WSJ: Making Billions Overnight, He Bets Big on Bitcoin to Turn It Around

By: blockbeats|2025/02/06 16:15:04
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Original Title: The Man Making Billions From the Wildest Bitcoin Bet
Original Author: Gregory Zuckerman, WSJ
Translation: Luffy, Foresight News

WSJ: Making Billions Overnight, He Bets Big on Bitcoin to Turn It Around

MicroStrategy CEO Michael Saylor

Michael Saylor's company has not launched any popular products or services. What he and MicroStrategy have done is to sell new shares and bonds at a historically rapid pace, then invest all the funds in Bitcoin, vowing to do so repeatedly.

Over the past year, MicroStrategy's stock price has risen by about 690%. The 59-year-old chairman holds about 10% of the company, worth around $9.7 billion, and personally holds about $1.9 billion worth of Bitcoin.

Saylor has become a public face of the recent Bitcoin frenzy, with nearly 4 million followers on X Platform (formerly Twitter). To celebrate Bitcoin breaking $100,000, Saylor hosted a New Year's Eve party at his waterfront mansion in Miami, inviting hundreds of cryptocurrency community members, with his luxury yacht moored nearby. At the party, six dancers dressed in gold costumes performed. Prominent figures from various fields and investment heavyweights gathered, including former Legg Mason fund manager Bill Miller, Fortress Investment Group Chairman Peter Briger, and Capital Group's key portfolio manager Mark Casey. The event was live-streamed on YouTube to tens of thousands of Bitcoin enthusiasts, with Saylor hosting the party in a black suit jacket and a Bitcoin-themed T-shirt.

The enthusiasm for Saylor's company is so high that it has led to a perplexing situation: MicroStrategy holds about $47 billion worth of Bitcoin, but its stock market value has reached $97 billion. It's as if investors were spending $2 to buy a $1 bill. Equally surprising is that experienced investors are among the largest buyers, including the well-established mutual fund company Capital Group, which held about 8% of MicroStrategy as of September 30, and Norway Bank Investment Management, managing $1.5 trillion in assets from the Norwegian Government Pension Fund, holding nearly 1% of MicroStrategy.

Fans say that this premium reflects their belief that Saylor will continue to profit from his Bitcoin bet. They believe that Bitcoin's limited total supply of 21 million coins will increase its value. SYZ Capital partner Richard Byworth holds MicroStrategy stock personally and states that Saylor, by issuing stock at a high price and selling bonds to the company at favorable terms, is able to create value for shareholders while expanding MicroStrategy's Bitcoin reserves.

"This premium is reasonable and will continue to exist," said Wall Street veteran Jordi Visser, who previously worked at Morgan Stanley and recently bought MicroStrategy stock. "No other company can do what he has done. They now own about 2% of the Bitcoin supply; who else can own more?"

However, Saylor's strategy also comes with significant risks. He has ridden the investment waves, sometimes losing billions of dollars of personal wealth in a single day when the wave peaks and crashes.

Saylor declined to comment for this article.

Saylor, who has never been married, will turn 60 next month. He has faced setbacks in his career and clashed with financial regulatory authorities. Last year, he agreed to pay $40 million to the District of Columbia to settle an income tax dispute. Previously, Washington officials claimed he was, in fact, a District resident, not a resident of Florida or Virginia as he had claimed, and therefore should pay taxes to the District.

Saylor's father was a career Air Force officer. Saylor studied Aeronautics and Astronautics at MIT and participated in the Air Force Reserve Officer Training Corps. A few years after graduation, in 1989, he co-founded MicroStrategy in Tyson's Corner, Virginia, with a college friend. It started as a data mining software company.

During the late 1990s Internet bubble, MicroStrategy rose rapidly. His stock was worth about $10 billion, enough for him to throw lavish parties for employees and others, as well as organize Caribbean cruises. MicroStrategy also bought domain names such as Mike.com, Michael.com, Hope.com, and Voice.com, selling Voice.com for $30 million.

But everything came crashing down when the Internet bubble burst in 2000. As regulators examined industry revenue recognition practices, MicroStrategy was forced to restate its revenue and earnings. The failure was so dramatic that it even caught the attention of tabloids: in March of that year, the New York Daily News ran a story titled "Loses $6 Billion in a Day" with a photo of the then 35-year-old Saylor, looking neat in a suit and tie but with a bewildered expression on his face.

