> I really appreciate how he's always searching for things that went/go/will go wrong even thought everything seems to go so well for Pixar.

Of course, the fact that things are going fairly well makes it easier for him to find and focus on things that aren't going well.

It's a virtuous circle wrt technical debt. The less you have, the more effort that you can apply to each bit that you do have. And, if things are going well, the less that you spend in total on reducing your technical debt.