Michael Saylor’s Strategy Moves to Raise $21 Billion for Bitcoin Buying Spree

Michael Saylor’s Strategy (MSTR) has made yet another bold move, filing for a massive $21 billion preferred stock offering to fund more Bitcoin purchases. Despite Bitcoin’s latest price dip and mounting losses on recent acquisitions, the firm remains committed to its accumulation strategy. However, investors seem uneasy, with MSTR shares taking a hit in pre-market trading.

The $21 Billion Stock Offering: What’s the Plan?

The newly filed stock offering will allow Strategy to issue and sell shares of its 8% series A perpetual strike preferred stock at just $0.001 per share. This move is part of the firm’s ATM (at-the-market) program, which will gradually sell stock depending on market conditions.

One major takeaway from Strategy’s SEC filing is how the proceeds will be allocated. The company has outlined three primary uses:

• Increasing its Bitcoin holdings
• Funding general corporate expenses
• Strengthening working capital reserves

Michael Saylor remains confident in his vision, continuing to double down on Bitcoin regardless of market corrections.

Bitcoin Holdings: 499,096 BTC and Counting

Strategy’s Bitcoin portfolio is massive, currently sitting at 499,096 BTC. At the current market price, this stash is worth $41.41 billion, with an average purchase price of $66,357 per Bitcoin. While the firm’s long-term Bitcoin strategy has yielded significant returns, its most recent buys are underwater.

The biggest concern? All Bitcoin purchased since November 2024—nearly 247,000 BTC—was acquired at an average of $94,035. With Bitcoin now hovering around $80,000, that segment of the portfolio is down about $3 billion in unrealized losses.

One market watcher commented, “Saylor’s conviction is impressive, but at some point, the market will test just how deep his pockets really are.”

MSTR Stock Under Pressure as Bitcoin Falls

As Bitcoin prices declined over the weekend, Strategy’s stock felt the impact. MSTR shares dropped 6.38% in pre-market trading on Monday, reflecting concerns about the company’s heavy exposure to Bitcoin.

Some analysts see more downside ahead:

• If Bitcoin falls to $75,000, further selling pressure on MSTR stock is likely.
• A drop below the company’s average Bitcoin purchase price of $66,357 could force Strategy to consider selling off BTC to stabilize its stock price.
• Any large-scale Bitcoin liquidation by Strategy could create a ripple effect, accelerating market declines.

One trader noted, “If Bitcoin dips below $66,000, we could see a domino effect where Strategy is forced to sell, pushing prices even lower.”

Saylor’s Push for a “Strategic Bitcoin Reserve”

Beyond his company’s Bitcoin buying spree, Saylor has been vocal about his belief that the U.S. government should start acquiring BTC. He has been advocating for Trump’s administration to allocate 25% of the global Bitcoin supply over the next decade.

While this proposal remains purely speculative, it highlights how deeply Saylor believes in Bitcoin’s role as a strategic asset.

His message? Bitcoin isn’t just a store of value—it’s a national security priority.