Market expert Shanaka recently explained how a historical event is unfolding with MicroStrategy and its Bitcoin strategy. This comes as the company faces a negative valuation from Wall Street while MSCI considers whether to remove MSTR from its indices. 

MicroStrategy’s Market Cap Drops Below the Value Of Bitcoin Holdings

In an X post, Shanaka noted that MicroStrategy, which is the world’s largest corporate Bitcoin holder, is now worth less than its BTC holdings. The company currently holds 650,000 BTC, valued at around $60 billion, while the MSTR stock has a market cap of $55 billion. The expert noted that Wall Street is valuing the company at a negative based on this. 

He further remarked that this is the sustained NAV inversion since MicroStrategy began the Bitcoin model in 2020. Shanaka noted that the company has created a $1.44 billion emergency reserve to pay dividends. This came after the CEO Phong Le admitted that they might have to sell BTC to fund dividend payments if the mNAV drops below 1. 

MicroStrategy’s woes could deepen as MSCI will decide by January whether to expel the company from global stock indices. MSCI is considering whether companies that hold Bitcoin should be regarded as funds or trusts rather than as companies. JPMorgan estimates the company could see $8.8 billion in outflows if other index providers make a similar move.

Shanaka described the math as “merciless,” noting that MicroStrategy has $8.2 billion in debt, $7.8 billion in preferred stock, and $16 billion in total obligations against a $45.7 billion shell. Meanwhile, the company currently holds its BTC at an average cost of $74,436, which the expert noted is 15% above breakeven. As such, he remarked that one sustained drop erases every gain since 2020. 

Shanaka stated that MicroStrategy’s current situation is not just about one company but about whether corporations can hold sound money without being destroyed by the very system they sought to escape. He added that the largest experiment in corporate Bitcoin adoption is breaking in real time. 

Saylor Confirms Talks With MSCI Over Potential Exclusion

According to a Reuters report, Michael Saylor confirmed that MicroStrategy is in talks with MSCI over a potential exclusion from their indices. MSCI is expected to decide by January 15 whether to remove digital-asset treasury companies that buy Bitcoin and other crypto assets, amid concerns that they are classified as investment funds.  

Saylor opined that MicroStrategy’s potential exclusion from MSCI indices won’t make any difference. He explained that his company is currently leveraged by a multiple of 1.11 and could survive a 95% Bitcoin crash. Meanwhile, it is worth noting that Phong Le has stated that it is unlikely they will sell any BTC over the next three years following the creation of the USD reserves, which should be sufficient for dividend payments during this period.

Bitocin treasury companies continue to accumulate a significant amount of BTC despite current market conditions and now control around 5% of the total BTC supply. These companies are led by Michael Saylor’s Strategy and Metaplanet, which have recently raised fresh capital to buy the dip. 

Bitcoin Treasury Companies Now Hold Over 1 Million In BTC

Bitcoin Treasuries data shows that the top 100 public Bitcoin treasury companies currently hold 1,058,929 BTC, while all public companies combined hold 1,061,697. Notably, Strategy is the largest public Bitcoin holder with 650,000 BTC. Michael Saylor’s company yesterday announced another 130 BTC purchase for $11.7 million. 

Meanwhile, the second-largest Bitcoin treasury company is BTC miner MARA holdings, which holds 53,250 BTC. Tether-backed Twenty One Capital, Metaplanet, and Bitcoin Standard Treasury Company complete the top 5, with 43,514, 30,823, and 30,021 BTC, respectively. Meanwhile, companies like Coinbase, Bullish, and Trump Media are among the top 10 largest BTC treasury companies. 

It is worth noting that these public companies account for only a part of the Bitcoin treasuries. Further data from Bitcoin Treasuries shows that there is currently 4 million BTC in treasuries as a whole, including the coins held by governments, private companies, exchanges, DeFi platforms, and ETFs.  

BlackRock is currently the second-largest Bitcoin holder, only behind Satoshi Nakamoto. Strategy is third on the list, while Binance and the U.S. government complete the top 5, with BTC holdings of 628,868 and 323,588, respectively. The 4 million BTC held by these treasury companies as a group accounts for 19% of the total Bitcoin supply. 

Bitcoin treasury companies such as Strategy and Metaplanet have raised new capital amid the recent crash to buy more BTC. Saylor’s company recently raised $836 million from its STRE offering, which it used to buy 8,178 BTC. Meanwhile, Metaplanet raised $130 million to expand its BTC treasury. 

More Companies Set To Adopt Bitcoin

More Bitcoin treasury companies are set to emerge as $10 trillion asset manager, Vanguard, will start offering BTC ETFs from today. Notably, some companies gain BTC exposure through these ETFs rather than buying Bitcoin directly. On-chain analytics platform Arkham Intelligence revealed that the largest U.S. bank, JPMorgan, holds $300 million worth of BlackRock’s BTC ETF. 

Meanwhile, it is worth mentioning that Bitcoin treasuries such as Strategy are coming under immense pressure amid the current market downtrend. Strategy’s CEO, Phong Le, admitted that they might have to sell Bitcoin as a last resort to fund dividend payments if their mNAV drops below 1x and they can no longer raise capital. 

At the time of writing, the Bitcoin price is trading at around $87,000, up in the last 24 hours, according to data from CoinMarketCap.

Strategy CEO Phong Le has revealed the instance in which his company may be forced to sell its Bitcoin holdings. This comes amid concerns about the MSTR stock crash, which puts the company at risk of seeing its mNAV drop below 1. 

Strategy CEO Reveals When They Will Sell Bitcoin

During an interview on the ‘What Bitcoin Did’ podcast, the Strategy CEO said they could sell Bitcoin to fund dividend payments on their preferred shares if the mNAV is trading below 1. He alluded to the BTC yield, which is their primary KPI, and that under 1x mNAV, it is more “creative” to sell their BTC holdings to pay the dividends. 

The Strategy CEO explained that they typically raise capital when their mNAV is above 1 to fulfill their obligations, even when it is below 1. He alluded to the 2022 crypto winter when they bought back their Bitcoin-backed loans as proof that they had prepared in advance for such market conditions. However, when they are unable to raise capital, Phong Le stated that they will have no option but to sell their BTC holdings. 

Strategy data shows that their mNAV is currently at 1.19. Meanwhile, the company currently holds 649,870 BTC, worth around $55 billion. With the MSTR stock on a downtrend, Michael Saylor’s company still faces the risk of seeing its mNAV fall below 1 for a sustained period. TradingView data shows that the stock is now down over 40% year-to-date (YTD) from a 2025 high of around $455. 

There were recently rumors that Strategy supposedly sold some of its Bitcoin holdings, which Saylor quickly denied. The company then went on to make one of its largest purchases this year, buying 8,178 for $836 million. This formed part of the proceeds from the company’s STRE offering. 

Saylor Teases Another Bitcoin Purchase

In an X post, Michael Saylor teased another Bitcoin purchase from Strategy. He posted the company’s BTC portfolio tracker with the caption, “What if we start adding green dots?” It is worth noting that these conventional Sunday posts have usually preceded a BTC purchase announcement by the company the following day. 

Based on this, Strategy likely bought more Bitcoin between November 24 and 30 last week. This comes amid the Bitcoin downtrend, with the flagship crypto again dropping below the psychological $90,000 level. Besides the BTC crash, the possibility of an exclusion from MSCI indices is another factor that paints a bearish picture for Saylor’s company. The MSCI will decide by January next year whether treasury companies like Strategy should remain in their indices. 

At the time of writing, the BTC price is trading at around $86,000, down over 5% in the last 24 hours, according to data from CoinMarketCap.