Saylor has always been a prominent figure in the Bitcoin space, and the above image shows him speaking at a conference in 2023

Later that year, Saylor, along with two other executives and the company, paid $11 million to settle accounting fraud charges brought by the U.S. Securities and Exchange Commission (SEC) over a financial restatement. The SEC alleged that the company had overstated its revenue and income, showing profits instead of losses, but Saylor and others neither admitted nor denied the allegations.

In July 2002, MicroStrategy's stock closed at 45 cents, a significant drop from its peak of $313 in 2000, and the company was facing debt issues.

During a lunch at a Hamptons villa in New York, venture capitalist Rick Rickertsen expressed sympathy to Saylor and asked him if he was worried about losing his company.

“It’s possible,” Saylor said, “but I would start over.”

Saylor restructured MicroStrategy's debt and implemented a 10-for-1 stock split to avert the crisis. Over the years, Saylor had been on the lookout for the next big opportunity. At one point, he made a significant personal gain by investing in stocks like Google and Apple, but he dismissed Bitcoin, once tweeting in 2013 that Bitcoin was “days numbered.”

By 2020, MicroStrategy's stock had remained almost unchanged for years with dim growth prospects. The company had a market capitalization of only $1.5 billion but was still profitable with around $500 million in cash.

During the COVID-19 pandemic in 2020, Saylor contemplated what to do with the company's cash from his home in Miami. Concerned that government spending to maintain economic stability might lead to inflation, Saylor revisited Bitcoin and became a staunch supporter. Soon, he proposed to the board to buy Bitcoin with the cash, a move the board agreed to mainly because the company seemed to have no better options. They believed that at least this move would attract some beneficial attention.

“The company was at a standstill at the time, with little to no Wall Street attention,” Rickertsen, who later became a board member, said. “The future looked bleak.”

That year, Saylor took half of the company's cash, about $250 million, and bought Bitcoin at a price of around $11,000 per coin. He himself also put in over $100 million. However, the Bitcoin price soon dropped to $9,000, resulting in a paper loss of about $40 million for MicroStrategy.

"Most of our board members were like, 'Oh my God, what have we done, we're going to get sued,'" Rickertsen said, "Saylor was also very worried."

This panic did not last long. The price of Bitcoin started to rise, breaking $26,000 by the end of 2020. MicroStrategy borrowed billions of dollars to buy more Bitcoin, including a $205 million loan at a floating interest rate of 8.27%, which was challenging loan terms at the time.

Then, by the end of 2022, the cryptocurrency exchange FTX collapsed, causing the Bitcoin price to drop below $17,000, and MicroStrategy's stock price also fell to around $17. The company's cost basis for the held Bitcoin was around $30,000, resulting in a paper loss. Rumors spread that the company was in trouble. However, Saylor and the company doubled down on their bet.

With Saylor doubling down on the strategy of raising funds through stock and bond offerings to purchase Bitcoin, and with the continued rise in the price of Bitcoin, the company's stock price began to soar. According to investment bank Benchmark Company analyst Mark Palmer, in just 2024, MicroStrategy raised $23.2 billion through stock and bond sales.

Saylor's rhetoric may be somewhat repetitive and simplistic, but his belief in Bitcoin has always been unwavering. He emphasizes that Bitcoin's supply is limited, a characteristic that sets it apart from the U.S. dollar and even gold. Saylor believes this makes Bitcoin perform better in resisting inflation. He also states that Bitcoin's digital nature makes it more convenient and cost-effective for holders to store and use, without the need for intermediaries, making it a "revolutionary" form of currency.

Some mutual funds and other institutions have internal rules prohibiting the purchase of Bitcoin and Bitcoin ETFs, making MicroStrategy's stock their indirect path to betting on Bitcoin. Even some large conservative investors view the stock as a potential way to gain an advantage over competitors who are unwilling to enter the cryptocurrency space.

Indeed, Saylor is adept at creating various types of equity and debt investment products, such as bank loans, convertible bonds, common stock, etc., to ensure a continuous influx of funds.

