The problem is that not everyone is an investor in normal society. For example, I'm in the UK, and most people don't invest cash into anything, never mind cryptocurrency. I am dumb enough to see if I can do it from $1000 a month into a wallet to beat estimates, but I will also manage that account because you need to manage it.
Most people don't invest cash into anything based on what they told you or what you see, but they can be investing in other things without making it public, and you will think they are not making any investment. We are in a digital world where anything is possible.
As someone stated, Saylor can happily buy whenever it's fine; it's not his money, but DCA is only easy if you understand the concept and understand you should also secure some gains.
You are also wrong here, saying it's not his money is as if he don't have any penny in that company when he is a share holder in that company, even if he holds less than $10 in share value, his money is still there, and mind you, he owns a higher level of share in microstrategy, and he is one of the decision-makers who don't have money; they can't hold such a position even if he is the founder of the company.