I've played Figgie a fair bit and don't think it's a good tool for teaching epistemics outside of a Jane Street trading internship.
To actually learn with it, you first need a number of motivated playing partners. They need to be quite skilled for their actions to be informative, and the game sucks before they reach this point. In my experience people don't reach this skill level within their first couple hours of play. It also requires N custom-made decks for N rounds of play, or for everyone to install a specific app. So it's really only practical for a t...
Love this idea, and +1 on Jon Gjengset and Neel Nanda.
For finance though, I'm skeptical of your recommendations (DeepFuckingValue and Martin Shkreli). The former made his money pumping-and-dumping meme stocks, and I get the impression the latter has been selected for fame (like recommending Neil deGrasse Tyson to learn physics).
In general, I think finding good resources in finance requires a much stronger epistemic immune system than nearly any other field! There's so much adverse selection, and charlatans can hide behind noisy returns and flashy slide dec...
I feel like we're the blind men with the elephant more often than we'd like to admit. A lot of the time when two people make conflicting claims about society, really they're both right about their substrate of society and the world is just twice as big as either thought.
Another shocker for most people: 20 million people in the US live in trailer parks. People with similar life circumstances tend to accumulate in similar places, only see those places, and thus vastly underestimate the diversity of life experience. (This is also true of everything in https://www.lesswrong.com/posts/KpMNqA5BiCRozCwM3/social-dark-matter)