1) Most bootstrappers don't have the money to pay someone else full time.
2) Most bootstrappers don't have enough experience to know what to build themselves, much less be able to communicate to someone else to do it.
3) Most developers without years of experience are overconfident in their ability to communicate and manage people.
Glad it has worked for this guy, though.
3) Yes, this is something that you learn overtime. Start small, start now :) I have written this article that presents a way to start outsourcing for a lower cost than development : http://47hats.com/2011/07/outsourcing-101-for-startup-founde...