Sometimes I ask myself, “If I had already achieved financial freedom, what would I do now?”.
An interesting insight is that you can actually do many of those things already.
I don't like Saylor, and I don't support him. But... he is not an investor when it comes to Bitcoin, he is a capital raiser.
The best time to raise capital is when the market is euphoric. By coincidence, that's also when assets are highly valued.
So, his average entry price is not the result of bad investment decisions, but rather a side effect of the strategy itself.