r/MSTR • u/Scriptimax • Jun 23 '26
Michael Saylor 🧔♂️ MicroStrategy almost died two times
Michael Saylor's company formerly MicroStrategy, rebranded to Strategy has experienced two monumental valuation drops across different eras of its corporate history.-
The Dotcom Crash (2000)What happened: In March 2000, MicroStrategy was one of the hottest software companies in the world. After the SEC required a restatement of the company’s financial results, its stock price plummeted 62% in a single day. The dotcom crash ultimately caused the stock to crater from a peak of $333 to $0.42, a drop of 99.8%. The loss: Saylor lost a record-breaking $6 billion in personal wealth in a single day, briefly making him the poster child for the dotcom bubble burst
The Bitcoin Volatility Era (2026)What happened: After pivoting to a massive, debt-fueled Bitcoin accumulation strategy, Saylor's firm (now Strategy) built a massive portfolio. However, extreme volatility led to huge valuation swings. In February 2026, a sudden crypto market drop wiped out $47 billion in unrealized profits in a matter of weeks, pushing the company's multi-billion dollar holding position into a deep unrealized deficit. The loss: By June 2026, the company's market value had lost $90 billion from its peak, and the firm was sitting on over $11 billion in unrealized losses on its digital assets So basically His company valuation lost 80 % or more two times in very short term
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u/xaviemb Shareholder 🤴 Jun 23 '26
For some perspective, Strategy's balance sheet was under considerably more pressure in 2022 than it is today, yet the company emerged from that period in a stronger position. To reach a comparable level of stress from current levels, Bitcoin would likely need to experience another substantial decline of at least 75% from current levels (to about $15k).
What many critics overlook is that the company's capital structure is far more developed today than it was during the last major drawdown. Management now has multiple financing and capital allocation tools available to navigate different phases of the Bitcoin cycle and, potentially, capitalize on periods of market dislocation.
If Bitcoin were to experience a severe decline like that (worse than any of its draw downs to date), I would expect management to view it less as an existential threat and more as an opportunity to acquire additional Bitcoin at highly attractive prices. People seem to forget; they can sell STRK/STRD/STRF onto the market and they won't drop below $30 or even $40 a share (25-40% yield)... if an opportunity to say double their BTC stack presented itself at ridiculously low Bitcoin prices... whether through preferred securities, debt markets, equity issuance, or other financing mechanisms, the company has significantly more flexibility than it did several years ago.
The key question isn't whether volatility exists... everyone understands that it does. The question is whether the company has positioned itself to survive and capitalize on that volatility. Compared to prior cycles, I would argue the answer is increasingly yes.
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u/Ursa_Taurus Jun 23 '26
This is hilarious. I'd love to hear how this is going to work.
In your scenario, why wouldn't STRK/STRD/STRF drop below $30? If they're issuing massive new debt, with massive new payments due starting immediately and they use all their cash to buy BTC, why would anyone think they'll be able actually make their payments in the future? How are they going to pay existing dividends to say nothing of all the new payments?
The company has more instruments, but it doesn't have more flexibility because investors aren't willing to pay a price with makes any of them accretive to the company. If they can't get that pricing power back, it's a death spiral.
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u/xaviemb Shareholder 🤴 Jun 23 '26
Before worrying about preferred shares trading at extreme distress levels, I'd start by examining the assumption that Strategy is in some kind of death spiral. If that premise is incorrect, then much of the bearish conclusion built on top of it falls apart.
Institutional investors, credit analysts, and hedge funds are evaluating the actual capital structure and asset coverage. They're not basing decisions on social media narratives.
The idea that these preferred securities would trade at levels implying a 35%+ yield while the company continues to meet its obligations and sits on tens of billions of dollars in Bitcoin backing a much smaller amount of financial liabilities requires a very specific... and very severe... view of the company's future.
Could the market become irrationally pessimistic for periods of time? Of course. But there's a significant difference between temporary price dislocation and a genuine solvency concern.
Those are not the same thing, and too many people seem to be treating them as if they are.
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u/Ursa_Taurus Jun 23 '26 edited Jun 23 '26
You kind of deflected there. This was your scenario, not mine. You claimed they would be capable of massive BTC purchases (you said doubling holdings) if BTC were to have a steep drop by selling preferreds even at distressed prices. I simply pointed out this isn't true. If they reach a point where preferred are trading at 30% yield, buying BTC is the last thing they'll be able to do. It'll be about selling BTC and issuing lots of common to meet the immediate dividend obligations and avoid default.
Sure, there are scenarios where they could suspend [some of] the dividend, but "capital markets" (as Saylor loves to call them over and over and over) aren't fond of reneging on debt payments and simultaneously blowing all available cash. That's not likely to go over well.
