Michael Saylor is not backing down. The MicroStrategy co-founder is preparing to issue another $4.2 billion in preferred stock to support his latest Bitcoin bet — while also providing reassurance to investors concerned about potential dilution of their holdings.

The plan was announced Thursday alongside second-quarter earnings results, addressing a major question about the company's stock: How long can Saylor continue his strategy of raising funds at high premiums to keep buying Bitcoin?

To appease shareholders, MicroStrategy has promised not to issue new common shares at less than 2.5 times net asset value, except for debt interest payments or preferred stock dividends. Meanwhile, Saylor will continue to opportunistically raise funds when premiums are high, using proceeds from stock sales to purchase more cryptocurrency.

This represents a win-win strategy: setting a floor price to reassure skeptical shareholders while replenishing the company's treasury to continue Bitcoin acquisitions. This dual approach puts Saylor in direct confrontation with hedge fund managers like Jim Chanos, who have been betting that the company's premium will collapse.

"This should provide comfort to common shareholders who were concerned about potential dilution," said Brian Dobson, managing director of disruptive technology equity research at brokerage Clear Street. "The market has responded positively to MicroStrategy's equity products. The company's large-scale fundraising demonstrates market demand."

Through these and other financial maneuvers, the once-obscure software company has transformed into a leveraged Bitcoin proxy.

The strategy also demonstrates Saylor's mastery of capital markets during the digital asset bull run: using self-imposed limits to pacify critics while arming the company with ammunition to continue Bitcoin purchases.

The company, formally known as MicroStrategy Inc., has already raised over $10 billion this year through stock and structured securities issuances, helping build a balance sheet with $74 billion worth of Bitcoin. Since Saylor first purchased cryptocurrency, the company's stock has soared 3,300%, outperforming Bitcoin itself, forcing hedge funds into a high-stakes confrontation over whether Saylor's premium-driven strategy can continue.