If you'd like to reduce all your history to a single "Initial import" commit, simply remove .git directory and create a new local repository (keeping a backup of the old one). git init . && git add . && git commit -m "Initial import".
Such new repository won't have a common ancestor with the one you've pushed to GitHub, so you'll have to git push --force your newly created repository.
You could rebase and squash everything if you wanted to (except the initial commit) but why bother? Simply delete your .git directory, run git init to recreate it, git add everything, and git commit to make a new initial commit.
Jefromi's answer will work, but if you want to keep your existing repo configuration, or even leave around the commits just in case, you could do the following:
git checkout master
git branch backup optionally leave another branch here in case you want to keep your history.
git reset --soft $SHA_OF_INIT_COMMIT this will update what HEAD is pointing to but leave your index and working directory in their current state. You can get the SHA with git log --pretty=format:%h --reverse | head -n 1, and make this one step with git reset --soft $(git log --pretty=format:%h --reverse | head -n 1)
git commit --amend change your initial commit to point to the current state of your repo.