I am not sure if you have the same problem, but for me it was because the path to the exe contained non ASCII characters. This is why it works in most systems but crashes on others. There is an open pull request to fix that https://github.com/rougier/freetype-py/pull/177.

Here is an easy way to reproduce; the exe worked fine until I added non ASCII characters to its parent folder. To be clear, a non-ASCII character will cause this regardless of where it is in the path (for example, if the exe is inside the user's folder and the username has non ASCII characters)