Massive respect. Michael Saylor, the legend, started buying Bitcoin for the first time on August 10, 2020. By December 8, 2025, over 5 years, he bought Bitcoin 89 times, accumulating a total of 660,624 BTC at an average cost of $74,696 per coin, with a total investment of $49.346 billion. His current holdings are up about $10 billion in profit. Back in 2013, Michael Saylor was still posting about dissing Bitcoin, saying it was just a money-laundering tool and would eventually go to zero. But after changing his perspective in 2020, he went all in and never looked back. This guy is either all out or all in, no in-between.