Digital Asset News host Rob discusses bear market mindset, perma-bear and perma-bull track records, and crypto market conditions in mid-2026
A solo commentary episode from the Digital Asset News channel, hosted by Rob.
Summary
Mid-2026 bear market conditions set the stage for a solo examination of perma-bear and perma-bull track records in crypto and traditional markets. A clip of billionaire investor Jeremy Grantham being challenged on-air by CNBC's Joe Kernen on Squawk Box illustrates how repeated bubble warnings since 2009 caused listeners to miss enormous gains. Rob then contrasts this with Tom Lee's overly optimistic Bitcoin price predictions, arguing that neither extreme serves investors well. He shares his own dollar-cost averaging strategy, notes that the average BlackRock IBIT ETF investor is now down 40%, and observes that the current drawdown of 52% compares favorably to the 68% drawdown seen at the same point in the previous four-year cycle.
Key Takeaways
FULL TRANSCRIPT
Bear Markets and the Perma-Bear Problem
Rob: Bear markets can be a little bit concerning, especially if this is your first one or maybe your second one. For those who have been around for quite some time — their third or fourth — this is no big deal. So I think it's something to reiterate and talk about, especially as we start to go into the doldrums that is the bear market.
Today, what I want to talk about is a reference we had yesterday on the show. There is a great podcast called Diary of a CEO. They've got some really great guests on there, and one of those was billionaire investor Jeremy Grantham. We talked about this yesterday because I had watched the whole episode. It was very good, very well put together — an hour plus long — and Jeremy lays out essentially what he thinks is a bubble and where things are going. It is true he has called bubbles from back in the dot-com era, 2007, 2008, and 2009. The problem is, as with most predictions, nobody gets it 100% correct.
One of the things we always have to be aware of are the perma-bulls, who never shut up about just how high Bitcoin, crypto, traditional markets, equities, and AI are going to go — as compared to the perma-bears. With this one, Jeremy is a massive, massive perma-bear. I think it might have been Tesla, or maybe someone else — I forgot who brought it up yesterday — but they said, "Hey, just remember that this same gentleman was on Squawkbox," and the things that were said really make your eyes open.
So I had to do a little digging, and thankfully Finance A Lot put it all together for us. I want you to take a listen to this for about three minutes and just realize that sometimes the perma-bears don't get it right all the time, and neither do the perma-bulls.
The Squawkbox Clip: Jeremy Grantham vs. Joe Kernen
Jeremy Grantham: What represents a form of exchange, and the way that Bitcoin is structured —
Joe Kernen: There are people that would argue with you that it has a hard fact that some people have made a lot of money — like a chain letter. What does crypto do?
Jeremy Grantham: I don't understand the question. What is the use of crypto? It pays no dividend. It doesn't represent an asset you can put your fingers on. There is nothing there. It is just an idea that it will go up in price if you trust me. When on an island, when shells were used to represent an hour of work —
Joe Kernen: This is completely faith-based.
Jeremy Grantham: It represents faith. It represents proof of work.
Joe Kernen: You're going to be totally wrong on Bitcoin too. You can be wrong on everything you've —
Jeremy Grantham: Proof of unnecessary work shouldn't be worth a bucket of warm spit. And it will not be.
Joe Kernen: It's only been 20 years so far, so someday you might be right about this.
Jeremy Grantham: Well, look, Warren Buffett's in the same camp.
Joe Kernen: I know. So is Charlie Munger. But you want me to list ten people that aren't in that camp?
Jeremy Grantham: I'm just suggesting that there are a lot of smart people who also have that view.
Joe Kernen: A lot of smart people have a different view. The point is it hasn't outlived a general bull market. We've been in a bull market since March of '09, right? And when we get into a bear market — which Joe may think we never will be again — a serious market of down 50, 60, 70 percent. Do we think it will prosper?
Jeremy Grantham: Anybody that listened to you from 2010 — you've done a grave disservice to them.
Joe Kernen: So if you feel fine with that, that's what you do for a living. That's fine. I don't have a problem. Andrew invited you on. I'm just pointing out the facts of the situation.
Jeremy Grantham: Someday you might be right — like a broken clock. This may be a huge bubble that we're in. But you've said it again and again and again and again and again.
Joe Kernen: These are your track record.
