I hope Chad Saylor actually waits for a DIP before deciding to purchase more Bitcoin. Buying in any price currently will merely raise his cost-basis, WHICH will put his investment in trouble of liquidation.
That makes sense to me (except that trying to time the market is extremely tricky), but I don't think that's the way Saylor thinks--and as long as he can secure financing for his bitcoin purchases, I doubt he's all that concerned about what price he's buying in at. He thinks cash is trash, right? Well, if that's your philosophy then DCAing goes right out the window, does it not?