Strategy's $1.5 Billion Cash-Flow Gap Sparks Concern Over Preferred Dividends

Grayscale's head of research, Zach Pandl, has highlighted a cash-flow problem at Strategy, the company led by Michael Saylor. According to Pandl, Strategy owes approximately $1.5 billion in annual preferred-stock dividends against roughly $477 million in software revenue for 2025.

This means that dividend obligations outweigh revenue by more than three to one, leaving the company with a significant gap to cover. To address this issue, Strategy sold 32 BTC for $2.5 million in May at an average price of $77,135 per coin, its first bitcoin sale since 2022.

Pandl emphasizes that this is not a crypto problem but rather a cash-flow issue. He notes that the preferred stock obligations are denominated in dollars and must be paid regardless of the performance of Bitcoin.