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Strategy’s stock is crashing — down nearly 60% over the past year — but Michael Saylor says he “won’t back down” from his massive Bitcoin strategy. Despite the steep decline, new data shows that Strategy is still up roughly 16% on its 649,870 BTC stack, purchased at an average price of $74,430. And over a five-year period, MSTR has outperformed giants like Apple and Microsoft by a massive margin, soaring more than 500%.

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Transcript
00:00Welcome to The Deep Dive, the show that gives you the critical insights you need without the hours of reading.
00:05We cut through the noise so you can get straight to what matters.
00:07And hey, if you find what we do valuable, if we save you time, just a quick reminder that hitting that like button or subscribing really does help us out.
00:15It tells the algorithm that this is useful stuff.
00:17Yeah, it lets us keep doing these deep dives into, well, into the absolute chaos of finance and crypto.
00:24And today we have a truly magnificent paradox for you.
00:29It's all about microstrategy or MSTR.
00:32Right. The world's largest corporate holder of Bitcoin.
00:36Their entire identity is basically built on this massive stack of BTC.
00:40A stack which, and this is the key part, is still firmly in profit.
00:44Yet, and here's the paradox, the stock is an absolute catastrophe.
00:48Yeah.
00:49I mean, critics are lining up screaming that the whole strategy is collapsing.
00:52Exactly. So our mission today is to figure out why.
00:55Why is there this total disconnect between a stock that's bleeding out and a core asset that's doing just fine?
01:01It's the ultimate head scratcher.
01:03Because if you just look at the stock ticker, you see disaster.
01:06But if you understand how big money actually operates, the story changes completely.
01:13Okay. So let's start with the pain.
01:14Because, wow, is it brutal.
01:17We really have to quantify this drawdown.
01:19It's what everyone is looking at.
01:21Over the last year, MSTR stock is down, what is it, around 60 percent?
01:25About 60 percent, yeah.
01:27It crashed from highs of, you know, around $300 down to about $170.
01:31And even if you just look year to date, it's still a 40 percent loss.
01:35And that's the headline, right?
01:36That's all the ammunition the skeptics need.
01:38They see that 60 percent drop and say, see, we told you.
01:42The leverage is blowing up the company.
01:44They argue the market is pricing in some inevitable failure, a liquidity crisis.
01:51And look, for any other company, numbers like that would signal a five-alarm fire, a total failure of the business model.
01:57Right. If we stopped the deep dive right here, the conclusion would be simple.
02:01Michael Saylor failed.
02:03But we can't stop here.
02:04No, because that conclusion is just plain wrong.
02:08You have to look past the stock ticker, which is just sentiment is just trading, and look at the actual balance sheet, the reality.
02:16OK, so let's flip the script.
02:17Let's move from the stock price to the assets themselves.
02:19Because the minute you do that, the panic just seems, well, it seems completely unhinged.
02:24It really does.
02:25Their whole reason for being is the Bitcoin treasury.
02:28And that treasury is deep in the green.
02:30That's the crucial insight.
02:31We pulled the data from BitcoinTreasuries.net, and the numbers are clear.
02:37Their average purchase price for all that Bitcoin, it sits at about $74,430.
02:42OK, and at the time these sources came out, what was Bitcoin trading at?
02:46Around $86,000.
02:47So MicroStrategy isn't just not losing money.
02:51They're up a very healthy 16% on their entire stack.
02:55So the whole narrative that the strategy is underwater or blowing up is just false.
03:00Completely false.
03:00Their capital is working.
03:02It's profitable.
03:03So we have a $170 stock that screams failure tied to an underlying asset that's sitting 16% in profit.
03:12Which proves the point.
03:13The problem is structural.
03:15It's a trading mechanism issue.
03:17It's not a fundamental failure of the thesis.
03:20And we should probably add even more context, right?
03:22Yeah.
03:22Because this recent crash, as painful as it is, doesn't erase the company's insane historical performance.
03:29Oh, absolutely.