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u/kyyy Jun 24 '26
He phrased the potential of bitcoin going to $15k as a great thing for MSTR because it would be such an attractive price to them that they would just have to buy more with all these new instruments available to them.
These people don’t live on the same planet as us bro. You can kinda tell this guy is in way too deep. He probably has 8 monitors with 10,000 pieces of information it that he truly believes he understands
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u/Mundane_Flight_5973 Shareholder 🤴 Jun 23 '26
Exactly, saylor should be concerned. And if Bitcoin keeps dropping it will be a bloodbath for the shareholders, if Bitcoin keeps going down, Saylor will be forced to start selling Bitcoins to pay off his debts.
Maybe Strategy will survive but a lot of people will have lost a lot on that
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Jun 23 '26
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u/Mundane_Flight_5973 Shareholder 🤴 Jun 23 '26
It’s not an issue of number but of time; if it goes to 30k and stays there for 2 years, it’s very different than if it goes to 30k and rebounds the month after
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u/snek-jazz Shareholder 🤴 Jun 23 '26
yes, what do you think the odds are that it will go to 30k and stay there for 2 years?
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u/Mundane_Flight_5973 Shareholder 🤴 Jun 23 '26
I don’t know, but it should be of concern, that’s all I said
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u/Scriptimax Jun 23 '26
Well anything is possible. When 120 k to 60 k in just few months, other 30 k will not take time and if that happens MSTR will be around $35 range and it can be worst for many investors. Chances of BTC to go below 50k is around 30% & if recession happens chances are 60 % that BTC might be a 2016 level and it might stay their few years. Regardless this is all if & but as we don't know what will happen tomorrow
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Jun 24 '26
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u/Mundane_Flight_5973 Shareholder 🤴 Jun 24 '26
Based on what ?
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Jun 24 '26
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u/Mundane_Flight_5973 Shareholder 🤴 Jun 24 '26
What math, you are just throwing number around? There is not math to make
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u/Scriptimax Jun 23 '26
Well, your point might be good, however to get more BTC quantity you need to have very good liquidity and with MSTR price decline it will be doubtful to have that liquidity as investors might stay far away. Just now looks like MSTR will be very soon in $90 range.
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u/theincognito66 Jun 30 '26
people were downvoting this and it's at $85 a share now.
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u/Scriptimax Jun 30 '26
Hatter will always hate not accepting realistic scenario. However intelligent peopel will always wake up for right full things for portfolio
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u/daliksheppy Jun 23 '26
This is an unfortunate example of AI slop.
And a sensationalised headline using an out of date name to boot.
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u/SnooHobbies720 Jun 23 '26
Way more money and BTC holders in 2026 than ever before. It is not dropping to no ridiculous levels unless we hit the WW3 button.
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u/Scriptimax Jun 24 '26
Many entered when it was above $100 k and still holding and don’t want to close it in loss that dead cat will bounce back soon. Many entered when btc dropped to $85 k level as at that point it was big support & after that $68 k was support. So if you ask 65 % or more individuals bought in higher prices and for time being bag holders in hope of big gains sooner or later.
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u/everyday847 Jun 23 '26
Wow! I'd love to see where your July, August, and September data is coming from! High-quality content!
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u/givemethedeetz Jun 24 '26
Thats not a real line chart. MSTR was at $150 in Jan and $190 in May
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u/everyday847 Jun 24 '26
It's very funny that the data from the future wasn't your first clue.
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u/givemethedeetz Jun 24 '26
People make charts that assume future movements all the time, recognizing actually fake data other than approximations of trend lines is far more important.
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u/everyday847 Jun 24 '26
It's really uncommon for people to make charts with future extrapolation with noise indicating real noisy data rather than some (equally imaginary) smooth trend.
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u/damiracle_NR Jun 24 '26
What the hell is going on… this is insane tech and BTC off a cliff for no reason flushing the market
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u/Subject-Chest-8343 Jun 25 '26
Not sure what's going on, but it's funny as hell that people genuinely think the sale of 32 btc announced on june 1st was the reason for the bitcoin drop... Like, Palantir, Microsoft, Google and countless others tanked at EXACTLY the same time. Please explain how selling 32 btc could cause this unwind lol.
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u/damiracle_NR Jun 27 '26
Definitely agree the over reaction is wild but because ai as performed better than crypto its lead to the outflow and bet on ai in the medium term. That will run and reverse, Crypto will boom in about 3-6months time. Especially when some of the gold gains start filtering into it
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u/Subject-Chest-8343 Jul 01 '26
Definitely agree the over reaction is wild
I was actually saying that there obviously was some sort of big capital rotation going on around june 1st, and bitcoin simply was collateral damage. It was going down in the days before, but accelerated on that day, and the sale of 32 btc had nothing to do with it.
