Michael Saylor's Bitcoin Strategy Backfires on Over 100 Public Companies
More than 100 publicly traded corporate treasuries borrowed billions in the first half of 2025 to buy digital tokens, following Michael Saylor's strategy of transforming corporate cash into Bitcoin holdings. Initially, stock prices of these companies rose significantly beyond the asset values they held. However, Bloomberg data reveals that the medians of these crypto treasuries have fallen 43% year-to-date, lagging behind Bitcoin's 7% decline, while the S&P 500 and Nasdaq 100 gained 6% and 10% respectively.
Strategy Inc., the Saylor-led model, attracted high-profile investors including the Trump family and employed a funding model reliant on convertible bonds and preferred shares, raising over $45 billion industry-wide. This created annual fixed obligations of approximately $750–$800 million that crypto holdings cannot generate cash flow to cover. Strategy itself raised $1.44 billion in stock proceeds to cover roughly 21 months of dividends as a reserve.
One notable example, SharpLink Gaming, pivoted to crypto by naming an Ethereum co-founder as chairman and acquiring large Ether holdings. Its stock surged approximately 2,600% before crashing 86% from its peak, with its market capitalization falling below the value of its Ethereum holdings.
Regarding ongoing financial management, Saylor and Strategy signaled potential Bitcoin sales to fund dividends. Phong Le stated that Bitcoin could be sold if necessary, and Saylor indicated that selling equity or Bitcoin derivatives would depend on whether equity trades above or below the net asset value of Bitcoin.
Strategy's Bitcoin holdings total about 650,000 BTC, worth over $56 billion, representing more than 3% of Bitcoin's maximum supply. However, accumulation has sharply declined from 134,000 BTC in 2024 to 9,100 BTC in November 2025, with only 135 BTC added in December.
