Digital Asset News host Rob discusses Bitcoin's record options expiry, market capitulation signals, and on-chain analysis
Rob from Digital Asset News covers Bitcoin's largest-ever quarterly options expiry, current market capitulation, and cycle analysis.
Summary
Rob, the host of Digital Asset News, opens by noting that Bitcoin has shown surprising resilience despite the largest quarterly options expiry in history — roughly $10.6 billion in contracts — with the price holding near $59,955 and only down modestly. He walks through on-chain analysis suggesting Bitcoin is near a major inflection point, with analyst Hyperion Desimus (Chris Sullivan) pointing to a potential final low between $54,000 and $57,000, or possibly a wick to $48,000, before any recovery within the next 90 days. Rob also covers a montage of high-profile capitulation moments from prominent figures including Mark Cuban, contrasts them with Grant Cardone's continued accumulation strategy, and addresses the macro bear case by highlighting investor Jeremy Grantham's warning on the AI bubble and potential broad market collapse (from a Diary of a CEO interview). Rob closes with a public service announcement about an AI-assisted email scam detection method using Claude connected to Gmail — including a real-world example of a fake Blockwire Media / Coinbase impersonation scam — and an extended discussion of custody best practices distinguishing cold storage vaults (IT Trust, Tandem) from small day-to-day soft wallets like MetaMask.
Key Takeaways
FULL TRANSCRIPT
Bitcoin's Record Options Expiry and Price Resilience
Rob: I have to say that Bitcoin is putting out some pretty good resilience. What I'm talking about today is there was a report from Bitcoin News saying it's going to be a problem and it's going to be volatile. It says: record $10.6 billion Bitcoin options expiry hits today. Now, this was actually a couple of hours ago, and I believe that Bitcoin News was actually incorrect — this has already happened, just three or four hours ago, as the options expiration hit today. Today's market saw the largest quarterly Bitcoin options expiry in history. Let me say that again: the largest Bitcoin options expiry in history, with roughly almost $11 billion in contracts set to expire.
Options expiry is important because traders and market makers often need to buy or sell Bitcoin to hedge their positions as contracts settle, which can significantly increase volatility. Now we have that. We're going to take a look at why people are capitulating right now and why there's a big sell-off — these things are actually happening. But I have to tell you, as these things have gone through, just take a look at the price action today. Not too bad. We were actually above $60,000. Right now we're at $59,955. In the last 24 hours we're actually up almost a percentage point. Now the last hour or so we've retraced just a little bit. But if we have the largest options expiry in history and we didn't go down magnificently, and here we are — that's not too bad. I can see there's a little bit of resilience, and I think a lot of people have already sold if they were going to sell.
Now there are still some people out there who are going to sell like crazy, and maybe that's for you. I can't tell you what to do. I'm not a financial advisor — even though the title kind of does look like financial advice: "Don't Sell Today." But I will tell you, I just think that we are around the timing of the bottom. I still think it can go down further. I still think there might be a bubble on the horizon. But as far as just how low it could go, well, it's anybody's guess.
The Cost of Not Taking Profits: Ethereum OG Wallet Story
As this goes out, I want to congratulate the people that took the advice which is right below me — the rules. The very last rule is to take profits, because nobody ever went broke taking profits. And I want you to remember this story going into the next cycle.
This is a story about Ethereum OG wallets — plural — finally selling after eight years, locking in an estimated $27 million worth of profit after they fumbled generational wealth of $150 million. Now, congratulations to them. Would anybody really be that ticked off if they lost $123 million? Yeah, you'd probably be a little ticked off. But on the good note, you have $27 million. This is the problem with people who are round-tripping their bags. This happens more often than not. So remember these types of stories as they come through. Take a little bit of profits off the table when you can.
I've been on a text insider group and one of the members talked about how they were happy that they actually took the advice and took some profits. They said — to be accurate — "Overall, Bull Mania saved me over $500,000 by selling my alts, and if I would have sold my Bitcoin, you would have saved me over $2 million." So again, as we go through this, we can kind of get away from that context of "never sell your Bitcoin" that Michael Saylor was spreading for so long. Even he sells now. I know people will say, "Ah, but the minutiae, Rob — remember, Michael Saylor didn't sell his Bitcoin. He sold Strategy's Bitcoin. Totally different thing." Sure. But he still sold. So that's where I'm going with this. Again, take some profits when they actually come up. A little bit late for that now, I understand. But congratulations to the person that took that advice.
