The Black Swan

Sloppy writing, and the author goes out of his way to make sure you see the chip on his shoulder.

If you can get past that, there are some really good ideas in here. Key takeaways:

Guassian distribution doesn’t apply to technology (money, publishing, stock market, etc…) but all the standard tools assume it.
Use barbell strategy for coping with non-guassian distribution: play very safe and add a couple of long shot bets with large upside. Stay clear of “low risk” options because the type of risk it’s exposed to can’t be predicted or priced adequately (see: GFC)