In a recent conversation, Michael Saylor, executive chairman of Strategy (MSTR), elaborated on the company’s long-term ambitions regarding its Bitcoin holdings. He stated that the primary objective is to enhance Bitcoin exposure on a per-share basis for its shareholders, aiming to achieve this goal within a seven-year timeframe.
Saylor suggested that selling some Bitcoin, especially near the company’s cost basis, could be strategically beneficial in mitigating potential tax implications for investors holding STRC shares. Presently, Strategy boasts nearly 850,000 Bitcoin on its balance sheet, valued at more than $65 billion, making it the largest corporate holder of Bitcoin globally.
During an interview, Saylor emphasized that various financial models that focus solely on equity, credit, or Bitcoin yield suboptimal outcomes. He hinted at the possibility of selling Bitcoin within the year, stating, “I think it’s not unlikely that we’ll sell some bitcoin between now and the end of the year.” His comments echoed sentiments made during the company’s Q1 earnings call, where he explored the idea of divesting Bitcoin to either acquire U.S. dollars or to invest in debt that could be advantageous for Bitcoin per share.
Despite Saylor’s insights, MSTR’s stock experienced a decline of 2.75% in morning trading, while Bitcoin’s price slipped below the $77,000 mark, reflecting a bearish sentiment among retail investors. Conversations surrounding both MSTR and Bitcoin on platforms like Stocktwits indicated a low level of excitement.
Amid concerns over the tax implications of potential Bitcoin sales, CEO Phong Le reassured investors that selling at the company’s cost basis would avoid significant tax consequences for the STRC preferred stockholders. He explained that the tax treatment for STRC would remain unaffected, stating, “Sell Bitcoin at cost basis, break even, no tax.”
In addition to discussing financial maneuvers, Saylor and Le expressed admiration for Strive (ASST), supported by Vivek Ramaswamy, for its decision to offer daily dividends on its preferred stock (SATA). Saylor commented on the potential growth of ASST, stating, “Would like to see ASST get 10x bigger.” As for Strategy, the company is considering increasing the frequency of its own STRC dividends and has opened a proposal for semi-monthly payouts. Saylor noted that if there is a demand for daily dividends from MSTR shareholders, the company would contemplate making that shift.
As Strategy navigates its cryptocurrency holdings and potential sales, the corporate landscape for Bitcoin investment continues to evolve, with growing interest in dividend structures and shareholder benefits.