On-Chain Analysis: Bitcoin Near a Major Inflection Point
Moving back into the all-time lows discussion — Quant says Bitcoin is near a major inflection point as rare on-chain signals align. This was from Hyperion Desimus, Chris Sullivan. The quote states:
"We have literally checked every single box except for a final pattern. Either we have to break above the $82,000 pivot to confirm — which would be more to the upside, and it's not going to happen anytime soon — or we have one final low, call it between $54,000 and $57,000, perhaps a wick to $48,000, to capitulate. One of those two conditions we expect to happen in the next 90 days."
How interesting that we're going to go down — it's almost as if there's a cycle to it. Now, as you know, on this channel I still believe in the four-year cycles. I also believe we're in the matrix, and I can just tell you that things have been playing out all the way from 2013 on. All-time high to all-time high. All-time low to all-time high. Just look at those days — 168 days, 160 days, 162 days. That's from 2015 on, all-time high to all-time low: 411 days, 365, 366. And I expect the same thing to happen around October 6, 2026, as we've got another 10% or so to go — maybe 70%. But who knows?
So if we take this and go, "Oh, look at that" — all you had to do was take a look at the four-year cycle and you would have done pretty well. What does that mean for today? Look, we can go through indicators all day long, but I think we all knew that if we just would have sold with the four-year cycle, we would have been just fine.
Moving Averages as a Framework for Buying Decisions
Let's just keep this super simple. Here are the averages — here's what the traders look at, and this is what they're trying to find. This is Bitcoin. This is the 200-week moving average. I cannot make this any simpler. We are right between the 200-week moving average and the 250-week moving average. Right in between. We fell below it just like we thought we would. The 200-week moving average is $62,000. The Bitcoin price right now is $59,000. At the 250-week level, that's $57,000. A $57,000 Bitcoin — maybe it'll happen, maybe it won't.
Let me just show you back in the day as a quick reminder of where we came from. This was 2022 — it was stuck between this range for quite a long time. Now, you can be a gambler and say, "You know what? I'm going to wait for the 300-week moving average and then I'll buy and dump everything in there." You can do that — doesn't sound too bad, actually. Or you can take a peek at what I was doing, which is buying every Monday, increasing the buys as we go into these moving averages and these risk levels. Or you can be a total degenerate and say, "I'm waiting for the 350-week moving average. If it doesn't hit, it doesn't hit." There's a plethora of different ways that you can do this.
I will say that there is a lot of capitulation going on right now. I don't know if we can go as low as the 350-week moving average of $47,000 — and it's funny how that works, right? $47,000, and here they are over here talking about $48,000 to capitulate. We'll see.
ETF Flows Signal Continued Capitulation
As far as capitulation goes, the ETF flow is not giving us much confidence. Look at these red days. I was not aware that BlackRock was selling so feverishly. I know people say, "It's not BlackRock, Rob — it's the individuals that are buying." That's not true. BlackRock has some. Investment advisors have some. I did a whole video on it — it's called Crypto Critical Videos, I think it's number seven or eight — and it talks about who is actually selling. It's not just retail. So we can see here: $30 million, $96 million, $172 million, $239 million, $265 million. That is another indicator of the capitulation that is happening.
Capitulation Montage: High-Profile Sellers and Bearish Voices
This is my favorite part, and I'm not here to say that I know anything more than anybody else. I'm not that smart. But I know that when you stick around, it seems like the same things keep happening over and over again. This is a nice little montage — shout out to Bitcoin News for putting this together from some big names out there who are just losing their mind. Mark Cuban being the first one. Just take a listen to this.
Mark Cuban: "I think Bitcoin has lost the plot. When I started buying Bitcoin — and I've sold all of it — I bought the dip. And now I can't keep buying the dip. I have no money left to buy the dip. The dip. Great. What do I buy the dip with? What am I going to pay for the dip? If I keep buying the dip, it keeps dipping. You've got no money to buy the dip. You're out of dip. This is the most bearish thing. I have zero desire. So last night I sold my Bitcoin. I sold my Bitcoin yesterday. I was holding a good amount of coins. I'm completely out of Bitcoin. 100% out of Bitcoin."
