IMO his big win was getting an iPhone app dev (who can actually execute) agree to make an app for him on the premise of splitting revenue. Either this was real early time of the "App goldrush" before anyone knew money could be made or the dev was a friend (post seems to imply it was a random twitter follower).

Anybody with a reputation as a good iPhone app dev get the age old "idea guy" proposition at least 3 times a week: "I got a great app idea.. I'll give you some of the $ if you code it just for me."