MicroStrategy (MSTR) Could Survive a Brutal Crypto Winter, but Shareholders Wouldn't Be Happy About It

Strategy Inc. MSTR executive chairman, Michael Saylor, says the company, formerly known as MicroStrategy, could survive a brutal crypto winter

Strategy Inc. (NASDAQ:MSTR) executive chairman Michael Saylor says the company, formerly known as MicroStrategy Inc (NASDAQ:MSTR), could survive a brutal crypto winter, but its shareholders wouldn't be too happy about it.

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 keeps piling on debt and preferred-stock financings to buy more Bitcoin, already the world's largest corporate holder of the token at 568,840 coins worth about $59 billion.

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.

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

According to Benzinga Pro, here are the top 3 Bitcoin-holding public companies as of August 2023:

*

Strategy Inc (NASDAQ:MSTR): 128,000 BTC (as of August 2023)

*

Coinbase Global (NASDAQ:COIN): 64,000 BTC (as of August 2023)

*

Riverbank (OTC:RIBC) (as of August 2023)

Economist Peter Schiff, a critic of all things Bitcoin, has questioned Strategy's Bitcoin playbook and predicted "fireworks" if Bitcoin were to drop in value. Schiff recently said that a significant BTC slump could soon even push MSTR "into the red."

However, JPMorgan analysts expect continued Bitcoin upside into late 2025, driven by sector-specific momentum and weakening gold sentiment. Major U.S. exchanges like Coinbase (NASDAQ:COIN), Kraken, and Gemini are expanding regulated crypto derivatives offerings to institutional investors, all adding to the crypto king's momentum.

Shares of Strategy closed 4.73% lower at $397.03 on Thursday. The stock is up 32.34% since the beginning of 2025.

Benzinga Edge Point: Edge Stock Rankings indicate that Strategy has a Momentum in the 97th percentile.