Michael Saylor’s once-swaggering Bitcoin strategy seems to be coming to a close as share issuances continue to become more convoluted.
Over just seven days, MicroStrategy (NASDAQ: MSTR) raised $74.6 million by selling 728,479 shares of two perpetual preferred issues—STRK with an 8% coupon and STRF with a 10% coupon.
All the raised proceeds were virtually then plowed into buying 705 BTC at an average price of $106,495.
“Strategy has acquired 705 BTC for ~$75.1 million,” Saylor boasted on X, lifting the company’s hoard to 580,955 BTC purchased for $40.68 billion at about $70,023 each.
The purchases come after a recent buying spree: from April 14–20, the firm raised roughly $555.5 million by selling 1.8 million common shares and 91,213 shares of its 8% STRK preferred, then spent $555.8 million to acquire 6,556 BTC at an average $84,785. Then, from May 19–25, it generated another $427 million via 847,000 common shares plus 678,970 STRK and 104,423 STRF preferred shares, using the proceeds to purchase 4,020 BTC at an average $106,237.
The recent purchase might be smaller in comparison but it tells a lot about the company’s strategy. After weeks of criticism over relentless common-stock issuance, the most recent Bitcoin buy was financed exclusively through at-the-market sales of said preferred shares.
That pivot reflects growing pressure to stop pounding MSTR’s common float. Saylor’s switch lets him claim “no fresh common dilution,” but the relief is cosmetic: STRK carries an 8% cash coupon and can convert into common stock once MSTR trades near US$1,000, while STRF’s 10% coupon is permanent, cash-only, and non-convertible.
The authorisations still sitting on the shelf are enormous—about $20.7 billion of STRK and $2.1 billion of STRF—and that is where the real math bites. Fully drawn, the two series would demand roughly $1.9 billion in annual dividends, a sum the cash-flow-negative business cannot generate organically.
With a blended over 9% preferred cost, management effectively needs Bitcoin to appreciate roughly 14% a year after tax just to break even before operating losses are considered.
READ: MicroStrategy’s Debt Problem Grows On Bitcoin Acquisition Strategy; Saylor: “It’s Not Debt”
Preferred proceeds spare common shareholders for now, but the rich coupons must eventually be paid either with more securities sales or, paradoxically, by selling the very Bitcoin the company vows never to touch.
Saylor is already teeing up a third layer of leverage—the 10% non-cumulative Series A “STRD” perpetual preferred—aiming to raise roughly $250 million. The prospectus makes no secret of its uses: more Bitcoin purchases and, crucially, buybacks of MicroStrategy common shares to keep the market‐price-to-NAV premium aloft. Although the board can skip STRD’s dividend without piling up arrears, holders get a redemption put if the company undergoes a “fundamental change.”
As observers put it, the move can turn fresh STRD cash into Bitcoin buys and share support for existing holders while leaving a 10% coupon that can only be paid by selling still more securities—or by liquidating Bitcoin. They allege that Saylor would want to recycle STRD proceeds into common-share repurchases to keep MicroStrategy’s market-price-to-NAV premium elevated.
Saylor’s rhetoric remains defiant. At the Bitcoin 2025 conference in Las Vegas, Saylor derided on-chain proof-of-reserves as “a bad idea,” warning that disclosing wallet addresses would expose custodians and investors to “50 pages of security problems.” Separately, in December 2024, he trumpeted Bitcoin’s alleged 60% risk-free returns, citing a decade-long average price surge to claim holders could “double their capital every 18 months.”
Information for this story was found via the sources and companies mentioned. The author has no securities or affiliations related to the organizations discussed. Not a recommendation to buy or sell. Always do additional research and consult a professional before purchasing a security. The author holds no licenses.
