What is the most amount of money you have lost as a business?

[Shortie]

When you start a business, even a small business you will always run into the issue of either losing money as well as making money. Every business will have a downfall eventually and end up losing more than they make at some point even if they don't always expect it. 

Has your business ever lost more money than it has gained? If so, how much did you lose, and do you know what caused it? Were you able to pull back from it?