Second speaker: "I sold all my Bitcoin. And I suffered absolutely massive financial losses."
Third speaker: "Well, it's unwinding all of crypto. We're seeing Bitcoin collapse below $60,000 again. The fact that Michael Saylor is allowed to walk around free right now is absolutely criminal. Somebody needs to arrest him. If I see this guy, I'm going to perform a citizen's arrest and lock this guy up, because this is absolutely criminal, Michael."
Rob: That is opinion, and that's what's going on. I think people are starting to lose it, and that's pretty much normal for massive bear markets. So we'll see where it goes. But this is feeling like a lot of 2022 vibes — not as bad as 2018, but 2022 vibes for sure.
And I will remind you — people will say, "Well, this is it, we're going to the low point." I have to give you all sides of this. I wouldn't be doing my job if I didn't. So let's just say for the sake of argument that we go way far down and there is a massive AI bubble and there are different things going on that maybe we aren't aware of. That's why I like to look at all different sides as much as possible.
Jeremy Grantham's Warning on the AI Bubble and Market Collapse
There was a great interview on Diary of a CEO with investor Jeremy Grantham, and he has called a lot of the bubbles and a lot of the collapses. He goes through in a very systematic way and talks about just how bad things are because of this AI bubble. He is pretty much out of the market — which is another billionaire out of the market. So it's interesting to see. Basically, he says: don't invest in US companies, get out of AI because that's going to collapse, and also get out of markets completely because they're all going to collapse. I'm going to have you watch that video — I think I linked it in the description, but if I didn't, it's the Diary of a CEO, the latest one, about 3 million views or so. Give it a whirl and see where you land, because you can't just take advice from one person or get information from one person. You have to get a whole consensus to see where things are going, and it could get very bad.
Grant Cardone Continues to Accumulate Bitcoin
However, there are some people that still believe it won't get that bad. This is Grant Cardone, and I'm surprised he's still around, honestly — I give it to him. He continues to buy Bitcoin. He's a total believer now. He's selling real estate cash flow — which he has a lot of — and putting it into Bitcoin. This is essentially what I'm doing as well. The flow that comes in from our short-term and medium-term rentals, that's the money I use to buy Bitcoin. It's great. I have this ability because I've been investing my whole life and doing these things — actually selling and taking profits off the table to get into real estate, which gives me money that I can then put into Bitcoin. There are plenty of ways to do this, but this isn't a bad way.
And as a reminder, people will say, "Well, he's just lucky." He's not. Cardone Capital held roughly $200 million in Bitcoin as of May, built from a thousand-coin purchase in 2025 and later additions, alongside thousands of residential units. Basically, Grant almost bought the top and here he is still doing it. I know the people that don't like Grant Cardone and say he's a bad person. That's not the point. The point today is that there are people that still believe in it. And I've got to tell you, a lot of people would have given up just like what we saw with all those others.
AI-Assisted Scam Detection: A Public Service Announcement
Now, a little public service announcement. I'm a big hater of scams and scam artists. I just despise them, and it's a big problem. I got this email today from "Rebecca Scholler, Coinbase Sponsor Inquiry." Now, I know what you're thinking — "Come on, Rob, Coinbase isn't reaching out to you." But I've got to tell you, it was a very compelling email. I was like, "Ah, maybe so." And before I even answered, I just did this little trick. And I think when we're talking about AI and how it's used, everybody's looking for the killer use case. So watch this — I think this is important for everybody.
When I opened up this email, it was super early. I was a little groggy, looking through it, and I was like, "Yeah, maybe I'll just respond to this." And there are going to be times when you're just not at your sharpest. So here's a way to use Claude and AI to make things relatively easy.
So I told Claude — because Claude has a connection to my Gmail account — "Hey, look at this recent email from Rebecca Scholler and tell me if it's legitimate or not. It sounds pretty good. Maybe it's nefarious." And Claude said, "Yeah, let me search that, read the full thread, verify." And it says, "Hey, this is a textbook crypto sponsorship impersonation aimed at YouTubers." The domain is a lookalike. And this is where it got me — because I have heard of Blockwire Media before, and a couple of friends have actually told me about it. So when I saw it, I thought it might be legitimate. But hers was "Block-Dash-Wire Media" or something like that. And Claude says, "Scammers register near-identical domains to borrow a legitimate company's reputation." And it says, "Watch out — this is a fake campaign. It requires you to pay upfront." And it pretty much laid out what the next steps were going to be and how they were going to screw me over. I was like, "That's pretty good."
