Strategy Inc. (NASDAQ:MSTR) executive chairman, Michael Saylor, says the company, formerly known as MicroStrategy, could survive a brutal crypto winter, but its shareholders wouldn’t be too happy about it.
What Happened: In a new Financial Times film and subsequent interviews, Saylor warned that if Bitcoin (CRYPTO: BTC) “fell 90 per cent and stayed there for four or five years, we would still be stable,” yet equity investors “would suffer because they’re levered.”
The alert comes as MicroStrategy — already the world’s largest corporate holder of the token at 568,840 BTC worth about $59 billion — keeps piling on debt and preferred-stock financings to buy more.
Saylor’s endgame is simple. “Whoever gets the most bitcoin wins. There is no other endgame,” he told Yahoo Finance in a separate sit-down. To keep buying, MicroStrategy sold $580 million of dividend-paying preferred shares in January and another perpetual-preferred slug in March — cash it can deploy straight into crypto.
The balance sheet now holds just $60.3 million in cash against tens of billions in digital assets, its latest 10-Q shows. Former Bank of America ECM chief Craig Coben tells FT that Strategy’s focus on “new money” raises “questions about the sustainability” of the bet if prices crater.
See also: Michael Saylor’s Bitcoin Strategy—’Infinite Money Glitch’ Or A Reflexive Leverage Bet?
Saylor shrugs at the skeptics, even trolling them on X: “Sell a kidney if you must, but keep the Bitcoin.” But Saylor’s own warning shows just how thin the ice could get if the next crypto winter proves deeper and longer than the last.
Top 3 Bitcoin-Holding Public Companies
| Company Name | Amount Of BTC Held | Value In U.S. Dollars |
| MicroStrategy | 568,840 BTC | 59.16 billion |
| Marathon Digital | 46,374 BTC | 4.82 billion |
| Riot Platforms | 18,692 BTC | 1.94 billion |
Why It Matters: Economist Peter Schiff, a fierce critic of all things Bitcoin, has consistently questioned Strategy’s Bitcoin playbook, recently predicted “fireworks” if Bitcoin were to drop in value. Schiff stated that a significant BTC slump could soon even push MSTR “into the red.”
That said, JPMorgan analysts expect continued Bitcoin upside into late 2025, driven by sector-specific momentum and weakening gold sentiment. Major U.S. exchanges like Coinbase, Kraken, and Gemini are expanding regulated crypto derivatives offerings to institutional investors, all adding to the crypto king’s momentum.
Price Action: Shares of MicroStrategy closed 4.73% lower at $397.03 on Thursday. The stock has gained 32.34% since the beginning of 2025, according to data from Benzinga Pro.
Benzinga Edge Stock Rankings indicate that Strategy has a Momentum in the 97th percentile. Click here to see how rivals like Coinbase stack up in comparison.
Photo Courtesy: Bukhta Yurii On Shutterstock.com
Read next: Eric Trump: Bitcoin Accumulation Is ‘A Race To The Top’
