Michael Saylor’s Strategy keeps doing what many investors fear most, buying Bitcoin when it looks expensive. Despite constant criticism for “buying the top,” the firm continues to prove that conviction can outperform timing.

In its latest filing, Strategy revealed it purchased 487 BTC between November 3–9 for $49.9 million at an average of $102,557 per coin, right after Bitcoin hit $106,000 before sliding below $100,000.
While that timing looks off, there’s logic behind it. The company’s purchase windows often align with internal liquidity events, like stock sales or financing rounds. These periods usually occur when Bitcoin markets are most liquid, often during rallies, making large buys smoother to execute.
For Saylor, short-term price swings mean little. His focus is on steady accumulation and treating Bitcoin as a long-term monetary asset, not a trade.
And so far, it’s worked. Strategy now holds over 641,000 BTC worth around $68 billion, up roughly $20 billion on paper since its first buy in 2020.
Critics may call it reckless, but the results tell another story, a corporate strategy built on conviction, not timing, and a belief that Bitcoin’s future value far outweighs today’s price chart.
Disclaimer: This content does not constitute trading or investment recommendations. It’s essential to conduct your own research before purchasing any cryptocurrency or investing in any services.















