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There's something both terrifying and mesmerizing about watching Michael Saylor's grand experiment unfold in real-time. MicroStrategy—now rebranded as simply "Strategy"—isn't just another tech company dabbling in crypto. It's a true believer that went all-in, mortgaging its future on a single conviction: Bitcoin is the future of money.
The Numbers Tell a Story of Faith Under Fire
Strategy holds 713,502 Bitcoin. Let that sink in. That's roughly 3% of every Bitcoin that will ever exist, sitting in one company's digital vaults. They paid an average of $66,384.56 per coin for this treasure chest. Right now, with Bitcoin hovering around $68,567 after briefly dropping below $61,000 this week, they're barely in the green on paper.
But here's where it gets real: MSTR shares have crashed 72% from their November 2024 peak. The market isn't just questioning Saylor's strategy—it's screaming doubts. The stock now trades at 0.814 times its net asset value, meaning investors value the company at less than the Bitcoin it holds. That's the market's way of saying, "We don't trust this can last."
The Tightrope Walk
Here's what keeps me up at night thinking about this: Strategy's entire playbook depends on continuously raising money to buy more Bitcoin. When Bitcoin goes up, the stock soars, they issue more shares at inflated prices, buy more Bitcoin, rinse and repeat. It's a beautiful flywheel—until it isn't.
Now, trading below net asset value makes new equity raises less attractive. The machine that powered their accumulation is sputtering. They've got $2.19 billion in cash reserves tucked away for emergencies, and $8.2 billion in convertible debt they'll eventually need to face. CEO Phong Le says they're fine unless Bitcoin crashes to $8,000 and stays there for five or six years —but that's cold comfort when you're watching the price swing wildly every day.
Why This Matters to All of Us
Whether you own a single Satoshi or have never touched crypto, Strategy's fate matters. They own so much Bitcoin that if they were ever forced to sell—really sell, in a panic—it would be like dropping a boulder in a pond. The waves would reach every corner of the crypto market.
But flip that coin over: if Saylor is right, if Bitcoin does what believers think it will, Strategy won't just survive—it'll become legend. Thirteen of fourteen analysts still rate MSTR as Buy or Strong Buy, with an average price target of $452 —that's 270% higher than today's price. They're betting on redemption.
The Human Element
What strikes me most is the sheer audacity of it all. While other companies hedged and diversified, Saylor looked at Bitcoin and said, "This. Only this." There's something deeply human about that kind of conviction—foolish or brilliant, only time will tell.
Bitcoin crashed over 35% between January and April last year before rebounding to a record high in May. The cryptocurrency has always been a story of death and resurrection. Maybe Strategy is just living that pattern in corporate form, with shareholder money instead of personal savings.
The thing is, we're all watching a real-time test of whether corporate treasuries can ever truly embrace Bitcoin's volatility. Institutional demand has reversed materially, with U.S. exchange-traded funds becoming net sellers in 2026. The smart money is getting cautious. But Saylor never claimed to be playing it safe.
What Comes Next
Strategy's Q4 earnings this week will tell us whether they're doubling down or pulling back. The next year or two will answer the question that matters: Was Saylor a visionary who saw the future first, or a cautionary tale about what happens when conviction overwhelms prudence?
I don't know which way this story ends. But I know I can't look away. Because buried in all these numbers and charts is something very human—the eternal tension between faith and fear, between holding on and letting go. Strategy bet everything on Bitcoin not just being right, but being right enough, soon enough.
We're about to find out if that faith was justified.