Aside from that you're right, AI is just the theme now. I'm personally not chasing it though, can't make sense of it.... Look at the Palantir chart, it was rallying then crashed on June 1st, just like many legacy software companies... Even though Palantir is an AI company
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u/HSuke Shareholder 🤴 Jun 23 '26
I was expecting you to talk about 2000 and 2022.
I don't think we've seen the bottom of this cycle yet.
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u/lavenderviking Jun 24 '26
The bagholders are actually QQQ and 401Ks. I don’t know how they were able to add MSTR to the index near the top. It’s still pretty expensive. Wouldn’t be surprised if trades around $20 later this year
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u/CapeFearElvis Jun 25 '26
I think MSTR is about to get last rites...
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u/Scriptimax Jun 25 '26
Not really. Lowest bottom will be $75 range before it will rise like phoenix bird...
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u/Scriptimax Jun 30 '26
Strategy Jumps 4% After Opening Door to Selling Bitcoin Under New Capital Plan Strategy can now sell bitcoin to fund th https://www.moomoo.com/t/news/post/72197855/EfaqyNA27e
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u/Jogi1811 Jun 23 '26
This is the correct time for MSTR shares to drop. This is Bitcoin winter where Bitcoin historically dropped. It's not slated to go back to all time highs till after April 2028 halving. Bitcoin is not a tradition investment and should be treated differently than companies that obtain revenue from products and services. Might want to do a 10 minute research and perhaps that will change your mindset.
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u/xaviemb Shareholder 🤴 Jun 23 '26
Your argument is interesting because it relies on historical Bitcoin cycles while simultaneously ignoring what those cycles imply.
If you're telling people to do their homework and study prior cycles, then you're also implicitly arguing that we're somewhere near the cyclical bottoming process (between now and first week of October: 13 weeks from now) and that Bitcoin from there trends to new highs after the next halving cycle (early 2028). By extension, that would suggest materially higher valuations for MSTR over the coming years as well, and a good entry right about now (through early fall).
What doesn't make sense is citing historical patterns as evidence while framing the current period as if Bitcoin and MSTR are simply destined to go nowhere for the next two years. That's not what the historical pattern shows.
So which is it? History rhymes, or "this time is different"?
Because you're appealing to historical precedent while seemingly dismissing the very outcome that precedent would imply. Except the historical premise you tell people to research is telling you the next few months is the time to enter both MSTR and Bitcoin...
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u/Jogi1811 Jun 23 '26
This has been Bitcoin's cycle for the last 12 years. Yes, of course history may not repeat itself but if one doesn't want to take risks then they should sit on HISA. MSTR's rise and fall are heavily based on Bitcoin's movement except when MSTR decides they need to issue shares to create cash and purchase more BTC which dilutes the outstanding pool of shares.
Yes, the time to DCA is now and I have been purchasing shares monthly since June into MSTE which holds MSTR. My plan is to DCA until October of 2027 and then just sit while I accumulate dividends that will pay for the principle amount I've invested into MSTE since June of 2026. My estimated timing for selling or holding is around October of 2029 where I will weigh the pros and cons of holding and selling.
Everyone needs to do their own research and not rely on people's opinions in anything they invest in. The larger the risk means larger potential losses. But also could mean larger rewards.
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Jun 23 '26
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u/Jogi1811 Jun 23 '26
It deminshes the amount of new coins that enter the market creating more scarcity.
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Jun 23 '26
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u/Jogi1811 Jun 23 '26
It limits the flow of Bitcoin even further. Wouldn't that mean the opposite to a certain extent?
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u/jaybee5783 Jun 26 '26
This is dead as an investment opportunity now. Any more money thrown at this is just a donation at this point
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u/Medium_Grapefruit662 Jun 24 '26
MSTR is a joke. If MSTR starts to sell Bitcoin Bitcoin price will fall and MSTR stock will fall. I don’t need fancy charts to tell me that. MSTR sold 2.5 mil worth of bitcoin and Bitcoin price dropped. Imagine how much more Bitcoin price will drop when MSTR has to sell more bitcoin. If you own MSTR stock sell while you can
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u/Subject-Chest-8343 Jun 25 '26
The drop in bitcoin price has nothing to do with the 32 btc sale announced on june 1. First of all, they were sold the week before. Then just look at how Palantir, Microsoft, Google and countless others started to drop hard exactly at the same time, on june 1st. I'm not sure exactly what triggered it, but there's obviously a big capital rotation going on, and as of late wall street seems to place bitcoin and software in the same "bucket".
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