In a lot of ways he is, despite witnessing a lot of how the sausage is made directly. Honestly, I think at at least half of it is wanting to convince himself that the world still functions in ways that make sense to him rather than admit that it's mostly grifters grifting all the way down.

This is a good heuristic, and it's how most things in life operate. It's the reason you can just buy food in stores without any worry that it might hurt you[0] - there's potential for million ${local currency} fines, lawsuits, customer loss and jail time serving as strong incentive for food manufacturers and vendors to not fuck this up. The same is the case with drugs, utilities, car safety and other important aspects of life.

So their boss may be naive, but not hilariously so - because that is, in fact, how the world works[1]! And as a boss, they probably have some understanding of it.

The thing they miss is that AI fundamentally[2] cannot provide this kind of "correct" output, and more importantly, that the "trillion dollar companies" not only don't guarantee that, they actually explicitly inform everyone everywhere, including in the UI, that the output may be incorrect.

So it's mostly failure to pay attention and realize they're dealing with an exception to the rule.

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[0] - Actually hurt you, I'm ignoring all the fitness/healthy eating fads and "ultraprocessed food" bullshit.

[1] - On a related note, it's also something security people often don't get: real world security relies on being connected - via contracts and laws and institutions - to "men with guns". It's not perfect, but scales better.

[2] - Because LLMs are not databases, but - to a first-order approximation - little people on a chip!