Billionaire Michael Thaler has been in trouble before, but never like this. The stock price of Saylor’s company Strategy, which owns more than 3% of the world’s Bitcoin share, fell sharply. To make matters worse, the company faces the dual headwinds of a bearish cryptocurrency market and impending rule changes, which could trigger a massive sell-off in its stock. On Monday, the company announced a $1.2 billion reserve fund to meet upcoming interest and dividend obligations, but that did little to boost its stock price. All of this has prompted new attacks from Thaler’s critics, who say Strategy’s unusual business model, which revolves around selling stock to buy Bitcoin, is unsustainable or even a Ponzi scheme.
Thaler has weathered storms in the past. They included an accounting scandal in 2000 that nearly bankrupted one of his previous companies and left him in dire straits. $6 billion in losses His personal fortune in one day. Thaler’s defenders, meanwhile, view critics as knee-jerk Bitcoin detractors who don’t understand the currency or the corporate finance techniques behind Strategy’s operations.
Siler will probably get out of this jam like he has in the past, but the stakes are higher this time. Strategy’s acquisitions have helped fuel the cryptocurrency’s record gains in recent years and made Saylor a major evangelist for Bitcoin. That means any move by Strategy to sell off some of its holdings – something its CEO suggested last week might happen – would not only depress prices but could trigger a crisis of confidence and a broader sell-off. Meanwhile, a further plunge in Strategy’s stock price could not only threaten its future viability but also lead to the collapse of dozens of other companies that emulate its business model. The coming months may prove once and for all whether Thaler is a pioneer in the crypto-finance space, as his supporters claim, or just another high-stakes gambler whose luck has run out.
An $8 billion sell-off looms
The cryptocurrency industry likes to refer to October as “uptoberbut failed to deliver its usual double-digit price gains this year. Instead, the month brought one of the largest losses in the history of the industry, and for Strategy, the month brought additional bad news, with financial giant MSCI proposing a new rule on October 10 to exclude it from a series of popular indexes.
The delisting process, expected to take effect in February, will force fund managers around the world to sell off their holdings in Strategy and other companies whose assets contain 50% or more of cryptocurrencies. November, JPMorgan warns The rule change could lead funds to sell $2.3 billion worth of Strategy shares, with the selloff potentially climbing to Over $8 billion If other index compilers follow MSCI’s example.
Growing awareness of MSCI’s plans has triggered a sell-off. Shares of MSTR (the MSTR ticker reflects Strategy’s previous name, Microstrategy) are down about 50% since Oct. 1. This has caused a key metric called mNAV, which reflects the value of a cryptocurrency company’s shares relative to its Bitcoin holdings, to fall below 1 multiple times recently. For a company whose mNAV reached around 2.45 mNAV a year ago, the current numbers highlight that Strategy stock’s long-term premium over Bitcoin has disappeared.
In response to so much bad news, most CEOs issued a series of low-key statements asking for patience. But Thaler is no ordinary CEO, and he responded by increasing the number of memes he posted on social media. The memes glorified Bitcoin and depicted Thaler in an AI-generated action hero pose, which led to many of his followers retweeting the memes or posting their own versions of the memes.
These meme strategies have served Thaler well in the past, turning strategies into momentum plays during bull markets. But the stunt has failed to stem the stock’s recent slump, with Thaler posting a rare gaffe on social media last month. To counter rumors that the company was selling Bitcoin, Thaler shared a photo of himself riding a life preserver in stormy seas as a burning ocean liner sank behind him. Critics, including Thaler fans, pointed out that the meme suggested that the Captain of the Strategy rescued himself when he got into trouble, rather than sinking with his ship.
long term holding pic.twitter.com/sQysm4i88t
— Michael Saylor (@saylor) November 14, 2025
Regardless of Thaler’s intentions, the minor controversy raised questions about whether Strategy would sell its Bitcoin holdings — a move the company said was unthinkable but which in recent weeks seemed prepared to accept.
Sell Stocks to Buy Bitcoin
At the end of November, Strategy acquired 130 Bitcoins, bringing its total reserves to 650,000, which at early December prices would be worth approximately $58.5 billion. For context, this equates to around 3.1% of Bitcoin Total supply: 21 million coins (95% of which has been mined) and makes Strategy the largest holder of the currency, aside from its creator Satoshi Nakamoto, whose 1.1 million coins are believed to have been lost forever.
According to Saylor, the company paid an average price of $74,436 per Bitcoin and spent a total of approximately $48.4 billion, including fees and expenses. In order to achieve this goal, Strategy needs a source of capital, and given that Bitcoin does not generate any revenue, the company’s preferred strategy is to sell common stock to fund its purchases.
A big advantage of this approach is that, unlike debt, common stock does not impose any financial obligations on the company. That’s not the case with preferred shares, of which Strategy also issues a large amount, forcing it to pay regular dividends to shareholders. Those obligations include about $200 million in payments due as of Dec. 31, most of which is owed in the form of dividends (Strategy, like most companies, also carries some debt).
To project a sense of financial stability, Strategy took the unusual step of building up what it called $1.4 billion in U.S. dollar reserves in early December, which Saylor said would be enough to cover its dividend obligations for the next 21 months.
