The Wolf Of All Streets - Bitcoin SHATTERED A $6B ETF Record – $10.6B Friday Expiry Hits

Episode Date: June 24, 2026

Bitcoin is staring down its biggest day of the week: a $10.6 BILLION Deribit options expiry Friday with nearly 80% of positions out-of-the-money, clustered around a $60K put and $80K call — meaning the next 48 hours will decide whether the relief rally extends or collapses. CryptoQuant publicly called on Saylor to STOP buying as Strategy's dividend obligations QUADRUPLED to $1.2B annually. Add the dollar at a 7-month high, Meta secretly building a prediction market called Arena, the CFTC suing Kentucky as the federal-state war hits 9 states, and the CLARITY Act with 4 unresolved sticking points and 5 weeks until Senate recess — and Friday's $10.6B expiry is the single most important catalyst of Q3. We break down what $60K vs $80K means for the rest of the cycle, whether Saylor will actually pause, and which catalyst could break the floor before Friday. Learn more about your ad choices. Visit megaphone.fm/adchoices

Visit BetMGM casino and check out the newest exclusive. The Price is Right Fortune Pick. BetMDM and Game Sense remind you to play responsibly. 19 plus to wager. Ontario only. Please play responsibly. If you have questions or concerns about your gambling or someone close to you, please contact connects Ontario at 1-866-531-2,600 to speak to an advisor,

free of charge. BetMGM operates pursuant to an operating agreement with Eye Gaming, Ontario. Bitcoin just shattered an ETF out for. record for 30 days over $6 billion exiting crypto ETFs. Meanwhile, we have the $10.68 billion Friday Options expiry hitting this week. Does that matter or not? I wrote about it in my newsletter. We can talk about that. But I've got one of the best guests to talk about all things markets. Dan Gunsberg joining today. Let's go. What is up, everybody? Welcome to the show. I hope you're all having a wonderful Wednesday.

I was literally just going to say Thursday. That's how good I am at this. Oh, we just transformed to a lakehouse. It's nice. Want to come to my lakehouse? It's nice. It's nice like house. What's up, Dan?

How are you? I'm moving well, Scott. How are you? Great to be back here with you. Yeah, man. Been a while. Let's first talk about, I guess, the main hits, and then we can dive into prediction markets.

And, of course, you know, what else happening markets? So Bitcoin drops towards 62,000 as chip sell off deepens for a second day. Okay, I don't find that that interesting. I guess what's notable is what's in the title, which is also from this article, $6 billion in outflows clearly not much interest in buying at these prices in this area. And of course, the $10 billion expiry coming on Friday. This is not the biggest of all time. People are talking about it like it is.

I think we had a $27 billion one in December or something like that. But listen, you're an old options trader, right? So I think you can give some insight as to this. I sort of gave my shot at it, basically why it's a nothing burger in my newsletter today and how we always talk about max paid and put call ratio. I think from a trading perspective, it's, you know, as you get close to expiry, all the theta decays out of the market and, you know, right before expiration, pending on which way the market's leaning pending on which way the new max paying point,

people are looking to establish is will determine which way things trade. I think from a trading perspective for trader, it's a it's a great time to be trading, generally getting some very good two-way volatility. But, you know, from an investor or somebody is holding options longer term generally in nothing. Yeah. So I mean, I think it's actually more interesting to watch how people reposition sort of after they close, right? Absolutely. That's that's what That's what I think you have to watch. It will set a tone, understand where the news is in the cycle, what it's currently digested in the market, and what may be sticking out there, you know, hiding out there

that could change, you know, investors or traders' opinions on where the market's going next. Yeah, that makes perfect sense. I mean, what do you make of just this general trend of outflows from the ETFs? I think we kind of had two catalyst people consistently watched for the bull run, which was ETF inflows, right? Which is a bit of an egg problem, but, and of course, strategy. And both of those two things are clearly massively under pressure.

