Perpetual Revolution: New Strategies to Overcome the Conversion Debt Crisis June 2, 2028

The new crypto industry has just discovered an innovative blueprint to tackle one of the biggest funding challenges: how to replace maturing convertible debt with more flexible and perpetual instruments. Strive (ASST), a leading Bitcoin asset management company, has demonstrated this concept by issuing $150 million in perpetual equity to fundamentally restructure its debt position.

This approach creates new opportunities for other companies facing urgent financial deadlines, including MicroStrategy (MSTR), which carries a convertible debt burden of $8.3 billion—almost all of which is still not due or has just been converted. With the perpetual strategy, CEOs and CFOs now have a new weapon to avoid outdated refinancing scenarios.

How Strive Is Changing the Game with Perpetual Shares

Recently, Strive set the offering price for its Variable Rate Perpetual Preferred Stock (SATA) at $90 per share, allowing for the issuance of up to 2.25 million shares in aggregate. This transaction combines a public issuance with a private debt exchange—a sleek and efficient structure.

The company plans to use the proceeds to pay off Semler Scientific’s senior convertible notes secured by Strive, with approximately 930,000 new SATA shares directly exchanged for the convertible debt. The remaining funds will be used to redeem the remaining convertible debt, pay off Coinbase loans, and buy additional Bitcoin. The key innovation here: instead of traditional refinancing, Strive converts maturing liabilities into perpetual shares that have no conversion features or maturity date.

Why Perpetual Equity Outperforms Traditional Convertible Debt

Strive’s perpetual shares provide a variable dividend of 12.25% forever without a maturity date. For existing bondholders, they effectively relinquish the equity conversion option in exchange for a higher-yield, perpetual, fully liquid instrument with seniority over common stock. It’s a win-win: debt holders get a more attractive yield and clear liquidity, while the company eliminates the ongoing refinancing risk.

From a financial reporting perspective, this also improves leverage metrics—since preferred shares are counted as equity rather than debt, the balance sheet appears healthier to investors and credit rating agencies.

MicroStrategy and the June 2, 2028 Deadline: Opportunities Abound

Strive’s strategy paves the way for MicroStrategy to adopt a similar approach on a much larger scale. MicroStrategy has a $3 billion tranche of convertible debt with a put date on June 2, 2028, and a conversion price of $672.40—about 300% above the current stock price of around $160.

The June 2, 2028 deadline provides a sufficient window for CEO Michael Saylor to begin implementing a similar perpetual equity strategy. If the stock price does not reach the conversion level ($672.40) at maturity, MicroStrategy must pay the principal in full—an expensive scenario if done through traditional refinancing. By using perpetual equity like Strive, MicroStrategy can convert its debt burden into a long-term instrument that no longer hangs like the Sword of Damocles.

The Future of Refinancing: Perpetual Equity Replaces the Old Model

The blueprint set by Strive shows that traditional refinancing—constantly borrowing back maturing debt—may soon become obsolete. With perpetual equity, companies are no longer at the mercy of financial market cycles or interest rate fluctuations. These instruments provide long-term stability while offering preferred shareholders attractive yields.

For MicroStrategy and other large companies with significant convertible debt burdens, the perpetual strategy is not just a financial option—it’s a strategic necessity before urgent deadlines like June 2, 2028, arrive. A new era of corporate debt management may have begun.