This Achievement is for losing 10 Scenarios. This is pretty simple. You just need to fail 10 UNIQUE Scenarios. This is easily combined with "The Creator" Where you create 10 Scenarios. Create 10 Scenarios with win trigger to play X amount of weeks and the lose trigger to have less than $0. Waste your money in all of them to fail to unlock this. Also do not forget to select the "Publish" Radio button to add it to your available Scenarios.
IMPORTANT!!! Your Scenario MUST have a Win and Lose Trigger to count towards these achievements.