Saylor’s financial wizardry could undermine the safety net for long-term holders.

Michael Saylor’s High-Stakes Bitcoin Bet Faces Fresh Pressure

March 28, 2025 — For nearly five years, Michael Saylor has been Wall Street’s most unrelenting Bitcoin bull. Through his company, Strategy (formerly MicroStrategy), he’s stacked over 506,000 BTC, building a digital war chest now worth $44 billion. But after the recent market pullback, the heat is turning up on Saylor’s bold financial engineering.

Bitcoin’s tumble from above $109,000 to its current level around $87,000 has narrowed Strategy’s cushion. The company’s average cost per bitcoin is now $66,000, meaning it’s still in the green—for now. But one more slip in BTC’s price could turn the biggest corporate crypto play into a paper loss.

The real tension, however, lies in how Strategy has financed its massive crypto buys. Saylor’s team has issued common stock, convertible notes, and recently, preferred shares with dividend commitments of up to 10% annually. It’s a creative blend of funding strategies that has worked—so far.

But critics are beginning to ask: What happens when the music stops?

“Strategy’s structure is clever, but it’s not invincible,” said Quinn Thompson, founder of Lekker Capital. “There’s no immediate threat of liquidation, but if the company has to keep issuing equity to meet dividend obligations, it could damage shareholder value.”

Indeed, Strategy doesn’t rely on its software business to cover these financial promises—it mostly leans on new stock issuance. And with Saylor no longer holding voting control as of 2024, some worry activist investors could step in if MSTR begins to trade at a significant discount to its bitcoin holdings.

Adding another layer of risk are the leveraged ETFs tied to Strategy’s stock—MSTX and MSTU—which now account for over $3 billion in MSTR exposure. These funds amplify both gains and losses. If they face outflows, Strategy’s share price could suffer a rapid decline.

Still, Saylor’s playbook remains intact. By courting both risk-seeking and income-focused investors through varied instruments, Strategy has created demand across the spectrum—from volatility hunters to yield chasers.

As Jeffrey Park of Bitwise puts it, “Strategy’s capital stack is like a playground seesaw. But when the market sentiment shifts, the tilt can be brutal.”

For now, Saylor is still in control of the narrative. But if Bitcoin continues to slide or investor appetite wanes, even the most calculated bet can turn precarious.

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