“His genius is in creating different products for different audiences,” said Brett Messing, a partner at SkyBridge Capital, a firm that manages funds with significant Bitcoin investments and provides advisory services to a fund holding MicroStrategy stock.

Over the past month or so, Saylor has been aggressively promoting MicroStrategy and Bitcoin on TV shows, popular podcasts, industry conferences, and other venues. “If you’re not buying Bitcoin at the highs, you’re missing out on an opportunity to make money,” he recently tweeted.

“He’s bombastic in public and detailed in private,” said Matt Hougan, Chief Investment Officer at Bitwise Asset Management, recounting how last summer, he heard Saylor speak at a dinner with 12 investors. His firm manages an ETF holding MicroStrategy stock.

If Bitcoin continues to rise, the premium on holding MicroStrategy stock may persist. However, if Bitcoin prices crash, MicroStrategy’s stock may follow suit. Even if the premium disappears, the stock could still be affected as long as Bitcoin prices remain stable. Skeptics point out that similar investment vehicles, such as closed-end funds, often trade below the value of their underlying assets, not at a premium.

Nevertheless, the company may not be facing a going-concern issue. MicroStrategy currently has $7.26 billion in unsecured debt, most of which is issued at very low rates. The company holds 450,000 Bitcoins at an average cost of around $62,000 per coin. The value of the Bitcoins held by the company would only fall below its debt if Bitcoin dropped below $16,000 and stayed around that level at debt maturity.

Just over a week ago, Saylor unveiled a novel way for MicroStrategy to raise funds from investors to support its Bitcoin purchase plans. He announced that the company would issue $2 billion in “perpetual preferred stock” this quarter. The news prompted analyst Palmer to reiterate his $650 price target for MicroStrategy stock, about 65% above the current price.

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China's Central Bank and Eight Other Departments' Latest Regulatory Focus: Key Attention to RWA Tokenized Asset Risk


Foreword: Today, the People's Bank of China's website published the "Notice of the People's Bank of China, National Development and Reform Commission, Ministry of Industry and Information Technology, Ministry of Public Security, State Administration for Market Regulation, China Banking and Insurance Regulatory Commission, China Securities Regulatory Commission, State Administration of Foreign Exchange on Further Preventing and Dealing with Risks Related to Virtual Currency and Others (Yinfa [2026] No. 42)", the latest regulatory requirements from the eight departments including the central bank, which are basically consistent with the regulatory requirements of recent years. The main focus of the regulation is on speculative activities such as virtual currency trading, exchanges, ICOs, overseas platform services, and this time, regulatory oversight of RWA has been added, explicitly prohibiting RWA tokenization, stablecoins (especially those pegged to the RMB). The following is the full text:


To the people's governments of all provinces, autonomous regions, and municipalities directly under the Central Government, the Xinjiang Production and Construction Corps:


  Recently, there have been speculative activities related to virtual currency and Real-World Assets (RWA) tokenization, disrupting the economic and financial order and jeopardizing the property security of the people. In order to further prevent and address the risks related to virtual currency and Real-World Assets tokenization, effectively safeguard national security and social stability, in accordance with the "Law of the People's Republic of China on the People's Bank of China," "Law of the People's Republic of China on Commercial Banks," "Securities Law of the People's Republic of China," "Law of the People's Republic of China on Securities Investment Funds," "Law of the People's Republic of China on Futures and Derivatives," "Cybersecurity Law of the People's Republic of China," "Regulations of the People's Republic of China on the Administration of Renminbi," "Regulations on Prevention and Disposal of Illegal Fundraising," "Regulations of the People's Republic of China on Foreign Exchange Administration," "Telecommunications Regulations of the People's Republic of China," and other provisions, after reaching consensus with the Cyberspace Administration of China, the Supreme People's Court, and the Supreme People's Procuratorate, and with the approval of the State Council, the relevant matters are notified as follows:


  I. Clarify the essential attributes of virtual currency, Real-World Assets tokenization, and related business activities


  (I) Virtual currency does not possess the legal status equivalent to fiat currency. Virtual currencies such as Bitcoin, Ether, Tether, etc., have the main characteristics of being issued by non-monetary authorities, using encryption technology and distributed ledger or similar technology, existing in digital form, etc. They do not have legal tender status, should not and cannot be circulated and used as currency in the market.


