Michael Saylor has spent over $50 BILLION accumulating Bitcoin over the last 5 years.
For the first time, that position is now underwater. $ZEUS
Most people believe this doesn’t matter — that Saylor has unlimited liquidity and can always “buy the dip.” $BTC
That assumption is dangerously wrong.
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🔍 HOW STRATEGY REALLY WORKS
MicroStrategy didn’t start as an extreme Bitcoin vehicle.
In fact, a decade ago, Saylor publicly said Bitcoin would go to zero.
Over time, he transformed the company into a leveraged Bitcoin acquisition engine:
1️⃣ Raise capital (shares, converts, preferreds)
2️⃣ Buy Bitcoin
3️⃣ BTC rises → MSTR trades at a premium
4️⃣ Use that premium to raise more capital
5️⃣ Repeat
This loop worked only because prices were going up and capital was cheap.
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⚠️ WHAT BROKE THE MACHINE
Bitcoin has now fallen below Strategy’s average cost (~$76K).
At the same time:
MSTR’s NAV premium collapsed
Share issuance became heavy dilution
Convertible note buyers demand much stricter terms
Each “Strategy buys BTC” headline now gets sold into
The reflexive flywheel has stalled.
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🧨 THREE SCENARIOS WHERE BTC SELLING BECOMES LIKELY
1 . Market Cap < BTC Treasury Value
Selling company equity destroys Bitcoin yield per share. Arbitrage breaks.
2️⃣ Capital Access Dries Up
Debt and equity markets become unavailable or prohibitively expensive.
3️⃣ Preferred Dividend Pressure
Without a NAV premium, dividends can no longer be rolled forward via new issuance.
At that point, selling Bitcoin becomes mathematically rational, not optional.
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📉 HISTORY RHYMES
This isn’t Saylor’s first collapse.
In the early 2000s, MicroStrategy stock fell over 90% after excessive leverage during the dot-com bubble. Saylor personally lost billions.
Now, one public company has turned itself into a 700K BTC leveraged proxy.
If this structure unwinds, the selling pressure will not be small.
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⚠️ This isn’t fear — it’s structure.
#Bitcoin #BTC #MicroStrategy #MSTR #CryptoRisk