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• Strategy, formerly MicroStrategy, is approaching its 100th Bitcoin purchase as part of its ongoing accumulation plan.
• The company continues to add to its Bitcoin holdings despite significant unrealized losses on its existing position.
• To fund purchases, Strategy is shifting toward issuing preferred stock and common shares, increasing attention on shareholder dilution.
• The milestone comes at a time of high Bitcoin price volatility and intense debate over corporate exposure to digital assets.
Strategy (NasdaqGS:MSTR) operates as a business intelligence and software company, while also running one of the largest corporate Bitcoin treasuries. Its focus on Bitcoin sets it apart from most public companies that either hold modest digital asset positions or avoid them entirely. Recent swings in crypto markets keep the risk profile of this approach in clear view for equity holders.
As the 100th Bitcoin purchase approaches, investors are weighing the trade off between potential upside from a larger Bitcoin stack and the impact of ongoing equity and preferred stock issuance on existing shareholders. The evolving mix of debt, preferreds, and common stock gives investors more to track in terms of capital structure, liquidity, and how tightly their exposure is tied to Bitcoin price moves.
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? Beyond the headline: 2 risks and 2 things going right for Strategy that every investor should see.
This 100th Bitcoin purchase underlines that Strategy is running a Bitcoin treasury-first business model, with the software segment sitting alongside a very large digital asset position. The company now holds more than 717,000 Bitcoin, with a reported unrealized loss of around US$6.8b and a US$12.44b net loss in Q4 2025 largely tied to digital asset marks. Funding new purchases through common equity and high-yield preferred stock links shareholder outcomes more tightly to Bitcoin price swings and to how efficiently management can raise capital without eroding Bitcoin per share.
The Risks and Rewards Investors Should Consider
• ?? Ongoing issuance of common shares and preferred stock can dilute existing holders, especially if the stock price is weak when capital is raised.
• ?? The Bitcoin-focused, leveraged balance sheet and complex “digital credit” structure mean Strategy’s equity can be more volatile than holding Bitcoin directly.
• ? Management reports a sizeable Bitcoin stack that is not pledged as collateral, along with about US$2.25b of cash and no major debt maturity until September 2027, which provides some flexibility.
• ? For investors who want amplified exposure to Bitcoin, Strategy’s treasury model offers a way to access that through a listed equity with an existing software business alongside it.