Books

I'm halfway through Nate Silver's On the Edge. The book's a bit tribal and self-aggrandizing for tech, but Nate is a measured guy and the tone is ok. Without being too antagonistic or bashing, he does a cool comparison between risk-takers & the professional managerial class and the implications at large. Worth the read

I like how he frames gambling as basically being on the lookout for mispriced markets and capitalizing on these with appropriately sized bets. He makes a good case for taking more risks wish I previously saw as more of a vice than a virtue.

Totally. Had a similar take about making a good case for why it's rather a virtue