I mean, is strategy the only buyer in the market that seems to be that in all my circles, it's the common. Everybody gives the, the egg analogy, like I'm the only buyer of eggs. And it, that story seems to be holding. So it's going to be really interesting to see. And, you know, I think everybody who is active. with Bitcoin or in the digital asset space or just that far up on the risk curve, who is going to come in and start supporting it?

What narratives need to be in the marketplace? I think things like even like interest rates and recent Fed speak is obviously adding, you know, could be pouring kerosene on self-pressure as well. Interestingly enough, you know, if you look at the Bitcoin curve, which every time on the show I talk about this, I think it's still, you know, somewhere over 5% that if you were just going to hold Bitcoin from like June expiration, which is now out to next June, the yield that it's paying is somewhere close to 5%. So the curve is still showing higher Bitcoin price further out, which is very,

which I find interesting. Usually if we're in a real bare market, the futures curve gets very flat, or it will even, you know, go back-radated. So interesting to see that it's still there. So maybe there is still long-term bullish sentiment for Bitcoin, which obviously we all know how it's built and how it's programmed. But given the fact that the main narrative is there's one buyer in the market and its MSTR is not the best important at the moment. I wonder what the June 27 is, I guess, not much higher than here.

Yeah, still, I guess, in Cicango. Yeah, I think it's settled yesterday somewhere close to 66,000. 566, yeah, that's what I guess. So, yeah, there's a lot of takes on what Sailor should be doing here, obviously. You know, sailor best bet maybe to halt strategies, Bitcoin buying spree. Interestingly, this got picked up on Bloomberg,

basically because of CryptoQuant, who said, yeah, you should pause Bitcoin, purchases, rebuild cash reserves, and adopt a systematic framework for purchase timing. There's a lot of takes on what he should be doing. Everybody from the peanut gallery. It's really easy to do it other than, you know, that fight is not really that much has changed.

All that changed was sentiment. So, yeah, I mean, okay, STRC is trading way below par. So that's changed, I guess. But that's just a buying machine turned off. That's not like some systemic risk, which is how a lot of people are talking about it. I guess the question is, you know, and before STRC, what he's doing now was how he was buying Bitcoin.

right? He would like slightly dilute micro strategy when it's in a premium. He would buy some Bitcoin. The only difference is he's adding back to the cash. So I guess the big question mark is what happened when he closed that $1.3 billion convert, you know, the 2028 or 29? For some reason when he did that and the cash reserves went down, that's when everything seemed to change. Yeah, I don't really know exactly what happened, but or it could be a timing with, you know, kind of the sentiment of the rest of the market. What is, you know, I think I was reading earlier that, you know, just from overall analyst estimates, which, you know, who knows how accurate, those are always going to be,

that they were saying something around like if Bitcoin falls towards 30,000, that there might need to be another substantial share issue is just to meet obligations. So, interesting to see what, you know, if this really is going to have some type of cascading effect or not. I think they could have to go pretty low, but 30 is pretty low. I can't imagine he wouldn't be sweating at 30, one way or another. Like, I don't know that he'll blow up. I think they can pay their dividends, but like, you know, strategy here is sitting at a, you know, cycle low.

It's down 81% from the peak. And listen, I'm not a sailor hater at all. Everybody knows that. I'm actually just kind of like, I think it's going to be fine. I always think it's going to be fine because that's the base case. I agree. And this feels normal for Bitcoin. I mean, for all of us that have been here long enough, 80% peaked to valleys, you know, Gartner's style cycle, chart patterns.

This is the stuff that people wait for. When, you know, when Bitcoin's at 120,000, everyone's like, oh, I'm going to buy it when he gets down to, you know, down to 60s. So Sailor, so strategy going 80% peak to low. Maybe, maybe for some, it's a, it's a signal. And I think, you know, in Sailor's defense, he's. I don't think he's looking at what the next three months look like. No. Talk to him in five years, seven years, ten years.

