FYI, this achievement may not pop in your first game. I had a number of achievements that should have popped, but took 2 games to show up. The game may not recognize too many achievements in one game.
For this one, it popped in-game when I crossed $20,000. It didn't wait until the end of the game.
There's an archive of all of the episodes and answers here, sorted by season: http://www.j-archive.com/listseasons.php
Hope it helps. It's frustrating.