Part way through Hoagies section, there is a section where the founding fathers are standing outside after a short cutscene of them jumping out of a window.
Walk to the chronojohn area. Select one of them with your mouse cursor.
Press Y Nd select the talk function. This will pop the achievement.
An Amendment from ZX KNIGHT - THank you, I did not know this.
Worth noting that if you go back into the main room with the fire and take the quill own it will trigger them coming back in and you won't be able to get the achievement.
Update, Not too sure why this was rated as bad. If t is not correct please let me know and I will delete this comment.