Michael Saylor went full degen on Bitcoin, turning his company into the biggest corporate BTC whale. From taking on debt to dropping $5.7B in a single buy, he’s all-in. Now holding 499K BTC, he’s up $2.8B, but if Bitcoin dips 20%, it’s game over. Genius or crazy?
Back in 2020, Michael Saylor made a wild move—he flipped MicroStrategy into a Bitcoin-hungry machine. Fast forward to 2025, and the company now holds 499,226 BTC worth $35.9 billion. What started as a “let’s see how this goes” play turned into a full-blown crypto obsession.
Saylor didn’t just throw spare cash into BTC—he took on debt, sold shares, and went all-in. The biggest flex? A record-breaking 55,500 BTC buy in 2024 worth $5.7B. Even when Bitcoin tanked below $16K in 2022, he didn’t blink. Now, with BTC at $82,589, he’s sitting on an unrealized profit of $2.8B.
But it’s not all sunshine. If Bitcoin drops below $66,380, his entire investment turns red. A 20% dip could wipe out profits, and we all know crypto is wild like that. But Saylor? He’s calling Bitcoin the future of money, a financial revolution. Some say he’s a visionary, others think he’s a lunatic—but one thing’s for sure: no CEO has ever gone this deep into Bitcoin.
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