Little Big Workshop

You can get this achievement at any point, you just need to let your finances slip below 0 and then recover. The game allows you to dip down to -5000 before you go bankrupt, so you can easily just sit on an order while you already have very low funds, wait to dip just below 0, then sell your order and recover, netting you the achievement.

If you wish to get this and 2 other achievements quickly, start up a new game. Once its loaded, skip the tutorial to get Too Cool for School. Next, hire 3 workers, buy some basic workstations, and no breakroom. Get started on an order, I did an order of 20 small drawers, and set your game to the fastest speed. After a bit you'll earn Horrible Working Conditions as all your workers will collapse. Next, get a simple breakroom going, and stay on the fastest speed. From there, just wait a few minutes and you'll go below 0 and should have at least a few items ready to ship. Just ship them off and as soon as their gone you'll get this achievement as well. 3 achievements in as little as 5 minutes.