Michael Saylor’s $84B Bitcoin Gamble: Is MicroStrategy’s Mega-HODL Paying Off?

MicroStrategy’s all-in Bitcoin bet now holds $84 billion in BTC—but is the strategy still working, or just riding the hype cycle?

The Breakdown:

- Saylor’s firm holds 1.2% of all Bitcoin. That’s not conviction—that’s a corporate cult.

- With an average buy-in of $35K, they’re sitting pretty… unless the market remembers this is a company that once sold ‘business intelligence’ software.

- The real play? Turning a legacy tech firm into a leveraged Bitcoin ETF before the SEC could even blink.

Bottom line: When your balance sheet moonlights as a crypto hedge fund, ‘strategy’ is just a fancy word for ‘diamond hands.’

Strategy’s 42/42 Plan To Increase Bitcoin Holdings

During its latest earnings call, Strategy introduced what it calls the 42/42 Plan, which is a roadmap aimed at raising $84 billion in capital over the next two years. The funding will be split equally between equity and fixed-income instruments, all designated to be used for further Bitcoin acquisitions. 

This initiative follows a $21 billion at-the-market equity offering that recently brought in over 301,000 BTC in recent months, sending the company’s share price soaring by 50%. As of April 28, 2025, Strategy holds 553,555 BTC, acquired at a total cost of $37.9 billion and an average price of $68,459 per coin. Of this total, 107,155 BTC have been bought in 2025 alone, making it the company’s most aggressive buying year to date despite only four months having passed. The firm’s internal disclosures also note an average cost of $66,384.56 per bitcoin. 

The latest acquisition round included 15,355 BTC purchased at an average price of $92,737 on April 28 at $1.42 billion. These aggressive purchases have positioned Strategy as the world’s second-largest institutional holder of Bitcoin, just behind BlackRock. 

Interestingly, Strategy’s playbook for building a BTC-heavy balance sheet is not slowing down. Even as the company reported its fifth consecutive quarterly net loss, investor sentiment is still optimistic. The company reported an unrealized $5.9 billion loss in the first quarter of 2025. However, its stock is up by approximately 32% since the beginning of the year and has outperformed the Nasdaq 100 index, which is down nearly 6% over the same period. 

How Strategy Is Doing On Its Current BTC Holdings

Strategy’s market value is now deeply influenced by Bitcoin’s price direction. The company’s BTC portfolio has yielded a 13.7% return so far in 2025, generating a paper gain of $5.8 billion. Despite the crypto market volatility, the company updated its BTC yield target from 15% to 25% and a $15 billion profit goal by the end of the year. 

At the time of writing, Strategy’s Bitcoin strategy continues to pay well, and the company’s stock has been rising in tandem with Bitcoin’s recent rally. MSTR is currently up by 3.35% in the past 24 hours and is currently trading at $394.37. Bitcoin, on the other hand, is trading at $96,500.

Featured image from Unsplash, chart from TradingView