MicroStrategy (MSTR) Stock Crisis: Bitcoin Holdings Now Worth More Than Entire Company

MicroStrategy's market cap plunges below its Bitcoin stash as shares crater to 52-week lows—raising existential questions about its crypto-heavy strategy.

Wall Street's favorite Bitcoin proxy just became a cautionary tale. The enterprise software-turned-crypto hoarder now carries a market valuation lower than its BTC holdings, with shares down 60% from 2025 highs.

When your treasury strategy becomes your entire business model, maybe it's time to update the investor presentation.

TLDR

• Strategy Inc (NASDAQ:MSTR) shares fell 5.90% to $211.35 on Thursday as Bitcoin dropped 3% to $98,588, with crypto-linked stocks declining across the board.
• The company’s market cap briefly dropped below $65.3 billion, falling under the $66.6 billion value of its 641,692 Bitcoin holdings for the first time.
• EVP Shao Wei-Ming sold 2,600 shares for $581,535 at $223.67 under a pre-scheduled trading plan, continuing a pattern of retirement-related sales totaling over $24 million since October.
• Analysts suggest Bitcoin’s traditional four-year halving cycle may be weakening, with the market now 1,080 days past its previous low without the expected euphoria period.
• Strategy’s stock premium has collapsed from 3x its Bitcoin holdings to roughly equal value as investors shift to direct Bitcoin exposure through ETFs rather than leveraged corporate structures.

Strategy Inc shares dropped Thursday as Bitcoin’s decline dragged down crypto-linked stocks. The company’s stock fell 5.90% to $211.35, trading NEAR its 52-week low of $219.68.

MicroStrategy Incorporated, MSTR

Bitcoin slipped 3% to $98,588. The drop comes as traders debate whether Bitcoin’s typical four-year market cycle is losing its power.

Analyst Scott Melker noted that Bitcoin’s previous market peaks occurred between 1,060 and 1,070 days after a major cycle low. The market is now about 1,080 days past its last low. But there hasn’t been a period of euphoria yet.

Altcoins remain quiet. Sentiment stays negative. Many investors already left the market early.

Melker suggests traders may have diluted the cycle’s impact by front-running it. Bitcoin could enter a mature, liquidity-driven phase lasting until 2026.

Strategy’s Market Cap Drops Below Bitcoin Value

On November 13, Strategy’s market capitalization briefly fell below the value of its bitcoin holdings. This created what analysts call a negative premium.

The company holds approximately 641,692 Bitcoin. At current prices fluctuating between $98,000 and $105,000, the holdings are worth about $66.6 billion.

Strategy’s market cap dropped to around $65.3 billion intraday. This marks a rare moment where investors valued the company’s equity at less than its digital assets.

For years, Strategy’s stock traded at a premium to its Bitcoin holdings. Investors paid extra for leverage and growth potential. That premium has now disappeared.

The shift reflects growing caution around corporate Bitcoin structures. Investors increasingly prefer direct Bitcoin exposure through ETFs rather than Leveraged corporate vehicles.

Strategy financed its Bitcoin purchases through convertible debt and equity issuances. This aggressive approach amplified exposure during rallies. It also introduced dilution risks for shareholders.

The company’s capital structure includes billions in convertible bonds and preferred equity. This leverage magnifies both gains and losses.

ByteTree noted that Strategy was once 3x ahead of Bitcoin in value. Now it’s just 50%. Retail investors previously bought Strategy as a Bitcoin proxy when ETFs were restricted.

With spot Bitcoin ETFs now accessible worldwide, money flows to simpler, low-fee vehicles instead.

Executive Continues Pre-Planned Stock Sales

EVP and General Counsel Shao Wei-Ming sold 2,600 shares for $581,535 at $223.67 on November 14. The transaction occurred under his Rule 10b5-1 trading plan.

JUST IN: Strategy's Executive Vice President Shao Wei-Ming just sold 2,600 $MSTR shares at $223.67 for $581,535. pic.twitter.com/Xba5vs8i4g

— BitcoinTreasuries.NET (@BTCtreasuries) November 14, 2025

This follows his sale of 10,668 shares on November 10 and 11. Those trades generated about $2.58 million in proceeds at prices between $234.74 and $249.55.

Shao’s 2025 sales have been substantial. In July, he sold 52,500 shares worth more than $21 million. In October, he sold 30,000 shares for roughly $10.7 million.

The consistent sales are tied to his personal retirement planning. They follow a pre-established trading schedule structured before his retirement announcement.

After these transactions, Shao directly holds 12,726 Class A shares plus multiple series of preferred stock.

BitMEX Research clarified that Strategy’s enterprise value, including debt, remains about $76 billion. That’s roughly 20% above the market value of its Bitcoin holdings.

The company released its third-quarter results in October. Strategy expanded its holdings to 640,808 Bitcoin as of October 26. The company generated a 26.0% Bitcoin Yield and $12.9 billion Bitcoin Gain so far this year.

Analyst ratings remain mixed. Monness, Crespi and Hardt changed their rating from Sell to Neutral on November 10. Canaccord Genuity and HC Wainwright maintained Buy ratings but adjusted price targets to $474 and $475 respectively.