Jason Buck (@JasonMutiny on Twitter), Co Founder and CIO of Mutiny Funds, stopped by for the first in person interview on The Business Brew.  Mutiny is releasing the Cockroach Portfolio, a portfolio designed to survive any market conditions.  See https://mutinyfund.com/ for details.   In this episode Jason discusses his history as an entrepreneur, which took a hit in the Great Financial Crisis.  That event caused Jason to think about whether it was possible to hedge entrepreneurial risk.  After years of thought, the Cockroach Portfolio was born. The goal of the Cockroach Portfolio is to keep wealth in all market conditions.   This conversation goes all over the place.  We hope you enjoy.    ~4:05 - Trading VIX ~9:00 - Jason's history as a real estate entrepreneur ~10:00 - How often "black swans" occur ~16:50 - Jason describes thinking about hedging macro/entrepreneurial risk ~18:00 - Shannon's Demon - see also https://quant.stackexchange.com/questions/38473/intuitive-explanation-for-shannons-demon ~22:30 - How would Buffett behave if he were starting today? ~23:35 - The $SHIT ETF ~29:17 - What it's like to lose everything ~32:00 - Keeping wealth vs. making wealth ~37:50 - The Hypomanic's Edge ~41:00 - How Jason and Taylor "solved" the problem they wanted to solve ~48:07 - Be so good they can't ignore you ~49:20 - Selecting the right partners ~55:00 - Building the Cockroach Portfolio the right way ~1:04:00 - Playing better games than stock picking; compounding capital without tax ~1:09:00 - What lies do we tell ourselves? ~1:13:00 - Laying asymmetric bets ~1:17:00 - Mental health and whether substances risk mental health ~1:18:00 - General mental health discussion and habits to keep healthy ~1:29:00 - General podcast and Pirates Of Finance Discussion; see https://www.youtube.com/channel/UCsfk98XxbnjTCLkROQZ5zWg/featured ~1:37:00 - Back to Mutiny Fund and how it's structured ~1:40:00 - Avoiding big drawdowns