Michael Saylor hints at buying more Bitcoin despite $11 billion unrealized losses

Strategy (NASDAQ: MSTR ) executive chairman Michael Saylor has signaled that the company may be preparing to increase its Bitcoin ( BTC ) holdings despite carrying approximately $11 billion in unrealized losses on its cryptocurrency portfolio. The indication came on June 7 after Saylor shared the company’s Bitcoin accumulation chart a move widely interpreted by market participants as a sign that another purchase could be imminent. A good time to add more dots. pic.twitter.com/4cRmmtbzKv — Michael Saylor (@saylor) June 7, 2026 The post comes during a challenging period for the company, which has faced growing scrutiny over its leveraged Bitcoin acquisition strategy. Strategy remains the largest corporate holder of Bitcoin, with approximately 843,706 BTC on its balance sheet. The company built its position through a combination of debt financing, equity offerings, and operational cash flows. Recent weakness in Bitcoin has left Strategy facing substantial paper losses, with its average purchase price estimated at $75,700 per BTC. Turbulent week for Strategy Saylor’s latest signal follows a turbulent week for the company, which disclosed the sale of 32 Bitcoin to meet dividend obligations tied to its preferred stock. Although the transaction represented only a small fraction of its holdings, it marked Strategy’s first known Bitcoin sale in years and raised investor concerns. The disclosure contributed to a sharp sell-off in Strategy stock, with shares falling about 28% over the past week as investors reassessed the risks associated with the company’s capital structure and Bitcoin exposure. At the same time, criticism of Strategy’s business model has intensified. Skeptics have questioned the sustainability of relying on debt and preferred stock issuances to fund continued Bitcoin purchases, particularly during periods of prolonged market weakness. Concerns have centered on the company’s ability to meet dividend obligations without resorting to additional financing or future asset sales. Despite the pressure, Strategy continues to maintain Bitcoin as its primary treasury reserve asset. The company has consistently defended its long-term conviction in cryptocurrency and remains committed to expanding its holdings whenever market conditions allow. Investors are expected to receive further insight into Strategy’s plans during the company’s annual shareholder meeting scheduled for June 8. The post Michael Saylor hints at buying more Bitcoin despite $11 billion unrealized losses appeared first on Finbold.