Every people have their own phrase including Michael Saylor. Think about it, if you just have $100 per week and you can only use $20 while $80 for filling your needs, that $20 is the money you can afford to lose. You will not add more money because that money is for your needs.

You don't have to follow what Saylor do because you are different. Not to mention about the amount of money between you and Saylor have, but there is another different that can not work if you use it.