As Stated before just talk to Tommy Torini in The Tops.
You must recruit all of them not just one, also when you do this make sure you go back and talk to Tommy after each one because if you recruit all of them and then return to talk to Tommy it will glitch and you will get all of the rewards, but the quest will not complete no matter how many times you talk to him.
I did all of them then talked to Tommy 3 times in a row including doing it after clearing cache and off line. Each time it glitched and the quest did not complete.
So as a side note! When you do this Side Quest save after each one just in-case you need to fall back for some reason and do one at a time.
This glitch may not happen in every case, but it is a heads up if anything.
Note: I have obtained this achievement on another account. It was compromised so I had to switch to another.