It never seemed to me that he was looking for a good time to buy, although it seems to me that he would have been very happy if he could have invested a lot more money while the price was under $20k. Of course, his company already has a very nice amount of BTC, and when you have that in mind, it's easy to plan your next move. Be that as it may, even though Saylor remained optimistic even when it looked like the price was going to go towards $10k, I'm sure it's a lot easier for him today than it was a few months ago.