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Author Topic: Saylor pivoting away from BTC?  (Read 161 times)
legiteum (OP)
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May 28, 2026, 05:53:50 PM
Merited by ingiltere (1), ABCbits (1)
 #1

https://finance.yahoo.com/markets/crypto/article/bitcoin-falls-to-75000-as-token-decouples-from-tech-rally-133920137.html

While the market didn't react immediately to MicroStrategy making two moves that should have been very bearing for BTC, the story above (and the video) seems to indicate that the market is only now absorbing the news.

The two moves in question are:

1) MSTR buying its own bonds back instead of making another BTC purchase;

2) Saylor making it clear that they have no policy that forbids them from selling their Bitcoin in the future, which is a massive departure from his previous statements indicating they would never ever ever sell their Bitcoin.

Taken together, these two announcements multiply each other: they start to create a script that has MSTR pulling completely away from Bitcoin and into AI or some other business.

When I think of this situation, I think about Saylor and his management team as individuals. They are flying high, but they also live in fear: if BTC dropped severely, they could be in very big trouble, and maybe even legal trouble personally (at minimum they will know that they will be targets for lawsuits and political retaliation). And Bitcoin is a pure-meme instrument with absolutely no fundamentals, so it depends entirely on what the market thinks is "cool"--which could change overnight. This has been compounded in the last few years as Bitcoin has attached itself to the fortunes of Donald Trump and his party--and public sentiment can shift dramatically when it comes to politics (say if Trump started a really unpopular war that spiked gas prices and caused inflation... or something).

If somebody--or some plan--offered them an offramp from this high-risk situation, my feeling is that they might just take it. And if they took it, they would have to unwind MSTR very very carefully and slowly, but... the two moves above would be the first ones you would make.

Right now, if MSTR sold all of their BTC, they would just about break even, based on the prices where they bought. Of course, MSTR itself moves the market, so they couldn't simply just sell everything because they would damage their own asset price. So yeah, anything major they do would have to be done... carefully.

Saylor needs to give the market some good news here soon, or this narrative is going to grow some legs and start running...



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May 28, 2026, 06:05:37 PM
 #2

Perhaps Saylor's words aren't entirely credible, given his mixed opinions on Bitcoin since he first became known. Initially, he criticized Bitcoin, then he invested in it. Ultimately, his decisions regarding Bitcoin aren't exactly driven by ideology. I assume, based on his actions over the years, that he only sees money; for him, it's currently a way to maximize capital, and his actions will always be based on money. Today he supports it, tomorrow he might see another investment that generates more and decide to abandon Bitcoin.

So I believe the market will only be influenced by his actions, not his opinions.

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Dunamisx
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May 28, 2026, 06:11:35 PM
 #3

Don't always trust microstrategy by his words because they are unpredictable, once it is not making profit to him, and that is why you always see that you will continue with bitcoin investment as long as he is much convinced that it is a profitable assets, this same man has been the one campaigning against bitcoin until he begin to show interest and turn an investor himself, so just take any of these recent action as to his own kind of profitability based on his mentality, while such is just his own strategy.

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bangjoe
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May 28, 2026, 06:18:04 PM
 #4

Like a company and like investing they will definitely take profits or change where they invest, even though they have said that they will accumulate 1 million bitcoins, it does not necessarily go with the original plan, they may change the plan in the implementation period, the company is dynamic they are just looking for a place to make a profit according to their own judgment, and they can switch at any time, don't think that they will save forever.
Like us when investing in bitcoin, there is no plan to keep it until it is brought to death, surely at a certain time you will sell it or give it as an inheritance or you enjoy it yourself after getting a profit.

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May 28, 2026, 06:37:35 PM
Merited by Don Pedro Dinero (1)
 #5


Taken together, these two announcements multiply each other: they start to create a script that has MSTR pulling completely away from Bitcoin and into AI or some other business.
Sorry how does Buying back their bonds and choosing to sell in the future multiply and give AI?

I'm not really a fan of his work but I understand how buying and hoping Bitcoin rises
Is important to them.
The bond was bought back cheaper and it's reducing their debt
They would sell it's just preparing people to know that it's in the table if it gets ugly.

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They are flying high, but they also live in fear:
I would say they have stopped being delusional and a little big realistic
To know that some caution is needed.

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And Bitcoin is a pure-meme instrument with absolutely no fundamentals,
Okay.

