Bought a book for Cocoa programming to learn Obj-C. Alright, but not a deal breaker.
First gig I offered for $200 flat rate to get the portfolio rolling, through a HN post: https://news.ycombinator.com/item?id=6382405
First app idea was actually a game, I learned what was necessary to build it (https://itunes.apple.com/gb/app/firework-flare/id513766705?m...).
Biggest challenge: going from basic programming knowledge to having to use design patterns, strange (at the time) syntax.