Strategy's shares fell 9.45% over the past week despite intense market interest in its Bitcoin-linked financing machine, as reported by Smart Investor Picks. The pullback comes as Bitcoin struggles to decisively clear the $82,000–$83,000 level and has slipped back below $80,000, rekindling worries about volatility and earnings stability. Trading in the company's preferred stock, STRC, exploded to a record $1.53 billion in daily volume and hit the $100 mark, underscoring strong demand for its 11.5% dividend and its role in funding Strategy's vast Bitcoin purchases. However, this surge in liquidity failed to lift the common stock, with investors instead focusing on the risks tied to the group's highly leveraged Bitcoin strategy.
Michael Saylor has indicated that Strategy may sell Bitcoin when necessary, marking a significant departure from his long-standing 'never sell' message. According to reports from The Wolf of All Streets podcast, Saylor emphasized that Strategy must demonstrate Bitcoin's utility as a working asset rather than a locked reserve. The company currently holds approximately $65 billion worth of Bitcoin and needs to show it can access this liquidity when needed to protect the asset that supports most of the company's value. In an interview on the podcast, Saylor explained that if the company announced it would never sell its Bitcoin reserves, credit rating agencies might stop recognizing them as assets. He believes that failing to utilize market liquidity diminishes the asset's value, as 98% of the company's business model is based on this very asset.
The strategic discussion follows Strategy's first-quarter results, which reported a $14.5 billion headline operating loss when Bitcoin dropped roughly 23%, even though the loss was largely on paper due to new accounting rules forcing BTC to market. As reported by The Wolf of All Streets, Strategy held 818,334 BTC as of May 3, with an average purchase price of about $75,537 per coin. The company also raised $11.68 billion year to date. In a notable development, Strategy filed a plan to repurchase approximately $1.50 billion of its 2029 convertible notes, with the estimated cash repurchase price at about $1.38 billion. The expected settlement date is around May 19, 2026.
Despite the selling debate, Strategy has maintained its Bitcoin acquisition strategy with unprecedented aggression. According to reports, the company purchased 535 BTC for about $43 million between May 4 and May 10, at an average price of approximately $80,340 per BTC. This purchase increased total holdings to 818,869 BTC as of May 10. The company is now preparing to scoop up over 3,000 additional coins in a single week—more than double new supply from miners. The company's approach remains tied to market prices, financing access, and investor demand, with Saylor noting that any Bitcoin sale would be followed by purchasing 10 to 20 more Bitcoin. Strategy has been purchasing Bitcoin since August 2020, making it one of the longest-running Bitcoin accumulation strategies in corporate history.
The debate highlights growing scrutiny of Strategy's treasury model, particularly regarding dividend costs and STRC growth. As reported by The Wolf of All Streets, Strategy added attention to the issue after filing its note buyback plan, which lists Bitcoin sales as a possible funding option for debt retirement. The company now holds more than 818,000 BTC after fresh buys, with aggressive accumulation funded through STRC and sizable convertible debt. The preferred program is nearing a $28.3 billion cap with major repayments looming from 2027, leaving markets uneasy about long-term funding and the cost of those rich dividends. Wall Street still broadly rates the stock a Strong Buy with large upside potential, but this week's 9.45% slide shows investors are demanding a higher risk premium for such a concentrated bet on one volatile asset.
