Strategy Raises Billions, Doubles Down on Bitcoin Accumulation

Michael Saylor’s Strategy doubles down on Bitcoin, securing $10.7M worth just days after unveiling a $21B capital raise plan.

Editorial Team (ET)May 6, 2025

Michael Saylor’s Strategy has once again expanded its Bitcoin holdings, acquiring $10.7 million worth of the cryptocurrency. The move comes just a week after unveiling plans to raise up to $21 billion through preferred stock sales, a strategy designed to further cement its position as one of the largest institutional holders of Bitcoin.

This latest purchase, disclosed in a filing with the U.S. Securities and Exchange Commission (SEC), adds 130 Bitcoin to the company’s ever-growing digital asset portfolio. Purchased at an average price of approximately $82,981 per Bitcoin, the addition brings Strategy’s total Bitcoin holdings to a staggering $41.6 billion.

A High-Stakes Financial Strategy

Strategy, formerly MicroStrategy, has transformed from an enterprise software company into a leveraged Bitcoin proxy under Saylor’s leadership. The company has aggressively acquired Bitcoin since 2020, funding purchases through equity and debt offerings. Initially relying on common share sales, the company has since pivoted to raising funds via preferred stock and fixed-income securities.

The move to issue up to $21 billion in preferred shares is part of a broader financial strategy aimed at securing $42 billion by 2027. With this capital, Strategy plans to continue accumulating Bitcoin at a scale few institutions can match. The company’s approach reflects Saylor’s unwavering confidence in Bitcoin as a hedge against inflation and a strategic reserve asset.

Wall Street’s Embrace of Bitcoin

Saylor’s conviction in Bitcoin remains unshaken. Speaking at a Miami Beach conference, he emphasized that Bitcoin has reached a historic entry point, citing Wall Street’s increasing acceptance of the digital asset. According to Saylor, U.S. banks and institutional investors are now poised to embrace Bitcoin, which will, in turn, drive global adoption.

Since Strategy’s pivot to Bitcoin, its stock has skyrocketed by approximately 2,300%. Over the same period, Bitcoin itself has gained more than 600%, underscoring the strength of Saylor’s long-term bet. However, despite these gains, the company’s stock has faced short-term volatility.

Market Volatility and Institutional Bets

The market remains on edge amid broader economic uncertainties. Strategy’s shares fell 3.7% to $286.52 on Monday, reflecting skittish investor sentiment driven by concerns over tariffs and macroeconomic conditions. Bitcoin has also seen a recent dip, down approximately 11% since December.

Hedge funds have played a crucial role in the demand for Strategy’s convertible debt, engaging in arbitrage strategies that involve buying the bonds and shorting the stock. These complex financial maneuvers highlight the stock’s volatility, a characteristic that both attracts and deters different classes of investors.

The Future of Strategy’s Bitcoin Bet

Despite the short-term fluctuations, Saylor remains resolute. He believes that once macroeconomic conditions stabilize, Bitcoin will surge with unprecedented momentum. His assertion that “Bitcoin will rip forward with a vengeance” reflects a deep-seated belief in the cryptocurrency’s long-term potential.

Strategy’s aggressive accumulation strategy sets it apart from traditional companies. While most corporations remain cautious about Bitcoin exposure, Saylor has made it the company’s defining feature. This bold approach has yielded enormous returns for investors who have stuck with the stock, but it also carries risks tied to Bitcoin’s inherent volatility.

Conclusion

Michael Saylor’s Strategy continues to push the boundaries of corporate Bitcoin investment. With $41.6 billion in Bitcoin holdings and an ambitious plan to raise billions more, the company is redefining the role of digital assets in corporate finance. While market conditions remain uncertain, Strategy’s unwavering commitment to Bitcoin signals that the company is playing the long game.

Bitcoin

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