Strategy’s stock dropped 4% over the past month, even as Bitcoin rose 3%, raising fresh questions about Michael Saylor’s multi-billion-dollar crypto play. Since 2020, the company has been buying bitcoin using a mix of borrowed money and new shares.
That pivot pushed the software firm into the spotlight as a bitcoin-heavy operation. The stock had soared 2,800% since the bitcoin buying spree began. But now, the numbers are heading the wrong way, and confidence in the Strategy model is starting to crack.
Other companies that copied Saylor’s approach are bleeding harder. Japanese hotel operator Metaplanet has lost 36% in the same 30-day stretch. KindlyMD, a healthcare startup now holding bitcoin, is down 87%. Medical tech firm Semler Scientific fell 12%.
Even Trump Media & Technology Group, now linked to a bitcoin treasury, lost 8%. A new crypto vehicle by Cantor Fitzgerald, tied to Twenty One Capital, dropped 17% before even going public. Twenty One is backed by SoftBank and Tether.
Public bitcoin holders lose value as market cools
All these companies had seen wild gains earlier in 2025, so the downturn is putting pressure on this whole “bitcoin treasury” trend. Gus Galá, analyst at Monness, Crespi, Hardt & Co., said in an email that “at a certain point there are too many strategies pursuing the same promised land and a finite amount of investor demand for similar exposures.”
This rush was fueled by three things: crypto prices going up, the Trump administration’s looser rules, and changes in accounting that made holding bitcoin more attractive on paper.
But as Kevin O’Leary, investor and TV figure, explained, “The majority of the market can’t hold bitcoin, but they can hold equities.” That’s why institutions prefer stocks that hold crypto, instead of holding the asset directly.
Norway’s Norges Bank, the world’s biggest sovereign wealth fund, owns 2.9 million shares of Strategy. It doesn’t hold any bitcoin ETFs. State-run retirement systems like CalPERS also own Strategy stock but steer clear of direct crypto exposure.
So far, more than 180 public companies have added bitcoin to their books. That’s 5% of all existing bitcoin. Of those, 94 have followed Strategy’s playbook.
But about 25% of those are now valued below the coins they hold, says Vetle Lunde, head researcher at K33 Research. “It’s been just a very wild ride,” Vetle said, “and now I think the bitcoin treasury space is getting quite saturated.”
This price drop could lead to bigger problems. If these companies stay worth less than their own bitcoin, it might lead to investor unrest — or even forced sales of the crypto holdings.
Skepticism grows around Strategy’s future debt funding
Even Strategy is feeling the pressure. Short seller Jim Chanos, known for calling out Enron, said on Bloomberg’s Odd Lots podcast, “It makes kind of no sense” that Strategy trades higher than bitcoin itself.
Gus, the analyst, added that Strategy may be running out of ways to keep funding these massive buys. The firm relies heavily on convertible debt, where bondholders can trade debt for shares if the stock pops.
But recent bond deals aren’t looking good. The company’s 2024 convertible note only becomes worthwhile if the stock doubles to $672, and it’s currently trading below face value.
Raising high-grade debt isn’t easy either. Gus said Strategy’s profit is made of unrealized crypto gains, which makes bond markets uneasy. Issuing more equity would just dilute shareholders.
“It all works as long as bitcoin goes up,” Gus said. “But then when bitcoin stops doing that, if it stops doing that, it stops working.” He added that smaller firms trying to mimic Strategy’s model, especially those with no real business operations, are in even worse shape.
“They are likely to struggle more,” Gus said, “to raise capital, market themselves as Michael Saylor has marketed Strategy, and drive premiums to their stocks’ multiples.”
Not everyone is down. American Bitcoin, the crypto miner backed by Eric Trump, is up 16% this month. GameStop, now holding bitcoin too, gained 12%. Still, even companies losing big are digging in.
David Bailey, Trump’s friend, told investors, “The entire public Bitcoin treasury space has been tested in recent months, yet this is exactly when conviction matters most.”
