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

By: blockbeats|2025/02/06 08:15:04
0
Share
copy
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.

Original Article Link

You may also like

$COIN Joins S&P 500, but Coinbase Isn't Celebrating

On May 13, S&P Dow Jones Indices announced that Coinbase would officially replace Discover Financial Services in the S&P 500 on May 19. While other companies like Block and MicroStrategy, closely tied to Bitcoin, were already part of the S&P 500, Coinbase became the first cryptocurrency exchange whose primary business is in the index. This also signifies that cryptocurrency is gradually moving from the fringes to the mainstream in the U.S.



On the day of the announcement, Coinbase's stock price surged by 23%, surpassing the $250 mark. However, just 3 days later, Coinbase was hit by two consecutive events: a hack where employees were bribed to steal customer data and a demand for a $20 million ransom, and an investigation by the U.S. Securities and Exchange Commission (SEC) into the authenticity of its claim of having over 100 million "verified users" in its securities filings and marketing materials. These two events acted as mini-bombs, and at the time of writing, Coinbase's stock had already dropped by over 7.3%.


Coincidentally, Discover Financial Services, being replaced by Coinbase, can also be considered the "Coinbase" of the previous payment era. Discover is a U.S.-based digital banking and payment services company headquartered in Illinois, founded in 1960. Its payment network, Discover Network, is the fourth largest payment network apart from Visa, Mastercard, and American Express.


In April, after the approval of the acquisition of Discover by the sixth-largest U.S. bank, Capital One, this well-established digital banking company of over 60 years smoothly handed over its S&P 500 "seat" to this emerging cryptocurrency "bank." This unexpected coincidence also portrayed the handover between the new and old eras in Coinbase's entry into the S&P 500, resembling a relay race scene. However, this relay baton also brought Coinbase's accumulated "external troubles and internal strife" to a tipping point.


Side Effects of ETFs


Over the past decade, cryptocurrency exchanges have been the most stable "profit machines." They play a role in providing liquidity to the entire industry and rely on trading fees to sustain their operations. However, with the comprehensive rollout of ETF products in the U.S. market, this profit model is facing unprecedented challenges. As the leader in the "American stack," with over 80% of its business coming from the U.S., Coinbase is most affected by this.



Starting from the approval of Bitcoin and Ethereum spot ETFs, traditional financial capital has significantly onboarded users and funds that originally belonged to exchanges in a more cost-effective, compliant, and transparent manner. The transaction fee revenue of cryptocurrency exchanges has started to decline, and this trend may further intensify in the coming months.


According to Coinbase's 2024 Q4 financial report, the platform's total trading revenue was $417 million, a 45% year-on-year decrease. The contribution of BTC and ETH's trading revenue dropped from 65% in the same period last year to less than 50%.


This decline is not a result of a decrease in market enthusiasm. In fact, since the approval of the Bitcoin ETF in January 2024, the inflow of BTC into the U.S. market has continued to reach new highs, with asset management giants like BlackRock and Fidelity rapidly expanding their management scale. Data shows that BlackRock's iShares Bitcoin ETF (IBIT) alone has surpassed $17 billion in assets under management. As of mid-May 2025, the cumulative net inflow of 11 major institutional Bitcoin spot ETFs on the market has exceeded $41.5 billion, with a total net asset value of $1214.69 billion, accounting for approximately 5.91% of the total Bitcoin market capitalization.


Chart showing the trend of net outflows for Grayscale among the 11 institutions


Institutional investors and some retail investors are shifting towards ETF products, partly due to compliance and tax considerations. On one hand, ETFs have much lower trading costs compared to cryptocurrency exchanges. While Coinbase's spot trading fee rate varies annually in a tiered manner but averages around 1.49%, for example, the management fee for IBIT ETF is only 0.25%, and the majority of ETF institution fees fluctuate around 0.15% to 0.25%.



In other words, the more rational users are, the more likely they are to move from exchanges to ETF products, especially for investors aiming for long-term holdings.


According to multiple sources, several institutions, including VanEck and Grayscale, have submitted applications to the SEC for a Solana (SOL) ETF, with some institutions also planning to submit an XRP ETF proposal. Once approved, this may trigger a new round of fund migration. According to a report submitted by Coinbase to the SEC, as of April, the platform's trading revenue from XRP and Solana accounted for 18% and 10%, nearly one-third of the platform's fee revenue.



However, the Bitcoin and Ethereum ETFs passed in 2024 also reduced the fees for these two tokens on Coinbase from 30% and 15% to 26% and 10%, respectively. If the SOL and XRP ETFs are approved, it will further undermine the core fee revenue of exchanges like Coinbase.