Jeremy Grantham: It isn't my track record. I can go through and give you quarterly letters which I have written — prepare yourself for a market melt-up — a market melt-up in 2018. That's already eight years. That proves you don't know what you're talking about, and there are plenty of others like that. I don't know where to go with that. Joe, you can take them on here.
Joe Kernen: I said my piece. You've got your 1929 book out. Maybe it happens at some point. Maybe it doesn't. Hopefully it doesn't. The market at this point — the S&P is pushing 8,000 eventually — and you've probably been bearish for 80% of that.
Jeremy Grantham: I've been saying that the market is overpriced by long-term standards.
Joe Kernen: We were at 2,300 at the bottom in April of 2021. Did you ever turn bullish? Remember the people who were here for you when nobody else was. Joe Kernen was here for you.
Rob's Take on Perma-Bears and Perma-Bulls
Rob: Congratulations, Joe, from Squawkbox. That was a hellacious comeback. Now, just because he said that doesn't mean Joe was 100% correct, and it doesn't mean that what Jeremy was talking about was 100% incorrect. But you have to take the good with the bad. When you are a perma-bear, just say, "Look, I've called this many times and this is where we're at. Yes, I missed this. Yes, I missed that." We all make mistakes. Look at me — I used to talk about Voyager and Celsius, how great those were. Didn't work out too well. So with these types of things, it's always somewhere in the middle.
And if we're going to talk about the ultimate bear misconception, I think it would be best to also take a look at the ultimate bull misconception. Tom Lee — you gotta love Tom Lee, but boy, these price predictions were something.
The Tom Lee Clip: Bitcoin Price Predictions
Tom Lee: I think there's a lot of upside into year-end — into your 150 target.
Interviewer: Yeah, 150, maybe 200, even 250 this year?
Tom Lee: Essentially permanent holders of Bitcoin coming in, so it should be good. Can easily get to 200,000 before year end. I know it's a big move — it's almost a double.
Interviewer: A double from here. Let's just take a quick pause. A double from here. So everybody listening to this — we're at $111,000 — and you think by Christmas time effectively we could be at 200,000?
Tom Lee: That's right.
Interviewer: I think it's still very likely that Bitcoin is going to be above 100,000 year end, and maybe even above that to a new high. I think crypto prices have bottomed. I think Ethereum, which is around —
Dollar-Cost Averaging and the Bear Market Mindset
Rob: Okay, I'm not going to rub it in, but you get the point. These are the things that actually happen, so just take it with a grain of salt.
Now, I am in the camp of the four-year cycles. I still say we have a little bit downward to go. But does this mean you should just wait for the absolute bottom? I don't know. I'm not a financial adviser. I can't tell you exactly what to do. I can tell you what I'm doing personally. I buy every Monday — something fires off over on Cash App. I take a look at the price of Bitcoin, I take a look at the risk levels. If the risk levels go down, it means the price has gone down, and I buy some more.
The biggest thing I can tell you is that there is one thing we do pretty well in the bear market — we all know how to dollar-cost average, we all know how to buy. The big trick is to shift your mind at some point and start to think about when to take profits. And for you, that could be at any different time.
I can just remind you that I never made a boatload of money in the bull markets. Usually in bull markets, everything's overpriced. I just think things are way too expensive. The only time I've done well is when I've gone into the bear market when nobody wants to go — when everybody is selling and everybody is saying this is the worst time — and I've bought on the way down. That is it. That is the reality check of bear markets. Nobody wants to do it. Only the strong survive. That's pretty much where we're at.
ETF Investors and Strategy's Drawdown
Rob: As far as the bear market goes, the ETF people are also feeling it. This is from Woo Blockchain — really great follow. They state this: the BlackRock IBIT averages a 40% loss so far. ETF president Nate Geraci, citing Bloomberg, said BlackRock's IBIT once reached $44.4 billion in assets after rapidly attracting inflows following its 2024 launch. And I've got to remember — I didn't think we'd get a launch either, but January 2024 came and boom, the spot ETF came through and it was a wild ride.
By mid-2025, the average investor had gained about 30%, and for traditional finance, that is huge — 30% in really no time at all. Unfortunately, they listened to the perma-bulls and thought it would never go down. Following the recent sharp decline in Bitcoin, the average BlackRock spot Bitcoin ETF investor is now down 40%. And that is when everybody listens to the perma-bears. It's just a cycle, and that's pretty much where we're going.
