Hosted by
Bill Brewster

Bill Brewster is a private investor. He cohosts the podcast Value: After Hours with Tobias Carlisle and Jake Taylor. Tobias, Jake and Bill met at a Berkshire Hathaway meeting and formed a lasting friendship. And, as it turns out, people really like the podcast.

While Bill tries to replicate Warren Buffett and Charlie Munger’s thought processes, he is heavily influenced by Bill Miller III, Stan Druckenmiller, and others. This podcast is his attempt to dig deeper into other investing/business philosophies and share the knowledge with the world.

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 here 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 
  • ~22:30 – How would Buffett behave if he were starting today?
  • ~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
  • ~1:09:00 –  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
  • ~1:37:00 – Back to Mutiny Fund and how it’s structured
  • ~1:40:00 – Avoiding big drawdowns


Disclaimer: Bill manages a portfolio under the name of Sullimar Capital Group. This podcast is for informational and educational purposes only. Nothing in this podcast or on SullimarCapital.Group is investment advice. All information in this is opinion based, potentially biased, and requires verification.

Bill and his guests make no representation, warranty or undertaking, express or implied, as to the accuracy, reliability, completeness or reasonableness of the information contained in these podcasts. Any assumptions, opinions and estimates expressed constitute the participant’s judgment as of the date thereof and are subject to change without notice. Any projections contained in the information are based on a number of assumptions as to market conditions and there can be no guarantee that any projected outcomes will be achieved. This podcast does not accept any liability for any direct, consequential or other loss arising from reliance on the contents of this presentation.

This podcast series DOES NOT CONSTITUTE AN OFFER TO SELL OR THE SOLICIATION OF AN OFFER TO BUY ANY SECURITIES MENTIONED OR DISCUSSED. Seek the your financial, tax, legal, accounting, or other advisor’s advice before making any investment decisions. We are not your fiduciary or advisor.

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Episode 35