Michael Saylor is easily one of the worst investors of his era. Don’t believe the hype and noise the maxis push while pretending he’s some master guru. During the 2000 dot-com bubble, he lost more money than almost anyone. 99% of his net worth was wiped out after he piled into high-risk bubble stocks that became worthless, and after MicroStrategy was forced to restate its financials due to SEC-flagged accounting issues. Fast-forward two decades, and he’s pinned the entire future of his company on Bitcoin. Before doing a complete 180, he publicly dismissed Bitcoin and compared it to speculative digital fads that flame out. Then he magically reinvented himself as its loudest evangelist, using the mania to pump attention into MicroStrategy. It’s the same playbook he ran 25 years ago, but most people either forget or never knew. His actual investment performance is horrible. His first Bitcoin buy was around 11,000. Bitcoin has surged a whopping 1,074% since then, yet MicroStrategy’s average cost basis is so inflated from nonstop buying that his unrealized gain is only about 22% over roughly 5 years. That’s around 4.4% annualized... He’s badly underperforming almost every major index and professional manager. A basic GIC would have outperformed Saylor’s return... The position he built is massively leveraged and structurally fragile, and his increasingly extreme public messaging reflects that pressure. You don’t tell people to mortgage their homes for Bitcoin unless you’re desperately trying to keep momentum alive. My view: Bitcoin is cracking and could drop extremely low, even below 10,000. If that plays out, Saylor’s entire strategy is exposed, and the community will turn on him fast. His bet is dangerously concentrated, debt-fueled, and dependent on endless upside. Anyone treating him as a financial oracle should step back and look at the numbers.(Jacob King)