Michael Saylor's Bitcoin Strategy: Risks and Resilience

# Michael Saylor's MSTR is Barely Ahead on BTC Bet, but Threat of Imminent Danger Overblown Bitcoin's Plunge Brings Strategy's Holdings to Near Breakeven, but Key Test Lies 18 Months Ahead ------------------------------------------------------------------------------------------------ Michael Saylor's company's balance sheet isn't at imminent risk of collapse, but further capital-raising efforts could surely be hindered unless conditions improve. -------------------------------------------------------------------------------------------------------------------------------------------------------------------- Nov 22, 2025, 9:00 p.m. ## The Bitcoin Rollercoaster and MicroStrategy's Position Liquidation calls from the sidelines are growing louder for MicroStrategy (MSTR) as bitcoin tumbles and the company's common stock has plunged nearly 70% from last year's peak, calling into question — for some — the firm's ability to continue to meet its obligations. Throughout 2025, MicroStrategy has relied on perpetual preferred stock as its primary financing vehicle for bitcoin purchases, while mostly using at-the-market (ATM) common share issuance mainly to cover its preferred dividend obligations. Led by Executive Chairman Michael Saylor, the company issued four U.S.-listed preferred series during the year: Strike (STRK) pays an 8% fixed dividend and is convertible into common stock at $1,000 per share. Strife (STRF) carries a 10% fixed non-cumulative dividend and ranks as the most senior of the preferreds. STRD also pays 10% but on cumulative terms and sits junior in the structure. Stretch (STRC), the newest series, debuted in August at $90 with a 10.5% fixed cumulative dividend and now trades just above its offer price. As of Nov. 21 STRK trades near $73, an 11.1% current yield, with a 10% decline since issuance. STRD has been the weakest performer, falling to about $66 for a 15.2% yield and a 22% total return loss. STRF is the only series still above issue, trading around $94 and delivering roughly an 11% gain, reflecting its senior standing. ### Nearly Back to Breakeven on Bitcoin Holdings Bitcoin's plunge over the past weeks has market participants focusing on the roughly $74,400 level at which MicroStrategy — after more than five years of accumulation — would actually be in the red on its bitcoin holdings. While that's surely an important level for talking points, a decline below $74,400 surely does not mean the company would face a margin call or need to engage in forced sales of any part of its BTC stack. The nearest structural pressure point is almost two years out on September 15, 2027, when holders of the $1 billion 0.625% convertible senior notes receive their first put option. The notes were priced when MSTR traded at $130.85 and carry a conversion price of $183.19. With the stock now at about $168, holders would be unlikely to convert and would probably seek cash repayment, potentially requiring MicroStrategy to raise or liquidate assets unless the share price rises meaningfully before 2027. ## Navigating Market Volatility: MicroStrategy's Strategic Levers Even if the MSTR share valuation premium to bitcoin holdings (the mNAV) collapses further and maybe even goes to a discount, MicroStrategy still has a clear path to cover the annual preferred dividend bill. The company can continue to issue common shares via ATM offerings, or sell small slices of its bitcoin treasury, or even pay dividends in-kind with newly issued stock. This isn't to say all is well. While preferred dividends are not at immediate risk, use of any of the above options would surely dent investor confidence in MicroStrategy even further, likely putting an end — for at least a temporary time — to any efforts to raise additional capital for more bitcoin purchases. ### The Broader Market Context: Tokenization and Financial Innovation The current market volatility, as seen with MicroStrategy's situation, highlights the dynamic nature of digital asset investment. For businesses and fanpage administrators navigating this space, staying informed is crucial. This is where innovative solutions for **market intelligence** come into play. At **RWA Times**, we understand the challenges of discerning signal from noise in rapidly evolving sectors like **tokenization** and **digital assets**. Our **RWA Times Intelligence Engine** utilizes advanced AI to categorize, analyze, and score financial news, providing a structured and data-driven view of the market. We help businesses cut through the clutter, identify emerging trends, and make informed decisions. Consider the complexities faced by companies like MicroStrategy. Understanding the interplay between asset prices, financing mechanisms, and regulatory sentiment is paramount. Our platform offers: * **Structured Taxonomy:** A comprehensive 40-topic hierarchy to classify news, ensuring relevance to specific areas like **asset types**, **legal frameworks**, and **institutional adoption**. * **Advanced Scoring:** Beyond simple sentiment analysis, we evaluate **novelty**, **uncertainty**, and **relevance** to the **RWA mandate**, giving you a quantitative edge. * **Transparent Reasoning:** Our AI provides clear explanations for its analyses, fostering trust and enabling deeper understanding. In an era where information is abundant but actionable insight is scarce, having a tool that intelligently decodes the financial landscape is invaluable. Whether you're exploring **tokenized real-world assets (RWAs)**, **digital securities**, or new financing models, **RWA Times** equips you with the intelligence to lead. ### Conclusion: Resilience in a Dynamic Market While Michael Saylor's conviction in Bitcoin remains a high-stakes gamble, MicroStrategy has demonstrated a degree of resilience. The company has multiple avenues to manage its obligations, even if current market conditions are challenging. The true test for MicroStrategy's long-term strategy, and its ability to attract further capital, will likely unfold over the next 18 months, particularly as the 2027 convertible notes approach their put option. This situation serves as a potent reminder for businesses operating in or considering the digital asset space: thorough risk assessment, diversified strategies, and robust information management are not just beneficial, they are essential for survival and growth. --- ### Explore Smarter Market Intelligence for Your Business Are you struggling to keep up with the pace of financial innovation and the influx of digital asset news? **RWA Times** offers the clarity and insights you need to make confident business decisions. Our AI-powered platform transforms raw financial news into actionable intelligence, tailored for professionals navigating complex markets. [**Learn More About RWA Times Intelligence Engine**](/) --- **Related Content:** More For You Protocol Research: GoPlus Security  What to know: * As of October 2025, GoPlus has generated $4.7M in total revenue across its product lines. 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