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if Trump started a really unpopular war that spiked gas prices and caused inflation... or something
I'm curious what won't be affected directly or indirectly?

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if MSTR sold all of their BTC, they would just about break even, based on the prices where they bought
Lol I don't even know where to start
Keeping Bitcoin price not changing say they magically sold it OTC
Do you think their stock would be the same?
And no they would be at loss not just from this or overhead cost but from the fact that their average cost is higher than current price.

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bitbollo
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May 28, 2026, 06:42:59 PM
 #6

It's a very interesting argument Smiley and the evolution would impact for sure the price of bitcoin.
Unfortunately we had to prepare to any possible scenario (including an heavy dump).
For sure behind a seller there is always a buyer. Having more "strategy" would just keep btc suriviving...

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hugeblack
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May 28, 2026, 08:53:16 PM
 #7

2) Saylor making it clear that they have no policy that forbids them from selling their Bitcoin in the future, which is a massive departure from his previous statements indicating they would never ever ever sell their Bitcoin.
I don't know, but did anyone truly believe they would never sell, at least not at some point in the future? If anyone did, they'd be better off staying away from investing.

Saylor needs to give the market some good news here soon, or this narrative is going to grow some legs and start running...

Sometimes, making negative statements is necessarily to buy at a low price or manipulate the market.


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legiteum (OP)
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May 28, 2026, 09:31:10 PM
 #8

Perhaps Saylor's words aren't entirely credible, given his mixed opinions on Bitcoin since he first became known. [...]
Don't always trust microstrategy by his words because they are unpredictable, [...]

Well, I don't take him on faith, but statements like this are often legally binding, so he can't always just say things that aren't true. If his investors ever lost a lot of money, they would sue him and reference his past public statements.

In particular, if MSTR sold a ton of its BTC today, after he made that statement, then he could say that he warned investors. Without that statement, he could be sued if he sold.

Unlike politicians, he can't always just... lie and get away with it.

Sorry how does Buying back their bonds and choosing to sell in the future multiply and give AI?

I was just using that as an example of another business he could pivot into. It could be AI or some other fintech, or anything.

Quote
Quote
if Trump started a really unpopular war that spiked gas prices and caused inflation... or something
I'm curious what won't be affected directly or indirectly?

Again, just an example. The point is that BTC could be hit by macro factors like political winds changing, which could drop the price by 80%, which would put MSTR in big financial trouble most likely. This would be a great source of fear by Saylor and his team.

Quote
Quote
if MSTR sold all of their BTC, they would just about break even, based on the prices where they bought
Lol I don't even know where to start
Keeping Bitcoin price not changing say they magically sold it OTC
Do you think their stock would be the same?
And no they would be at loss not just from this or overhead cost but from the fact that their average cost is higher than current price.

I agree, which is why I said they would have to do it very slowly and carefully (say writing down their BTC while building up their new business in order to equalize the losses).

Oh, and just to be clear, if BTC really tanked, I think they'd be absolutely screwed no matter what they did, and the plan I'm envisioning here has a good chance of failing no matter how careful they were. I'm just musing about their motivations, that's all.


I don't know, but did anyone truly believe they would never sell, at least not at some point in the future? If anyone did, they'd be better off staying away from investing.

Well, as an investment that's based on Bitcoin, but isn't Bitcoin, and trades at a premium of Bitcoin, I personally never understood why anybody would ever want to buy this stock--but that's just me. He's obviously gathered a lot of buyers for his stock somehow. Don't ask me how.


Quote
Saylor needs to give the market some good news here soon, or this narrative is going to grow some legs and start running...
Sometimes, making negative statements is necessarily to buy at a low price or manipulate the market.

Possibly, but he'd need to be, again, very very careful about doing stuff like this. I've said many times that whales can--and probably do--manipulate the BTC market. But if Saylor himself does it, since he's so high-profile, that would involve a lot of risk. In his case, based on how he finances his purchases,  he doesn't have a lot of time to float the money, and he also can't sell without getting on the market's radar.






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May 28, 2026, 09:37:40 PM
 #9

We have to be realistic, everyone will sell their Bitcoin at some point. They won't hold onto it forever. They have to take profit.
Maybe Saylor wants a more diversified portfolio because he's heavily invested in BTC. Putting all their eggs in one basket has paid off so far, but it won't always be that way. We all trust Bitcoin but from a corporate perspective it makes sense for them to shift their investments to areas where they can make money faster if they've found more profitable opportunities. MSTR sells, someone else buys. This doesn't harm Bitcoin. After all there are plenty of buyers in the market.

