
@ AVB
2025-03-29 17:58:33
A flash of inspiration
<img src="https://blossom.primal.net/f1adbb3992b05ba7bbb9e3ff3b61d27e6e58b1564e628dd136afee4e57b3449c.jpg">
Sometimes the mind takes you to strange places. The other day, I stumbled across Madonna’s “Vogue” video, you know “strike a pose” and all that jazz, and it got me thinking. Not about her music (which, let’s be honest, hasn’t aged as gracefully as her PR team might hope), but about Michael Saylor and Bitcoin.
Bear with me here, there’s a connection there. Madonna built an empire and her iconic name on catchy tunes and reinvention, even if her catalog feels a bit thin these days. Saylor? He’s doing something similar—taking an old act, dusting it off, and teaching it a new trick. Only instead of a microphone, he’s wielding Bitcoin, and Wall Street’s playing the role of the music industry, propping up the star despite a shaky back catalog (his initial business software).
Old school meets new moves
Think of Saylor as that veteran artist who’s been around for a few decades and think of bitcoin as a new style of music, a genre or a gimmick that’s popular with the kids. Old music stars sooner or later pick up on that, and even bring people in to do a cross-over song, a mix or god forbid, a duet.
MicroStrategy, his software company, was never a top hit scoring machine. More of a album full of B-sides that faded into obscurity (for those who don’t know, look up what a B-side song was). But then he stumbled onto Bitcoin, the shiny new genre that’s got the attention and attracted people because of the underlying asset (our tunes are here to stay).
It’s not just a pivot; it’s a reinvention. Like an aging pop star learning to rap, Saylor’s taken his old-school business and remixed it into something attracting a decent audience at conferences for example. Like Madonna or the former Prince fulling arenas. He’s voguing alright; with bold moves, big loans, the support of his own music industry and a spotlight for his (sometimes Madonna lyrics like) ramblings.
The Saylor trick: a ray of light on bitcoin
Here’s the play: Saylor’s turned MicroStrategy into a Bitcoin hoarding machine. Forget software licenses; his game is borrowing billions—through corporate bonds and stock sales, only to buy and hold Bitcoin. Bitcoin will outshine gold, bonds, even the S&P 500, Saylor says. It’s a gamble, an honorable one if you’re a bitcoiner, but it’s dressed up as a vision, and it’s got a self-fulfilling prophecy in it. Not only that, such a prophecy can only fully come to fruition if he’s not the only buyer of last resort of any significance. A music industry isn’t a real industry if there was only Madonna dancing on stage as the only mainstream artist.
We had Prince, Michael Jackson, Taylor Swift, Bruno Mars or Dua Lipa and hundreds of other artists over time, vying for your money, attention span, and streaming minutes. The more Strategy buys, the more the Bitcoin crowd cheers, the higher the price climbs, and the more attention he gets. Speaking gigs, headlines, cult status—it’s a win-win, at least on paper. Strike the pose, indeed.
The McDonald’s trick: value under the surface
It’s not the first time Michael Saylro remixes a tape from another artist so to speak. Let’s pivot to McDonald’s for a second, because there’s a parallel here. You think Big Macs when you think McDonald’s, but their real value hustle is actually real estate.
They own prime land, lease it to franchisees, and rake in rent—billions of it. The burgers? Just a tasty front for a property empire. Saylor’s pulling a similar move, but instead of buildings, his asset is Bitcoin. MicroStrategy’s software gig is the fries on the side — nice to have, but not the main course. He’s borrowing against the future value of BTC, betting it’ll keep climbing, just like McDonald’s banks on steady foot traffic and picking strategic (pun intended) locations. The difference? McDonald’s has a fallback if real estate tanks. Saylor’s all-in on bitcoin. (So far so good, if there’s one thing to go all-in on, it’s bitcoin anyway). That on itself is not an issue. But it’s important to know that the “location” is the asset for some while bitcoin is the “asset” for Strategy. Mc Donald’s assets are easy to spot: there are restaurants all over the place. Madonna’s concerts are also easy to spot: they sell out arenas left and right. Strategy’s bitcoin asset is less easy to spot, as we can’t see them, neither can we verify them. More on that later.