Saylor announced the reserve fund during a Dec. 1 investor presentation, adding with typical bravado, “We intend to continue to accumulate Bitcoin.” However, in the near future, this goal may become desirable and Strategy may find itself selling Bitcoin instead.
“We can sell Bitcoin and we will sell Bitcoin if we need to fund dividend payments below 1x mNAV,” Strategy CEO Phong Le said in a statement. podcast Last Friday. This is an extraordinary statement from a company that is predicated on the ever-increasing value of Bitcoin. More notably, Thaler, who often exhorts people to hold Bitcoin with the buzzword “HODL,” reiterated on Monday that Strategy may sell some Bitcoin.
On Tuesday, Strategy CFO Andrew Kang qualified the statement, saying the company plans to treat Bitcoin as a last resort and only if mNAV remains below 1 for “an extended period of time.”
Regardless of the specifics, Strategy’s admission that Bitcoin could be sold in conjunction with a new U.S. dollar reserve fund sparked a new wave of vitriol from Strategy’s critics. Among them was gold industry advocate and long-time cryptocurrency critic Peter Schiff, who claimed that the company was headed for bankruptcy and that Thaler was Wall Street’s “biggest liar.”
Today is the beginning of the end $mstrer. Saylor was forced to sell shares and, instead of buying Bitcoin, purchased U.S. dollars simply to fund MSTR’s interest and dividend obligations. The stock is broken. the business model is a fraud, and @saylor He is the biggest liar on Wall Street.
— Peter Schiff (@PeterSchiff) December 1, 2025
If Schiff’s view (which is hard to agree on) is correct and Strategy must liquidate, the broader cryptocurrency market could be hit hard, as the sell-off will almost certainly trigger a downward spiral in Bitcoin prices. Even if Strategy Group only sells part of its holdings, it could trigger a chain reaction hundreds Other so-called digital asset treasuries (data transmission technology) do the same thing.
But even as skeptics label Strategy and the DAT model as houses of cards built on financial deception, others see them as early leaders in the emerging cryptocurrency banking category.
“That’s where all the bad news is”
Whatever one thinks of Seiler, there’s no denying that he’s a natural performer. In a speech announcing the new dollar reserve on December 1, he showed off a futuristic spaceship in bright green and orange colors with a Bitcoin-powered reactor at its core. “Think of (the dollar reserve) as a dollar battery. We’re basically using a nuclear reactor to spin a generator to charge the battery,” Thaler explained.
strategy
To Thaler’s critics, all of this smacks of the worst kind of sales pitch. Others saw a visionary using compelling metaphors and images to help the public understand complex new financial mechanisms.
The latter includes Sebastian Bea, a former long-term BlackRock executive and Olympic rower and current president of digital asset library ReserveOne. Bea said Saylor is pursuing a sophisticated long-term strategy and has a team of corporate finance experts, including board member Peter Briger, who has a distinguished career at Goldman Sachs and Fortress Investment Group.
Against this backdrop, Thaler’s plan to purchase the growing supply of Bitcoin by accessing capital markets to purchase stocks, commodities, and derivatives makes sense. As he and Strategy’s chief financial officer explained this week, the plan includes bringing in revenue by lending Bitcoin and selling covered call options.
However, for this to work, the value of Bitcoin must continue to appreciate. The concept strikes crypto skeptics as absurd, but cryptocurrency advocates rightly point out that Bitcoin has grown faster than almost any other asset over the past decade, and with the emergence of large entities like sovereign wealth funds, Bitcoin is poised for long-term gains. University Endowment Fund Add it to their portfolio. In the latest bullish sign, Vanguard Group, which for years resisted adding cryptocurrencies to its portfolio –Choose to add Bitcoin and other cryptocurrency ETFs this week.
If Bitcoin does continue to appreciate, Strategy will be able to continue to draw credit from the residual value, much like the company would with real estate in an ideal market. Of course there will be a downturn, but according to Bea, Strategy is “already planning for it” and has a healthy overall gearing ratio.
Bea added that the recent wave of digital asset finance companies resembles a new type of bank, and their models are evolving rapidly. He noted that some cryptocurrencies, including ReserveOne, are based on cryptocurrencies such as Ethereum, which, unlike Bitcoin, does provide yields, which provides additional breathing room on the financial side of the business. Bea acknowledged that MSCI’s upcoming move to exclude DAT from the index is a significant headwind and said crypto-asset-based companies will take time to develop.
Cosmo Jiang, a partner at Pantera, a venture capital firm focused on cryptocurrencies, similarly believes that digital asset treasuries—including Companies focused on Solana What he supports – will become a permanent feature of the financial landscape.
“We are seeing the origins of a whole new business category,” Jiang told wealthadding that DAT is expected to generate significant revenue from the rapidly growing world of decentralized finance.
in a separate comment BloombergJiang said the industry is currently at a low point, but the current downturn for Strategy and similar companies is temporary. “We’re in a moment now where all the bad news is coming out, and the bears’ voices are the loudest in the room.”
However, Jiang pointed out that many companies are unlikely to survive the recent wave of cryptocurrency hoarding, and that this business model requires not only a large number of tokens, but also extensive experience in capital markets and corporate financing.
He predicts that “there will be two or three big winners” for each major cryptocurrency. If this is the case, the coming months may determine whether one of these is a strategy.