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Strategy (MSTR) Bitcoin Sale Countdown: The End of Saylor’s “Never Selling” Era?

Published 01 December 2025
Giuseppe Ciccomascolo
Authors

Key Takeaways

  • Strategy Inc. holds around 650,000 BTC as of December 2025, over 3% of total Bitcoin supply.
  • Bitcoin accumulation has been funded primarily through equity and high-yield perpetual preferred issuances.
  • Critics, including Peter Schiff and Scott McClintic, argue the model resembles a leveraged pyramid or Ponzi-like structure.
  • Critics view Strategy as a pioneering digital-asset treasury, providing leveraged exposure to Bitcoin.

Strategy Inc. has become synonymous with one thing: ultra-leveraged Bitcoin accumulation. What began in 2020 as a treasury hedge under the leadership of Executive Chairman Michael Saylor has evolved into one of the most aggressive Bitcoin-backed financial structures globally.

As of December 2025, Strategy holds 650,000 BTC, representing more than 3% of the entire Bitcoin supply, acquired through a steady stream of equity and debt sales.

But a quiet shift in late November has sparked a wave of market anxiety. For the first time, Strategy’s leadership acknowledged a scenario where the company might sell Bitcoin to meet its obligations. For a company whose identity is built around “never selling,” the admission was seismic.

With critics calling the company a “leveraged pyramid” and supporters praising it as a visionary digital-asset treasury, the question now hangs over markets: Is Strategy a revolutionary Bitcoin corporation—or a debt-fueled Ponzi waiting to collapse?

This educational deep dive breaks down the mechanics behind Strategy’s model, the controversy over its sustainability, and the significance of its new willingness to sell BTC.

Inside Strategy’s Business Model: The Mechanics Behind Its Massive Bitcoin Purchases

Since 2020, Strategy has employed a primary lever to build its massive Bitcoin war chest: raising capital to purchase Bitcoin, issuing additional securities, and acquiring more Bitcoin.

In 2025 alone, Strategy raised approximately $20 billion through the issuance of newly issued common stock and a series of high-yield perpetual preferred shares. The company describes its strategy as “strategically accumulating Bitcoin using equity and debt financings.”

Strategy Bitcoin holdings
Strategy holds 650,000 Bitcoin as of Dec. 1, 2025. | Credit: Strategy

As of Dec. 1, 2025, Strategy held 650,000 BTC with a cost basis of roughly $50 billion. The company’s enterprise value hovers around $66 billion, backed by approximately $71 billion in Bitcoin collateral. In effect, Strategy operates like:

  • A Bitcoin investment trust.
  • Leveraged through equity dilution.
  • Supporting a suite of high-yield securities relying on continued liquidity.

As long as the stock trades above the value of its Bitcoin holdings, Strategy can issue shares at a premium and use the proceeds to buy more BTC. This is why a metric called mNAV (Market Net Asset Value) has become central to Strategy’s survival.

Strategy’s Current Situation

The financial newsletter The Kobeissi Letter noted that Strategy now holds approximately $55 billion worth of Bitcoin, offset by $8 billion in debt and roughly $1.4 billion in cash reserves. Despite those impressive figures, the company’s market capitalization stands at just $45 billion, implying that investors are pricing in a substantial level of risk.

Strategy's Current Situation
Strategy’s Current Situation (as of Dec. 1, 2025) | Source: @KobeissiLetter on X.

In effect, the market is valuing MicroStrategy at less than the net worth of its Bitcoin holdings — a striking signal of skepticism toward the company’s highly leveraged crypto strategy.

Understanding mNAV: The Key Metric Driving Strategy’s Risk and Value

Before diving into the controversy surrounding Strategy’s liquidity risks, it’s essential to understand the metric at the center of the debate: mNAV, or market Net Asset Value. This single number determines whether Strategy can continue its aggressive Bitcoin-acquisition model, or whether the company may eventually be forced to sell the very asset it built its identity around

As volatility rises and investor confidence wavers, mNAV has become the pressure gauge everyone is watching.

Strategy basic mNAV
Strategy (MSTR) basic mNAV. | Credit: Protos

mNAV = Strategy’s market cap ÷ value of its Bitcoin holdings

  • mNAV > 1 = The market values Strategy above the worth of its Bitcoin.
  • mNAV < 1 = Strategy trades below the value of its Bitcoin treasury.

This ratio is the lifeblood of Strategy’s business model. When mNAV is high, the company can easily raise new capital through stock or preferred issuances to buy more Bitcoin. But when mNAV falls toward 1, or worse, below it, the entire engine breaks down.

