Saylor's Case for Microsoft: Bitcoin Over Bonds

In the fast-evolving world of corporate finance, few ideas have sparked as much debate as Michael Saylor's bold suggestion to Microsoft: swap its conservative bond investments for Bitcoin.

In the rapidly evolving landscape of corporate finance, few propositions have generated as much discussion as Michael Saylor's bold suggestion to Microsoft: swap its conservative bond investments for Bitcoin.

As the CEO of MicroStrategy (NASDAQ:MCRL) and a fervent Bitcoin proponent, Saylor is on a mission to persuade major corporations to embrace the world’s leading cryptocurrency.

At Strategy World 2025, Saylor, known for his contrarian takes, continued his argument for Bitcoin over bonds.

“Microsoft should be powered by digital capital,” Saylor stated, highlighting Bitcoin as the “highest-performing uncorrelated asset.”

He challenged the conventional corporate strategy of focusing on low-yield bonds and stock buybacks, asserting that these leave equity weaker and shareholders vulnerable to volatility.

In contrast, Bitcoin's fixed supply and autonomous monetary policy provide a superior hedge against inflation and bear markets, in an age where macroeconomic stability is increasingly crucial.

Bitcoin News: Saylor’s Case for Microsoft: Bitcoin Over Bonds

Saylor's argument at Strategy World 2025 is based on Bitcoin's superior performance. According to TradingView data, Bitcoin achieved a five-year average annual return of 53%, significantly outperforming Microsoft's 6% average (148% total) over the same period.

Further analysis reveals even greater disparities: 62% annual gains for Bitcoin versus 18% for Microsoft—and bonds encountered a 5% yearly loss, lagging behind by 19%. Such stark contrasts highlight the potential of reallocating corporate reserves.

Saylor refers to Bitcoin as “digital capital”—a revolutionary asset that could transform how companies manage their treasuries.

On the other hand, Saylor in January described bonds as "toxic," highlighting their negative real yields and potential to destroy capital over time.

He noted that corporate reliance on low-yield sovereign debt fails to keep pace with inflation and market returns, making bonds a drag on balance sheets. For companies with substantial cash holdings, parking funds in U.S. Treasuries or corporate debt can erode value.

Saylor has been practicing what he preaches. MicroStrategy last week added 1,895 BTC to its treasury holdings.

The company now holds 555,450 BTC, acquired for over $38 billion in cash at an average price of $68,550.

The latest purchase was executed at an average price of $95,167, indicating continued confidence in Bitcoin's long-term prospects despite recent price fluctuations.

MicroStrategy's market capitalization has skyrocketed from approximately $1.2 billion in August 2020 to over $105 billion in May 2025—a rally of more than 8,650%.

The company's aggressive Bitcoin acquisition strategy is a key driver of this transformation. As MicroStrategy continues to build its treasury and capitalize on new investment opportunities, we can expect further updates on their Bitcoin holdings and the overall performance of their investment strategy.

Microsoft (NASDAQ:MSFT), with $104.8 billion in cash and equivalents as of FY25, is an ideal candidate for Saylor's vision.

He claims that redirecting the $200 billion returned to shareholders over five years into Bitcoin could increase Microsoft's enterprise value by as much as $5 trillion.

However, Microsoft's board remains skeptical. In December 2024, a shareholder proposal to invest just 1% of its cash in Bitcoin was rejected, receiving minimal support.

The board, backed by proxy advisors, highlighted Bitcoin's volatility and Microsoft's preference for a cautious investment approach.

The Risks: Volatility and Regulation

Bitcoin's potential is closely tied to its volatility. Its price has been notoriously unstable throughout its history, and while it reached highs above $108,000 earlier this year, it has also experienced sharp declines of 70% from all-time highs.

Regulatory uncertainty adds another layer of complexity, as governments around the world are still grappling with the best way to oversee cryptocurrencies.

Microsoft has already dabbled in crypto, accepting Bitcoin for payments since 2014. However, the tech giant's treasury is still heavily invested in traditional assets.

With $104.8 billion in cash at its disposal and no immediate need for capital gains realized from Bitcoin to support operations, the company has the flexibility to make changes.

Ultimately, it comes down to leadership style and risk appetite. Microsoft's leadership prioritizes stability and has shown little interest in venturing into speculative assets.

Saylor's pitch at Strategy World 2025 raises a broader question: Is Bitcoin a viable asset class for corporations, or is it too unpredictable for mainstream adoption?

MicroStrategy's success in pivoting its entire strategy around Bitcoin seems to support the former, while Microsoft's continued