Strategy Hits Four-Month Low, Michael Saylor Under Pressure

Strategy shares tumbled about 15% in the past week to hit a four-month low as Bitcoin’s sharp decline piles pressure on CEO Michael Saylor’s ability to sustain the company’s relentless buying spree.

MSTR stock is now at its lowest price since April, intensifying concerns about Saylor’s ability to fund additional purchases without diluting shareholders or taking on costly debt.

This comes after Bitcoin tumbled more than 6% in the past week to trade at $113,495 as of 10 a.m. EST.

Strategy currently owns more than 629k Bitcoins that are worth about $71 billion at current prices, according to Bitcoin Treasuries. It is the biggest corporate holder of Bitcoin in the world.

How Will Strategy Fund More Bitcoin?

Some analysts and investors are worried about the outlook. When share prices are falling, it’s harder for Strategy to sell new shares or raise cheap debt for Bitcoin purchases without hurting current shareholders.

🚨MicroStrategy is the biggest BUBBLE ever

No roadmap, no innovation, just buying BTC with borrowed funds

I compared it to Apple, Nvidia and Coinbase and was shocked

Here’s when $MSTR will collapse and what it means for crypto👇🧵 pic.twitter.com/rry5Mkq9ly

— Coin Shot ☁️ (@CoinSh0t) August 17, 2025

These concerns are being discussed widely on social media and in the crypto community.

A Tougher Backdrop for Crypto Stocks

The bigger financial picture is making life harder, too. Just a few months ago, investors were pouring money into Bitcoin ETFs and crypto stocks like Strategy. Now, they are getting cautious with Bitcoin ETFs recently seeing strong outflows.

Investors are also worried about things like a possible liquidity squeeze by the US Treasury market, stubborn inflation, and higher interest rates around the world.

Stock prices for other crypto-linked companies like Coinbase and Marathon Digital are also down. Some market experts think these issues will stick around through September, a month that often brings more selling.

What do you mean “if” BTC value keeps rising? BTC’s value is built upon the inflationary nature of fiat. Unless we experience sudden reversal of inflation, Bitcoin, as codified in the protocol, will continue to appreciate against all current forms of fiat.

— Penn Nguyen (@IHeartYou5970) August 20, 2025

Many traders are waiting to hear what Fed Chair Jerome Powell says about the outlook for interest rates in a speech at the Jackson Hole summit on Friday before deciding on their next moves.

Bitcoin Still at the Heart of Saylor’s Bet

Still, Saylor is not backing down and his team is not changing its strategy.

“We have been through more than 10 major corrections in Bitcoin, and we continue to believe in its future as a global monetary asset,” he said.

They believe that owning more Bitcoin, bought with a mix of debt and new shares, will beat holding traditional assets like cash or bonds.

Saylor believes that drops in price are just bumps in the road amid a long-term uptrend, especially as more people and companies start to buy Bitcoin and the future supply decreases.

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