Yeah, I tried every speed on the drill press, starting from the lowest. Nothing wanted to go through though.
I'm not sure yet what I'm going to do about it. I haven't really gotten the chance to sit down and try to think of something. The clip still works great, so it's not as if it's unusable. If I think of a good fix, I'll post it here, just in case anyone else runs into the same problem (not likely... I'm sure everyone here has better tool skills than me

).