Things can go very south from the moment he decides to sell. It can happen slowly and even silently I presume, so Saylor can only expose the sale in quarterly reports where we finally find out. Or he can crash the market and cause a lot of panic.
Another question comes too, who will he sell his Bitcoin to? If he owns over 2 percent of the total supply, I see banks having a growing interest in the accquisition of his large stash of Bitcoin at one point. As a bank, having the opportunity to own this much of the supply through one single transaction from a single party may be something they may attempt if they want to finally get involved with Bitcoin. For Saylor, if Bitcoin becomes worth more than 250-300 thousand, selling it all in one chunk may be an excellent opportunity.
What happens then? Saylor sold. SHAME ON HIM! Bank purchased his stash. THE NEW BULLISH HERO! Or is it?
My fear was always that the banks will do the best they can to own as much of the Bitcoin supply as possible. And not only banks, there are multiple entities whose hands I rather not have so much Bitcoin centralized in. I get why people are hyped about Saylor but I also do not. Years ago we would have not cheered when a single party wanted to control a large chunk of the Bitcoin supply. It would have been a fearful event instead.
I have no idea what happened since then causing people to reverse their mind and cheer for it.