  The business activities related to virtual currency are classified as illegal financial activities. The exchange of fiat currency and virtual currency within the territory, exchange of virtual currencies, acting as a central counterparty in buying and selling virtual currencies, providing information intermediary and pricing services for virtual currency transactions, token issuance financing, and trading of virtual currency-related financial products, etc., fall under illegal financial activities, such as suspected illegal issuance of token vouchers, unauthorized public issuance of securities, illegal operation of securities and futures business, illegal fundraising, etc., are strictly prohibited across the board and resolutely banned in accordance with the law. Overseas entities and individuals are not allowed to provide virtual currency-related services to domestic entities in any form.


  A stablecoin pegged to a fiat currency indirectly fulfills some functions of the fiat currency in circulation. Without the consent of relevant authorities in accordance with the law and regulations, any domestic or foreign entity or individual is not allowed to issue a RMB-pegged stablecoin overseas.


(II)Tokenization of Real-World Assets refers to the use of encryption technology and distributed ledger or similar technologies to transform ownership rights, income rights, etc., of assets into tokens (tokens) or other interests or bond certificates with token (token) characteristics, and carry out issuance and trading activities.


  Engaging in the tokenization of real-world assets domestically, as well as providing related intermediary, information technology services, etc., which are suspected of illegal issuance of token vouchers, unauthorized public offering of securities, illegal operation of securities and futures business, illegal fundraising, and other illegal financial activities, shall be prohibited; except for relevant business activities carried out with the approval of the competent authorities in accordance with the law and regulations and relying on specific financial infrastructures. Overseas entities and individuals are not allowed to illegally provide services related to the tokenization of real-world assets to domestic entities in any form.


  II. Sound Work Mechanism


  (III) Inter-agency Coordination. The People's Bank of China, together with the National Development and Reform Commission, the Ministry of Industry and Information Technology, the Ministry of Public Security, the State Administration for Market Regulation, the China Banking and Insurance Regulatory Commission, the China Securities Regulatory Commission, the State Administration of Foreign Exchange, and other departments, will improve the work mechanism, strengthen coordination with the Cyberspace Administration of China, the Supreme People's Court, and the Supreme People's Procuratorate, coordinate efforts, and overall guide regions to carry out risk prevention and disposal of virtual currency-related illegal financial activities.


  The China Securities Regulatory Commission, together with the National Development and Reform Commission, the Ministry of Industry and Information Technology, the Ministry of Public Security, the People's Bank of China, the State Administration for Market Regulation, the China Banking and Insurance Regulatory Commission, the State Administration of Foreign Exchange, and other departments, will improve the work mechanism, strengthen coordination with the Cyberspace Administration of China, the Supreme People's Court, and the Supreme People's Procuratorate, coordinate efforts, and overall guide regions to carry out risk prevention and disposal of illegal financial activities related to the tokenization of real-world assets.


  (IV) Strengthening Local Implementation. The people's governments at the provincial level are overall responsible for the prevention and disposal of risks related to virtual currencies and the tokenization of real-world assets in their respective administrative regions. The specific leading department is the local financial regulatory department, with participation from branches and dispatched institutions of the State Council's financial regulatory department, telecommunications regulators, public security, market supervision, and other departments, in coordination with cyberspace departments, courts, and procuratorates, to improve the normalization of the work mechanism, effectively connect with the relevant work mechanisms of central departments, form a cooperative and coordinated working pattern between central and local governments, effectively prevent and properly handle risks related to virtual currencies and the tokenization of real-world assets, and maintain economic and financial order and social stability.


  III. Strengthened Risk Monitoring, Prevention, and Disposal


  (5) Enhanced Risk Monitoring. The People's Bank of China, China Securities Regulatory Commission, National Development and Reform Commission, Ministry of Industry and Information Technology, Ministry of Public Security, State Administration of Foreign Exchange, Cyberspace Administration of China, and other departments continue to improve monitoring techniques and system support, enhance cross-departmental data analysis and sharing, establish sound information sharing and cross-validation mechanisms, promptly grasp the risk situation of activities related to virtual currency and real-world asset tokenization. Local governments at all levels give full play to the role of local monitoring and early warning mechanisms. Local financial regulatory authorities, together with branches and agencies of the State Council's financial regulatory authorities, as well as departments of cyberspace and public security, ensure effective connection between online monitoring, offline investigation, and fund tracking, efficiently and accurately identify activities related to virtual currency and real-world asset tokenization, promptly share risk information, improve early warning information dissemination, verification, and rapid response mechanisms.


