Michael Saylor and Jack Mallers Debate Strategy's Bitcoin Valuation Metrics at BTC Prague

Strategy, formerly MicroStrategy, began as a business-intelligence software company before co-founder and Executive Chairman Michael Saylor redirected its balance sheet toward Bitcoin. It made an initial $250 million purchase in August 2020 and subsequently funded further acquisitions through common stock, convertible notes and preferred shares. The structure turned MSTR into a leveraged corporate vehicle for Bitcoin exposure, but unlike a spot ETF, investors also assume operating, financing, governance and capital-structure risks.

As of Aug. 28, 2026, Strategy held 840,447 Bitcoin acquired at an average price of $75,653, with the reserve valued at about $66.79 billion. Since May, the company has sold 6,948 Bitcoin for roughly $432.5 million to help fund preferred dividends and STRC repurchases, replacing Saylor’s long-standing “never sell” posture with a goal of never becoming a net seller. Strategy now weighs Bitcoin sales against equity issuance based on relative cost, while separate USD Reserve and unrestricted USD Cash pools provide liquidity for debt, dividends, buybacks and market opportunities.

Software company Strategy, the world’s largest publicly traded corporate holder of Bitcoin, has long been known for an uncompromising buy-and-never-sell strategy. Executive Chairman Michael Saylor’s proposal to sell Bitcoin to fund dividends breaks with that previous pledge and signals a more flexible approach to capital management. The move shows the company confronting the realities of capital markets and has prompted investors worldwide to reassess the viability of crypto-heavy balance sheets.

Strategy reported a first-quarter net loss of $12.54 billion and still holds 818,334 Bitcoin. To raise funds for dividends, the company sold 3,588 Bitcoin for the first time between June 29 and July 6, 2026, generating about $216 million. The move raised market concerns: JPMorgan warned that the policy would add “two-way risk” to crypto markets, while Fortune warned that Strategy could fall into a death spiral.

Strategy, formerly MicroStrategy, has long financed Bitcoin purchases through debt and issuances of common and preferred stock, making Bitcoin holdings per share an important measure of shareholder value for investors. The dispute centers on whether issuing additional shares, while expanding the company’s assets, also dilutes existing shareholders by increasing the number of shares outstanding.

Strategy disclosed on June 8, 2026, that it had sold more than 1.4 million MSTR shares and raised about $181 million. It spent $101.3 million to buy 1,550 Bitcoin between June 1 and June 7. BTC Yield fell to 12.8% from 13.0%. Saylor said on June 9 that the transaction remained accretive after accounting for an additional $100 million in cash, which brought reserves to $1 billion.

MicroStrategy, now known as Strategy, brought crypto assets into its corporate treasury strategy in August 2020 when it spent $250 million to buy 21,454 Bitcoin. The move made Michael Saylor a leading advocate of corporate Bitcoin adoption. His arguments have influenced institutional allocation and community governance, with the central debate focused on balancing scarcity, security, capital inflows and technological expansion.

In his latest long-form article, Saylor divides Bitcoin supporters into four groups: maximalists, fundamentalists, capitalists and technologists. He argues that dominance by any single camp could create an imbalance. Saylor calls for “disciplined expansion” to connect Bitcoin with the global economy while preserving the core protocol and the values of decentralization. The article disclosed no new transaction dates, amounts or changes in Strategy's Bitcoin holdings.

Strategy, formerly known as MicroStrategy, has gradually become a publicly traded company that accumulates Bitcoin through debt and share issuance since adding the cryptocurrency to its balance sheet in 2020. Founder Michael Saylor became executive chairman in 2022. Because his wealth is primarily tied to his existing shareholdings, it rises and falls with Strategy's stock price and Bitcoin, underscoring how closely his personal interests are aligned with the company's strategy.

In a proxy statement filed with the U.S. SEC on April 17, 2026, Strategy disclosed that Saylor received a salary of $1 in each year from 2023 through 2025, with no stock awards, options or bonuses. In 2025, he also received $787,031 in security and other compensation, bringing his total compensation to $787,032. By comparison, Chief Executive Phong Le received total compensation of $13,784,204 that year.

Strategy, formerly known as MicroStrategy, raises funds through debt, common-share issuance and preferred stock to buy bitcoin, making BTC its core treasury asset. Michael Saylor argues that as long as bitcoin’s long-term annualized return exceeds the 2.05% cost of its preferred stock, the company can continue paying dividends without issuing additional common shares and diluting shareholders.

According to its latest disclosure, Strategy holds more than 760,000 bitcoin and remains the world’s largest publicly traded corporate holder of the cryptocurrency. Saylor recently hinted again at further purchases. At its current pace of accumulation, the company is buying close to three times the amount of new bitcoin supply created over the same period, indicating that it continues to use low-cost preferred stock to expand its BTC position.