The hybrid star: Madonna meets McDonald’s
So, picture this: Saylor’s a cross between Madonna and a fast-food landlord. He’s the aging music icon who’s learned a flashy new dance, but underneath the glitter, he’s running a McDonald’s-style value play. It’s brilliant, in a way. Bitcoin’s scarcity fuels the hype, and his borrowing keeps the show on the road. Madonna’s legacy still sells records her name holds value, and McDonald’s can lean on its food business and brand, if the property game stumbles they can easily pivot back to basics and earn like they’ve always done on selling food and franchise income/licensing. Saylor? His software arm’s is rather dismal. If Bitcoin falters, there’s no encore that can him.**a flash of inspiration**
Sometimes the mind takes you to strange places. The other day, I stumbled across Madonna’s “Vogue” video, you know “strike a pose” and all that jazz, and it got me thinking. Not about her music (which, let’s be honest, hasn’t aged as gracefully as her PR team might hope), but about Michael Saylor and Bitcoin.\
\
Bear with me here, there’s a connection there. Madonna built an empire and her iconic name on catchy tunes and reinvention, even if her catalog feels a bit thin these days.\
Saylor? He’s doing something similar—taking an old act, dusting it off, and teaching it a new trick. Only instead of a microphone, he’s wielding Bitcoin, and Wall Street’s playing the role of the music industry, propping up the star despite a shaky back catalog (his initial business software).
**Old school meets new moves**
Think of Saylor as that veteran artist who’s been around for a few decades and think of bitcoin as a new style of music, a genre or a gimmick that’s popular with the kids. Old music stars sooner or later pick up on that, and even bring people in to do a cross-over song, a mix or god forbid, a duet.
MicroStrategy, his software company, was never a top hit scoring machine. More of a album full of B-sides that faded into obscurity (for those who don’t know, look up what a B-side song was).\
But then he stumbled onto Bitcoin, the shiny new genre that’s got the attention and attracted people because of the underlying asset (our tunes are here to stay).\
\
It’s not just a pivot; it’s a reinvention. Like an aging pop star learning to rap, Saylor’s taken his old-school business and remixed it into something attracting a decent audience at conferences for example. Like Madonna or the former Prince fulling arenas.\
He’s voguing alright; with bold moves, big loans, the support of his own music industry and a spotlight for his (sometimes Madonna lyrics like) ramblings.
**The Saylor trick: a ray of light on bitcoin\**
\
Here’s the play: Saylor’s turned MicroStrategy into a Bitcoin hoarding machine. Forget software licenses; his game is borrowing billions—through corporate bonds and stock sales, only to buy and hold Bitcoin. Bitcoin will outshine gold, bonds, even the S&P 500, Saylor says.\
It’s a gamble, an honorable one if you’re a bitcoiner, but it’s dressed up as a vision, and it’s got a self-fulfilling prophecy in it. Not only that, such a prophecy can only fully come to fruition if he’s not the only buyer of last resort of any significance. A music industry isn’t a real industry if there was only Madonna dancing on stage as the only mainstream artist.\
\
We had Prince, Michael Jackson, Taylor Swift, Bruno Mars or Dua Lipa and hundreds of other artists over time, vying for your money, attention span, and streaming minutes.\
The more Strategy buys, the more the Bitcoin crowd cheers, the higher the price climbs, and the more attention he gets. Speaking gigs, headlines, cult status—it’s a win-win, at least on paper. Strike the pose, indeed.
**The McDonald’s trick: value under the surface\**
\
It’s not the first time Michael Saylro remixes a tape from another artist so to speak.\
Let’s pivot to McDonald’s for a second, because there’s a parallel here. You think Big Macs when you think McDonald’s, but their real value hustle is actually real estate.
They own prime land, lease it to franchisees, and rake in rent—billions of it. The burgers? Just a tasty front for a property empire. Saylor’s pulling a similar move, but instead of buildings, his asset is Bitcoin.\
MicroStrategy’s software gig is the fries on the side — nice to have, but not the main course. He’s borrowing against the future value of BTC, betting it’ll keep climbing, just like McDonald’s banks on steady foot traffic and picking strategic (pun intended) locations.\
The difference? McDonald’s has a fallback if real estate tanks. Saylor’s all-in on bitcoin. (So far so good, if there’s one thing to go all-in on, it’s bitcoin anyway). That on itself is not an issue. But it’s important to know that the “location” is the asset for some while bitcoin is the “asset” for Strategy.\
Mc Donald’s assets are easy to spot: there are restaurants all over the place. Madonna’s concerts are also easy to spot: they sell out arenas left and right.\
Strategy’s bitcoin asset is less easy to spot, as we can’t see them, neither can we verify them. More on that later.