One of the biggest thing that I've said to the critics is that, you know, they're freaking out that as of two weeks ago, he was doing things that were dilutive to strategy shareholders. I have that exact same salonamug right over there. I might have just been drinking on it. I think I have the exact same one. I think I just had coffee from it right before the show. Maybe that's a signal. Yeah, that's our signal by Salana. I don't know what signal it is.

But I find it interesting is that, you know, he had like a week when he started doing this, you know, adding to the cash reserve and buying Bitcoin with it under the 1.22 premium to NAV or whatever. That people are saying it's dilutive. And I'm like, yeah, but you don't judge someone's strategy on a week of dilutive behavior.

And it's been, when it's been non-dilutive, I think on a year-to-date basis, it's like 40 to 15% up. Yes. So like, you know, yes, he's doing something this week that may be a sign of stress, but that doesn't mean that like he's going to do it every week and all of a sudden everything's going to be diluted. It's just like this short-term kind of analysis of every move when he's probably,

as you said, playing five-year chess. Exactly. And I just think it's general investor psychology to really key in when, you know, obviously your positions are under extreme pressure like a strategy position would be if anybody bought it in the last year but to you know you start seeing every down move and then you analyze

everything that happens in the actual short run as opposed to seeing the forest through the trees which is I think where Sailor's head is you know it is he you know it given that Bitcoin has another cycle

which, you know, every single time we're in a bear. It, you know, it always proves what's wrong in the longer. So he's going to end up being on the right side of this trade, actually. Yeah, so I want to talk, I want to talk prediction markets because I know that you, I think it really suits your style. So I was saying that you're loving participating, but like, you know, for people don't remember, you've probably been on the show 50 times. But in the beginning days, like it was really in the very early days of Hero where you just had up-down contracts.

I mean, it was basically an entire gamified. Will Bitcoin be higher or lower than based over a certain time period, which really, to some degree is the first iteration, I would say, of prediction markets. And you saw this. I mean, how long was seven, eight years ago, nine years ago? It was seven. Yeah, it was eight years ago now. Right. I mean, so that's wild.

And now obviously, so we have prediction markets. it's in every jurisdiction. Every exchange now has a plan. I don't even know if I have the story. I do. So one of those is that meta is coming in with the arena, which I think is hilarious that he's so late again. It's like, you know, like metaverse.

But arena is a pretty cool name. But then I saw this today, which actually kind of blows my mind. CBOE introduces CBO predicts, launching first product to new prediction market suite. So like these are the guys who like, you know, the 100 plus year old incumbent, and they're adding, you know,

while the S&P open, close higher or lower than X today? It's amazing to see. Look, just to go back on what you were saying, yeah, our thesis very early on when we got into crypto, when I got into crypto full-time leaving the traditional trading world, was that there would be, our take was a little bit different. There would be this convergence of trading with gaming, like trading at the end.

the day was a big game, was kind of our thesis. And the best way to express that was in a more simplified way of trading, which prediction markets offer. And so we came up with that up-down concept. We actually pioneered it in crypto. And then if you remember, there was in the very early days, there were platforms like Auger in, you know, that were blockchain specific. Auger was was very early as well. And then things like Iowa electronic markets. markets, you know, predict it. There were in trade. There were some great platforms that were out there very early.

And then I just think it's, you know, it's just the nature of the bees. It took, it took time to finally get to the surface. And it's really interesting to see. I think now the incumbent exchanges, CME, ICE, you know, ICE is, are they partnered with OKX now? They just said they've done a bunch of announcements there. Yeah. Yeah. And I think CBO is in a position where if they don't offer it, they're not going to look very good because it is rapidly becoming just another part of the fabric of the derivative market world.

The big question to me still, that is outstanding is obviously this debate between is it a financial product or is it betting. And that is something that we always struggled with with Hero was, what is it? It sits right in the middle of this kind of Venn diagram of trading with gaming or betting. And it was always very challenging to define it. And at the time, you remember, their regulators wouldn't even look at it. They're just like, we don't even really have a category to define this. and so it's really interesting that somebody's fine, you know, that Salick came in and was taking.