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May 28, 2026, 09:53:44 PM
 #10

Sometimes, making negative statements is necessarily to buy at a low price or manipulate the market.

They would hurt more
They usually get their funds for buying through ATM and STRC recently
So if they manipulate to make it lower
They would loss more since their stock is more volatile than Bitcoin.
They gain more when it rises
Since with that they can easily issue more shares as investors start flocking in
As a result of Bitcoin Bullishness.


Oh, and just to be clear, if BTC really tanked, I think they'd be absolutely screwed no matter what they did, and the plan I'm envisioning here has a good chance of failing no matter how careful they were. I'm just musing about their motivations, that's all.
Yeah
No matter how fancy or strategic they need Bitcoin to perform well than Bitcoin needs them.
If it tanks, shares is affected their investors face more brunt
Since they are kinda just printing.

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May 28, 2026, 10:13:18 PM
 #11

Taken together, these two announcements multiply each other: they start to create a script that has MSTR pulling completely away from Bitcoin and into AI or some other business.
Taking from the potential effect of the news possibilities to negatively drive the Bitcoin market to be bearish can be true in regards to how the market directions also relies on Speculations and investors sentiments.

But coming to think of it, the market can not just keep reacting towards every cause of macroeconomic news or the institutional adoption news as that of Micro Strategy.
Moreover the news does not imply that the institution will be backing away from their Bitcoin investment journey, they are only expanding their portfolios over their other assets and bonds.











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May 28, 2026, 11:46:04 PM
 #12

If that's the decision, that's a good thing. At least one of the people influencing the volatility has been reduced.

Our concern might be how he disposes of his holdings, whether it's the same as when they make gradual purchases, announcing it publicly. Furthermore, blockchain intelligence tools will also be monitoring trusted wallets associated with this company. If they want to sell at a good price, they should do their best to suppress the noise.

 
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May 29, 2026, 12:02:53 AM
 #13

For the fact that Michael Saylor paused buying bitcoin to repurchase its own bonds doesn't mean he's pivoting away from BTC. This is someone that has been buying bitcoin consistently since 2020, so pausing further buy for now and concentrating on buying back its own convertible bonds at a percentage off the retail price could be a strategy he wants to use and strengthen his company for massive purchase of bitcoins in the near future.

Quote
Saylor making it clear that they have no policy that forbids them from selling their Bitcoin in the future, which is a massive departure from his previous statements indicating they would never ever ever sell their Bitcoin.
Did he ever said they won't sell their bitcoins? i don't think he did but even if he said that it could just be to encourage others to hold their bitcoins without thinking of selling because he can't tell me that they will never sell their bitcoins, that's not possible. He can say that they don't have intention of selling anytime soon but not permanently.
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May 29, 2026, 12:09:10 AM
 #14

I don't see the update of the Strategy selling part of their bitcoin to be that overwhelming as such bad news because it's neither not to be expected that they'll hold their portfolios forever. Definitely time to take profits in the future will surely come because they're not just investing to make big names in the industry but to grow in financial richness to assist their needs.
Moreover if the sales has to even cause bearishness, that shoulwd'nt be a call for alarm after all such events as high trading volumes has severally occurred that at the falling of the market price, it creates entry events that others would be interested to buy their bitcoin at the cheap rate.

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May 29, 2026, 12:43:53 AM
 #15

We have to be realistic, everyone will sell their Bitcoin at some point. They won't hold onto it forever. They have to take profit.
Maybe Saylor wants a more diversified portfolio because he's heavily invested in BTC. Putting all their eggs in one basket has paid off so far, but it won't always be that way. We all trust Bitcoin but from a corporate perspective it makes sense for them to shift their investments to areas where they can make money faster if they've found more profitable opportunities. MSTR sells, someone else buys. This doesn't harm Bitcoin. After all there are plenty of buyers in the market.

This isn't Michael Saylor, himself, personally buying some Bitcoin. Instead he has created a company specifically devoted to purchasing Bitcoin, which is what he has asked invetors to invest in. Strategy is a Bitcoin holding company, and MSTR is purchased for the purpose of exposing yourself to BTC.

And MSTR is a single largest holder of Bitcoin outside of Satoshi (aka the US government Smiley). So this isn't just some investor diversifying his portfolio.

