Most of us have been in that same painful regretful shameful confidence bursting situation more than just a few times. However, I’ve learned the most about investing in penny land from my massive mistakes. Those mistakes cost a lot, but will make you a better investor by forcing you to avoid that mistake by going in with a plan on how much you are willing to lose and where you will jump out on your gain. This isn’t just coach speak either. I’m being honest.