Everything changed when the "never sell" mantra finally cracked. For years, Michael Saylor was the guy you could count on to hold Bitcoin through a nuclear winter. But lately, the vibe around MicroStrategy (now formally just "Strategy") has shifted into some pretty weird territory. If you’ve been watching the tickers, you know the score: MicroStrategy shares drop is the headline, but the "why" is where it gets messy.
The drama really kicked into gear when CEO Phong Le—who usually plays the pragmatic straight-man to Saylor’s digital-gold-evangelist—admitted that the company might actually sell some Bitcoin. Not just for fun, but to cover dividends and keep the lights on if things get desperate.
The "Never Sell" Era is Officially Over
Honestly, it feels like a bit of a betrayal for the die-hard Bitcoin maxis. Since 2020, MSTR wasn't just a stock; it was a crusade. You bought it because you believed Michael Saylor would rather sink with the ship than offload a single satoshi. But reality is a brutal teacher. The company has moved away from that pure "buy and hold forever" stance into what they’re calling a "capital markets platform."
Basically, they’ve started building a massive cash pile—about $2.25 billion as of mid-January 2026—just to make sure they can pay dividends on their new preferred shares without being forced to dump Bitcoin during a market crash.
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It’s a smart move on paper, but it signals a shift from a "Bitcoin treasury" to a "complex financial instrument." And investors? Well, they’re kinda freaked out. The stock has been underperforming Bitcoin itself for months. When the company hinted that they’d sell BTC if their market value dropped below the value of their holdings (the mNAV), the "proxy premium" that used to keep the stock price high just evaporated.
Why MicroStrategy Shares Drop Despite the Massive Stash
It’s a weird paradox. The company owns over 687,000 Bitcoin. That’s more than 3% of every Bitcoin that will ever exist. At current prices, we’re talking about over $60 billion in digital assets. So why is the stock struggling?
- The Dividend Pressure: Strategy now has to pay out roughly $800 million a year in interest and dividends. That’s a massive nut to crack for a company whose software business only brings in about $500 million in revenue. The math just doesn't work without either selling stock or selling Bitcoin.
- The MSCI Scare: For a few months, everyone was terrified that MSCI (the big index people) would kick Strategy out of their global indexes. They argued that because Strategy holds so much crypto, it’s basically an unregistered investment fund, not an operating company. While MSCI hit the pause button on that decision in January 2026, the threat is still lurking.
- The Proxy Problem: Back in 2021, if you wanted Bitcoin in a brokerage account, you bought MSTR. Now? You can just buy a spot ETF. The "scarcity" of MSTR as a way to play Bitcoin is gone, and the market is re-pricing the stock accordingly.
Selling Bitcoin for Dividends: A Necessary Evil?
Let’s talk about that dividend reserve. In December 2025, the company funneled $748 million into a USD reserve. By early 2026, that grew to over $2 billion. Saylor and Le are trying to build a bridge. They want to attract "real" institutional investors who demand dividends, but to do that, they have to prove they have the cash to pay them even if Bitcoin drops to $50,000.
But here’s the kicker: to get that cash, they’re mostly selling more MSTR shares. It’s a bit of a loop. They sell shares to buy Bitcoin, then they sell more shares to build a cash reserve to pay dividends to the people who bought the shares.
Some analysts, like those at TD Cowen, think this is genius—it creates "digital credit." Others see it as a house of cards that only stays up if Bitcoin keeps going to the moon. If Bitcoin stays flat while the company keeps issuing shares, the value of each share gets diluted into oblivion.
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What the Experts Are Saying Right Now
If you look at the analyst desks, opinions are split right down the middle. Dan Dolev over at Mizuho recently set a price target of $403, which is pretty bullish considering where we are. On the other hand, the market sentiment (measured by the Crypto Fear and Greed Index) hit some of its lowest levels in years late in 2025.
There's a lot of "show me" energy in the market right now. Investors want to see if this "capital markets platform" actually generates value or if it’s just a very expensive way to hold a lot of Bitcoin.
What You Should Actually Do
If you’re holding MSTR or thinking about jumping in, you’ve got to realize this isn't the same trade it was three years ago. It’s much more technical now.
- Watch the mNAV: If the market cap of the company stays below the value of the Bitcoin they hold (an mNAV under 1.0), it means the market has zero faith in the software business or the management's strategy.
- Keep an eye on the Series A Preferred (STRC): This is the ticker for the preferred shares. If those start to tank, it means the market thinks the dividend reserve isn't big enough.
- Monitor the 50-day moving average: Technically, the stock has been trying to find support. If it can’t hold the line during these "re-balancing" phases, the drop could get uglier.
The bottom line? Strategy is trying to grow up. They’re trying to move from being a "Bitcoin pirate ship" to a "Bitcoin bank." That transition is messy, it’s loud, and it’s why the stock is swinging like a pendulum.
To stay ahead of the next move, you should download the latest SEC 8-K filings directly from the MicroStrategy investor relations site to track the exact size of the USD reserve versus their upcoming debt maturities.
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Actionable Insight: Track the "Bitcoin Yield" metric that the company reports quarterly. If this number starts to trend toward zero or goes negative, it indicates that the dilution from new share offerings is outstripping the growth of their Bitcoin holdings, which is a major red flag for long-term equity holders.