Quote
Saylor making it clear that they have no policy that forbids them from selling their Bitcoin in the future, which is a massive departure from his previous statements indicating they would never ever ever sell their Bitcoin.
Did he ever said they won't sell their bitcoins? i don't think he did but even if he said that it could just be to encourage others to hold their bitcoins without thinking of selling because he can't tell me that they will never sell their bitcoins, that's not possible. He can say that they don't have intention of selling anytime soon but not permanently.

Yes, there's a meme going around on the SM platforms of the many MANY times Saylor said he would never ever EVER sell their Bitcoin.

Of course that never made any sense since... why make an investment you never intend to sell? The implication was that MSTR would be a simple holding company for BTC, which is how people treated it, but now it seems like he is saying that MSTR is going to be... something that is not that?

https://www.google.com/search?q=did+michael+saylor+say+he+would+never+sell+his+bitcoin&oq=did+michael+saylor+say+he+would+never+sell+his+bitcoin








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May 29, 2026, 05:23:45 AM
 #16

This kinda shows his change of strategy from just buying bitcoin to become a company that is more stock focused.

He even put a bitcoin cushion for his new product paying high dividend from new buyers and if somehow company isn't able to pay the dividend, selling bitcoin is okay.

But then again, we should all realize that Strategy is a company and a company seeks profit, should've seen this coming from miles away.

However, their product and their notion towards bitcoin signals that they aren't pivoting from bitcoin but creating a business on top of it.

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May 29, 2026, 08:59:13 AM
 #17

Taken together, these two announcements multiply each other: they start to create a script that has MSTR pulling completely away from Bitcoin and into AI or some other business.

Are there any publicly known indication MSTR will switch their business (to AI or something else)? The news you shared doesn't mention anything about it.

Right now, if MSTR sold all of their BTC, they would just about break even, based on the prices where they bought. Of course, MSTR itself moves the market, so they couldn't simply just sell everything because they would damage their own asset price. So yeah, anything major they do would have to be done... carefully.

If they plan to sell their BTC in massive scale, they would use OTC to reduce the impact on market/bitcoin price. But if address claimed to be owned by MSTR send lots of Bitcoin, that alone may affect market/bitcoin price.

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May 29, 2026, 09:23:19 AM
 #18

The bond was bought back cheaper and it's reducing their debt.

Are you sure about that?

The original plan was that the share price would rise so much that, once the strike price was reached, the bond would be converted into MSTR shares, meaning that both the company and the bondholders would come out ahead. The company would benefit because it would receive the funds years in advance to invest in Bitcoin, which tends to appreciate in value over the long term, and the bondholder would benefit significantly from the conversion at the strike price.

But if I’m a bondholder, I’m not going to let Saylor give me less money for it now. If I wait until the deadline, he’ll pay me my money back (if the stock doesn't reach the strike price). Am I really going to accept less money now, meaning I’ll have been financing Saylor at a loss all this time?

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May 29, 2026, 04:00:52 PM
 #19

Buying back convertible bonds while they're trading at a discount is just normal balance sheet management, it doesn't mean he's souring on BTC. And "no policy forbids us from selling" is basically legal honesty, no company should ever have a clause that bans them from ever selling an asset, that's not the same as planning to.

I'm not saying it's impossible he ever pivots away from BTC, but it feels like you're stacking two fairly ordinary moves into a narrative that isn't really there yet.

 
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May 29, 2026, 04:13:01 PM
 #20

Buying back convertible bonds while they're trading at a discount is just normal balance sheet management, it doesn't mean he's souring on BTC. And "no policy forbids us from selling" is basically legal honesty, no company should ever have a clause that bans them from ever selling an asset, that's not the same as planning to.

I'm not saying it's impossible he ever pivots away from BTC, but it feels like you're stacking two fairly ordinary moves into a narrative that isn't really there yet.

It is normal for a diversified company, but what wasn't normal was his public stance before this week: that he would never ever EVER sell any of his Bitcoin.

Before this week, MSTR was a pure Bitcoin play: essentially another Bitcoin ETF. Now MSTR is... something else.

Given that MSTR is the single largest holder of BTC besides Satoshi/USA (who are not active traders to say the least), and given that Saylor himself has been, by far, the #1 public marketing agent for Bitcoin in the last five years, I don't think you can simply write this off as just "some business doing business stuff".

I agree the narrative isn't fully there yet, but... these are signs....


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