Saylor's 'Working ₿etter' Tweet Signals Strategy's Return to Bitcoin Buying

Strategy's Colossal Bitcoin Treasury

Strategy's treasury remains the largest corporate Bitcoin holding in the world by a massive margin. As of its last official update on May 25, 2026, the company holds 843,738 BTC, representing approximately 4.02% of Bitcoin's total 21 million supply .

The firm's total cost basis for this massive position is approximately $63.87 billion, with an average purchase price of $75,700 per Bitcoin . Its largest single acquisition to date was a $2.54 billion purchase in April 2026. To fund its buying spree, Strategy has aggressively used capital markets, recently retiring $1.5 billion in convertible debt at an 8% discount and issuing billions in new preferred and common stock .

The Upcoming June 8 Shareholder Vote

The timing of the post is closely linked to a pivotal proxy vote scheduled to conclude on June 8, 2026. Strategy is asking shareholders to approve an amendment to the dividend structure of its Variable Rate Series A Perpetual Stretch Preferred Stock (STRC) .

• The Proposal: Change STRC dividend payments from a monthly schedule to a semi-monthly schedule, meaning investors would receive payouts twice a month instead of once .
• The Rationale: The goal is to reduce "reinvestment lag" and stabilize the STRC price near its $100 par value by making the income stream more frequent, predictable, and liquid .
• Key Details: The popular 11.5% annualized dividend rate remains entirely unchanged, as do the total annual obligations of approximately $1.2 billion . Approval requires a "FOR" vote from both STRC holders and MSTR common shareholders . If successful, the first semi-monthly record date would be June 30, with the first payment on July 15 .

Saylor has publicly urged shareholders to support the proposal, and the "Working ₿etter" post serves to keep the Bitcoin narrative and retail enthusiasm high just as he seeks this structural change .

Current Market Context: Buying the Dip?

The signal to buy comes during a period of market weakness. As of early June 2026, Bitcoin is trading in the $73,000–$73,800 range, down significantly from its ~$80,000 levels in mid-May . The cryptocurrency closed out May down more than 3.5% .

This price decline has pushed Strategy's position into an unrealized loss on paper. With a blended average cost of $75,700 per BTC, the firm's $63.87 billion treasury was facing an estimated $1.6 billion unrealized loss as prices fell . Broader market headwinds, including geopolitical tensions and persistent outflows from Bitcoin ETFs, have weighed on sentiment, with Polymarket traders pricing a 64% probability that BTC would remain in the $70K–$72K range on June 2 .

This environment creates the type of opportunity Saylor has historically seized. The "Working ₿etter" signal suggests Strategy is preparing to deploy fresh capital—likely from its ongoing capital-markets programs—to accumulate more Bitcoin at a discount to its own average cost, turning a market dip into a buying opportunity while simultaneously building momentum for its corporate governance goals.