Investing in a Price Round

i once raised a five five million dollars on a convertible note with a hundred million dollar cap for basically a company that was at a seed stage. The subsequent round happened relatively quickly at a price that was high but it was not a hundred million dollars. It created this enormous misalignment of team past investor and new investor who were trying to get the same amount of capital from different sources. i think  the time element is incredibly important because my example is very much like with five million we could have lasted a lot longer than 90 days obviously right?