  (6) Strengthened Oversight of Financial Institutions, Intermediaries, and Technology Service Providers. Financial institutions (including non-bank payment institutions) are prohibited from providing account opening, fund transfer, and clearing services for virtual currency-related business activities, issuing and selling financial products related to virtual currency, including virtual currency and related financial products in the scope of collateral, conducting insurance business related to virtual currency, or including virtual currency in the scope of insurance liability. Financial institutions (including non-bank payment institutions) are prohibited from providing custody, clearing, and settlement services for unauthorized real-world asset tokenization-related business and related financial products. Relevant intermediary institutions and information technology service providers are prohibited from providing intermediary, technical, or other services for unauthorized real-world asset tokenization-related businesses and related financial products.


  (7) Enhanced Management of Internet Information Content and Access. Internet enterprises are prohibited from providing online business venues, commercial displays, marketing, advertising, or paid traffic diversion services for virtual currency and real-world asset tokenization-related business activities. Upon discovering clues of illegal activities, they should promptly report to relevant departments and provide technical support and assistance for related investigations and inquiries. Based on the clues transferred by the financial regulatory authorities, the cyberspace administration, telecommunications authorities, and public security departments should promptly close and deal with websites, mobile applications (including mini-programs), and public accounts engaged in virtual currency and real-world asset tokenization-related business activities in accordance with the law.


  (8) Strengthened Entity Registration and Advertisement Management. Market supervision departments strengthen entity registration and management, and enterprise and individual business registrations must not contain terms such as "virtual currency," "virtual asset," "cryptocurrency," "crypto asset," "stablecoin," "real-world asset tokenization," or "RWA" in their names or business scopes. Market supervision departments, together with financial regulatory authorities, legally enhance the supervision of advertisements related to virtual currency and real-world asset tokenization, promptly investigating and handling relevant illegal advertisements.


  (IX) Continued Rectification of Virtual Currency Mining Activities. The National Development and Reform Commission, together with relevant departments, strictly controls virtual currency mining activities, continuously promotes the rectification of virtual currency mining activities. The people's governments of various provinces take overall responsibility for the rectification of "mining" within their respective administrative regions. In accordance with the requirements of the National Development and Reform Commission and other departments in the "Notice on the Rectification of Virtual Currency Mining Activities" (NDRC Energy-saving Building [2021] No. 1283) and the provisions of the "Guidance Catalog for Industrial Structure Adjustment (2024 Edition)," a comprehensive review, investigation, and closure of existing virtual currency mining projects are conducted, new mining projects are strictly prohibited, and mining machine production enterprises are strictly prohibited from providing mining machine sales and other services within the country.


  (X) Severe Crackdown on Related Illegal Financial Activities. Upon discovering clues to illegal financial activities related to virtual currency and the tokenization of real-world assets, local financial regulatory authorities, branches of the State Council's financial regulatory authorities, and other relevant departments promptly investigate, determine, and properly handle the issues in accordance with the law, and seriously hold the relevant entities and individuals legally responsible. Those suspected of crimes are transferred to the judicial authorities for processing according to the law.


 (XI) Severe Crackdown on Related Illegal and Criminal Activities. The Ministry of Public Security, the People's Bank of China, the State Administration for Market Regulation, the China Banking and Insurance Regulatory Commission, the China Securities Regulatory Commission, as well as judicial and procuratorial organs, in accordance with their respective responsibilities, rigorously crack down on illegal and criminal activities related to virtual currency, the tokenization of real-world assets, such as fraud, money laundering, illegal business operations, pyramid schemes, illegal fundraising, and other illegal and criminal activities carried out under the guise of virtual currency, the tokenization of real-world assets, etc.


