TYSONS CORNER, Virginia, May 9, 2026, 18:04 (EDT)
Michael Saylor, executive chairman at Strategy Inc, tried to recast a potential bitcoin sale as a tactical move to shore up the company’s capital structure—rather than a step back from its bitcoin-focused playbook—after he floated the idea that Strategy could “sell some Bitcoin to fund a dividend.” His comments come as others with bitcoin on their balance sheets, like Nakamoto, Empery Digital, and Sequans, have already trimmed their bitcoin stashes amid the latest crypto slide. Fortune
This shift is significant: Strategy isn’t just a software firm with a hefty bitcoin stash anymore. The company’s financing now involves ongoing requirements tied to several lines of preferred stock—these securities take priority over common shares and tend to come with dividends. In its latest quarterly filing, Strategy acknowledged software revenues alone won’t meet either its near- or long-term liquidity demands. Instead, it pointed to a mix of cash on hand, bitcoin sales, and new offerings of both common and preferred shares, along with other financing options, as potential funding sources. SEC
With markets shuttered for the weekend, investors are left to process the recent move ahead of Monday’s open. Strategy last changed hands at $187.59. Bitcoin hovered close to $80,777, anchoring the stock’s performance to the cryptocurrency that’s become its main reserve.
Strategy’s first-quarter numbers showed a staggering net loss: $12.54 billion, or $38.25 per diluted share. That’s a much wider gap than the $4.22 billion loss posted last year. As of May 3, the company held 818,334 bitcoins—market value pegged at $64.14 billion. “Adoption of Bitcoin continues to grow in 2026,” CEO Phong Le said. CFO Andrew Kang added that preferred dividends had been paid “on time and in full” for 23 consecutive distributions. Strategy
The following vote drills deeper into cash flow mechanics. In documents for its annual meeting, Strategy is proposing a shift for STRC, its “Stretch” variable-rate preferred, replacing monthly dividends with twice-monthly payouts—no change to the total economics. “Same dividend economics; more frequent payments,” Kang said.
Wall Street’s appetite for the trade hasn’t faded. On May 7, Lance Vitanza at TD Cowen bumped his price target up to $395 from $385 and stuck with a Buy. Joseph Vafi at Canaccord Genuity also moved higher, hiking his target to $224, previously $185. Benchmark’s Mark Palmer trimmed his target back to $570 from $705, but kept the Buy call. TheStreet
The wider environment remains challenging. According to Reuters, bitcoin’s previous drop, worries over the Middle East, doubts about AI valuations, and a lack of clarity on Fed policy all dragged on digital assets this week—even as banks and asset managers kept expanding into crypto-linked products. Reuters
The risk here is clear. Strategy flagged volatility in bitcoin prices, shifting financing conditions, tax rules, securities regulation, crypto market liquidity, and its own capital-raising capacity as factors that could drive outcomes away from what management expects. A significant bitcoin selloff—or just speculation that one may happen—can weigh on the asset at the core of Strategy’s valuation. SEC
Strategy wants investors to focus on its flexibility rather than fret about distress. Still, the bigger issue looms: can a business whose core is relentless bitcoin accumulation offload even a fraction without altering how the market perceives its fundamental bet?