As a reminder, Strategy is down almost 80% now. In the first iteration in 2020 and 2021, MicroStrategy — now called Strategy — was down 85%. So if they can hang on to just a 78.56% decline in the past year, not too bad, I'll be honest with you.
Unfortunately, we've also got STRIFE — the financial instrument from Strategy that is supposed to be pegged around $100 — which is now below $75. That is a negative 25%, even though it was supposed to be stable. I think there are going to be some more problems as this comes about. I think 2022 is essentially mirroring what we're seeing right now, and there has to be — or possibly will be — some collapse.
Regulatory Outlook and Polymarket
Rob: Don't worry, people will tell you good news is on the horizon — the GENIUS Act is coming. I just don't think it is. Even on Polymarket, just roughly a month ago they were pegging it at almost 65%, and as of today, as far as clarity being signed into law in 2026, we're now saying around a 41% chance. But take that with a grain of salt, because Polymarket is a prediction market — they also called for a massive flow for certain Democrats in the traditional establishment to win in New York, and it looks like that didn't happen. Polymarket gets it wrong sometimes. That's pretty much it.
The Positive Case for Bear Markets
Rob: So where are we? Can I give any good news, or am I just going to be negative today? The positivity is this: as bad as it is, I prefer bear markets. I like you guys when you come into the live stream. I like chatting with you. You're not tourists. You're seasoned veterans. I can't stand tourists these days. It's just refreshing because we're all on the same page. We all know how the playbook goes.
Taking a look at these four-year cycles — I had Claude build me this nice little slider — and we can see that over four years it pretty much lines up. Four-year lows, four-year highs, roughly. And then as a quick reminder: this time four years ago, we were down 68%. As of today, June 27, 2026, we're only down 52%. Even though we don't go up as high, I still see that there's more stability. It's all how you play it. I think these are the good days. I think there's more positivity ahead of us, but we have to get through the bear market, and I for one am okay here.
Q&A with Live Chat
Rob: All right, let's get into a little Q&A and go over your questions.
Damon — that interview with Diary of a CEO, which he's talking about — yes, Damon is right. This was a hellaciously good interview. The way it's put out by Jeremy Grantham, he's like the expert and it's going to go this way and we're going to have a massive bubble and it's going to pop and everything's going to go to hell in a handbasket. When you listen to it — and it's almost two hours long — you really get into it. But then you of course remember the Jeremy and Joe Kernen back-and-forth on Squawkbox. It was a pretty good back-and-forth and we can kind of see where things really actually were, because perma-bears are perma-bears and that's what it is. I'm not saying we can't go into a massive collapse — it could happen, definitely. But it's good to hear two sides of the same story.
Meme says a lot of smart people said we didn't need cars — horses and buggies worked fine. And then this is the big thing about AI. I was listening to Hershey Finance and he had a good point about ATMs. ATMs came out in the late '60s, early '70s, and the banks put them in and were saying the ATMs would just replace the cash teller. What they found was that people didn't trust them at first, and then they realized that with the ATMs and the different problems, they actually had to hire more people to service their new customers — because this actually brought in more people who liked doing this. And that continued from the '70s, '80s, '90s, all the way until around 2006 or 2007, when they started to see a decline in the actual teller. But at that point, everything had been climbing anyway. So it took 40 years.
So when we talk about AI and how people say we don't need this new technology, we don't need Bitcoin, we don't need this new advancement in AI — people think it's going to just destroy everything. It doesn't. It takes a little bit longer than what people think. That was a good reference.
Here's the old man yelling at clouds thing. It's not like Jeremy Grantham didn't have good points to say on the show — he made a lot of sense. But again, when you keep pounding the table like Michael Burry — "this is the bubble, okay now it's the bubble, now it's the bubble, okay maybe not that, now it's the bubble" — before you know it you've said it 37 times. And then once you actually hit a bubble, it's "see, I told you the whole time." And just like Joe talked about — you're telling me the bubble you were warning about since 2009, through essentially a 15-year bull run, and you missed out on all those gains just to sit on the sidelines? Come on. As a friend of the show, the guy from Coin Bureau puts it — you've got to risk it for the biscuit.
