Michael Saylor has completely transformed his tech company Strategy into a “money-making machine” that bets on Bitcoin, but as the cryptocurrency market declines, this high-stakes gamble is facing severe tests. This article is adapted from The New York Times original titled “Michael Saylor’s Strategy Is Having to Sell Bitcoin,” translated by Dongqu.
(Background: Michael Saylor vows: “Even if I have to sell a kidney, I won’t sell Bitcoin,” MicroStrategy’s Bitcoin profits drop to $6.6 billion)
(Additional context: Software sales sluggish, relying on Bitcoin to become a legend! Decoding MicroStrategy Strategy and Michael Saylor’s financial magic)

Table of Contents

• The unfulfilled dream of a fighter pilot
• “Breaking free from economic slavery”
• An economic anomaly
• How will everything collapse?

If Bitcoin becomes worthless tomorrow, whether I hold 1%, 2%, 3%, or 0.5% doesn’t matter; it’s all worthless anyway.

If you just take a quick glance at Michael Saylor at his Tuscan-style estate in Miami, you might think it’s just another private gathering of the wealthy. The scene features unlimited Iberian ham, a spacious Versailles-style banquet hall with an electronic music DJ; docked nearby are at least three yachts belonging to Saylor, and at the entrance, a row of smiling staff members are holding shoes for guests.

However, by dinner time, the scene becomes absurd. On New Year’s Eve 2024, in front of a giant screen set up on the billionaire’s lawn, hundreds of guests witness the host’s eyes emitting green laser beams.

On the screen, Saylor’s face is composited into famous movie clips like Gwai Gwai and The Lord of the Rings. He is edited as a hero, shooting laser beams from his eyes, turning a host of crypto skeptics like Bill Gates and bank executive Jamie Dimon “to ashes.”

“Buy it!” Saylor’s virtual image shouts as opponents fall one by one.

The Bitcoin community has never lacked passionate believers, even outright scammers. But recently, the most watched and also most criticized figure in the industry is none other than Michael Saylor. This ambitious business magnate has been accused of tax evasion, and in just six years, he transformed his originally mediocre tech company Strategy into a “money-making machine” betting on Bitcoin.

Strategy’s main business is selling enterprise software that helps clients organize sales data into more intuitive reports. Today, this business has become a negligible subsidiary: Saylor has woven a web of various financial instruments and lending agreements, deploying almost all available company funds into the crypto market. This is a highly volatile, relatively lightly regulated domain, completely unrelated to the company’s original business.

Just looking at this move, whether it’s courageous or reckless, people might give completely opposite answers. But undeniably, this operation was highly successful for a long period: Strategy’s stock was initially ignored, but last year, as the crypto market rebounded, the company’s Bitcoin holdings surpassed the gold reserves of the Fort Knox vault, accounting for a significant portion of the global supply, and the stock price soared to $474 per share.

At that time, 60-year-old Saylor’s net worth on paper exceeded $10 billion, earning him titles like “Digital Navy Captain” and even more directly “Bitcoin Savior.” On social media, he further fueled the flames, posting sensational messages predicting the dollar’s imminent collapse and advising the public never to abandon cryptocurrencies. He once tweeted on X platform: “Even if I have to sell a kidney, I will hold onto Bitcoin.” Eric Trump, son of President Trump, even hosted him at Mar-a-Lago.

But all this was just the prelude. Over the past year, Strategy rapidly launched and promoted a series of investment products claiming to turn Bitcoin, known for its extreme volatility, into a stable investment target for the masses.

Saylor travels around the world on private jets, speaking in obscure financial jargon, promising fixed double-digit returns to investors buying specific types of company stocks, and comparing its safety to bank deposits.

Of course, this is ultimately not real bank deposits, but just putting your money into the crypto market.

As the chairman of Strategy and holding nearly half of the company’s shares, how Saylor justifies his promises is complex. And as the crypto market turns downward, the company’s investment projects continue to adjust, making the logic behind them increasingly obscure.

This “guru” who once advised everyone never to sell Bitcoin now hints that the company might have to sell Bitcoin to repay loans. Strategy has begun borrowing, but the borrowed money is not used to buy more crypto; instead, it has accumulated billions of dollars in cash.

In the eyes of skeptics, this is the latest sign that Saylor is just a complete con artist, and his scam is about to be exposed in front of everyone.

Today, Strategy’s stock price has fallen two-thirds from its peak, far outpacing Bitcoin’s decline. The crypto community is increasingly anxious: if one of the market’s biggest “whales,” Strategy, begins to sell Bitcoin, the entire market could collapse. This would not only affect mainstream financial institutions like Fidelity, Barclays, and Cantor Fitzgerald that do business with Strategy but also cause countless ordinary investors who followed Saylor’s advice to suffer losses.

Moreover, dozens of companies are following suit, increasing their crypto holdings, including Trump Media & Technology Group. The collapse of Strategy would undoubtedly spell disaster for them.