And then I tried something: "Hey Claude, can you do a search every 24 hours in the morning on my Gmail account and check for any suspicious emails that come through, even though we have a heavy spam filter, because I don't want to get scammed?" And Claude said, "I'll set up a daily morning scan — created now." Awesome. Well, that was easy.
So that's the beauty of AI. Some people think it's very confusing — it doesn't have to be. That would be the big one to implement. And if you're looking for how to set that up, links in the description for my second channel. I'll make it as simple as I possibly can.
The reason I bring this up is this: if you orange-pilled somebody, you're responsible for that somebody. If you convinced your mom or your dad or your significant other, and they get scammed, it's on you. So have Claude help you out. Make sure it can filter out all the suspicious emails, and maybe you can even say, "Hey, Claude, I got a call from so-and-so — is this legitimate?" It'll tell you.
Custody Best Practices
Custody is kind of important. Don't do anything on a MetaMask wallet. Just do what I do — I use Tandem and IT Trust. I don't even use a Ledger anymore. I just don't like that company.
And you know, if you don't take custody seriously, you get people losing their life savings. Before you say, "Well, I'll just keep my seed phrases in my Dropbox" — stuff like that can happen. Good luck.
As a reminder, IT Trust uses the same custodial service that BlackRock and Saylor does, which is Coinbase Prime. And the great thing about that is when you have IT Trust custody for you, they don't charge you to send it over. Now, when you sell it, they're going to charge you 1%. But I'd rather pay 1% than 100%. And you can call them and talk to them. They're open right now. Talk to Tommy. Tell them Rob sent you. And you can ask, "Hey, what's up with this custody? I don't want to get screwed over." And maybe you want to do a Roth IRA. Links in the description.
Strategy (MicroStrategy) and Michael Saylor's Legal and Financial Risks
I keep thinking of MicroStrategy — now Strategy — as a potential next collapse. I know people are really ticked off at Saylor because of the way he marketed Strategy to more of retail. And as a reminder, Strategy and Michael Saylor are being sued right now by an independent group for alleged instances of poor marketing practices. So if you haven't heard about that story, we'll cover that tomorrow. A bunch of investors are not too happy.
But if you look at Strategy's stock price from 2020 to 2021 and then into 2022, it was an 85% reduction from its peak. Massive run, then massive drop. Now if we take a look at the peak — which I think was around $438 to $460, correct me in the comments — in 2025, to where we're at today, it has gone down significantly. And I will say Strategy did make it through the last bear market, but they didn't have these financial instruments that they have right now — preferred shares targeting 11.5%, 12.5% yield and beyond. So we'll see if Michael Saylor makes it through this. It's good for the market, but who knows?
Live Q&A
Rob: Slow Noob says: "You know how Rob was talking about him being on Squawk Box? He was completely destroyed by Joe." Oh, I've got to watch that. See, this is what I love about these sessions — getting to talk to people live. Thank you, Slow Noob. Very nice.
"I didn't even install internet banking for my dad because I knew he would get in trouble." That's actually not a bad plan. Even us — all of us, even those who are very tech-savvy — how many people have you seen who are prominent in crypto, who have been around for quite some time, and gotten screwed over? A lot of people that I know. And even me — I had my MetaMask wallet hacked not too long ago. I don't know how that happened. I did a computer scan and everything came back fine. Good news was it wasn't that much in there. That still ticks me off, but thankfully I didn't put everything into MetaMask.
"I did watch the video of the Asian guy — the tech dev or something — saying he was getting out. He said he messed up bad and over-leveraged." I think that's what it is. And what we're talking about, if you're just coming in here, we had these guys — this is like the story of capitulation. The people who use leverage are the most vocal when they're winning, but when they lose — I'll give it to that guy, I don't know his name, but at least he had the guts to come in and say that he got wrecked.
"Do you use Trezor?" I don't. But you know who likes Trezor a lot is Guy from Coin Bureau — he's always talking about it. I just don't like the device. I'd rather just use a card or just have somebody else custody it for me. And I've got to tell you, if you're a hacker trying to get into IT Trust, I couldn't even get into it myself in under two weeks. So good luck. And I'm the real person. But people will say, "Oh, I don't want them to have my money." They can do whatever they want with it as far as custody goes — not rehypothecation, they don't do that. But if it makes it difficult for me to get it, imagine how hard it is for a hacker.
