Perpetual Stock Strategy: How Aggregate Offerings can Solve the Challenge of Saylor's $8 Miliar Debt

The crypto market is moving volatile at the end of January 2026. Bitcoin saw a significant drop of 5.09% to $84.87K, recording a new low for the year, while the tech stock index also weakened as Microsoft fell more than 11% after its earnings report. In these volatile market conditions, innovative financial strategies emerged that attracted the attention of industry players. Bitcoin asset management firm Strive (ASST) introduced an aggregate offering approach that could be a blueprint for other companies to face the challenges of convertible debt refining.

Strive Launches $150 Million SATA Aggregate Offering

Strive announced plans to expand its preferred equity aggregate offering beyond its initial target of $150 million. Through this mechanism, the company will issue a Series of Variable Perpetual Preferred Shares (SATA) at a fixed price of $90 per share. The enhanced aggregate offering allows for the issuance of up to 2.25 million SATA shares in total, combining a public issuance with a privately negotiated debt exchange with certain securities holders.

The allocation of funds from this aggregate offering is designed to pay off Semler Scientific’s 4.25% Convertible Senior Notes due in 2030. Strive targets to execute swap agreements with bondholders representing approximately $90 million of aggregate principal amounts. In the exchange transaction, approximately 930,000 newly issued SATA shares will be exchanged directly for convertible bonds. The remainder is used to redeem the remaining convertible debentures, pay off loans under the Coinbase Credit facility, and fund additional bitcoin purchases.

Perpetual Equity Restructuring: Mechanisms and Benefits

The essence of this strategy is debt substitution with a fixed maturity into preferred shares that are perpetual (perpetual). SATA comes with a variable dividend set at a rate of 12.25% and has no maturity or obligatory conversion features. Since preferred shares are treated as equity instead of debt in the financial statements, these instruments increase the reported leverage ratio as well as provide greater financial flexibility.

The perpetual equity structure presents an attractive tradeoff for both parties. For bondholders, they relinquish their equity conversion option but get instruments with higher yields (12.25%), full liquidity, and seniority against common stock. For issuers like Strive, they eliminate the risk of future refinancing because there is no maturity date hanging over. This creates a favorable equilibrium in a challenging refinement landscape.

A similar structure can be applied to address another $3 billion tranche of conversion that has a put date of June 2, 2028 at a conversion price of $672.40, well above the current share price. This perpetual equity approach offers a flexible alternative to traditional refinancing or complex restructuring.

Potential Implications for MicroStrategy and Michael Saylor

The model applied by Strive has direct relevance to the MicroStrategy (MSTR) situation. CEO Michael Saylor’s company currently carries a bond conversion expense worth about $8.3 billion. The value of MSTR’s perpetual preferred shares has recently exceeded the face value of its convertible debt, creating a new strategic option. The remaining largest convertible debt still outstanding is a $3 billion tranche with a put date of June 2028 and a conversion price of $672.40, about 300% above current market prices.

The use of aggregate offerings and perpetual preferred equity provides Saylor with an additional avenue to manage significant maturity risk. By applying the same model, MSTR was able to convert most convertible debt into perpetual equity, releasing long-term refinement pressure and increasing the flexibility of its balance sheet. This strategy will reduce reliance on volatile market conditions for large-scale refining.

Market Challenges and Reform Momentum

The current market volatility—with bitcoin dropping to $84.87K and the tech index weakening—is creating pressure on institutional players with large convertible debt exposures. In this context, the perpetual equity innovations that Strive demonstrated offer a template that can be adopted more widely. This approach allows companies to offload periodic refinement and adapt to the ever-changing capital landscape.

Strive success in executing this aggregate offering will serve as a reference point for other crypto and fintech companies facing similar debt conversion challenges. For Michael Saylor and MicroStrategy in particular, Strive example opens up opportunities to take proactive action in managing its $8.3 billion in existing debt, turning challenges into opportunities to strengthen long-term financial positions.