MSTR Today: Michael Saylor’s Bitcoin Bet Is Getting Wilder

Added: 2026-05-19

[00:00:00]Welcome to MSTR today in the Treasury Titans JLD here and it is Tuesday, May 19th and man, we are not happy about the Bitcoin price action. We are not happy about the MSTR price action, but we are not looking for days or weeks or months.

[00:00:21]We are looking at years and then decades because Michael Saylor will always be amplifying the orange. So, let's focus on the orange. And what did Michael Saylor do by the way? He just acquired 24,869 Bitcoin for $2 billion at $81,000 per Bitcoin and achieved a Bitcoin yield of 12.6% year-to-date.

[00:00:47]Um now strategy huddles 843,738 Bitcoin, which was acquired at $63 billion and the total average cost per Bitcoin is $75,700 currently.

[00:01:04]So, Michael Saylor still wants us to be focusing on stretching our income. So, let's see what he has for us today.

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[00:01:45]All right. Stretch has had its second strongest week ever raising just under $2 billion. Strategies funding has shifted almost entirely to the stretch ATM with the common ATM seeing only limited use recently. And you can see stretch here in black. While MSTR is in the orange, you can see going back quite a ways now. There hasn't been much orange compared with the black. Let's go all the way back to March 9th to see any significant orange. I still believe that MSTR will be having some orange coming up in the future because the capital base needs to be expanded as always. But man, this is a thing of beauty to see because it's called zero dilution. Now, 83 million was raised through MSTR, which is a lot of money.

[00:02:31]But compared to the 1.9 billion raised through stretch, we can definitely see the shift. You can say air may shares at 32 weeks remaining in 2026. Strategy is now estimated to reach a million Bitcoin by 11 24. You can see for the first time they dropped into the fours, 4,883 is the average weekly to goal, and I think they're going to get there.

[00:02:55]Mark says, "843,738 Bitcoin. MSTR alone now holds 4% of the total Bitcoin supply." And look at this growth. It is a thing of absolute a beauty. Chris says, "The dominant narratives around MSTR have all been bearish. Meanwhile, stretch just casually raised another 2 billion dollars in one week." What happens when the dominant narratives are all bullish and stretch is raising billions of dollars a day, which by the way will be happening. Um Ragnar says, "Strategy has officially surpassed 4% of all Bitcoin ever in existence. They now own 4.02 of the whole network, not even calculating and counting lost coins. And we all know there's a lot, a lot of lost coins." Um "Stretch just raised 2 billion in one week," says Chris. "These are the types of people we're competing against. High time preference, zero vision, zero rationality, extremely emotional MSTR bulls, we are so so early. And by the way, I am personally blocked by little because I went back and forth with him like back in the fall and basically I destroyed him. I'll just go ahead and say it. Um but look at this post. This was he posted this back in What's the date here?

[00:04:12]Um September 30th, he posted this. He wrote For the IPO investors, yes, they got a discount to our Saylor claims he will ATM the stock. Issue is there's virtually no demand for his preferreds because his common is wrecked and he's a liar. Nobody trusts him. I'd rather get paid less money, less percentage of a dividend to get paid by someone who is trustworthy. So again, this is a person who said there's virtually no demand for his preferreds. Okay, can you say 1 billion dollars of demand in 1 day?

[00:04:44]Absolutely living up to your name. Adam says, Saylor performing this on such a bloody red day for Bitcoin. So far off from the ex-dividend date is amazing. A sizable chunk of Bitcoin is going to be added over the next couple weeks.

[00:04:57]Domination, bullish bullish ASST. And by the way, it's so impressive, especially with stretch stretch dropping into the 98s.

[00:05:06]Yuck. But Saylor is performing amazingly and they've already out here They've already ATM'd 64 Bitcoin in this one day. I mean, they're blowing minds once again. Very cool, very incredible to see for sure. And we have a lot more coming up from Michael Saylor's mouth when we get back from thanking our sponsors.

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[00:08:03]We're very methodical in the way we operate our capital markets programs.

[00:08:08]That's a very federal one, so.

[00:08:09]So, with the um 2.2 tax loss, um so while Bitcoin now is say depressed in price, um 36 87% from its all-time high, would this be a good time to sell high cost basis Bitcoin? Is that um is that something that you're looking at? And is And also is the tax deferred within this calendar year or is it rolled over into other calendar years?

[00:08:35]>> the option to capture that that up to 2.2 billion dollar tax credit. The The value of the credit's changing every day, every minute, right?

[00:08:45]And uh we also have the option to calculate the mispricing of the convertible bonds, and there's a massive uh yield in that. We also have the option to to capture Bitcoin in a trade. Um we make that decision week by week, day by day. Ge- Generally on a weekly basis, we think strategically on a daily basis, we make our capital markets decisions.

[00:09:10]And uh we may uh we may not uh every you know, everything we do precludes us doing something else.

[00:09:20]And so we always have to consider you know, is this equity positive but credit negative? Or Or maybe it's screamingly good for the equity. It makes us a you know, $500 million, but it's a little bit bad for the credit.

[00:09:34]And so would I do that? Well, if the credit was super strong, then I would do something equity positive, slightly credit negative. If the credit was super weak, we wouldn't. Yeah. Right? So, sometimes we do things that are bad for the uh that that are equity negative, the credit a negative yield. For example, last year we raised $2.25 billion in US dollars. That was a negative yield, but it was but it was important to bring the credit to life.

[00:10:02]And so, Is it Is it Post Falls where that cash is held? Is that just on the balance sheet? Is that sitting generating yield?

[00:10:09]>> We're in the same certain money markets.

[00:10:11]So, we're we're in the same table money markets that anybody else with a large amount of corporate cash would be in.

[00:10:18]Um I think the point to be made there is if we think we need to support the credit, we do it. When we did it, it was equity negative, but then in the first 4 months of this year, we generated $5 billion of credit sales, and we generated a you know, like a a ford of a $5 billion Bitcoin gain. That's a net income equivalent. If you think Bitcoin's going up 11% a year, when we when we book a $5 billion BTC gain, it's $5 billion in net income. If you think Bitcoin's going up 22% a year, it's $5 billion in net income with another $5 billion coming over the next 7 years. And if you think Bitcoin's going up 30% a year, it's $5 billion up front, $10 billion on the back end.

[00:11:01]So, um sometimes we trade off a a negative in order to in the present to get a positive in the future.

[00:11:10]But on the other hand, if the credit markets change, then we might go back to the equity, and then the Bitcoin markets also have an impact. So, we have to weigh all of these things.

[00:11:23]I think the real message for the marketplace is is we think about the equity, we think about the credit, we think about the Bitcoin, everything we do, you know, over the long term over the long term, it's certainly Bitcoin positive. You know, we bought $62 billion of Bitcoin. We're the biggest buyer of Bitcoin in the world.

[00:11:44]We will probably be continue to be ad infinitum the biggest buyer of Bitcoin in the world.

[00:11:54]What's the second best? There is no second best.