Michael Saylor’s Strategy Soars Past Wall Street with Bitcoin-Powered Stock Surge

New York: While Wall Street explores new crypto investment tools — from tokenized funds to advanced ETFs — it’s Michael Saylor’s bold Bitcoin strategy that continues to deliver the biggest gains.

Saylor’s company, now known as Strategy (formerly MicroStrategy Inc.), has become a standout player by executing a simple yet high-impact formula: raise capital through stock and bond sales, buy Bitcoin, and ride the market’s wave — again and again.

So far in 2025, Strategy’s stock has climbed 26%, outpacing Bitcoin’s own 16% gain and outperforming nearly all 74 crypto ETFs available in the U.S., except one. The company’s shares currently trade at a significant premium above the value of its Bitcoin holdings — a valuation dynamic no ETF has been able to replicate.

“Saylor was first, early, and leveraged,” said Matt Maley, chief market strategist at Miller Tabak & Co. “He’s playing the Bitcoin market and the equity markets — and he’s doing it with precision.”

That premium fuels a feedback loop: as Strategy’s stock price rises, it enables the firm to raise more capital, which is then used to buy even more Bitcoin. This cycle strengthens its position as a crypto powerhouse.

Even leveraged ETFs like MSTX and MSTU — designed to track Strategy’s stock at twice the daily return — have failed to keep pace due to market volatility drag. While Wall Street races to design smarter, faster crypto investment vehicles, none have matched the aggressive self-reinforcing growth Strategy has engineered.

The firm currently holds over $60 billion in Bitcoin and recently announced plans to raise another $84 billion to expand its holdings. The rise of Saylor’s Bitcoin-centric play has helped push Strategy’s market cap from $1 billion to over $100 billion in just five years.

Despite growing competition, including Donald Trump’s media company announcing a $2.5 billion Bitcoin treasury plan, Strategy’s loyal retail investor base remains a key differentiator. For many crypto enthusiasts, the premium on Saylor’s stock isn’t just tolerated — it’s embraced as a mark of conviction.

“Strategy isn’t just a proxy for Bitcoin — it’s a belief system,” said Strahinja Savic of FRNT Financial. “It’s reflexive, narrative-driven, and turbocharged by the retail crowd.”

However, the trade is double-edged. When Bitcoin plunged in 2022, Strategy’s stock fell harder — and the firm has since increased its leverage. Any future crypto downturn could amplify losses just as it currently magnifies gains.

Still, the trend of corporate Bitcoin accumulation is growing. At least 30 U.S.-listed firms have followed in Strategy’s footsteps. Analysts at Bernstein expect as much as $330 billion in corporate Bitcoin purchases by 2030 — a development Saylor openly champions.

“It’s a phenomenal story,” Savic added. “Corporate adoption is one of the top reasons I’m bullish on Bitcoin.”