As of December 2025, Strategy’s mNAV has slipped to 0.9-1.0, meaning:

  • The market now values the entire company at or below its Bitcoin holdings.
  • Raising fresh capital becomes far more difficult.
  • Continued Bitcoin accumulation risks severe dilution to shareholders.
  • A sustained discount could undermine Strategy’s ability to meet its fixed obligations.

Analysts warn that mNAV “nearly vanished” in late 2025 for the first time in almost two years. If it drops further, some believe it could activate what they’re calling “the kill-switch scenario,” where Bitcoin sales become mathematically unavoidable.

Strategy Confirms Bitcoin Sale Option as Liquidity Risks Rise

For years, Saylor’s mantra was absolute: “We will never sell our Bitcoin.”

But on Nov. 29, 2025, CEO Phong Le quietly introduced a new possibility during an interview: if Strategy’s market cap falls below its Bitcoin value and the company cannot raise capital, it may sell high-basis Bitcoin to fund preferred dividends.

The company reinforced this message with a Dec. 1 announcement of a $1.44 billion USD reserve, created from stock sales, to cover 21 months of preferred dividends.

This move signals three major shifts:

  1. Short-term liquidity now matters more than ideology.
  2. Strategy is preparing for a world where capital markets tighten.
  3. Selling Bitcoin is no longer “impossible”; it’s a contingency plan.

Why Critics Claim Strategy (MSTR) Is a Ponzi-Like, Debt-Fueled Bitcoin Bet

As mNAV approached parity and news of possible BTC sales spread, long-time critics became louder.

Peter Schiff: “The Beginning of the End for Strategy”

Schiff called Strategy’s model “fraudulent” and compared it to a pyramid scheme, arguing:

  • Preferred shareholders depend on yields that “will never be paid long-term.”
  • The system relies entirely on new inflows—classic Ponzi dynamics.
  • If liquidity dries up, a “death spiral” could begin as investors dump securities.

Additionally, in Schiff’s view, the firm’s decision to sell stock not to buy more Bitcoin, but to raise U.S. dollars to cover interest and dividend payments, signals the collapse of its narrative. He argues that Strategy’s entire model, using equity and debt financing to maintain its Bitcoin position, has finally buckled under its own weight.

Peter Schiff on MSTR and Michael Saylor.
Peter Schiff on MSTR and Michael Saylor. | Source: @PeterSchiff on X.

“This is the beginning of the end,” Schiff has said, contending that the stock is broken, the business model unsustainable, and Michael Saylor’s strategy a form of financial sleight of hand. To Schiff, this isn’t innovation but illusion: a company propped up by hype and leverage, now forced to turn back to the fiat system it once scorned.

Scott McClintic, Crypto Analyst

McClintic warned Strategy is: “A financial pyramid that feeds on itself.”

He said lenders are “asking to fail” because the model only works if Bitcoin continues to rise.

Other Red Flags Critics Cite

  • Strategy’s rising share count massively dilutes shareholders.
  • Preferred dividends ($750-$800 million yearly) depend on a constant capital inflow.
  • Bitcoin price weakness could force liquidation.
  • The company behaves like a leveraged Bitcoin ETF with a software company attached.

For critics, the admission that BTC might be sold is not a prudent backup plan; it’s validation that the model is unstable.

Is Strategy (MSTR) the Next LUNA or the Ultimate Bitcoin Stress Test?

That disconnect has fueled speculation about what might happen if Bitcoin’s price were to stumble again.
“It’s hard not to see echoes of the past here,” said Sandeep Nailwal, co-founder and CEO of Polygon, who compared MicroStrategy’s position to the LUNA collapse of 2022. “If things turn, we could see another public, Wall Street–retail–entangled death spiral. Let’s hope Saylor can pull some magic out of his hat.”
Sandeep Nailwal on Saylor’s Bitcoin bet
Sandeep Nailwal on Saylor’s Bitcoin bet. | Source: @sandeepnailwal on X
Nailwal’s concern isn’t isolated. Critics have long warned that Strategy’s heavy leverage, combined with its near-total dependence on Bitcoin’s performance, creates systemic risk, particularly given its status as a publicly traded company.
Among the more vocal skeptics is market commentator Jacob King, who argues that CEO Michael Saylor has built a fragile narrative around Bitcoin as a corporate reserve asset. King accuses Saylor of hypocrisy, noting that after years of dismissing fiat currency, Strategy is now increasing its U.S. dollar reserves in response to Bitcoin’s volatility.
“The same people who called fiat worthless are now relying on it to survive,” King said. “It’s the ultimate contradiction.”
Strategy’s strategy has undeniably elevated Saylor into one of the most visible figures in corporate crypto adoption. But it has also tied the company’s fate tightly to Bitcoin’s fortunes, a bet that looks brilliant in bull markets and terrifying in downturns.

