Passing wire down through Exterior Wall
HazardousGlitch had a good suggestion. I don't think I was drilling into to top of a stud because I had tried several holes before posting.

Opened up the wall more so I could position the drill closer to the drywall and went through easily. Above I posted the wrong photo that didn't have the deep hole. Now you can see the deep hole (left bottom) and the successful hole (right by the old wire). You can also see my other failed attempts. 

Thanks for the help!