to position themselves in some way, either gear up with more money to compete or, you know, kind of land in a home that's got bigger resources. So I don't know, it's, it's, they are really interesting bellwether

right now of everything that's going on, you know, kind of at a high level of the industry. We're gonna go full Lord of the Flies with stable coins in the United States in the coming years, it's gonna be wild, because listen, we've already seen sort of shots across the bow publicly between circle and Tether. Now we obviously have Tether being you know, finally, they have their proof of reserves from Cantor Fitzgerald as we know, but

Howard Lutnick and Cantor Fitzgerald being partial owners. And obviously Tether now part of 21 with Jack Mullers and Softbank and Cantor Fitzgerald just getting more of I think a stamp of approval in the United States circle looking to come online as a public company. And then all of these banks trying to compete with that directly all in the context of wondering what will be allowed from the genius act or whatever stable coin legislation passes, everybody is

going to stable coin their faces off in the next few years. This is it's gonna be Bitcoin, Treasury companies and stable coins. That's what we're going to be doing. Absolutely. You know, stable coins have this, you know, incredibly strong product market fit. You know, the narrative has made them, you know, by by by investing in stable coins, you're also investing in America now, right? is sort of like the way that the narrative is resolved. So you know, by by by investing in stable coins, you're also investing in America now, right? Is sort of like the way that the narrative is resolved. So you know, from so many

different angles, there's there's going to be a ton of energy around it. I know that those were all of our topics. Someone said, why aren't you guys talking about why is the market dumping and not going up like it's supposed to? It's not supposed to do anything. But literally, I'm not gonna say there's the reason. But I can't recall a time when Bitcoin went up during a Bitcoin conference. Yeah, it's a rule.

It used to be consensus. Now it's just a rule for any big conference. It has to go down. Anybody who would be buying is playing double down blackjack. Yeah. I don't know if the four-year cycle still exists, but I'm pretty sure that the conference rule still exists. I wouldn't worry about it until it keeps going down for a week after this. Yeah, I'm not concerned about $105,000 Bitcoin, personally.

Yeah. No, but I actually I don't- I am a bit concerned about altcoins though. Listen, I think we will have our altcoin seasons, things will go crazy. But I'm telling you, that is not where the pumpers and dumpers and go crazy. But I'm telling you, that is not where the pumpers and dumpers and the the extractors are looking right now. That's those things go up and down because of the huge VC money and all the people that have been participating in them. Those people want Bitcoin related things right now. Yeah, yeah, I don't know. I just do in a quick search of various

channels to see if there's any specific catalysts. But look, we continue to have every other story is sending a different signal when it comes to tariffs and trade. And so there's that general background volatility, which just means one step forward, one step back pretty constantly. Also just a reminder, at Liber Liberation Day when all of the market uncertainty really kicked in Bitcoin was $82,000. It's now 105,000. Yeah. So if you're wondering about when it was supposed to go up, that's a time it probably was supposed to go down

and it's up big. So I would not worry about Bitcoin at the moment at all. That's all the stories that we have for you guys. Give NLW a follow and of course, check out the breakdown and we will be back next Friday for the Friday Five. Thanks, man. Later, guys. Have a great weekend. Let's go.