Michael Saylor is overleveraged and continuously doubles down on massive Bitcoin long positions every time it dips.
That sounds like a dangerous investing 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.
Michael Saylor will either by the biggest loser in Bitcoin Land, or he will be celebrated as making one of the greatest bets in the history of trading/investing. Zoom out, if he can pay the interest until the big surge to 6 digits, then there’s obviously higher probability for his bet to profit him billions.