Michael Saylor is overleveraged and continuously doubles down on massive Bitcoin long positions every time it dips.
That sounds like a dangerous trading strategy to me, specifically, the "double down" part. It's understandable to inject a little more cash in long positions on each correction, but adding large amounts of BTC unnecessarily increases the risk, especially since it's company money and I don't expect BTC to make more than 66% gains at the current price, which would place it at 75K. But even any profit beyond 33% at 60K is highly unlikely. When you think about how much money that adds up to in terms of net income for Microstrategy it doesn't really make sense.