Strategy and Strive Walk a Tightrope Between Bitcoin Buying and Preferred Stock Dividends

Companies that hold bitcoin on their balance sheets, led by Strategy and Strive, are juggling two needs at once. They want cash to keep buying, yet they also need investors to keep wanting the perpetual preferred shares they sell to raise it. Every new share adds to the dividend bill. Fidelity Digital Assets says these securities have paid for about 136,000 bitcoin over 20 months, more than 0.5% of the maximum supply. Fidelity sizes the bitcoin preferred market at roughly $12 billion, small beside a global fixed income market of $150 trillion. Strategy dominates with five share classes, starting with STRK in February 2025.

Dividend Costs, Buybacks and the Risks Behind Preferred Stock

CoinShares’ James notes that STRC, paying a variable dividend near 12%, raised $7.5 billion in 2026 through late July, and that money carries a recurring cost. Palmer calls demand reflexive, since buying depends on shares trading near par. Two Prime’s Alex Blume points to STRC dipping into the $70 range in late June, and says issuers must balance more bitcoin per common share, dollar dividends and avoiding bitcoin sales. It now trades near $99.40.

Buybacks Now Compete With Bitcoin Purchases

Strategy’s latest weekly update showed $193 million spent repurchasing STRC against only 267 bitcoin bought, and its repurchase authorization rose to $3 billion. Butterfill says buybacks cut future dividends but compete for capital today, and Strategy has already sold some bitcoin to cover payouts. He expects preferreds to amplify the cycle, helping when financing is easy and fading as sentiment sours.