Renowned short-seller Marc Cohodes predicts that Strategy will inevitably crash and calls Saylor a “mouthful of nonsense preacher, on the same level as Jim Jones (cult leader).”

“We’ve always kept our distance,” said Jan van Eck, founder of asset management giant Van Eck and a crypto investor. “This is just hype.”

Senior financial analyst Herb Greenberg describes Strategy as a “quasi-Ponzi scheme,” where late investors’ returns depend entirely on new investors’ capital.

Neither Saylor nor Strategy’s representatives have responded to this article.

A year ago, CNBC questioned Saylor about the Ponzi scheme allegations, to which he replied: “Like Manhattan developers, whenever real estate appreciates, they issue more bonds to develop new projects. That’s why New York skyscrapers keep rising; this model has lasted 350 years. I prefer to call it an economic model.”

The unfulfilled dream of a fighter pilot

Strategy Chairman Michael Saylor attended a meeting last year with President Trump and crypto industry leaders

For most of the history of cryptocurrency development, Saylor and his Strategy have never been involved.

This company, headquartered in the suburbs of Virginia, was formerly called MicroStrategy. Before the dot-com bubble burst in the early 21st century, it gained fame with a simple data processing software. This software helped companies like McDonald’s analyze customer information. Although its revenue and profit were not spectacular, as Saylor became a media regular, its stock became a darling of the market.

Saylor’s life story is quite legendary. Due to a heart murmur, his dream of becoming a fighter pilot was dashed, and he was known for boasting and making promises that often couldn’t be fulfilled.

In 1998, MicroStrategy went public. In an interview with Forbes, Saylor predicted that “every person’s life around the world, every moment, will be inseparable from our technology.” He also once envisioned developing brain-implant devices for employees.

As The Washington City Paper commented in 2000: “Apparently, Saylor’s persona is just an endless talk box.”

That same year, the U.S. Securities and Exchange Commission sued MicroStrategy for alleged fraud, accusing the company of manipulating accounting records to fabricate nonexistent profits. Saylor and his partners agreed to pay millions in fines but did not admit or deny the fraud allegations. The stock plummeted, and Saylor was forced to lay off staff, but he later led the company to transform into a mid-sized software provider and regain profitability.

Despite still being wealthy, Saylor began immersing himself in the activities of the rich. He founded the online university Saylor Academy, and combined three apartments in Georgetown into a super-luxury mansion. One of his yachts even appeared in the movie Gwai Gwai.

But Saylor’s passion for innovation never waned: MicroStrategy developed software for Apple’s iPad, and built a new business around social media data scraping. He also accumulated a large number of internet domain names, including michael.com and mike.com, which are still under his control.

However, by 2014, Saylor and the company faced another wave of controversy. Discontented hedge fund investors accused Saylor of partying excessively and neglecting management. The fund pointed out to the board that Saylor had turned MicroStrategy into a “Wall Street orphan” and emphasized that the company held over $350 million in cash, which could be invested for higher returns.

An anonymous attendee recalled that Saylor met with investors accompanied by lawyers and promised to devote more energy to the company’s business. He also assured that he would find suitable uses for the idle cash.

“Breaking free from economic slavery”

However, until the outbreak of COVID-19, Saylor made little real progress in this regard. At that time, MicroStrategy still held $500 million in cash. During the pandemic, Saylor moved to Miami and started long conversations by the pool with neighbor and early crypto evangelist Eric Weiss. Both later mentioned this experience in podcasts.

Years earlier, Saylor had tweeted that Bitcoin’s days were numbered. But after about a week of discussions, he completely changed his mind. He became convinced that the Federal Reserve’s measures to respond to the pandemic would lead to dollar devaluation, creating a digital currency alternative. His distrust of existing government institutions further strengthened this view, which is a common belief in the crypto community.

In the podcast, Weiss suggested that Saylor invest a small amount of personal funds in Bitcoin. In June 2020, Saylor suddenly called Weiss, shocked to tell him he had invested $100 million in Bitcoin, when the price was around $10,000.

MicroStrategy quickly followed. In August of the same year, the company announced it would use most of its cash reserves to buy Bitcoin and repurchase shares from dissenting shareholders.

Saylor publicly described this move as “breaking free from economic slavery.”

Meanwhile, there is an important background: during the pandemic, MicroStrategy’s core software business faced difficulties, with new customer signings plummeting and revenue dropping to its lowest in twenty years.

Using balance sheet funds for external investments is not unusual. For example, insurance companies operate large investment departments, investing premiums for profit and using the proceeds for claims; large retailers often buy real estate.

But MicroStrategy’s transformation was highly aggressive. To acquire cryptocurrencies, it used almost every means: frequently issuing new shares to the public, borrowing at low interest rates, and rapidly investing the raised funds into Bitcoin.

According to the company’s financial reports, by March 2021, MicroStrategy’s Bitcoin holdings were worth $1.9 billion; a year later, this rose to $2.9 billion; by the end of 2024, it skyrocketed to $23.9 billion.

Saylor’s language also changed accordingly. He began publicly describing Strategy as a “Bitcoin reserve company,” meaning its only mission is to invest heavily in cryptocurrencies.