**The hybrid star: Madonna meets McDonald’s**
So, picture this: Saylor’s a cross between Madonna and a fast-food landlord. He’s the aging music icon who’s learned a flashy new dance, but underneath the glitter, he’s running a McDonald’s-style value play.\
It’s brilliant, in a way. Bitcoin’s scarcity fuels the hype, and his borrowing keeps the show on the road.\
Madonna’s legacy still sells records her name holds value, and McDonald’s can lean on its food business and brand, if the property game stumbles they can easily pivot back to basics and earn like they’ve always done on selling food and franchise income/licensing.\
Saylor? His software arm’s is rather dismal. If Bitcoin falters, there’s no encore that can him.
The music’s made in-house
Michael Saylor’s strategy with Strategy, is a bold, all-in bet on Bitcoin as the ultimate store of value. Essentially combining what Mc Donald’s does with the strong believe in bitcoin’s future (and fueling that believe with the fitting rhetoric).
It works like this: Since August 2020, Saylor’s company has been buying up more and more Bitcoin, making it their main asset instead of traditional cash or investments, and by March 2025, they own 506,137 BTC—worth about $42.8 billion (at $84,000 per Bitcoin). This, after spending $33.7 billion to buy it over time (DCA), including a massive 218887 BTC purchase late 2024 for $20.5 billion, giving them over 2.41% of all Bitcoin ever to exist (way more than companies like Marathon, Coinbase, Tesla or Riot).
To pull this off, they’ve borrowed heavily: owing $7.2 billion, mostly to Wall Street investors through special IOUs1 called convertible notes, which don’t need to be paid back until 2027, through 2029. These can either be settled with cash or swapped for Strategy stock. (there lies one of the main issues in my opinion, as the main asset’s price in USD is directly impacting the stock price of MSTR). A small example of this repeated correlation happened on March 28, 2025 when Strategy’s stock (MSTR) dropped 10.8% from $324.59 to $289.41, which was mirroring Bitcoin’s move down from $85,000 to $82,000 earlier.
This debt they have can be called “risky” by any stretch, with a high leverage rate of 39-40%, meaning they’ve borrowed a big chunk compared to what they own outright, but here’s the genius of it: they don’t have to sell their Bitcoin if its price drops, and they can refinance (borrow more later) to keep the dance going. As long as they find investors willing to bet on the later bitcoin price surge, but more importantly, as long as the song is liked by the new audience. If Michael Saylor is our “Madonna”, then there’s still not Taylor Swift or Rihanna in sight.
The creditors (big players, not banks) win if Bitcoin soars, as Strategy’s huge stash (potentially 2.9%+ of the market) nets them massive profits, or even if it crashes, they’re still in the game with other ways to make profit (not on bitcoin), since they can afford the risk. If someone is willing to bet 4 to 8 billion dollars, they’re probably not spooked by losing it all. More so, these Wall Streat people in the correct entourage, can probably afford such a gamble, and can stomach to lose it all if something goes horribly wrong as well, instead of risking being left out of a growing market. But since they’re probably the same people steering and “owning” the USD market anyway, they’re just conquering positions in a new market. The fact that they’re not real bitcoin-ethos people, but just “suits” in finance, can make the suspicious bitcoiners watching all of this unfold, even more uneasy.
So, Strategy sits on $44 billion in Bitcoin with just $7.2 billion in debt, voguing confidently. And Saylor’s betting the song never gets old, he’ll do the B-sides and re-mastering his old albums if necessary, but if Bitcoin’s value ever fades (for whatever reason), the real question is how long they can keep striking poses before the music stops. Remember: all money (fiat, gold, silver, bitcoin, nicely made papers) is a matter of trust.
As I have trust in bitcoin itself, but not so much in Strategy, I’ve take some precautions. I've started my own sort of "Strategy crash fund", with fiat money that only will come into action when strategy is done. The crash that we'll see after that goes down, will be such a tremendous opportunity, that I'll pour in some more fiat, gladly, and that will be the exact moment I will actually “sell all my chairs” (from Saylor’s well-known quote).
Purchases
Strategy’s Bitcoin purchases, don’t seem to jolt the market much either, no matter the size of the order. They always have the same sound: “it’s OTC, it doesn’t impact the market that much”.
Still, it’s strange to see: no one has ever come forward to tell anyone “I’ve sold 15000 bitcoin from my old stack to Saylor”, neither do we see any clear evidence and on-chain moves.
