History is a great teacher, only to those who want to learn from it. When we look back to see the fate of some of the most expensive IPOs of the bull run that ended in January 2008, we find a common motif. Lofty valuations do not hold up for very long. Take a look at the four graphics below. These are some of the most expensive IPOs of recent times. These consist of diverse companies in unrelated industries. None of them were able to hold onto their high valuations for long. Keep in mind that these are not IPOs that have lost the most investor wealth. These are just the most expensively valued ones at the time of their listing.