Some might wonder what the point of this is. After all, anyone can buy Bitcoin directly through channels.

The answer has two layers. First, thanks to Strategy’s extensive leverage, when crypto prices rise, the company’s stock price increases far more than Bitcoin itself: for every $100 worth of Strategy stock sold, the company can borrow to buy over $100 worth of Bitcoin.

Second, the type of bonds used is crucial. Most of Strategy’s borrowing is through “convertible bonds.” These bonds, upon maturity, allow investors to exchange them for company stock instead of cash.

Typically, such bonds pay interest like other bonds. But in recent years, Strategy’s stock soared so much that some investors were willing to lend at near-zero interest rates in exchange for the promise of future stock appreciation.

Thus, Strategy can finance itself at zero cost, and the funds raised are naturally used to buy more Bitcoin.

Some call this model the “flywheel effect,” others call it the “infinite money-printing loophole,” terms used by financial practitioners.

But from another perspective, it could also be seen as a looming disaster.

An economic anomaly

Over the past year, Saylor and Strategy’s situation has undergone dramatic changes. The reasons are not just the fall in Bitcoin prices. More critically, Saylor has begun targeting a broader group he calls “Bitcoin curious.”

In early 2025, Strategy launched a series of “preferred stock” products, giving them cool names like “Surge” and “Expansion.” Investors could receive fixed cash dividends ranging from 8% to 11% over a set period.

This model sounds similar to traditional corporate bonds, like airlines paying bond interest from ticket sales and using financing to buy more planes.

But Strategy’s core mission is to buy Bitcoin and wait for its appreciation. This model itself does not generate any cash flow for dividends. Only when Bitcoin prices rise and drive the stock price higher can dividends be paid easily; if Bitcoin falls, the entire cycle breaks instantly.

Despite this fatal flaw, Saylor still promotes these investment products as safe and stable. Last fall, he claimed in a podcast: “It’s not high-yield bank deposits, but it’s close.”

Alexandre Laizet, vice president of Blockchain Group, once advised Saylor and later founded a listed company in Europe using a similar financing model. Laizet called this a “major breakthrough in traditional finance.”

“Of course,” he added, “we all know it’s not a bank deposit at all.”

How will everything collapse?

Saylor attended a Bitcoin conference in Las Vegas last year

Criticism of Saylor and Strategy has long been heard.

On one hand, investors are wary of Saylor’s track record. In 2024, he agreed to pay $40 million to settle tax evasion charges with the District of Columbia. Saylor even boasted about his tax evasion methods.

Famous investors and short-sellers like James Chanos, known for exposing Enron’s scandal, have repeatedly warned. Their concerns include: Strategy’s market cap peaked at over $120 billion last summer, far exceeding the total value of its Bitcoin holdings.

This means that even if the company liquidates all assets, it would not be enough to pay off shareholders, let alone debts.

In December last year, credit rating agency S&P downgraded Strategy to junk status.

S&P pointed out that in the first half of 2025, Strategy’s $8.1 billion “profit” was entirely from paper gains on Bitcoin holdings, not traditional corporate profits.

“If Bitcoin becomes worthless tomorrow,” Saylor declared at an event in Miami last December, “whether I hold 1%, 2%, 3%, or 0.5%, it doesn’t matter; it’s all worthless anyway.”

Adding to the pressure, new challenges keep emerging. In early October last year, trade tensions between the Trump administration and China caused Bitcoin prices to plunge 24%, and thereafter, Strategy’s stock halved.

According to company disclosures, in Q4 last year, the value of Bitcoin held by Strategy shrank by $17 billion.

As of this month, Strategy’s loans and preferred stock debts have reached $21 billion.

Within the next year, the company must pay investors over $844 million.

Even larger debt repayment pressures are looming. As early as next year, holders of convertible bonds offering near-zero interest rates will have the right to convert into stock at promised prices. Strategy has guaranteed that these stocks could be worth up to $672 per share.

Currently, the stock price hovers around $171. If the stock price does not reach the promised level by then, Strategy will have to raise funds to cover the difference. Over the next three years, the total maturity of such bonds will reach $5 billion.

Saylor has long abandoned the stance of “never sell Bitcoin.” Last month, Strategy announced a new stock issuance, but unusually, the raised funds were used to stockpile over $200 million in cash as an emergency reserve. The CEO Phong Le said in a crypto podcast, “If needed, we will sell Bitcoin.” Saylor also stated that this move is “rational.” However, the company has not yet sold any Bitcoin.

Some still believe in Saylor wholeheartedly. “Denying this is the future,” said former Strategy executive Ed Juline, “is like claiming the internet was just a fleeting trend.”

On New Year’s Eve 2025, Saylor’s villa did not host the grand party of last year. A former attendee recalled that Saylor told a group that he would only hold such a celebration again if Bitcoin reached $1 million. Currently, Bitcoin trades around $95,000.

Saylor’s long-term prediction is: by 2045, Bitcoin will reach $13 million.