• Strategy Inc. (MSTR) is preparing to sell part of its bitcoin holdings to improve liquidity, marking a shift from founder Michael Saylor's long-standing "never sell" mantra.
  • The move comes as the company faces near-term obligations and aims to optimize its capital structure, according to people familiar with the matter.
  • This reversal has sparked debate among investors, with some praising prudent financial management and others questioning the commitment to Strategy's bitcoin-centric strategy.

For years, Michael Saylor urged investors to never sell bitcoin—famously saying, "Sell a kidney if you must, but keep the bitcoin." Now, his company, Strategy, is preparing to sell part of its bitcoin holdings to remain solvent, according to people familiar with the matter. The irony is hard to miss: Saylor still appears to have both kidneys.

The decision marks a notable departure from Strategy's long-held “buy and hold forever” posture, which had become central to the company's identity. The enterprise software firm has aggressively accumulated bitcoin since 2020, positioning itself as a quasi-bitcoin investment vehicle. However, recent filings and insider sources indicate that the company is now executing a partial disposition to bolster liquidity and meet near-term financial obligations.

“We have to manage our balance sheet prudently,” a Strategy spokesperson said in a statement, when reached for comment. The company declined to specify the size or timing of the planned sales, but noted that any transactions would be “tax-efficient” and designed to “optimize shareholder value.”

Saylor himself has not publicly commented on the shift, though he remains a top voice on bitcoin. The move is seen as a pragmatic response to market conditions, where bitcoin's price volatility and the company's debt obligations have created pressure. Strategy has historically funded its bitcoin purchases through equity and debt offerings, and the current sales are expected to complement those mechanisms.

Analysts are divided on the implications. Some view the sale as a necessary liquidity measure that could stabilize the stock and support preferred stock distributions. Others worry it undermines the very thesis that has driven MSTR's premium valuation—that the company would never be a forced seller. “If you can't trust Saylor to hold, who can you trust?” quipped one crypto investor on social media.

The broader market impact remains uncertain. The potential sale adds supply to an already volatile bitcoin market, though the amounts involved are likely small relative to Strategy's roughly $15 billion in holdings. The company's shares fell 2% in pre-market trading following the news.

This development mirrors similar moves by other large corporate holders of cryptocurrency, who have periodically rebalanced or partially liquidated positions to address capital needs. However, given Saylor's vocal advocacy for never selling, the psychological impact on the crypto community could be outsized.

Correction: An earlier version of this article misstated the timing of Strategy's bitcoin sales. The company has not yet executed any sales but is preparing to do so.