Saylor Faces Doubts as MicroStrategy Piles Debt to Buy More BTC

MicroStrategy Faces Investor Scrutiny Over High-Leverage Bitcoin Strategy and Premium Valuation

  • MicroStrategy has taken on significant debt and dividend obligations to buy more Bitcoin, raising concerns among investors.
  • The company’s stock is trading at a 65% premium to the value of its bitcoin holdings, down from a higher multiple in late 2024.
  • Shareholders and social media users are calling for proof that MicroStrategy actually controls its reported 555,400 BTC.
  • Despite questions and new competition, Michael Saylor continues to pursue bitcoin accumulation using leveraged strategies.
  • MicroStrategy has outperformed bitcoin over the last five years, but experts warn of risks linked to high leverage and market competition.

MicroStrategy, led by Michael Saylor, continues to add large amounts of bitcoin to its balance sheet, using debt and dividend-yielding financial instruments. Investors are questioning this strategy as the company’s stock now trades at a notably lower premium to its bitcoin holdings compared to late 2024.

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According to recent data, MicroStrategy trades at a 1.65 times multiple of its net bitcoin value, down from a previous 3.4 times premium. Social media discussions focus on whether the company actually holds all of its reported 555,400 BTC, valued at over $30 billion. Shareholders are demanding "proof of reserves," but Saylor has argued during a Bitcoin 2025 talk that disclosing this information could undermine security for custodians, exchanges, and investors.

The company funds its bitcoin purchases through billions in new stock offerings, convertible debt, and preferred shares. As a result, MicroStrategy now holds more than $60 billion worth of bitcoin—four times more than a year ago. Its average purchase price per bitcoin is about $69,726, while the price recently reached $107,000, giving the firm over $20 billion in unrealized gains. Profitability doesn’t seem to be the main issue, according to the article.

Despite these gains, investors are focused on the future price of bitcoin, competition from other public buyers, and whether Saylor can keep raising low-cost funds. In 2025, several companies including Twenty One, Nakamoto, MetaPlanet, and others have tried to follow the same bitcoin buying strategy.

Some experts, including short-seller Jim Chanos, say MicroStrategy‘s shares are "ridiculously" overvalued compared to its assets. The company faces $8.2 billion in total debt and about $34.6 million in annual interest costs, even with a low average interest rate of 0.42%. Some observers also criticize "bitcoin yield per share" metrics, saying they can exaggerate profits by not factoring in the effect of new share sales.

Other public companies now compete with MicroStrategy by raising money to buy bitcoin, reducing its uniqueness in the space. Still, Saylor remains committed to bitcoin accumulation, even joking on social media about his dedication.

Despite concerns about high leverage and a 28-page list of official risk warnings in its latest filings, MicroStrategy stock has performed strongly compared to bitcoin. Over five years, the company’s shares are up 2,900%, while bitcoin has increased 1,100%. Loyal investors continue to bet that the company’s large bitcoin holdings and aggressive approach will keep it ahead in the market.

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