Strategy Faces $1.5B Annual Dividend Obligations Against $477M Revenue, Grayscale Research Head Says

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According to Grayscale's head of research (LowBeta), Strategy Inc. faces a fundamental cash-flow problem: roughly $1.5 billion in annual preferred-stock dividends outpace its software business revenue of $477 million by more than three to one. In a podcast with journalist Laura Shin, the research head argued the issue is "a cash flow issue, not a crypto issue," noting that bitcoin generates no yield to service dividend payments. Strategy sold 32 BTC for approximately $2.5 million in late May to fund preferred-stock payouts, marking its first bitcoin sale since 2022. The company's preferred-equity stack has swollen to roughly $15.5 billion as of mid-2026.
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