oh! so you played twice then. thank you for the dedication!
i don't see being unable to pay your debt as losing, necessarily. it's just an ending, a bad one, but still an ending. that's why when you die it says "THE END" and not "game over" or anything like that. i didn't want to make it feel like you were losing losing. but that's just my interpretation and i think it's totally valid to think of that as losing the game and feeling compelled to play it again.
there are actually 3 "endings" (it's just the final dialogue that changes). one if you can't pay, one if you pay (more than $800) and a sort of "special ending" if you get more than $1200.