As the crypto market once again swings between optimism and uncertainty, the question remains: is Strategy a visionary pioneer proving the long-term case for Bitcoin, or is it a ticking time bomb whose unraveling could ripple across both Wall Street and Main Street?

Why Supporters Say Strategy (MSTR) Is a Visionary Bitcoin Play

On the other side are analysts, crypto maximalists, and institutional investors who see Strategy as a pioneering digital-asset treasury.

Benchmark Analysts

Benchmark maintained a Buy rating with a target of $705, arguing:

  • Fears of insolvency are “misplaced noise.”
  • Strategy holds $55 billion in Bitcoin against mostly fixed obligations.
  • Bitcoin would need to fall 86% (to $12,700) for the company to fail.

Wall Street Consensus

Based on recent TipRanks data:

  • 12 Buy ratings
  • 2 Holds
  • Consensus: Strong Buy

Bill Miller

Veteran investor Bill Miller has accumulated preferred shares, stating that Strategy created a structure appealing to diverse investor profiles.

Crypto Enthusiasts

Bitcoin advocates often argue:

  • $MSTR behaves similarly to BTC in terms of leverage, significantly outperforming in bull markets.
  • A 10% rise in BTC can send MSTR up 20-30%.
  • Strategy’s approach accelerates Bitcoin’s institutionalization.

Supporters view Strategy as the “Berkshire Hathaway of Bitcoin” and Saylor as the first CEO to build a corporate balance sheet around digital gold.

MSTR Stock Performance: Why Strategy Trades Like Bitcoin With Leverage

Strategy’s price action reflects its leveraged relationship with Bitcoin:

  • 2024-early 2025 bull markets pushed MSTR to near $550 (all-time highs).
  • By November 2025, the stock dropped to $180-200, down by 70% from highs.
  • Bitcoin, by comparison, dropped only by 10-15% in 2025.
MSTR stock price performance
MSTR stock price performance since its debut in New York. | Credit: Yahoo! Finance

Strategy (MSTR) Stock Performance — 2025 Timeline

Here’s a rough 2025 timeline of Strategy (ticker MSTR), summarizing major stock-price moves from January through November (with December’s early info), and key events.

Month (2025) Approx. Closing Price (USD)  Notes
January 334.79 Strong start to the year; optimism around Bitcoin accumulation.
February 255.43 Sharp dip from January; volatility increases as crypto market softens.
March 288.27 Partial rebound as investor sentiment stabilizes.
April 380.11 Strong rally driven by renewed optimism and Bitcoin price strength.
May 369.06 Minor pullback but stock remains elevated.
June 404.23 Year-to-date high; market bullish on MicroStrategy’s Bitcoin holdings.
July 401.86 Stability near peak levels; confidence in strategy continues.
August 334.41 Noticeable correction as broader crypto sentiment turns cautious.
September 322.21 Gradual decline continues amid market uncertainty.
October 269.51 Steep drop; pressure builds from macro factors and Bitcoin weakness.
November 175–177 Significant sell-off; investors price in heightened risk.
December (early) 52-week range shows a low near $166.01 and high near $457.22 (though peak was early 2024) Shares near yearly lows; market remains wary of leverage and volatility.

This divergence highlights the mNAV collapse. When the premium is gone, the stock behaves like: Bitcoin × leverage × investor fear.

Preferred shares tell a similar story: yields spiked to 10-15% while prices slid to multi-year lows, showing investor uncertainty about the sustainability of payouts.

Is Strategy (MSTR) Really a Ponzi Scheme? A Look at the Business Model

Let’s first understand what a ponzi scheme is.

A ponzi scheme has three defining traits:

  1. Guaranteed returns.
  2. Payouts funded by new investor money.
  3. Collapse when inflows stop.

Critics argue Strategy exhibits #2 and #3, since:

  • Capital raises, not operating income fund preferred dividends.
  • Bitcoin purchases rely on constant stock and debt issuance.
  • If liquidity evaporates, the structure falters.

But Strategy lacks the key ingredient of a Ponzi:

  • It does not promise fixed returns to stockholders or guarantees of the Bitcoin price.
  • It fully discloses its financing mechanisms.
  • Its assets (Bitcoin) are real, liquid, and independently valued.