03:29Absolutely. You have to zoom out.
03:31If you look at MSTR over the last five years, it's returned over 500%.
03:36500%. Now put that next to, say, the titans of tech.
03:40Yeah.
03:40Apple over that same period.
03:42I think it was up about 130%.
03:44Microsoft 120%.
03:45I mean, it's not even in the same ballpark.
03:47MSTR's returns are in a different galaxy.
03:50Even if you shorten the timeline to the last two years, which have been painful, MSTR is still up 226%.
03:55While Apple's at, what, 43%.
03:57And Microsoft's at 25%.
03:59Yeah.
04:00I mean, it almost makes big tech look stagnant by comparison.
04:03It just proves that the core idea, turning MSTR into this levered way to get Bitcoin exposure, has worked incredibly well for long-term shareholders.
04:12So we have a long-term winner, profitable on its assets, trading like it's about to go bankrupt.
04:18Okay. This is where it gets really interesting.
04:20We have to move past the balance sheet and into institutional trading psychology.
04:25Why the brutal dump if the fundamentals are solid?
04:29The answer is all about how the big funds are using MSTR.
04:32And Tom Lee explained this perfectly.
04:34Big money doesn't see MSTR as a software company anymore.
04:37They see it as a tool.
04:38Exactly.
04:39A highly liquid tool to hedge their massive crypto positions.
04:42Hedge.
04:43So explain that.
04:43Why not just short Bitcoin itself?
04:45Why go through a stock?
04:46It's all about friction.
04:47For a giant hedge fund, shorting actual Bitcoin spot or even futures could be a huge headache.
04:52There are regulatory hurdles, capital requirements, custodial risks.
04:57It's complicated.
04:58But MSTR is just a stock.
04:59It's just a stock with a super liquid, easy-to-access options chain that every single trading desk is already set up to use.
05:06It's on the traditional market rails.
05:08They treat it like a turbocharged BTC ETF.
05:10Okay, so let's walk through that.
05:12A huge fund has, say, $500 million in long Bitcoin positions.
05:17They think the market might dip next week.
05:19Right.
05:19They don't want to sell their actual Bitcoin because that creates a taxable event and messes up their long-term strategy.
05:26So instead...
05:26So just short MSTR stock.
05:28Yeah.
05:28Or buy-put options.
05:29Precisely.
05:30They create a temporary short to protect themselves from volatility in their main asset, which is Bitcoin.
05:36And that creates this constant, you know, artificial sell pressure on MSTR.
05:41Pressure that has absolutely nothing to do with MicroStrategy's software sales or how profitable their treasury is.
05:47Nothing.
05:47The stock is basically a prisoner of institutional risk management.
05:51And this whole situation is being made worse by what's happening in the broader market, right?
05:55That liquidity slowdown that Wintermute warned about.
05:58Yeah.
05:58This is where the structural shorting meets a real-world headwind.
06:02Wintermute pointed out that the three main pillars of crypto liquidity stablecoins, ETFs, and digital asset treasuries are all drying up.
06:10And that third one, digital asset treasuries or DATS, that's where MicroStrategy lives.
06:15That's the category.
06:16It's basically corporations putting crypto on their balance sheets.
06:20And the inflow of new money into that category just fell off a cliff.
06:24Give us those numbers again because they are just shocking.
06:27So in September, you had $11 billion in new inflows into DATS.
06:31Well, $11 billion.
06:32Okay.
06:32By October, that dropped to $2 billion.
06:35Right.
06:35And by November, it was barely half a billion dollars.
06:38From $11 billion to $500 million.
06:40Yeah.
06:41In three months, that's not a slowdown.
06:44That's a full-on stop.
06:45It's a dead stop.
06:46And when that organic buying pressure vanishes, liquidity dries up.
06:50That makes the market more volatile, which, in a vicious feedback loop, means the big funds need to do more hedging.
06:56And where do they go to hedge?
06:57They go right back to shorting the easiest, most liquid proxy they can find.
