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Home » Struggling Software Sales: The Ascendancy of Bitcoin! Decoding MicroStrategy’s Strategy and Michael Saylor’s Financial Wizardry
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Struggling Software Sales: The Ascendancy of Bitcoin! Decoding MicroStrategy’s Strategy and Michael Saylor’s Financial Wizardry

May. 15, 20256 Mins Read
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Struggling Software Sales: The Ascendancy of Bitcoin! Decoding MicroStrategy's Strategy and Michael Saylor's Financial Wizardry
Struggling Software Sales: The Ascendancy of Bitcoin! Decoding MicroStrategy's Strategy and Michael Saylor's Financial Wizardry
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Financial Times Releases Video “Michael Saylor’s $40 Billion Bitcoin Bet”

On May 14, the Financial Times launched a video titled “Michael Saylor’s $40 Billion Bitcoin Bet,” focusing on the publicly traded company MicroStrategy and its founder Michael Saylor. The video delves into how MicroStrategy transformed from a business software company into the world’s largest holder of Bitcoin.

(Background: MicroStrategy invests another $1.34 billion to buy 13,390 Bitcoin, with over $40 billion in MSTR + STRK stock available for BTC accumulation.)

(Context: Michael Saylor discusses in depth why BTC is the strongest safe-haven asset in the world, without exception.)

MicroStrategy’s Astonishing Transformation: From Software Company to Bitcoin Dominator

MicroStrategy, originally a business software company established nearly 25 years ago, embarked on a dramatically different path under Michael Saylor in 2020: aggressively investing in Bitcoin. The video highlights that after investing $250 million in Bitcoin in mid-2020, MicroStrategy rapidly expanded its investment scale. By 2025, the company is expected to hold around $50 billion worth of Bitcoin, becoming the largest single entity holding Bitcoin among global enterprises.

This strategy has also resulted in a surge in the company’s stock price, which rose nearly 400% in 2024 alone, reaching a market capitalization of $100 billion, surpassing oil giant BP and significantly outperforming tech giants like NVIDIA, Meta, and Tesla. The video describes this transformation as “crazy and spectacular.”

Michael Saylor’s Bitcoin Belief: The Future of Digital Growth

In the documentary, Michael Saylor is portrayed as a high-profile Bitcoin evangelist, nicknamed “the man who never sells.” He believes that Bitcoin is “the best savings technology on Earth,” with its scarcity conferring unparalleled value. He predicts that Bitcoin’s price will reach $1 million in the next 10 years and could soar to $13 million in 20 years, asserting that its collapse is nearly impossible unless a “black swan event” occurs (such as a global electromagnetic pulse or alien invasion).

The film also reveals that Saylor actively promotes Bitcoin through social media platforms, even hosting a Bitcoin-themed party at his Miami mansion when the price surpassed $100,000. His AI-generated images, such as those depicting him in Bitcoin-branded clothing or on a football field, further enhance his public influence. The documentary emphasizes that Saylor is not just an investor but a leader who views Bitcoin as a faith.

“Infinite Capital Loophole”: The Magic of Financial Engineering

The documentary also details MicroStrategy’s financial strategy, referred to by supporters as the “infinite capital loophole.” The core of this strategy involves leveraging the premium of stock and Bitcoin holdings to create a self-reinforcing funding cycle:

  • Equity and Bond Financing: MicroStrategy raises funds by issuing stock and convertible bonds. In November 2024, the company raised $12 billion in just 50 days, showcasing impressive efficiency.
  • Low-Cost Debt: The company issues convertible bonds at low (1%) or zero interest rates, attracting institutional investors (such as hedge funds), effectively securing interest-free loans.
  • Premium Arbitrage: When the stock premium reaches twice the net asset value, MicroStrategy can exchange $1 of capital for $2 in Bitcoin purchasing power, equivalent to buying Bitcoin at a 50% discount.

The video explains that this strategy has driven up Bitcoin prices, further enhancing its stock price and creating a virtuous cycle.

Market Frenzy and Investor Mindset

Additionally, the documentary features investor Jeff Walton, who has concentrated 99% of his stock investments in MicroStrategy, reporting a 3,000% increase in his portfolio over the past two years. He predicts that MicroStrategy could grow into a $1 trillion or even $10 trillion company.

In this context, MicroStrategy’s stock is viewed by investors as a belief system rather than merely a financial asset. They are willing to pay a premium above the value of Bitcoin holdings, particularly evident when Bitcoin prices surge.

However, the documentary also points out that this frenzy carries risks: if Bitcoin prices decline, the premium may vanish, ultimately leading to dilution of shareholder value.

High Risks and Financial Challenges

The documentary does not shy away from discussing the risks associated with MicroStrategy’s strategy:

  • High Leverage Risk: The company relies on substantial debt, reporting nearly $6 billion in unrealized losses in the first quarter of 2025 due to a decline in Bitcoin prices. Although its capital structure is designed to withstand a 90% drop in Bitcoin for four to five years, equity holders will bear the brunt of the risk.
  • Cash Flow Shortages: Almost all raised funds are allocated to Bitcoin, leaving limited operational cash. If debt repayment is necessary, the company may need to sell Bitcoin or bring in new funds, which can be challenging when Bitcoin prices stagnate.
  • Controversial New Financial Products: In early 2025, MicroStrategy launched perpetual preferred stock (STRK) offering fixed returns, which performed well. However, the subsequent introduction of STRF (paying dividends only in cash) raised concerns as it could exacerbate liquidity pressure.

Thus, the documentary warns that this strategy is sustainable “as long as the music is playing,” but if Bitcoin prices collapse, the entire model may disintegrate.

Political Environment and Market Impact

The documentary also discusses how the Trump administration’s crypto-friendly policies in 2025 benefitted MicroStrategy. The government is considering establishing a “strategic Bitcoin reserve,” and the new SEC has relaxed regulations on digital assets, all of which have boosted Bitcoin prices. Interactions between Saylor and the Trump family also highlight the intersection of cryptocurrency and politics.

However, in February 2025, Trump’s tariff policies triggered fears of a global trade war, causing Bitcoin prices to drop by 25%, demonstrating that external factors could impact MicroStrategy. Therefore, despite the recovery of Bitcoin prices by the end of April, the documentary cautions investors about market volatility.

Investor Warnings and Future Outlook

Finally, the Financial Times notes that while Saylor and his supporters express optimism about Bitcoin’s future, the speculative nature of Bitcoin still carries risks, making it a “gold mine or a minefield.” The film quotes SEC Commissioner Hester Peirce, reminding investors: “If you lose money, don’t expect Grandma to bail you out.”


Related Reports

SOL Strategies CEO: We are not the Solana version of MicroStrategy; we are building the future with technology.

MicroStrategy invests another $180 million to acquire 1,895 Bitcoin, while BTC consolidates at $95,000 and U.S. stocks end a nine-day rally.

MicroStrategy spends $1.42 billion to acquire an additional 15,355 BTC, pushing total holdings beyond 550,000 Bitcoin, with MSTR soaring 27% in a month.

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