HN user
yes, creating an app to supplement an existing business (Men's wearhouse) can yield sub-optimal results at best. A better way to do it is to disrupt the model like IndoChino did. They realized that buying a suit is all about the materials and the fit and did everything possible(refunds, alteration fee) to ensure that customers were satisfied.
I am a fairly proficient ruby coder and I tried learning obj-c multiple times but just did not find my way around it. I wasn't thrown off by the syntax but more about the way the MVC model is built in obj-c. I was really confused by delegates and did not for some reason find obj-c intuitive. I was baffled in a few areas even with tutorials since I did not grasp some of the fundamentals. I think most people are not referring to the obj-c syntax as hard but to the overall framework. Again, I did not spend as much time/effort learning ruby/rails and felt comfortable the first week. My background is primarily Java/J2EE stuff before rails.