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.
I'm not worried about Saylor's strategy because she basically believes that BTC is a valuable asset. Loss or gains, are often calculated in conditions that have not been realized, meaning that even if the value of BTC in the future drops, the BTC assets never decrease. So far, MSTR's BTC assets are still in surplus and buying when prices are low, isn't everyone doing the same thing?