The expansion of ETF products is gradually weakening the financial intermediary status of cryptocurrency exchanges. From their original roles as matchmakers and clearers to now gradually becoming mere "on-ramps and off-ramps" for funds, exchanges are seeing their marginal value squeezed by ETFs.


Robinhood Takes a Stand, Traditional Brokerages Join the Fray


On May 12, 2025, SEC Chairman Paul S. Atkins gave a keynote speech at the Tokenization and Cryptocurrency Working Group roundtable. The theme of his speech revolved around "It is a new day at the SEC," where he indicated that the SEC would not approach enforcement and regulation the same way as before but would instead pave the way for cryptocurrency assets in the U.S. market.



With signs of cryptocurrency compliance such as the SEC's "NEW DAY" declaration, an increasing number of traditional brokerages are attempting to enter the cryptocurrency industry. One of the most representative cases is the well-known U.S. brokerage Robinhood, which began expanding its crypto business in 2018. By the time of its IPO in 2021, Robinhood's crypto business revenue accounted for over 50% of the company, with a significant boost from the Dogecoin "moonshot" promoted by Musk.


In Q1 2025 earnings report, Robinhood showcased strong growth, especially in revenue from cryptocurrency and options trading. Fueled by Trump's Memecoin, cryptocurrency-related revenue reached $250 million, nearly doubling year-over-year. Consequently, Robinhood Gold subscription users reached 3.5 million, a 90% increase from the previous year, with the rapid growth of Robinhood Gold providing the company with a stable source of income.



Meanwhile, RobinHood is actively pursuing acquisitions in the cryptocurrency space. In 2024, it announced a $2 billion acquisition of the long-standing European cryptocurrency exchange Bitstamp. Additionally, Canada's largest cryptocurrency CEX, WonderFi, which recently went public on the Toronto Stock Exchange, also announced its integration with RobinHood Crypto. After obtaining virtual asset licenses in the UK, Canada, Singapore, and other markets, RobinHood has taken a proactive approach in the compliant cryptocurrency trading market.



Furthermore, an increasing number of brokerage firms are exploring the same path. Futu Securities, Tiger Brokers, and others are also dipping their toes into cryptocurrency trading, with some having applied for or obtained the VA license from the Hong Kong SFC. Although their user bases are currently small, traditional brokerages have a natural advantage in user trust, regulatory licenses, and low fee structures. This could pose a threat to native cryptocurrency platforms in the future.



User Data Breach: Is Coinbase Still Secure?


In April 2025, security researchers discovered that some Coinbase user data was leaked on the dark web. While the platform initially responded by attributing it to a "technical misinformation," it still raised concerns among users regarding its security and privacy protection. Just two days before Dow Jones Indexes announced Coinbase's addition to the S&P 500 Index, on May 11, 2025, Coinbase received an email from an unknown threat actor claiming to have obtained customer account information and internal documents, demanding a $20 million ransom to keep the data private. Subsequent investigations confirmed the data breach.


Cybercriminals obtained the data by bribing overseas customer service agents and support staff, mainly in "non-U.S. regions such as India." These agents abused their access to Coinbase's internal customer support system and stole customer data. As early as February this year, blockchain detective ZachXBT revealed on X platform that between December 2024 and January 2025, Coinbase users lost over $65 million to social engineering scams, with the actual amount potentially higher.


Among the victims was a well-known figure, 67-year-old Ed Suman, an established artist in the art world for nearly two decades, having been involved in the creation of artworks such as Jeff Koons' "Balloon Dog" sculpture. Earlier this year, he fell victim to an impersonation scam involving fake Coinbase customer support, resulting in a loss of over $2 million in cryptocurrency. ZachXBT critiqued Coinbase for its inadequate handling of such scams, noting that other major exchanges have not faced similar issues and recommending Coinbase to enhance its security measures.


Amidst a series of ongoing social engineering incidents, although there has not been any impact on user assets at the technical level so far, it has raised concerns among many retail and institutional investors. Especially institutions holding massive assets on Coinbase. Just considering the U.S. BTC ETF institutions, as of mid-May 2025, they collectively hold nearly 840,000 BTC, and 75% of these are custodied by Coinbase. If we price BTC at $100,000, this amount reaches a staggering $63 billion, which is equivalent to the nominal GDP of two Iceland in the year 2024.


Visualization: ChatGPT, Source: Farside


In addition, Coinbase Custody also serves over 300 institutional clients, including hedge funds, family offices, pension funds, and endowments. As of the Q1 2025 financial report, Coinbase's total assets under management (including institutional and retail clients) reached $404 billion. The specific amount of institutional custodied assets was not explicitly disclosed in the latest report, but it should still be over 50% based on the Q4 2024 report.