  (XII) Strengthen Industry Self-discipline. Relevant industry associations should enhance membership management and policy advocacy, based on their own responsibilities, advocate and urge member units to resist illegal financial activities related to virtual currency and the tokenization of real-world assets. Member units that violate regulatory policies and industry self-discipline rules are to be disciplined in accordance with relevant self-regulatory management regulations. By leveraging various industry infrastructure, conduct risk monitoring related to virtual currency, the tokenization of real-world assets, and promptly transfer issue clues to relevant departments.


  IV. Strict Supervision of Domestic Entities Engaging in Overseas Business Activities


(XIII) Without the approval of relevant departments in accordance with the law and regulations, domestic entities and foreign entities controlled by them may not issue virtual currency overseas.


  (XIV) Domestic entities engaging directly or indirectly in overseas external debt-based tokenization of real-world assets, or conducting asset securitization activities abroad based on domestic ownership rights, income rights, etc. (hereinafter referred to as domestic equity), should be strictly regulated in accordance with the principles of "same business, same risk, same rules." The National Development and Reform Commission, the China Securities Regulatory Commission, the State Administration of Foreign Exchange, and other relevant departments regulate it according to their respective responsibilities. For other forms of overseas real-world asset tokenization activities based on domestic equity by domestic entities, the China Securities Regulatory Commission, together with relevant departments, supervise according to their division of responsibilities. Without the consent and filing of relevant departments, no unit or individual may engage in the above-mentioned business.


  (15) Overseas subsidiaries and branches of domestic financial institutions providing Real World Asset Tokenization-related services overseas shall do so legally and prudently. They shall have professional personnel and systems in place to effectively mitigate business risks, strictly implement customer onboarding, suitability management, anti-money laundering requirements, and incorporate them into the domestic financial institutions' compliance and risk management system. Intermediaries and information technology service providers offering Real World Asset Tokenization services abroad based on domestic equity or conducting Real World Asset Tokenization business in the form of overseas debt for domestic entities directly or indirectly venturing abroad must strictly comply with relevant laws and regulations. They should establish and improve relevant compliance and internal control systems in accordance with relevant normative requirements, strengthen business and risk control, and report the business developments to the relevant regulatory authorities for approval or filing.


  V. Strengthen Organizational Implementation


  (16) Strengthen organizational leadership and overall coordination. All departments and regions should attach great importance to the prevention of risks related to virtual currencies and Real World Asset Tokenization, strengthen organizational leadership, clarify work responsibilities, form a long-term effective working mechanism with centralized coordination, local implementation, and shared responsibilities, maintain high pressure, dynamically monitor risks, effectively prevent and mitigate risks in an orderly and efficient manner, legally protect the property security of the people, and make every effort to maintain economic and financial order and social stability.


  (17) Widely carry out publicity and education. All departments, regions, and industry associations should make full use of various media and other communication channels to disseminate information through legal and policy interpretation, analysis of typical cases, and education on investment risks, etc. They should promote the illegality and harm of virtual currencies and Real World Asset Tokenization-related businesses and their manifestations, fully alert to potential risks and hidden dangers, and enhance public awareness and identification capabilities for risk prevention.


  VI. Legal Responsibility


  (18) Engaging in illegal financial activities related to virtual currencies and Real World Asset Tokenization in violation of this notice, as well as providing services for virtual currencies and Real World Asset Tokenization-related businesses, shall be punished in accordance with relevant regulations. If it constitutes a crime, criminal liability shall be pursued according to the law. For domestic entities and individuals who knowingly or should have known that overseas entities illegally provided virtual currency or Real World Asset Tokenization-related services to domestic entities and still assisted them, relevant responsibilities shall be pursued according to the law. If it constitutes a crime, criminal liability shall be pursued according to the law.


  (19) If any unit or individual invests in virtual currencies, Real World Asset Tokens, and related financial products against public order and good customs, the relevant civil legal actions shall be invalid, and any resulting losses shall be borne by them. If there are suspicions of disrupting financial order and jeopardizing financial security, the relevant departments shall deal with them according to the law.


  This notice shall enter into force upon the date of its issuance. The People's Bank of China and ten other departments' "Notice on Further Preventing and Dealing with the Risks of Virtual Currency Trading Speculation" (Yinfa [2021] No. 237) is hereby repealed.


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