Although the Bitcoin treasury company Strategy (MSTR) has maintained its position in the Nasdaq 100 index, concerns about the sustainability of its business model are growing. Based on new analyses, the year 2028 is critical, where the company's survival will be determined.
The company's Bitcoin position is now so large that it can influence the entire market. Its holdings clearly exceed the scale of a typical 'whale'.
Tiger Research: 2028 is a real test
The cryptocurrency research company Tiger Research has identified the year 2028 as a key risk point in its analysis of the financial structure of the Strategy company.
The report highlights a significant change in Strategy's capital acquisition methods. Until 2023, the company used cash reserves and small convertible notes, keeping its Bitcoin holdings low at around 100,000 BTC. From 2024 onwards, Strategy significantly increased its leverage by combining preferred stocks, ATM programs, and large convertible loans. This created a feedback loop where rising Bitcoin prices enabled even larger purchases.
The problem: The options associated with these convertible bonds focus on 2028, causing redemption pressure of about $6.4 billion. Investors may demand early repayment, which the company cannot refuse.
No cash flow, no safety net
Tiger Research raises a fundamental vulnerability: Strategy used nearly all the capital it raised to buy Bitcoin instead of investing the funds in income-generating assets.
“If the funds had been invested in income-generating assets, the company would have a natural source of repayment,” the report states. “Now, focusing on accumulating Bitcoin leaves little cash for redemptions.”
If the financing reform is blocked in 2028, Strategy will have to sell about 71,000 BTC at a price of $90,000. This corresponds to 20-30 percent of the daily trading volume and may trigger a market-level downward spiral.
The bankruptcy threshold rises
Strategy's fixed bankruptcy threshold is $23,000 in 2025, which would require a 73% price drop. However, this level has steadily increased: from $12,000 in 2023 to $18,000 in 2024 as debt growth outpaces Bitcoin accumulation.
“The structural risk of Strategy appears small under normal conditions, but it focuses very heavily on 2028,” warns Tiger Research. “If financing arrangements fail, selling pressure could become so great that it impacts the entire Bitcoin market.”
The report states that new digital asset treasury companies face an even greater risk. They lack the multi-layered security mechanisms of Strategy, which emerged from survival during the 2022 bear market.
The stability of the Nasdaq 100 amid suspicion
At the same time, Strategy avoided removal from the Nasdaq 100 in the index's regular rebalancing announced last weekend. However, global index provider MSCI is evaluating Strategy's position in January, and some market watchers believe that the buy-and-hold Bitcoin model resembles more of a mutual fund than a technology company.
Strategy was the first to bring the Bitcoin treasury model to corporate use in 2020, leading to dozens of copycats worldwide. As Bitcoin's volatility pressures stock prices — Strategy has dropped 47 percent in three months — questions are growing about whether such leveraged positions can withstand upcoming debt obligations.
