How can I make sure he trusts what changes he sees? He says he really doesn't trust himself - because he felt like he "believed me before when I said I'd change" and ultimately things did not change. He feels stupid for trusting me so the issue is he doesn't even want to trust what's in front of his face for fear of "being duped again".
You can't make him do anything. All you can do is make the changes in you, and live them. This will take time.
One important thig is that you have to make the changes for YOU, and not because you want to influence him. He will see through it if you are only doing it for him.