Read that as both Nate and me seeing me as more optimistic than him, and wanting to settle it by experiment (actually making the change and seeing if it helps), but this being limited to upside instead of downside.

That is, if I propose a change that "totally won't hurt" and Nate is sure it'll hurt, then Nate will go with his gut, but if I propose a change that "totally will help" and Nate is sure it won't help, then Nate will see what happens when we try.