Yeah, yeah, exactly. He would have said Hero is completely compliant and legal in the United States. We would have been in the seven years. Exactly. Yeah. But that's it. Don't we think that, you know, who will win this game is a sports game? I think there's just nuance, right?

So, like, I understand why the states are a casino, know, although they're trying to block all this, but look at it and be like, dude, like, we spent millions of dollars in years, like fighting, like a draft Kings or a fan duel, like what they went through. And then, like, literally, like, you can just launch a sports contract. That's the exact same thing. Right. The CFTC comes in and says, that's ours.

Yeah. Fine. No, it's understandable. And it's understandable from the states as well for exactly what you're saying. And, you know, not only states, but Indian reservations, you know, anybody that is, getting paid or tax revenue from from sports betting. This obviously is a very sensitive subject for all of them and I think it's going to be highly debated for a long time here. One other quick point that I found interesting is that I've been fairly active

in the eye gaming space also is there the eye gaming space as a whole was very slow to pick it up as well. You know, a lot of a lot of of the big sports books and everybody. They were like, you know, everyone was like, you know, wait and C mode.

You know, that, that industry tends to move very slow. If you go back and look at sports books and, you know, or sorry, online casinos and things like, you're often seen the same slot machines,

the same games, the same everything. They're very slow to change because they're, you know, there's been great margins there and their position is why we're going to do things. So they were very slow to pick it up. And then suddenly everybody like was in,

was going 150 miles an hour, we're trying to get these to market. And this is not only, you know, onshore, this is all in the offshore role as well. So very interesting to see how heavily it's picked up, you know, big, big kudos to Kalshi and Pali Market that, you know, they stuck it out for the last few years. Yeah, we now, like I was going to say, the next kind of story there, and then I want to talk about how you're actually using these. But the next story there, I think, is the convergence of, you know, kind of crypto and

prediction markets as a crypto show, right? So, of course, like, Polymarket is literally called Poly because it was built on Polygon, which, by the way, if one know how dead all coins are, that you could have the most popular platform, basically on the planet named after cryptocurrency, and that coin goes down. It should probably tell you everything you need to know. But, like, listen, so, but coming in from the other side, like, we're now also because of Seelig, we're getting swaps everywhere, right? We're getting perps, I should say.

So perpetual swaps. So Calci launches perpetual slops, which swaps, swaps. which is like the most crypto-native product that we ever had and is basically a test for these on everything. I think Coinbase now said they're going to be offering them on stocks and everything. So we have this weird convergence of all things. Speculation, I'll say. This is a seriously transformative and disruptive moment for financial markets, I think.

I mean, you know, swaps tokenized assets, basically anything that's tokenized is going to be, it's going to have a perp on it now. And is that healthy? I don't know the answer to that. Like, you know, more than enough people, I'm sure are going to are going to use these for speculative purposes. Like, everyone.

Thank you. Exactly. All of retail. It's not like the, nobody's using it. Nobody's using it as a hatch. Yeah. Like, yes, there might be like somebody who's like, yeah, I see these interesting things. It's like, you can hedge your personal interest in politics.

Like, I'm a Democrat. A Republican wins. At least I get paid. like that's not hedging. Right. Scott, it just, at the end of the day,

it just furthers the thesis that this is all going. I am a staunch believer. And I, you know, you can't paint it perfectly in the future. But this is how we started with Hero back in 2018 was, this is all going to merge. The lines between speculation,

trading, gambling. I understand gambling on a RNG-based, you know, spin a slot machine. That is a different story to me. But there is this, there is this void, this white space in between the two segments, the two verticals that I think is going to continue to evolve.

Something like perps at the end of the day is going to feed that heavily. Something like prediction markets and what you can actually speculate on in prediction markets, going to feed that heavily. This line will be very blurred and will continue to blur for a long time. And I think ultimately, where you're going to start seeing capital flows and from retail is going to be more and more closer to that as things evolve. I can't even imagine 24-7-365 stock market with perps on top of that and how any hedge fund or institution on the planet manages that. Like, all my first. The millennium guys are all like

I guess we're going to hire a bunch of people to trade thin markets abroad but like I'm not showing up at work 400 hours there's not 400 hours a week. But you know I'm not showing up at work 200 hours a week. Exactly. Like I'm still going to go pick up my kids after what would have been market closed.

