Draw Inside not working for text objects that have been converted to paths?

Hi guys. Sorry to bother you again. Learning illustrator seems to be quite difficult and I keep encountering random issues that googling doesn't solve.

My issue today is that I have a three text objects that I have outlined (converted to curves), but I cannot draw inside them collectively. I can draw inside the individual letters but I want to be able to draw inside all letters at once (SEE VIDEO FOR CONTEXT: https://youtu.be/PgiEfAfN7f4)

Thanks for being patient and helping me learn!