"You're smarter than Claude. Everything is a scam." No, but I will tell you what I had used Claude for — I believe that software as a service is dying and now we're going to go into self-software as a service, where you're going to be able to make your own software. I had Claude do a scan of my computer and it found a couple of different things, and we wiped them out. It showed me how to do it. It was pretty great.
With these scams, it's good to have AI go right into the email itself. But I don't think software is going to be that big of a money maker as time goes on. I think it's going to be the people who know how to use AI and implement it and show businesses how to make it work. Because the most productive, the best asset you can have for your company is good employees — or you can be the best version of yourself, and AI just supercharges you. That's pretty much what it is.
It's like the example JD Vance gave — he talked about how the industrial revolution from 1860 into the early 1900s really changed things. You would think there would be fewer people with jobs because of automation, but he said no, it's totally the opposite. More people were actually being born, there was an increase in population, and there was an increase in jobs being taken by real people. Think of it like the Ford Model T. You could have three guys building one archaic vehicle, but then you put it on an assembly line and instead of taking all day to make one, you can crank off 20, 50, 100. And of course, if you do that, you increase the revenue — so what do you need? You need more people on the line to make things actually work. That's how I think AI is going to be. It will eliminate some jobs — no one's hiring a typewriter repairman in 2025 — but I think it's going to lead to more effective, greater revenue, and bigger businesses.
"Don't leverage. Got it." That's pretty good, Lone Wolf. Very nice.
"I don't want to buy anything using my cold wallet. I should just hold my coins and swap in and out or sell. That's it. How do you feel about that?" I think you're 100% correct. I always see it as there are two types of wallets. One is your vault — your bank vault. You don't put a bank vault in your back pocket and go to Walmart with your entire life savings. That would be ridiculous. What you do is you have a soft wallet with a couple of twenties, maybe some fives, maybe a dollar — and that's the wallet you use for day-to-day purchases. For me, it's the same thing. My Tandem and IT Trust — those are my vaults. That is where I keep the majority of my crypto and digital assets. My MetaMask, which got hacked — what did I keep in there? A couple of twenties, couple of fives, and a couple of dollars. So when my wallet got eradicated, it didn't crush me. You've got your vault and you've got your soft wallet. Plan accordingly.
"Rusty: yield farming itself is not a threat to the Tandem security model. However, it increases the risk because you are moving from pure cold storage to interacting with DeFi protocols and smart contracts." That's true. I did a video on how to integrate with a DEX on your Tandem because they had rolled that out, and I'm probably just going to delete that video because Rusty's right. Keep things cold is cold, warm is warm, hot is hot as far as storage goes.
"Jimmy: You going to be using Proton Mail, especially for your finances? Gmail has too many vulnerabilities." Yeah, I know people love Proton Mail. I've used it, but I still get scammy stuff out of there. I know people say, "Well, that's not mine — mine doesn't." Well, mine did. So inevitably, scammers and hackers will make their way through. I think we just have to do the smartest option we possibly can.
"Jack: Was going to try all options and realized after all the insiders manipulating markets, I'd have been harvested. Hope Bitcoin isn't really the same." I don't think so. I don't see it going to zero. I just see it — so far everything's been adding up the same way.
There is one thing I don't want to gloss over — remember in 2022 when we had some massive collapses? Luna depegging from its stablecoin, Voyager — great interface, horrible management — Celsius, and then of course the big one, FTX. It seemed like we had these columns that would just crumble and then everything from the foundation went all the way to the floor. I keep thinking of Strategy as the next potential collapse, but I know people are really ticked off at Saylor because of the way he marketed Strategy to retail. And as a reminder, Strategy and Michael Saylor are being sued right now by an independent group for said instances of marketing poor practices. If you haven't heard about that story, we'll cover that tomorrow. But if you look at Strategy's stock price from 2020 to 2021 and 2022, it was an 85% reduction from its peak. And I will say Strategy did make it through the last bear market, but they didn't have these financial instruments that they have right now. We'll see if Michael Saylor makes it through this.
"I started buying today — I've probably picked one of the better times to buy." Congratulations.