Michael Saylor’s Strategy outperforms Bitcoin. Is a reversal coming?

Michael Saylor’s Strategy is moving faster than Bitcoin itself. The company, formerly called MicroStrategy, has built its entire identity around Bitcoin ownership, stacking up 499,096 BTC on its balance sheet—almost 2.4% of all Bitcoin that will ever exist.

But while Bitcoin struggles to hold momentum, Strategy’s stock is soaring, leaving investors questioning whether this is a real shift or just a temporary bubble.

Strategy doubles down on Bitcoin while the market hesitates

Bitcoin has been the play for financial independence. With 21 million coins hard-coded as the max supply, it has been called digital gold, a hedge against inflation, and the future of money. It is decentralized, borderless, and immune to government interference.

Institutions have been piling in for years—Tesla, BlackRock, and even countries like El Salvador have put Bitcoin on their balance sheets. Adoption is still growing, and the network’s hash rate in 2025 is at all-time highs, making it nearly impossible to attack. Transactions are up, proving Bitcoin is being used, not just held.

But prices tell a different story. Bitcoin has struggled despite all the bullish fundamentals. And that has put companies tied to it—especially Strategy—under pressure. The firm is not just buying Bitcoin, it is using debt to buy more, making its stock a high-stakes leveraged play on Bitcoin’s future.

This move has worked so far. In 2024, Strategy was the second-best performing stock in the Russell 1000, delivering a 358.5% total return—three times Bitcoin’s own gains. Investors have been willing to pay extra for exposure to Bitcoin through Michael Saylor’s financial engineering.

As of March 14, 2024, Strategy’s 499,096 BTC was worth $42 billion, but the company’s market cap was sitting at $77.4 billion. Add in its debt, and the enterprise value was $84.6 billion. The stock was trading at double the value of the Bitcoin it holds.

Michael, who has been pushing the Bitcoin Standard for years, made no apologies for the company’s aggressive strategy. “We see Bitcoin as the best asset in the world, and we are structuring our company around that belief,” he said.

Leverage fuels growth, but the risks are stacking up

Strategy isn’t just betting on Bitcoin—it’s borrowing billions to buy more. That leverage has amplified the gains, but it also means the stock can crash twice as hard if Bitcoin drops.

Since the start of 2024, Bitcoin’s price has declined. But instead of following suit, Strategy has climbed 2.7% year-to-date. The stock isn’t just trading on Bitcoin’s value anymore—it has become a premium speculation play.

The danger? The premium could vanish overnight. If Bitcoin drops further, Strategy’s debt-heavy balance sheet could become a liability.

A trader looking to hedge against a potential drop might consider a June $250/$200 put spread, betting that Strategy’s stock price will fall. By buying one $250 put at $30 per contract and selling two $200 puts at $15 per contract each, the trader would make money if the stock lands between $150 and $250 by June.

But if Strategy collapses below $200, the trader is forced to buy shares at that price. With Strategy’s book value at roughly $150 per share, that could still be an expensive bet.

Wall Street braces for more volatility

Bitcoin is not the only asset facing pressure. The entire market is feeling the weight of uncertainty.

Deutsche Bank’s chief strategist, Binky Chadha, has warned that the sell-off in U.S. equities isn’t over.

“We see the sell-off in U.S. equities as having further to go,” Binky wrote. “With trade policy uncertainty likely to continue to weigh, at least until April 2, we expect positioning to continue to unwind.”

Binky believes that if the S&P 500 drops another 6.9%, it will put even more pressure on Bitcoin and Strategy. The benchmark index, which closed at 5,638.94 on Friday, is already 8% off its all-time high.

And it’s not just about trade policy. Executives at major corporations are cutting spending and lowering earnings forecasts.

The one thing that could stop the bleeding? Donald Trump.

Wall Street has long believed in a “Trump put”—the idea that Trump will adjust policies to stabilize markets if things get too bad. But Binky is not so sure.

“Compared to the level of consumer confidence, the current approval rating is high, implying plenty of room for downside with negative growth or inflation developments likely to speed the catch down,” Binky said. “We expect the net approval rating has to turn more significantly negative, at least -5%, before the administration starts to consider responding.”

For now, Trump’s policies have not been enough to stop the market’s decline. But Binky still holds a bullish year-end target of 7,000 for the S&P 500, suggesting that once the uncertainty clears, stocks—including Bitcoin and Strategy—could stage a major rebound.

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