Michael Saylor’s Strategy Eyes $100 Billion Bitcoin Fundraise via Preferred Stock

Michael Saylor, the bold leader behind Strategy, has laid out an extraordinary plan. He aims to raise a stunning $100 billion, perhaps even double that amount. This massive sum would fuel his company’s aggressive pursuit of more Bitcoin.

This ambitious fundraising hinges on what Saylor calls his “BTC credit model.” It’s a clever way to use Bitcoin as collateral. Strategy would issue special shares that pay dividends forever, essentially using their Bitcoin holdings to back these perpetual preferred shares. Bloomberg recently highlighted this unique approach. These shares are interesting because they mix features of debt and equity. They let a company bring in new money without just selling more common stock or convertible bonds.

Strategy, once known as MicroStrategy, made a big splash in 2020. They decided to put Bitcoin at the heart of their company treasury. This groundbreaking move has led them to amass 628,946 Bitcoins. Today, that hoard is worth about $73 billion, making Strategy the world’s largest corporate holder of the cryptocurrency.

Saylor is famous for his absolute commitment. He has always promised that Strategy will never sell a single Bitcoin, a promise he has kept. He even famously advises his followers to buy Bitcoin, suggesting they should “sell a kidney” if needed.

The company has been busy this year. Strategy secured nearly $18 billion so far in 2025 to boost its Bitcoin stack. This sum includes around $6 billion from four separate offerings of preferred shares. The most recent sale, nicknamed “Stretch,” pulled in $2.5 billion. It was one of the largest capital raises in the crypto world this year. With more than $22 billion coming from institutional investors last year and close to $40 billion since 2024, Saylor’s dream of reaching $100 billion or more doesn’t seem quite so outlandish.

A Strategy with Risks

While innovative, this fundraising model carries real risks. No other cryptocurrency investment company has tried it before. The biggest worry is Bitcoin’s wild price swings. If Bitcoin’s value plummets, it could make paying dividends on those perpetual preferred shares very difficult.

Some critics are wary. Jim Chanos, a well-known financial short-seller, has warned that Strategy’s stock price might be inflated. He noted that the company’s shares trade at a premium of more than 200% above its underlying assets. Chanos even suggested betting against the company. However, investors have shown great faith in Saylor’s long-term vision. Strategy’s stock (MSTR) has soared 350% since 2020.

In the second quarter of 2025, Strategy reported $14 billion in unrealized gains. This gain was thanks to Bitcoin’s recovery and some accounting adjustments. This strong performance backs up Saylor’s story. He plans to keep issuing preferred shares to buy more Bitcoin. He wants to do this without reducing the value of existing common shareholders’ stakes. Interestingly, about a quarter of the “Stretch” offering came from everyday retail investors. That’s unusual in a market typically dominated by big financial firms, as Bloomberg pointed out.

Reshaping Corporate Finance

Saylor is a polarizing figure. His supporters see him as a financial visionary. Skeptics might view him as an enthusiastic preacher. Regardless, his audacious move has ignited a craze for corporate Bitcoin treasuries. Over the past year, companies like Metaplanet and Trump Media have copied his approach. They too are now hoarding Bitcoin in their company funds, ushering in a new way of investing.

Today, more than 165 public companies globally hold some form of Bitcoin in their treasuries. Together, they own a staggering 971,000 Bitcoins. This shows that Saylor’s vision, though risky, continues to challenge traditional markets. It is clearly redefining the future of corporate finance.

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