Strategy’s $66B Bitcoin machine relies on capital markets, report shows

Strategy, the company formerly known as MicroStrategy, now sits on 840,447 BTC worth approximately $66 billion. That makes it the largest corporate Bitcoin holder on earth, controlling roughly 4% of Bitcoin’s total supply cap. An analysis from Regime Intelligence published on August 19 lays out the math behind the machine. Strategy carries about $22 billion in senior claims against that Bitcoin pile, split between $15.5 billion in perpetual preferred stock and $6.7 billion in convertible notes. Those instruments impose annualized cash obligations of around $1.76 billion, mostly from preferred dividends. The cash flow problem Strategy’s original business, enterprise analytics software, generates almost nothing relative to those obligations. Operating cash flow for the first half of 2026 came in at roughly $9.85 million. That covers about three days’ worth of annual obligations. Since its first Bitcoin purchase in August 2020, the company has raised an estimated $40 to $50 billion through equity and preferred issuances. The preferred stock, branded under names like STRC and marketed as “digital credit,” functions as a novel financial product that blends traditional fixed-income chara...