I believe that he should start to be careful in my personal opinion. He's not doing his purchases using 100% of his own capital/money. It's actually a leveraged trade using MicroStrategy stock as collateral.
I think you have not understood it well and I have already explained it in the thread but I think it is easy to get lost in such a long thread, so I will explain it again: the debt that MSTR has is unsecured, therefore there is no collateral backing it.
As of today MSTR finances bitcoin purchases in two ways:
1) ATM: it sells shares and with the money it buys bitcoin. These are newly created shares.
2) Convertible debt. The interest paid is ridiculous, 0% or close to 0%, and two things can happen, the share price can go up, so the convertible debt is converted into shares, or it can go down or stay more or less the same, so MSTR has to repay the debt, which is not much of a problem because the debt to equity ratio is quite low.
If his average entry price goes high enough because of Chad Saylor's new Bitcoin purchases, that could give the trade a higher probability for liquidation.
Nope. There is no liquidation because there is no secured debt. No margin calls.
Although I believe it's a historic investment that will be written in investment and finance books, he should still be very careful. What will he do during a -50% price crash?
Something similar to what he did in the previous -80% crash?
Will he scale down? Because that would indeed be very bearish. Instead of DCA at any price, it's probably better for him to wait, Buy the DIP, and HODL.
If Saylor has been so successful, it is precisely because he does not think like you. I know it is hard to understand, but that is precisely the basis of success.
