I am trying to get into Spitznagel's book Safe Haven but it is hard to know what to make of him. In the preface he basically says don't even try to do any of this type of tail hedging. This isn't a book about strategy. That has made it hard to be motivated to listen to him as what is the point? He does though mention his mentor, old veteran corn trader Everett Klipp. "was known as the "Babe Ruth" of the Chicago Board of Trade" https://en.wikipedia.org/wiki/Everett_Klipp He basically says Klipp would take a one tick loss if he wasn't up immediately and had no regard for his winning percentage. That might have been worth the entire book as that mode of thinking is quite interesting. For this thread , not that options are lottery tickets but I can honestly say I have never bought a lottery ticket or a put or a call and I never will. I feel like a trader has to basically be ignorant of the real hardcore quant derivatives literature or they would not want to trade with those that are not. I think of Tankov's Financial Modelling with Jump Processes and even that is probably massively outdated at this point.