Visualization: ChatGPT


Once this security barrier is breached, not only could the rate of user attrition far exceed expectations, but more importantly, institutional trust in it would undermine the foundation of its business. Therefore, after a hacking event, Coinbase's stock price plummeted significantly.


CEXs are All in Self-Rescue Mode


Facing a decline in spot trading fee revenue, Coinbase is also accelerating its transformation, attempting to find growth opportunities in derivatives and emerging assets. Coinbase acquired a stake in the options platform Deribit at the end of 2024 and announced the official launch of perpetual contract products in 2025. This acquisition fills in Coinbase's gap in options trading and its relatively small global market share.



Deribit has a strong presence in non-U.S. markets, especially in Asia and Europe. The acquisition has enabled Coinbase to gain a dominant position in bitcoin and ethereum options trading on Deribit, accounting for approximately 80% of the global options trading volume, with daily trading volume remaining above $2 billion.


Meanwhile, 80-90% of Deribit's customer base consists of institutional investors, with their professionalism and liquidity in the Bitcoin and Ethereum options market highly favored by institutions. Coinbase's compliance advantage, coupled with its already robust institutional ecosystem, makes it even more suitable. By using institutions as an entry point, it can face the squeeze from giants like Binance and OKX in the derivatives market.



Facing a similar dilemma is Kraken, which is attempting to replicate Binance Futures' model in non-U.S. markets. Since the derivatives market relies more on professional users, fee rates are relatively higher and stickiness is stronger, making it a significant source of revenue for exchanges. In the first half of 2025, Kraken completed the acquisition of TradeStation Crypto and a futures exchange, aiming to build a complete derivatives trading ecosystem to hedge the risk of declining spot transaction fee income.


With the surge of Memecoin in 2024, Binance, OKX, and various CEX platforms began massively listing small-market-cap, highly volatile tokens to activate active trading users. Due to the wealth effect and trading activity of Memecoins, Coinbase was also forced to join the battle, successively listing popular tokens from the Solana ecosystem such as BOOK OF MEME and Dogwifhat. Although these coins are controversial, they are frequently traded, with fee rates several times higher than mainstream coins, serving as a "blood-boosting" method for spot trading.


However, due to its status as a publicly traded company, this practice is a riskier endeavor for Coinbase. Even in the current crypto-friendly environment, the SEC is still investigating whether tokens like SOL, ADA, and SAND constitute securities.


In addition to the forced transformation strategies carried out by the aforementioned CEXs, they are also starting to lay out RWAs and the most talked-about stablecoin payment fields, such as the PYUSD launched through a collaboration between Coinbase and Paypal, Coinbase's support for the Euro stablecoin EURC by Circle that complies with EU MiCA regulatory requirements, or the USD1 launched through a collaboration between Binance and WIFL. In the increasingly crowded trading field, many CEXs have shifted their focus from just the trading market to the application field.


The golden age of transaction fees has quietly ended, and the second half of the crypto exchange platform game has silently begun.


Arthur Hayes: Why I'm Betting on ETH While the Market Is Obsessed with SOL

"I personally have also allocated 20% to gold, expecting the price of gold to potentially rise to $10,000-20,000 by the end of this market cycle."

Key Market Insights for May 16th, how much did you miss out on?

1. On-chain Flows: $111.3M inflow to Ethereum this week; $237.6M outflow from Berachain 2. Largest Price Swings: $ETHFI, $NEIRO 3. Top News: Data: Solana Network's revenue reached $7.9M on the 13th, surpassing the sum of all other L1 and L2 chains

CryptoPunks Changes Hands Twice, Did the Originator of NFTs Finally Find Its "Forever Home" This Time?

The original NFT pioneer CryptoPunks has once again officially changed ownership after being sold to the Bored Ape Yacht Club (BAYC) developer Yuga Labs.

May 16 Key Market Information Gap, A Must-Read! | Alpha Morning Report

1. Top News: Coinbase Faces Double Blow with 'SEC Investigation' and 'User Data Breach,' Stock Price Drops by 7.2% 2. Token Unlocking: $ARB, $AVAX, $PRIME, $ASTR, $1INCH

MOG Coin Skyrockets as Elon Musk and Garry Tan Embrace "mog/acc" Identity

「mog/acc」 is rapidly sweeping through various figures, from Elon Musk to Garry Tan, boosting the project's visibility and ultimately driving up the price.

Popular coins

Latest Crypto News

Read more