07:01MSTR.
07:02It's a perfect storm.
07:03Okay.
07:04I get the hedging argument.
07:05But doesn't that create a huge problem for a regular retail investor?
07:09If big money is just constantly dumping your stock to protect themselves, aren't you kind of perpetually screwed?
07:15That is the critical question.
07:17You're right.
07:17You're basically buying into a system where your stock carries this extra risk that Bitcoin itself doesn't have.
07:23The retail holder is absolutely caught in the crossfire.
07:26Which leads us perfectly into what the real risk is here.
07:30Right.
07:30So if the shorting is just noise, what's the actual existential threat?
07:34It's the one nightmare scenario.
07:36Forced liquidation.
07:38Exactly.
07:39MSTR used a lot of debt to buy its Bitcoin.
07:41The only way this strategy truly catastrophically fails is if the price of Bitcoin drops so low that they are forced to sell their holdings to cover debt payments or margin calls.
07:53That's the leverage risk finally coming home.
07:55It is.
07:56But analysts have run the numbers.
07:58They say MSDR is, quote, very far from that scenario.
08:02The way they structure their debt with convertible notes and secured loans gives them a pretty significant buffer.
08:07But the risk is always there.
08:09And this inherent risk is why some analysts made that really sharp distinction between owning the stock and owning the asset.
08:16Yes.
08:16The argument is that owning MSTR might actually be inferior to just owning Bitcoin directly.
08:22And it's not an insult to management.
08:25It's about structural risk.
08:27As one analyst put it, stocks can go to zero.
08:30Especially highly leveraged, heavily shorted stocks.
08:33Right.
08:34But Bitcoin as a network conceptually can't.
08:37It's a subtle point, but it's a huge one for anyone thinking long term.
08:41Speaking of conviction, though, Michael Saylor's response to all this market chaos has just been next level.
08:48Oh, it's defiance.
08:49Cure defiance.
08:50While everyone was panicking and rumors were flying that there was some...
08:53Which she called completely false.
08:55They went out and bought more.
08:56On November 17th, with the stock in free fall, they made one of their biggest purchases ever.
09:01What were the numbers on that buy?
09:03They bought 8,178 more Bitcoin for $835 million.
09:08I mean, think about that.
09:09He was essentially betting nearly a billion dollars against every single short seller out there.
09:14It's an incredible display of conviction.
09:16So what are their total holdings now?
09:17It's just staggering.
09:19649,870 Bitcoin worth around $56 billion.
09:25Saylor's message is basically, I won't back down.
09:28He sees the stock price as just noise.
09:30Okay, so let's wrap this up.
09:31What does this all mean for you, the listener?
09:33Try and make sense of this puzzle.
09:35Let's distill the key takeaways.
09:36First, MSTR stock is dumping mostly because of structural hedging.
09:40Big institutions are shorting it to protect their larger Bitcoin positions.
09:44It's artificial pressure.
09:45Second, despite that, the underlying Bitcoin treasury is healthy.
09:50It's profitable.
09:51The critics saying the strategy has failed are just wrong on the facts.
09:54Third, if you zoom out, long term performance is still phenomenal.
09:58Up 500% in five years.
10:00Crushing big tech.
10:02The strategy has worked over time.
10:04And finally, this whole situation is being amplified by the collapse in new corporate money
10:08coming into the space, which is making everything more volatile and fueling the need to hedge.
10:13Which brings us to our final provocative thought for you to think about.
10:16Given that MSTR's stock price is now so heavily driven by institutional hedging,
10:22does that make it a better or a worse indicator of real market sentiment for Bitcoin?
10:28In other words, is the MSTR stock chart just a reflection of Wall Street's risk management
10:32psychology now and not a true reflection of Bitcoin's value?
10:36Exactly.
10:37And is this constant short pressure now just a permanent feature of this turbo ETF that MSTR has become?
10:43A fascinating question to ponder.
10:44Thanks for joining us on this deep dive.
10:46We'll catch you on the next one.
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