Michael Saylor’s Big Bitcoin Gamble: How’s it Going?

Michael Saylor’s company, Strategy (formerly MicroStrategy), is making headlines again with its massive Bitcoin investment. They’re aiming to become a Bitcoin powerhouse, and their strategy is bold.

A $84 Billion Bitcoin Plan

Strategy currently owns over half a million Bitcoins, making them a major player in the crypto world. But they’re not stopping there. They’ve announced a plan to raise a whopping $84 billion over the next two years to buy even more Bitcoin! This ambitious plan, called the “42/42 Plan,” involves raising equal amounts through equity and fixed-income investments.

This follows a recent $21 billion equity offering that significantly boosted their Bitcoin holdings and their stock price. As of late April 2025, they held 553,555 BTC, acquired at an average price of around $68,459. They’ve been particularly aggressive this year, buying over 107,000 BTC in just four months. Their most recent purchase was 15,355 BTC at an average price of $92,737.

This aggressive buying spree has made Strategy the second-largest institutional Bitcoin holder globally, trailing only BlackRock.

Riding the Bitcoin Rollercoaster

Despite reporting a net loss for the fifth consecutive quarter (a $5.9 billion unrealized loss in Q1 2025), investor confidence remains high. Strategy’s stock is up significantly year-to-date, outperforming the Nasdaq.

How’s the Bitcoin Bet Paying Off?

Strategy’s success is directly tied to Bitcoin’s price. Their Bitcoin holdings have already yielded a 13.7% return in 2025, a paper gain of about $5.8 billion. Despite market volatility, they’ve raised their Bitcoin yield target from 15% to 25%, aiming for a $15 billion profit by year’s end.

Currently, Strategy’s stock price is rising alongside Bitcoin’s recent price increase. The company’s stock is performing well, and their Bitcoin strategy appears to be paying off – at least for now.