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August 22, 2025Understanding MicroStrategy’s Capital Structure
20 August 2025
Strategy (NASDAQ:MSTR) or previously MicroStrategy has built a unique financial ecosystem centered on Bitcoin as its primary treasury reserve asset. Under the leadership of Michael Saylor, the company has issued a range of securities - common stock (MSTR) and four perpetual preferred stocks (STRK, STRF, STRD, STRC) - to fund Bitcoin acquisitions and provide investors with diversified exposure to digital assets.

While the price performance of MSTR has been nothing short of spectacular in the last year 2 years, the underlying mechanics of the financials that support MSTR and the recent addition of new related securities have been dividing financial analysts and investors standing on two side of an irreconcilable chasm: those calling it the greatest ponzi of the century, and those calling it a feat of financial engineering.
The Five Horsemen of Strategy Inc
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MSTR: Common Stock
MSTR is Strategy’s common stock, representing equity ownership in the company. It’s the riskiest but potentially most rewarding security, offering leveraged exposure to Bitcoin’s price movements. Unlike preferred stocks, MSTR shareholders have voting rights but are last in line for payouts in a liquidation event. The stock’s value is tied to Strategy’s Bitcoin holdings (over 629,000 BTC as of August 2025) and its software business, though it trades at a premium to its Bitcoin assets. Investors in MSTR seek high growth, driven by Bitcoin’s performance, but face volatility and no guaranteed dividends.
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STRK: Convertible Preferred Stock
STRK, or Series A Perpetual Strike Preferred Stock, offers an 8% annual dividend ($8 per share) based on a $100 liquidation preference, paid quarterly if declared by Strategy’s board. Its standout feature is convertibility: holders can exchange 10 STRK shares for one MSTR share if MSTR’s price hits $1,000, providing equity upside. STRK sits above MSTR but below other preferred stocks in the capital structure, balancing yield and growth. It raised $563 million in February 2025, appealing to investors seeking Bitcoin exposure with downside protection. As MSTR approaches $1,000, STRK’s price may rise due to its conversion option.
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STRF: Income-Focused Preferred Stock
STRF, or Series A Perpetual Strife Preferred Stock, provides a 10% fixed dividend ($10 per share) on a $100 stated amount, paid quarterly starting June 2025, if declared. Unlike STRK, STRF lacks a conversion feature, making it a pure fixed-income security with greater price stability. It raised $711 million in March 2025, targeting income-focused investors like pension funds. STRF is senior to STRK and MSTR, offering lower volatility but no equity upside. If dividends are missed, they compound at 10% plus 1% annually, up to 18%.
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STRD: High-Yield, Higher-Risk Preferred Stock
STRD, or Series A Stride Preferred Stock, launched in June 2025, offers a 10% non-cumulative dividend ($10 per share), the highest yield among Strategy’s preferred stocks. It raised nearly $1 billion, reflecting strong demand. STRD is junior to STRF and STRK in the capital structure, increasing risk but appealing to yield-seeking, risk-tolerant investors. Its non-cumulative dividends mean unpaid amounts don’t accrue, unlike STRF. STRD’s performance is tied to Strategy’s ability to sustain dividends, heavily reliant on Bitcoin market conditions.
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STRC: High-Yield, Stable Preferred Stock
STRC, or Variable Rate Series A Perpetual Stretch Preferred Stock, was introduced in July 2025 via a $4.2 billion at-the-market (ATM) program. It offers a variable dividend rate, designed to compete with money market funds by providing high yield and price stability. STRC is non-callable under normal conditions but can be repurchased during tax events or fundamental changes. Its proceeds fund Bitcoin purchases and working capital, with some dividends supporting other preferred stocks. STRC targets investors seeking steady income with Bitcoin-backed exposure.
How They Work Together
Strategy’s capital structure is a financial engineering feat, using MSTR, STRK, STRF, STRD, and STRC to create a Bitcoin-backed yield curve. MSTR offers high-risk, high-reward equity exposure, while the preferred stocks cater to income-focused investors with varying risk profiles. STRK blends yield and growth, STRF prioritizes stability, STRD targets high yield with higher risk, and STRC competes with traditional fixed-income products.
The Concerns on Strategy Inc
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Digital Asset Volatility
Strategy's whole strategy is focused on Bitcoin price performance, and as we all know, digital assets is a very volatile asset class. Any drawdown on Bitcoin will be amplified multiple times on Strategy's listed securities which have an intrinsic leverage due to its capital structure.
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Negative Cashflows
STRK, STRF, STRD, and STRC, together have created a situation of negative cashflow on Strategy, whereby the dividend payments on those securities (in addition to existing Strategy's debt) exceed Strategy's ability to generate cash flow from operating activities, making the company dependent on its investing activities (buying Bitcoin and selling it higher) to be able to service its obligations.
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modified Net Asset Value (mNAV)
The mNAV metric estimates Strategy’s value based on its Bitcoin holdings and software business, and it often shows MSTR trading at a premium (e.g., 2-3x its Bitcoin NAV), raising fears of overvaluation among some investors.
Thoughts on Strategy Inc
This is one such case where the market can stay irrational longer than you can stay solvent, but is reminiscing of the situation that we had in the early days of the Greyscale Bitcoin Trust.
In the early days (2017-2020) the Greyscale Bitcoin Trust traded at a premium and even went peaked to as high as 130% of the NAV before sinking to discount of -48% in 2021. Though that type of NAV elasticity may seem illogical from an academic perspective it does happen in certain particular situation, and Strategy is one such situation.
Fortune favours the bold, but I would remain cautious around Digital Asset Treasury Companies (DATs) as mNAV does not have a floor at 1.0
by Nathaniel Tsang Mang Kin
Chief Operating Officer at Stewards Investment Capital
Disclaimer: This article is for informational purposes only and does not constitute financial, investment, or professional advice. Readers are encouraged to conduct their own research and consult with a licensed financial advisor before making any investment decisions. The mention of specific companies or financial instruments does not imply endorsement or a recommendation to buy or sell. Investments in digital assets or securities linked to digital assets, carry inherent risks and may not be suitable for all investors.
About Stewards Investment Capital
Stewards Investment Capital is a boutique investment advisory firm with a track record of over 25 years under the Stewards Group of Financial Companies. Strategically positioned in Mauritius, South Africa, and the USA, we tailor niche investment solutions to high-net-worth individuals and institutional investors.
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