I believe that the Heroic Failure must have something do to with death.
Perhaps you have to game-over a certian number of times
Perhaps you have to die pathetically, old king coal?
I'm sure it has something to do with the concept of a game-over, but whether it's a number of times or a particular death is unknown.
Also, the "Now who's Boss" one.....Has anyone considered it to be like the achievements in the game? One of the achievements requires you to kill 50 or so enemies with Mumbo. Perhaps this one is unlocked by killing a certain enemy or enemies a particular number of times.
That is what I think, you're welcome to accept it or not. ^^