Take their first buy in August 2020 for example. Totaling 21454 BTC for $250 million at $11,652 per BTC; Bitcoin sat at $11,500 to $11,700 so barely moved, inching to $12,000 weeks later due to broader trends.
Same story in December 2020 with 29646 BTC for $650 million, there, the price hopped from $19,000 to $23,000, but a bull market was already raging. Fast forward to February 2021 (19452 BTC, for $1.026 billion (!)), March 2024 (9245 BTC, $623 million), November 2024 (55500 BTC, $5.4 billion), and March 2025 (6911 BTC, $584.1 million)
Bitcoin wobbled 2-15%, but always in line with existing momentum, not Strategy’s announcements. Their biggest buy, for a total of $5.4 billion (!) is just 0.3% of Bitcoin’s $1.7 trillion market cap, it’s too small to register as a blip even. But compared to the liquidity on the market and the “availability” on the OTC market, it should. More so, OTC bitcoin is announced as “for sale” somehow. A person with +25000 bitcoin is not standing on the side of the street yelling “hey man, wanna buy some bitcoin?”. There are specialized firms doing that for them, and making these available. This date is also used by some insiders and people who know this very small market (there aren’t that many bitcoiners sitting on such an amount after 2024 I guess). Data from Binance OTC, Coinspaid, kraken OTC, is highly private of course, but still, anything being sold over there, to Strategy or anyone else, would take larger amounts off the open market and the OTC market, making a price impact, certainly withing 2 years, as Bitcoin mining companies sit on an average buffer of 6 months depending on market conditions.
Strategy funds all of this by selling shares (diluting the pool big-time) or issuing convertible notes, and while SEC filings make faking these buys near-impossible. And even if Saylor is the Bitcoin version of Bernie Madoff, he could get away with it, if enough people "in the know" are willing to support this way of infesting (and investing in) the bitcoin economy. This would have to be a clear orchestrated attack on bitcoin, purely on the financial level then.
I don't believe this to be the case, but mathematically we have to take it into account as a very slight possibility.
After all, a company like "WorldCom"2 managed to scam their way out of different audits for years, until the scheme got bust and a enormous amount of investors lost their money after their CEO went to jail3 for exchange fraud.
I believe this could be the case with Strategy, but I give it a 3% chance (this might be low, but it's there, we can't outright dismiss the possibility).
Water in the wine
Strategy has also massively diluted its stock to fund Bitcoin buys, jumping from 10 million shares in 2020 to about 285 million by March 2025—a 2,750% increase, this happened after raising $4.25 billion from 2020 onwards and $20 billion of their $42 billion "21/21 Plan" by early 2025.
After the 10-for-1 stock split in August 2024, the number of MSTR shares grew from 16.5 million in 2023 to 284898 by end of 2024, a 1625% rise !!!. Add to that about 275 million more shares added in total (including 120 million in 2024 alone) and 1.975 million extra in March 2025 for $592.6 million.
So more and more tap water is poured in the wine, and it means each share’s ownership slice shrinks as new shares flood in, mostly via "at-the-market" sales and convertible note conversions. This is partly offset by share splits, but still, the rise in the number of stock is significant, and a big factor in evaluating MSTR.
In December 2024, they proposed hiking authorized shares to 10.33 billion (plus 1 billion preferred), approved in January 2025, setting the stage for even more if they keep selling.
The trend is clear: relentless selling. They might say “we never sell bitcoin”, but the same doesn’t count for their shares… which derive their value from bitcoin’s fiat price. So shareholders are betting on Bitcoin’s rise to offset the watering down of the share they hold. The more you think of it, the more ludicrous it sounds. It’s a loop of trust where the stock itself can only thrive if the company itself is an active, useful middleman. And so far, it’s only doing so for other Wall street companies, the biggest holders of MSTR shares:
Vanguard Group Inc, BlackRock, Capital International Investors, Jane Street Group, Susquehanna International Group
This on itself is also “normal” of course. In the flow of things. Like every aspect by itself in the whole Strategy setup is just normal. But combining all the factors makes it look a bit more… suspicious to me.
Supporting bitcoin ?
The real head-scratcher comes next: their secrecy and lack of community involvement. Strategy claims to hold 506137 BTC, likely cold-stored with partners like BitGo or Coinbase Custody, but no public wallet addresses back these claims up. Odd for a firm swearing never to sell.
There’s also the real risk that these partners are partly selling paper bitcoin (bitcoin they don't hold the keys to, or "promised" bitcoin) to Strategy, and that they just assume everything is audited and OK.