Exactly. Like you don't want to wake up, you know, 65 years old, having not left your chair for the last 25 years. and trying to figure out what the hell happened, that your kids are now 30 and out of college, and you've been sitting at your desk trading perps 24 seconds. Yeah.

So are you using this? I use perps or prediction? I mean, generally, well, yeah. You know, some speculation, but I'll tell you what I use prediction markets for the most, is it's made watching golf very exciting. Exactly. Exactly. So I've actually said this recently. So I love the World Cup. I've finally gotten back into watching sports.

I pass the World Cup. But I used to watch every sporting event ever because I just loved sports. And I've given up on fandom, all that shit. I don't care. But now I can't watch a sporting event outside of seemingly the World Cup without having some skin in the game because I don't care. So like I don't even like I didn't watch. an NBA game probably for the last four years.

I just don't care. I guess I could bet on them and then I would care. Yes. You know, I do fantasy football, so I'll sometimes watch a football game just because, like, I want to win, not even because there's major money on the line, because I want to beat my friend. You realize it's, yeah, you know, most of betting like that, or

let's call it speculating for CFTC purposes, that, you know, you're getting a little dopamine kick. You're not, it's not, it could be $10, it doesn't have to be $10,000. And, you know, at least for me, that's not, what's that? It gives me something to win or lose. It gives you something to win.

It puts you on one side. Exactly. You know, I actually, just from being a trader forever, I enjoy figuring out some of the trading strategies around prediction, like in golf. I do, you know, I've done a lot of things where, like, you're buying, like, what I would call teeny options or, like, very low-priced option. because the delta between, you know, the number one player and number 50 player in the world is not very big. And so on any week, you know, there's a lot of very cheap optionality in the market.

And I saw all do things like buy those and then try to trade out of them and then use that to buy cheap offside again and see like what happens on Sunday. So things like that. It's like bringing back your trader mentality. Oh, man. It's the best. I think I saw on your feed once. It was like Rory was up, you know, the most he'd ever been up in 36 holes. And you were like basically shorting that is the easiest, selling that is the easiest trade in the world.

Yeah, because I was able early on to buy, you know, he comes out and makes, in the first three holes, he's like, you know, he's two over. And suddenly he goes hard off, hard offward and he's cheap to buy. So now I own Rory cheap. And then Rory kind of gets his sea legs under and makes a run. Now we're getting to the end of Saturday. He's trading 70. So I'm taking money off the table and then using that to buy a bunch of. to buy a bunch of horses that are, you know, a bunch of bikers in the Peloton, a bunch of golfers

that are not how people are using it, but this is how you should be using it if you want to have a really good time. This is, it makes it so fun and it just, it really adds a nice feature to sports at the end of the day. And look, I do it so small because it's, for me, it's just about getting the dopamine rush. I'm not going to ever make life changing money. I never try to, but that matters. Yeah, so there's one thing since you brought up golf and I know that this is something we've

talked about quite a few times. I even just brought up the site, golfing, because this is super cool. I don't know at what level you're involved in it at this point or what you're doing. I know you were kind of consulting early and investing and everything, but. Yeah, I, you know, I own some of it with the CEO, first of all, Jared Phillips, hands down, one of the best CEOs and like could not be a more perfect fit. He's a dude, anyways, yeah, but yeah, yeah. He's such an awesome dude. He's so passionate. He's running it beautifully. They're doing, very, very well. I think it's at $40,000.

This is crypto native. You can't tell that when you look at it, which I think is the beautiful part of it. It's on it, it rides crypto rails, correct? At the end of the day, basically, it's exactly what it says. It's a golf app that, you know, it gives you GPS.

