Traders copying Michael Saylor's dollar-cost averaging often buy on rallies instead of dips, pushing their average cost higher and bloating position size. When the market reverses, they're stuck with a large, expensive position that's hard to exit without taking big losses.
What actually happens when traders try to use Michael Saylor's style of DCA in a trading context? Well, they fall into a trap. They don't realize that they're in. Instead of buying more when prices fall, they keep adding. As prices rise, every purchase feels justified because the market is confirming their bias and belief. But mechanically, their average cost is creeping up. Every single buy. The position gets larger, it gets riskier, and of course, it gets harder to manage. Then, when the market finally turns, as it always does, they're stuck. There's no flexibility left, there's no room to exit. There's just a bigger position with a worse entry.