We can't estimate that, since we don't have any public MicroStrategy addresses or other ways to look at their holdings. This is for security reasons apparently, which raises another question: If they for example would show 300k+ BTC on-chain as proof, it’d boost trust, yet they don’t, hinting at a bigger play — maybe as a Wall Street-backed buyer of last resort for a new asset class.
Also Strategy’s software business and bitcoin “apps” (like the super simple Lightning email integration, and an on-chain digital ID system) is underwhelming to say the least (I literally know people that code such stuff on a free afternoon while they’re cooking dinner).
Their very minimal software innovation for the Bitcoin space, with basic Lightning features and an on-chain ID system, failing their their valuation as a 'Bitcoin company' in my opinion. More so, their business is ignoring the other innovation that would help bitcoin thrive. This is kind of a red flag for me. Why would a company sitting on +500 k bitcoin be hesitant about supporting the bitcoin eco-system more actively? They sure have the funds to do so, right? And they also have the right insights, info and spirit. Yet, they don’t.
They don’t fund developers for open-source projects, or Bitcoin’s growth in general (not publicly at least). So Saylor shines in talks, hyping Bitcoin’s future and Strategy’s stock, but it’s all the self fulfilling prophecy.
No grants, no real support for the community they lean on. It’s like they’re dancing to Bitcoin’s mixtape, raking in the spotlight, while giving little back. All the while some extremely needed projects lack funding, and most software companies in bitcoin who wish to innovate are begging and scraping funds together, in order to stay afloat. Something’s not ok with that. I can’t understand a company with that much power and money being part of this movement and loving bitcoin, while not actively supporting the development or the maintainers of the bitcoin software. (and yes, to keep their independence it’s best to keep it that way, that’s also an argument, but even then, giving out a grant to anyone that’s crucial in this industry, might help the whole ecosystem).
The show must go on—for now
The whole Strategy setup feels more and more like a performance to me. Saylor’s the star, doing the moves and Wall Street’s the record label, and we’re the audience, captivated by the spectacle and paying to see the show on occasion.
The suits keep funding him (free money, IOUs), just like the music industry props up a fading diva with a limited repertoire or drags a new star from her home studio on YouTube into the spotlights. H Saylor’s 21/21 Plan to the amount of $42 billion to snatch up more Bitcoin can be a grand finale that’s dazzling while the lights stay on.
Prediction: the music stops eventually
Here’s my take: Bitcoin will keep rising over a long period of time, and Saylor’s gambit will look like a genius move, until it doesn’t. All it takes is one big shot in Wall Street to find another shiny toy to play with, or another play to get their money working. The billions they’ve invested, will come back eventually, and if it doesn’t, it will mean the world has changed in their advantage as well in another way. Some people cannot lose, no matter what. Saylor’s now part of that, doing their bidding and doing his part for educating the other businesses.
He’s the only big buyer of last resort in this game so far. No one else is piling in with billions like he is. When the hype cools or the debt catches up, he’s got no real business to fall back on. The software? A relic. The Bitcoin bet can save him if the time is right, we’ll see about that. Time is his enemy not ally, and it always wins in the end. The pose can only hold so long. You can’t keep scoring free fiat, without either die on low valuation and dilution, or without at least 20 other Strategy-grade businesses jumping in to take their piece of the pie. So far, surprisingly, none of these two things happen. He keeps getting free fiat from Wall Street investors, and no other Saylor stands up. This can’t last forever. One of the two will happen by end of 2025.
Curtain call
Saylor’s a fascinating watch, a mix of investor-backed bravado, brains, and borrowed billions. Is it a masterstroke or a bitcoin version of Worldcom? I’m not sure. In any case, I would only invest in MSTR myself if the company has a real added value for bitcoin development and the bitcoin ecosystem. They could be the engine, the spirit, the core of bitcoin. Yet they’re just doing the poses. Let your body move to the rhythm.