A more accurate label is: A hyper-leveraged Bitcoin holding company with ETF-like characteristics.

So Strategy’s  model is risky, but not necessarily fraudulent.

Why Strategy (MSTR) Is Unique

Strategy stands out as a publicly traded company functioning like a leveraged Bitcoin ETF, yet retaining the flexibility of a traditional corporation. Unlike typical software firms, its balance sheet is dominated by Bitcoin, which it actively accumulates using a mix of debt issuance and equity sales. This hybrid model makes MSTR a bridge between Wall Street’s capital markets and the crypto ecosystem.
While critics compare its structure to a Ponzi scheme, but rather than fraud, the risk lies in market exposure and leverage: if Bitcoin prices fall sharply or liquidity dries up, MSTR’s model strains under its own weight.
Still, its approach is a rare experiment, a corporate entity using traditional finance tools to create a high-beta proxy for Bitcoin, blurring the line between a tech stock and a crypto asset vehicle.

Can Strategy (MSTR) Withstand a Bitcoin Price Decline?

The company now faces its most vulnerable moment since 2021:

  • mNAV is near parity.
  • Capital markets are less enthusiastic.
  • BTC is underperforming expectations.
  • Preferred dividends need $750-800 million per year.
  • Saylor and Le openly acknowledge the need for liquidity buffers.

If Bitcoin rebounds, Strategy could soar again.

But if Bitcoin stagnates, or worse, crashes, Strategy may be forced to:

  • Sell BTC.
  • Slash dividends.
  • Halt expansion.
  • Restructure obligations.

Any of these would shatter the narrative Saylor spent years building.

Why Strategy (MSTR) Is a High-Risk, Controversial Yet Unique Bitcoin Investment

So, is Strategy a Ponzi? The answer is more nuanced.

  • It’s not a literal Ponzi scheme.
  • But its sustainability is deeply tied to Bitcoin going up and capital markets staying open.
  • The business model magnifies both the upside and the catastrophic downside.

For investors, Strategy is not “safe Bitcoin exposure”; it’s leveraged Bitcoin with corporate debt attached.

And now that the company has admitted it might sell BTC, the myth of invincibility has broken.

Whether Strategy becomes a legendary success or a cautionary tale depends on one thing: Bitcoin’s next move.

FAQs

What is Strategy Inc. and what does it do?

Strategy Inc. is a publicly traded company that has made Bitcoin its primary treasury asset. Since 2020, it has raised capital through stock and high-yield preferred shares to purchase Bitcoin, effectively giving investors exposure to BTC via a regulated corporate structure.

What is mNAV and why is it important?

mNAV, or market Net Asset Value, is the ratio of Strategy’s market capitalization to the value of its Bitcoin holdings. An mNAV above 1 indicates the company trades at a premium to its Bitcoin, allowing it to raise capital to buy more BTC. An mNAV below 1 signals risk, as the market values the company less than its crypto holdings, potentially forcing BTC sales to meet obligations.

Why did Strategy announce a possible Bitcoin sale for the first time?

In November 2025, CEO Phong Le said that if Strategy’s market cap falls below its Bitcoin value and the company cannot raise new capital, it may sell high-basis Bitcoin to cover preferred dividends. This marks a shift from Michael Saylor’s long-standing “never sell” policy and reflects a focus on liquidity and risk management.

Is Strategy a Ponzi scheme or fraudulent?

Critics have called it “Ponzi-like” because it relies on new capital inflows to fund Bitcoin purchases and preferred dividends. However, Strategy fully discloses its financing methods and holds real Bitcoin assets, so it does not meet the legal definition of a Ponzi scheme. It is better described as a hyper-leveraged Bitcoin holding company.

Disclaimer: The information provided in this article is for informational purposes only. It is not intended to be, nor should it be construed as, financial advice. We do not make any warranties regarding the completeness, reliability, or accuracy of this information. All investments involve risk, and past performance does not guarantee future results. We recommend consulting a financial advisor before making any investment decisions.
Giuseppe Ciccomascolo

Giuseppe Ciccomascolo began his career as an investigative journalist in Italy, where he contributed to both local and national newspapers, focusing on various financial sectors.

Upon relocating to London, he worked as an analyst for Fitch's CapitalStructure and later as a Senior Reporter for Alliance News. In 2017, Giuseppe transitioned to covering cryptocurrency-related news, producing documentaries and articles on Bitcoin and other emerging digital currencies. He also played a pivotal role in establishing the academy for a cryptocurrency exchange website. Crypto remained his primary area of interest throughout his tenure as a writer for ThirdFloor.

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