Current theories of repeat entrepreneurship provide little explanation for the effect of failure as a “trigger event” in creation of successive ventures. Multiple failures offer potentially valuable insights to explore this relationship. New venture creation could potentially be the consequence or cause of failure. The relation also depends on whether the entrepreneur learnt from the preceding failures. Three questions were pursued: Are multiple failures driven by similar preconditions, is multiple failure the trigger or consequence of repeat entrepreneurship behaviour and what “entrepreneurial learning” is required before corrective action.