AVB
If you like : tip here / other writings
1 https://en.wikipedia.org/wiki/IOU
2 https://sc.edu/about/offices_and_divisions/audit_and_advisory_services/about/news/2021/worldcom_scandal.php
3 https://content.next.westlaw.com/Document/Ic6b4dd91644311dbbe1cf2d29fe2afe6/View/FullText.html?transitionType=Default&contextData=(sc.Default)#:\~:text=Rep.-,6,Criminal%20Charges**The music’s made in-house**
Michael Saylor’s strategy with Strategy, is a bold, all-in bet on Bitcoin as the ultimate store of value. Essentially combining what Mc Donald’s does with the strong believe in bitcoin’s future (and fueling that believe with the fitting rhetoric).\
\
It works like this: Since August 2020, Saylor’s company has been buying up more and more Bitcoin, making it their main asset instead of traditional cash or investments, and by March 2025, they own 506,137 BTC—worth about $42.8 billion (at $84,000 per Bitcoin).\
This, after spending $33.7 billion to buy it over time (DCA), including a massive 218887 BTC purchase late 2024 for $20.5 billion, giving them over 2.41% of all Bitcoin ever to exist (way more than companies like Marathon, Coinbase, Tesla or Riot).\
\
To pull this off, they’ve borrowed heavily: owing $7.2 billion, mostly to Wall Street investors through special IOUs[1](https://allesvoorbitcoin.substack.com/p/strategy-is-in-vogue#footnote-1-159855071) called convertible notes, which don’t need to be paid back until 2027, through 2029. These can either be settled with cash or swapped for Strategy stock. (there lies one of the main issues in my opinion, as the main asset’s price in USD is directly impacting the stock price of MSTR).\
A small example of this repeated correlation happened on March 28, 2025 when Strategy’s stock (MSTR) dropped 10.8% from $324.59 to $289.41, which was mirroring Bitcoin’s move down from $85,000 to $82,000 earlier.
This debt they have can be called “risky” by any stretch, with a high leverage rate of 39-40%, meaning they’ve borrowed a big chunk compared to what they own outright, but here’s the genius of it: they don’t have to sell their Bitcoin if its price drops, and they can refinance (borrow more later) to keep the dance going. As long as they find investors willing to bet on the later bitcoin price surge, but more importantly, as long as the song is liked by the new audience. If Michael Saylor is our “Madonna”, then there’s still not Taylor Swift or Rihanna in sight.
The creditors (big players, not banks) win if Bitcoin soars, as Strategy’s huge stash (potentially 2.9%+ of the market) nets them massive profits, or even if it crashes, they’re still in the game with other ways to make profit (not on bitcoin), since they can afford the risk. If someone is willing to bet 4 to 8 billion dollars, they’re probably not spooked by losing it all. More so, these Wall Streat people in the correct entourage, can probably afford such a gamble, and can stomach to lose it all if something goes horribly wrong as well, instead of risking being left out of a growing market. But since they’re probably the same people steering and “owning” the USD market anyway, they’re just conquering positions in a new market. The fact that they’re not real bitcoin-ethos people, but just “suits” in finance, can make the suspicious bitcoiners watching all of this unfold, even more uneasy.\
\
So, Strategy sits on $44 billion in Bitcoin with just $7.2 billion in debt, voguing confidently. And Saylor’s betting the song never gets old, he’ll do the B-sides and re-mastering his old albums if necessary, but if Bitcoin’s value ever fades (for whatever reason), the real question is how long they can keep striking poses before the music stops. Remember: all money (fiat, gold, silver, bitcoin, nicely made papers) is a matter of trust.
As I have trust in bitcoin itself, but not so much in Strategy, I’ve take some precautions.\
I've started my own sort of "Strategy crash fund", with fiat money that only will come into action when strategy is done. The crash that we'll see after that goes down, will be such a tremendous opportunity, that I'll pour in some more fiat, gladly, and that will be the exact moment I will actually “sell all my chairs” (from Saylor’s well-known quote).
**Purchases**
Strategy’s Bitcoin purchases, don’t seem to jolt the market much either, no matter the size of the order. They always have the same sound: “it’s OTC, it doesn’t impact the market that much”.\
\
Still, it’s strange to see: no one has ever come forward to tell anyone “I’ve sold 15000 bitcoin from my old stack to Saylor”, neither do we see any clear evidence and on-chain moves.\
\
Take their first buy in August 2020 for example. Totaling 21454 BTC for $250 million at $11,652 per BTC; Bitcoin sat at $11,500 to $11,700 so barely moved, inching to $12,000 weeks later due to broader trends.
