Henry Ford

Ford is known world-wide for his contribution to the world of engineering and motorized vehicles.  He invented and successfully established a market for the Ford Model T, the first affordable passenger vehicle.  Before this, however, he spent all of the money his first investors provided with nothing to show for it, bankrupted another Detroit Auto Company, and tried but failed to launch a political career.  In total, he failed and went broke five times before he succeeded.  Impressive fails!