For files over 20 or so megabytes, email just won’t do. Check out this article for 7 ways to send huge files.
I have no problem sending files up to 50mb with email (100mb if I know the person has a fast internet connection). I just break it up in multi part rar files.
Also for very large files you might want to consider sneakernet, which is basically sending storage devices via snail mail.
This blog post explains a bit about it: http://www.codinghorror.com/blog/archives/000783.html
Yes, I’ve done that before, except with MediaFire.
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