Same story in December 2020 with 29646 BTC for $650 million, there, the price hopped from $19,000 to $23,000, but a bull market was already raging.\
Fast forward to February 2021 (19452 BTC, for $1.026 billion (!)), March 2024 (9245 BTC, $623 million), November 2024 (55500 BTC, $5.4 billion), and March 2025 (6911 BTC, $584.1 million)\
\
Bitcoin wobbled 2-15%, but always in line with existing momentum, not Strategy’s announcements. Their biggest buy, for a total of $5.4 billion (!) is just 0.3% of Bitcoin’s $1.7 trillion market cap, it’s too small to register as a blip even. But compared to the liquidity on the market and the “availability” on the OTC market, it should.\
More so, OTC bitcoin is announced as “for sale” somehow. A person with +25000 bitcoin is not standing on the side of the street yelling “hey man, wanna buy some bitcoin?”. There are specialized firms doing that for them, and making these available. This date is also used by some insiders and people who know this very small market (there aren’t that many bitcoiners sitting on such an amount after 2024 I guess). Data from Binance OTC, Coinspaid, kraken OTC, is highly private of course, but still, anything being sold over there, to Strategy or anyone else, would take larger amounts off the open market and the OTC market, making a price impact, certainly withing 2 years, as Bitcoin mining companies sit on an average buffer of 6 months depending on market conditions.\
\
Strategy funds all of this by selling shares (diluting the pool big-time) or issuing convertible notes, and while SEC filings make faking these buys near-impossible. And even if Saylor is the Bitcoin version of Bernie Madoff, he could get away with it, if enough people "in the know" are willing to support this way of infesting (and investing in) the bitcoin economy. This would have to be a clear orchestrated attack on bitcoin, purely on the financial level then.
I don't believe this to be the case, but mathematically we have to take it into account as a very slight possibility.
After all, a company like "WorldCom"[2](https://allesvoorbitcoin.substack.com/p/strategy-is-in-vogue#footnote-2-159855071) managed to scam their way out of different audits for years, until the scheme got bust and a enormous amount of investors lost their money after their CEO went to jail[3](https://allesvoorbitcoin.substack.com/p/strategy-is-in-vogue#footnote-3-159855071) for exchange fraud.
I believe this could be the case with Strategy, but I give it a 3% chance (this might be low, but it's there, we can't outright dismiss the possibility).
**Water in the wine**
Strategy has also massively diluted its stock to fund Bitcoin buys, jumping from 10 million shares in 2020 to about 285 million by March 2025—a 2,750% increase, this happened after raising $4.25 billion from 2020 onwards and $20 billion of their $42 billion "21/21 Plan" by early 2025.\
\
After the 10-for-1 stock split in August 2024, the number of MSTR shares grew from 16.5 million in 2023 to 284898 by end of 2024, a 1625% rise !!!. Add to that about 275 million more shares added in total (including 120 million in 2024 alone) and 1.975 million extra in March 2025 for $592.6 million.\
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So more and more tap water is poured in the wine, and it means each share’s ownership slice shrinks as new shares flood in, mostly via "at-the-market" sales and convertible note conversions.\
This is partly offset by share splits, but still, the rise in the number of stock is significant, and a big factor in evaluating MSTR.\
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In December 2024, they proposed hiking authorized shares to 10.33 billion (plus 1 billion preferred), approved in January 2025, setting the stage for even more if they keep selling.\
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The trend is clear: relentless selling.\
They might say “we never sell bitcoin”, but the same doesn’t count for their shares… which derive their value from bitcoin’s fiat price.\
So shareholders are betting on Bitcoin’s rise to offset the watering down of the share they hold. The more you think of it, the more ludicrous it sounds. It’s a loop of trust where the stock itself can only thrive if the company itself is an active, useful middleman.\
And so far, it’s only doing so for other Wall street companies, the biggest holders of MSTR shares:
Vanguard Group Inc, BlackRock, Capital International Investors, Jane Street Group, Susquehanna International Group\
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This on itself is also “normal” of course. In the flow of things.\
Like every aspect by itself in the whole Strategy setup is just normal. But combining all the factors makes it look a bit more… suspicious to me.
**Supporting bitcoin ?**
The real head-scratcher comes next: their secrecy and lack of community involvement.\
Strategy claims to hold 506137 BTC, likely cold-stored with partners like BitGo or Coinbase Custody, but no public wallet addresses back these claims up. Odd for a firm swearing never to sell.
There’s also the real risk that these partners are partly selling paper bitcoin (bitcoin they don't hold the keys to, or "promised" bitcoin) to Strategy, and that they just assume everything is audited and OK.
