The better I get at AI, the less I trust it

The better I get at using AI, the less I trust it.

I know, I know — that sounds backwards. We’re being sold a future where increasingly capable AI assistants take more and more work off our plates. But after spending a frankly embarrassing amount of time building an elaborate AI-powered NFL betting project over the last few months — and especially after suffering through an infuriating $1,500 catastrophe this week — I’ve come to the opposite conclusion.

AI works best when you treat it like an idiot.

Some context: I co-host a small NFL player-prop show as a side project. Because I am apparently incapable of enjoying hobbies like a normal person, I started building an AI research system to augment my own analysis. I want to know ball on camera, obviously.

It started simply: Analyze the games. Find interesting player props. Tell me what you think. Let’s make some money!

That worked surprisingly well — until it didn’t.

Welcome to another edition of Prompt Mode, your weekly AI newsletter.