Flirting with Models

Jason Buck - Designing the Cockroach Portfolio (S6E1)

May 1, 2023

55:47

Creator website

AI Chapters

Episode notes

Introduction

2min

The Importance of Formative Experiences

3min

Mutiny Friends: The Entrepreneurial Experience

3min

How to Make High Highs and Low Lows

3min

How to Build a Diversified Portfolio for Entrepreneurs

3min

Harry Brown's Permanent Portfolio

2min

How to Define Long Volatility and Tail Hedging

2min

How to Be a 25% Long Ball Investor

3min

The Long Ball Tail Hedging Sleeve: A Blue Ocean for Value Investors

2min

10.

How to Monetize Options Trades

2min

11.

How to Avoid the Case of Tail Hedging

2min

12.

The Importance of Volatility in the S&P 500

3min

13.

The Importance of Monetization in Tail Hedging

2min

14.

How to Replace Gold With an Ensemble of CTA's

2min

15.

The Dispersion of CTA's

3min

16.

The Importance of Trend Following in Capital Allocation

2min

17.

The Importance of Having Strong Assumptions in Portfolio Design

2min

18.

How to Find the Right Leverage Level for Your Portfolio

5min

19.

How to Design a Portfolio That's Robust

3min

20.

The Best Use Case for an Entrepreneur's Portfolio

2min

21.

How to Make Your Fund Cataclysm-Proof

3min

Jason Buck is the co-founder and CIO of Mutiny Funds and maybe one of the most interesting people I know.

Jason made, and subsequently lost, a fortune in commercial real estate in the 2008 crash. This “ego destroying event” was the catalyst for him to completely rethink the idea of resiliency, both in business and investments.

Jason spent the better part of the 2010s developing the Cockroach portfolio, a modern take on Harry Brown’s permanent portfolio. A quarter stocks, a quarter bonds, a quarter CTA, and a quarter long volatility, Jason has designed the portfolio to provide all weather returns, with the possibility of serving as an entrepreneurial hedge.

We discuss the value of tail hedging, tail hedges versus long volatility trades, the limits of manager diversification, and managed futures/CTAs versus static commodity positions.

As a final note, this episode was recorded live at the Exchange ETF event in Miami.

Enjoy.