We can't estimate that, since we don't have any public MicroStrategy addresses or other ways to look at their holdings. This is for security reasons apparently, which raises another question:\
If they for example would show 300k+ BTC on-chain as proof, it’d boost trust, yet they don’t, hinting at a bigger play — maybe as a Wall Street-backed buyer of last resort for a new asset class.
Also Strategy’s software business and bitcoin “apps” (like the super simple Lightning email integration, and an on-chain digital ID system) is underwhelming to say the least (I literally know people that code such stuff on a free afternoon while they’re cooking dinner).
Their very minimal software innovation for the Bitcoin space, with basic Lightning features and an on-chain ID system, failing their their valuation as a 'Bitcoin company' in my opinion. More so, their business is ignoring the other innovation that would help bitcoin thrive. This is kind of a red flag for me.\
Why would a company sitting on +500 k bitcoin be hesitant about supporting the bitcoin eco-system more actively? They sure have the funds to do so, right? And they also have the right insights, info and spirit.\
Yet, they don’t.\
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They don’t fund developers for open-source projects, or Bitcoin’s growth in general (not publicly at least). So Saylor shines in talks, hyping Bitcoin’s future and Strategy’s stock, but it’s all the self fulfilling prophecy.\
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No grants, no real support for the community they lean on.\
It’s like they’re dancing to Bitcoin’s mixtape, raking in the spotlight, while giving little back. All the while some extremely needed projects lack funding, and most software companies in bitcoin who wish to innovate are begging and scraping funds together, in order to stay afloat.\
Something’s not ok with that.\
I can’t understand a company with that much power and money being part of this movement and loving bitcoin, while not actively supporting the development or the maintainers of the bitcoin software. (and yes, to keep their independence it’s best to keep it that way, that’s also an argument, but even then, giving out a grant to anyone that’s crucial in this industry, might help the whole ecosystem).
**The show must go on—for now**
The whole Strategy setup feels more and more like a performance to me. Saylor’s the star, doing the moves and Wall Street’s the record label, and we’re the audience, captivated by the spectacle and paying to see the show on occasion.\
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The suits keep funding him (free money, IOUs), just like the music industry props up a fading diva with a limited repertoire or drags a new star from her home studio on YouTube into the spotlights. H\
Saylor’s 21/21 Plan to the amount of $42 billion to snatch up more Bitcoin can be a grand finale that’s dazzling while the lights stay on.
**Prediction: the music stops eventually**
Here’s my take: Bitcoin will keep rising over a long period of time, and Saylor’s gambit will look like a genius move, until it doesn’t. All it takes is one big shot in Wall Street to find another shiny toy to play with, or another play to get their money working. The billions they’ve invested, will come back eventually, and if it doesn’t, it will mean the world has changed in their advantage as well in another way. Some people cannot lose, no matter what. Saylor’s now part of that, doing their bidding and doing his part for educating the other businesses.\
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He’s the only big buyer of last resort in this game so far. No one else is piling in with billions like he is. When the hype cools or the debt catches up, he’s got no real business to fall back on. The software? A relic. The Bitcoin bet can save him if the time is right, we’ll see about that.\
Time is his enemy not ally, and it always wins in the end. The pose can only hold so long. You can’t keep scoring free fiat, without either die on low valuation and dilution, or without at least 20 other Strategy-grade businesses jumping in to take their piece of the pie.\
So far, surprisingly, none of these two things happen.\
He keeps getting free fiat from Wall Street investors, and no other Saylor stands up.\
This can’t last forever. One of the two will happen by end of 2025.\
**\
Curtain call**
Saylor’s a fascinating watch, a mix of investor-backed bravado, brains, and borrowed billions.\
Is it a masterstroke or a bitcoin version of Worldcom?\
I’m not sure. In any case, I would only invest in MSTR myself if the company has a real added value for bitcoin development and the bitcoin ecosystem. They could be the engine, the spirit, the core of bitcoin.\
Yet they’re just doing the poses.\
Let your body move to the rhythm.
AVB
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[1](https://allesvoorbitcoin.substack.com/p/strategy-is-in-vogue#footnote-anchor-1-159855071) <https://en.wikipedia.org/wiki/IOU>
[2](https://allesvoorbitcoin.substack.com/p/strategy-is-in-vogue#footnote-anchor-2-159855071) <https://sc.edu/about/offices_and_divisions/audit_and_advisory_services/about/news/2021/worldcom_scandal.php>
[3](https://allesvoorbitcoin.substack.com/p/strategy-is-in-vogue#footnote-anchor-3-159855071)
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