Written by: Allard Peng
Compiled by: Saoirse, Foresight News
Recently, MicroStrategy's announcement that it may sell some Bitcoin to achieve operational goals has caused a stir in the market. The company had previously maintained a firm stance of never selling its Bitcoin holdings, with Michael Saylor even jokingly posting that he would rather sell assets than part with Bitcoin.
In reality, for companies holding Bitcoin reserves, selling is always an operational option. "Never selling" merely reflects a long-term investment philosophy, aligning with the prevalent long-term thinking in the crypto space. Even though the market generally advocates for hodling, selling Bitcoin remains a reasonable choice in numerous scenarios.
On a personal level, selling Bitcoin is often for lifestyle improvements, such as purchasing property, travel, children's education, or covering large, unexpected medical expenses. For corporations, however, the core tenet guiding all operational decisions is the enhancement of shareholder equity.
In the first quarter of 2026, Bitcoin miners sold a total of 25,376 Bitcoin, using the proceeds to pivot towards artificial intelligence (AI) businesses. Management deemed the risk-reward profile of AI projects more favorable than holding Bitcoin. This leads to a fundamental logic: when higher-return investment opportunities exist, selling Bitcoin to reallocate assets is rational. For hodling companies like MicroStrategy, selling Bitcoin can also create tangible value, specifically for five reasons.
Reason One: Increase Bitcoin Held Per Share
The amount of Bitcoin held per share is the core operational objective for companies with reserve assets. Periodic growth in this metric represents the Bitcoin yield rate. The conventional method is to purchase more Bitcoin to increase the total holdings; another approach is to buy back shares to reduce the number of shares outstanding. Both methods can push up the Bitcoin-per-share figure.
If a company's stock price is lower than its corresponding Bitcoin asset value, selling Bitcoin to repurchase shares can ultimately increase the Bitcoin held per share. The decline in total Bitcoin holdings would be smaller than the reduction in shares outstanding. When a company's operating cash flow cannot cover fixed expenditures like preferred stock dividends or bond interest, and the stock price is undervalued, selling Bitcoin to service debt and pay dividends can minimize the erosion of Bitcoin per share.
Reason Two: Optimize Capital Structure, Lower Financing Costs
Credit rating agencies significantly influence capital market flows. Adhering to their assessment criteria can help companies secure financing smoothly. Previous reports have analyzed viable ways to improve credit ratings, as a strong rating can effectively lower a company's financing costs.
Standard & Poor's (S&P) recognizes the value of cash reserves. MicroStrategy adopted this strategy accordingly. As of January 2026, the company's cash reserve reached $2.2 billion, substantially alleviating investor concerns about its ability to pay preferred stock dividends.
A company can sell Bitcoin to bolster cash reserves, meeting capital market demands and subsequently issuing bonds at a lower cost. Simultaneously, selling Bitcoin to repay debt can reduce senior liabilities, enhancing the appeal of preferred stock for financing.
In the long run, differences in financing rates widen through the effect of compound interest. Low-cost debt can reduce burdens and increase profits for business operations.
Reason Three: Legal Tax Planning
Currently, the U.S. has no wash-sale restrictions for Bitcoin. Companies can sell Bitcoin to realize a book loss, then repurchase it, lowering the asset's tax cost basis to offset tax liabilities. MicroStrategy employed this tactic during the market downturn in 2022.
This tax incentive remains effective. Companies can combine loss-harvesting for tax benefits with simultaneous share buybacks, debt repayment, or other operations to achieve multiple benefits.
Reason Four: Counter Negative Market Sentiment
The Bitcoin industry is relatively young, and various negative rumors persist. Unfounded claims suggest that if MicroStrategy sells Bitcoin, it would directly impact the entire crypto market, undermining the company's operational model of hodling.
If a company sells, for example, 50,000 Bitcoin and neither the market price nor its own stock price experiences significant volatility, it could shatter such rumors. This would help the capital market accept the business model of companies holding Bitcoin as a reserve asset.
The market possesses self-regulating capabilities. Sensationalism is often the domain of media and influencers. Professional investment institutions base decisions on actual research and are not swayed by one-sided narratives. This is the most subjective reason among the five.
Reason Five: Repurchase Preferred Stock at a Discount
This operational strategy is less discussed. When the price of a floating-rate financial instrument significantly deviates from its face value, a company can repurchase it at a price far below par, settling high-cost debt.
This operation is equivalent to closing out a short position on its own preferred stock without interest or borrowing costs. Taking the STR-C product as an example, issued with a face value of $100, if the price falls to $82, the company can use funds from selling Bitcoin to repurchase shares at this low price, earning a $18 difference per share. This gain is typically tax-free.
Price trend of STR-C since its initial public offering
A drop in preferred stock price does not necessarily coincide with a Bitcoin market crash. Leveraged trading can easily trigger chain reactions of selling. Companies can seize the opportunity to buy back shares at low prices, avoiding future funding drains from potential dividend rate increases.
Conclusion
A company selling Bitcoin should not automatically be viewed as a bearish signal. In many scenarios, divesting Bitcoin safeguards the interests of the company and its shareholders. Bitcoin possesses monetary attributes, providing companies with flexible capital allocation options. Utilizing assets rationally unlocks their maximum value.
