Michael Saylor’s Strategy Eyes $2.1 Billion Preferred Stock Sale Amid Bitcoin Surge

Michael Saylor’s crypto powerhouse, Strategy, is once again making waves—this time with a bold plan to raise up to $2.1 billion through the sale of 10% perpetual “strife” preferred stock, just as Bitcoin hits a record high of $111,000.

What’s Happening?

In a fresh filing on Thursday, Strategy confirmed it will launch an “at the market” offering of preferred shares. That means shares will be sold gradually over time, depending on market conditions, rather than all at once.

These preferred stocks offer a generous 10% dividend and will be available to retail investors at an initial liquidation price of $100 per share. It’s a move that’s expected to test the ongoing investor appetite for crypto-linked equity products—especially now, with digital assets on a hot streak.

The Bigger Picture

Strategy, formerly known as MicroStrategy, has become a bellwether for corporate Bitcoin investing. Under Saylor’s leadership, the firm has already raised billions via convertible bonds and equity offerings to fund massive Bitcoin buys. The company’s long-term goal? Raise $84 billion through various securities to further expand its BTC holdings.

So far, the demand has been impressive—and contagious. Several firms are now replicating Strategy’s model, issuing crypto-tied securities as a way to tap into Bitcoin’s growing mainstream appeal.

As of May 19, Strategy still had $19 billion in room for equity offerings and $35.5 billion for convertibles, according to regulatory filings.

Why It Matters

This new offering isn’t just another fundraising effort—it’s a litmus test for how deep investor interest runs in the current crypto bull market. With Bitcoin now comfortably above $111,000 and digital assets enjoying a major tailwind from a crypto-friendly U.S. administration, there’s growing belief that alternative finance models like this one could become the new norm.

Interestingly, earlier versions of these preferred shares were launched at $85 per share and have already returned 16% since inception, according to the company. That kind of return—combined with a 10% dividend—could be attractive to income-focused investors who want exposure to crypto without holding Bitcoin directly.

Strategy Stock Responds

Shares of Strategy jumped as much as 5.9% on Thursday and are now up over 40% year-to-date, reflecting strong investor confidence in both the company and the broader crypto market.

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