Kelby says: "Hey Rob, so many people are telling me they're waiting for the low before buying Bitcoin. That seems risky, but maybe I'm stuck in my ways of DCA-ing." They're not wrong, and neither is Kelby. If we take a look — and we talked about this yesterday as far as the moving averages — the 200-week moving average puts Bitcoin at $62,000 and the 250-week moving average puts it lower. We are squarely in between. Those are good times, I've got to tell you.
Now it might not be the absolute bottom, because if we look back at 2021–2022, that is essentially buying Bitcoin at $19,000 to $22,000. Would anybody complain right now if they had bought at $19,000 or $22,000? You'd be up 3x, and actually up 6x if you sold the top. Maybe people are waiting for the 300-week moving average, which would put the price at $54,000. You could do it. But I'll still buy a little bit now as we go down.
As a reminder — as we go down, the risk levels go down. Right now we're at 0.28. I start buying at 0.5. Below 0.4, I double up. At 0.3, I quadruple up. Now I have to 8x what I buy because we went below the 0.3 level — I didn't realize that. It's a good thing I need to change my Cash App settings. So I'll just be buying more as it goes down. If it goes to that $54,000 level, I'll probably be buying the same amount. But if it goes to $45,000 or $46,000, then I'll have to 16x what I buy. That's going to hurt the old pocketbook, but it'll probably be worth it in the end.
Yes, Michael Burry is a perma-bear, that's for sure.
Nemo says Jeremy Grantham only holds paper stock certificates and bars of gold. There's nothing wrong with that. I own gold. But even the gold bugs look at me like, "Do you own real gold, Rob, or do you own paper gold?" It's in my Roth IRA with iTrustCapital. So it's not quite in line with their ethos either.
Cavalier says it's over. Might be correct. You know, STRIFE can raise the yield to 14% and in a month they would stabilize. And A1 is correct — as we were talking about, STRIFE, which is Strategy's financial instrument, tries to peg everything to $100 and it's been pretty stable. Let me look over a year. Wow, that doesn't look good. It's been stable around $98, $101, $98, $95 — in February it dropped to $93 and everybody said it's over. But look at that now — that is quite a dip, 25%. A1's right though. They can raise the yield. Instead of getting 11.5% annually, they can say, "Okay, we're going to raise it to 14% or 15%." I think the big thing would be if they stop paying yields, but they say they have 17 months in reserves. So we'll see. That is concerning.
A1 also says he watched the Diary of a CEO and the Jeremy Grantham episode. He noted that Jeremy said he's put 95% of his wealth into an environment fund supporting green energy and green deals. So yeah — I like solar panels. I would invest in that, especially if they can put solar panels in space with SpaceX. I don't know how it's going to work, but that's the next big thing. We'll see.
Perry says the bubble should be in fiat printing — that's the M2 money supply. Reggie is right.
Aristotle — was it you who told me about the Joe Kernen back-and-forth on Squawkbox yesterday? I think it was you. It was highly entertaining. Jeremy didn't just benefit from the government for green energy deals in the US and other places in the world. He is a hustler and part of a dying breed of investors like Munger and Buffett.
Reggie also makes a correct point: if you raise the yield on STRIFE, you have to raise the amount of money going out. So that is a problem — it's not a long-term solution.
Meme says they'd love to have solar throughout Puerto Rico. It's a goal. Shout out to Elon Musk — it looks like Starlink will help power emergency communications across all 78 Puerto Rico municipalities. I actually have Starlink on my house with the transfer setup, and I've got to tell you — very stable, very good stuff, and relatively inexpensive.
And here's another thing: if you own SpaceX stock, why don't you have Starlink? If you own SpaceX stock, why do you still pay your provider for internet service? You should be getting Starlink. It kind of supports that, right? Because that's one of the three companies under SpaceX — SpaceX rockets, Starlink for internet, and xAI. Those three.
And lastly — pride and arrogance are never wrong and never learn from mistakes. Respectfully, Jeremy Grantham has potentially been a great investor. He's a legend and we give him the due diligence and accolades that he deserves. But again, taking a look at perma-bears and perma-bulls, it's usually in the middle, and that's where we should temper our expectations.