To be fair, those "ducks-in-a-row" questions are NOT easy to answer and it's easy for someone to fool themselves with a BS answer. Moreover, there are plenty of ridiculous ideas that someone would never think anybody would "pay for" that make tons of money in spite of themselves.

In the end it's all about taking calculated risks. Should the OP have learned more about the market he was trying to operate in AT SOME POINT before quitting his day job, hiring five "contractors" and writing 200000 lines of code in 9 months? Sure. Was it a worthwhile experience that gave him more wisdom? Hard to say. To be honest I am surprised he only blew 40K, it could have been a lot worse.