Earlier quoted context omitted.
DHH seems to have gotten plenty "filthy rich" hitting singles: http://david.heinemeierhansson.com/racing People who swing for the fences generally fly out to shallow center. You can score lots of runs hitting single after single after single.
Having a sports car fits into the "you can live a good life on hitting singles". Having your own private jet, is when you're filthy rich.
UPDATE: Link - http://www.luxist.com/2010/09/06/one-of-a-kind-pagani-zonda-...