Does it work out if we imagine that Prince and/or the person who wrote the post don't have the full picture of Cloudflares own involvement?

It becomes nuanced doesn't it? First thing is: to trust him fully is to understand what it means to trust him... that he knows his business well enough that he can intuitively feel things are wrong. That comes from not being checked out, so: he knows who is in his company and why, he knows the types of projects happening in his business and why, he has easy levers to gain real time information when something feels wrong, and - he monitors his business correctly. I trust Matthew because I know him, so I believe all those things are true. The final part is that trust is also about knowing that mistakes happen, and that they are being: sought out, addressed and owned. So when I say I trust him, it's because I believe everything aforementioned - it makes your scenario safe, at least to me.