It keeps all your stats for you. Very complex, very, very easy to use, but very complex in terms of feature set and what it automatically does for you. And then at the end of the day, pays you to play. So even if you're if you don't have a membership and you can, there's a free version, you can go play and it you will earn golf in points as you play your round. And when you finish that round, you'll have these points. And I think right now it's maybe

somewhere like six or seven dollars around very small, but something to get you started. And you can play a couple rounds of golf and suddenly you can go into the, the store, which is effectively a pro shop. And, um, you've earned enough points to buy a dozen balls. let's say. It's so. I know, because I, you know, like you, this was born out of, people probably already forget because we've had so many trends in crypto. But there was the play to earn, you know, I literally got to the point where it was like

poop to earn and, and sex to earn if you remember. That's how. Yeah, sex in. Yes, I remember that one. Steppen was like, I think maybe was. Step in. You walk and you exercise and you earn points for your steps and, yeah, pretty straightforward. I think Caitlin, who used to work with you, launched one as well, right?

that was a yeah she was she was she was a head of growth for something called moonwalk fitness which was a kind of an option similar concept

it's still one of the killer apps of crypto that just kind of died which is like you can be incentivized in a token for doing something you already do

in participating in a community yeah that one was great for walking it's a great concept still exists today yeah but golfing has been fantastic it's been amazing

to see the growth of it the app is incredible. And, you know, it's continuing to grow and it's really starting to get, like, its network is starting to capture velocity. And it's that, you know, I don't have the exact numbers, so I don't want to give them on here. But I know the revenue numbers are very strong. And, you know, as I was saying, you could, there's a free version, but then there's

memberships that, you know, once you're in, you can tear up on your memberships. And those give huge multipliers on the points that you earn. And there's people in there that are, you know, they're earning 40,000 points around because they have like the Diamond Tier membership. And it is making them a lot. It's, you know, the money that they would normally spend in a golf shop or going to the PGA Superstore, they're earning it, playing on, you know, just playing rounds of golf now, then going to our, going to ProShop and spending it. And it's just amazing to see the flywheel work. and the team is absolutely incredible. I would highly recommend that if you are a golfer, you go try it out.

This was an unintended pitch, guys, but it's awesome. I have the app as well. I just stopped playing golf with my problem right when you guys started. I decided that my mental health is more important. Didn't we do a... Might have been with you at Top Golf. Yeah, I was going to say, we did a Wolf of Wall Street session at sitting in front of Top Golf in Austin, Texas, I think. That was fun.

No, actually, like a long story, but my thumb went completely numb, like the whole side of my hand, and swinging a golf club became really painful. I had kind of a pinch nerve, so I just stopped, and then I'm going to Mac seemed like, because I just don't have five hours ever. Gunny was like basically a professional golfer for those who don't have the content. You try. Not quite there, but I definitely enjoyed the game. So, yeah, it's, you know, I will say that it is for my career, I would just, anybody's listening. And I think there's a trend. I think it was a Wall Street Journal article about this.

It did wonders for me in the trading world, you know, being a golfer and the camaraderie and the business development that happens on the golf course is second to none. So I would highly recommend anybody. Whatever walk of life that you are is learn to play golf, you don't have to be great, but learn, you know, learn the etiquette, learn how to play, learn how to, you know, I have friends I call it like good business golf. They know how to go out there, keep the ball moving. and it's a great sport for for business.

Yeah, the good etiquette part. Does that count throwing my club at people and cursing and? No, yeah. That's definitely out of the... Throwing my opponent in a lake. Maybe I guess it depends on what you're playing with, right? Yeah, yeah. No running over your opponents with golf carts or anything.

No, it just feels right sometimes. All right, man, well, I think we covered it all. We nailed it right to 930. It's great to have you. back on the show. We got to do this again very, very soon. Absolutely, Scott. Appreciate it, man. All right, man. Everybody else, I'll see you on the daily well afternoon and see you tomorrow. Thanks, man. Peace.