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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 decks for a very long time. I've worked at a top quant trader long enough to spot BS, and the KL-divergence between what competent looking YouTubers say and what actually works is extreme.

My recommendations would be:

  • Blogs with great tacit knowledge: bitsaboutmoney.com, thediff.co, Money Stuff
  • Trustworthy news sources: Financial Times, Bloomberg News, Reuters

Other recommendations:

  • Git version control: Scott Chacon's So You Think You Know Git videos