The Cockroach Portfolio

With the duo out conquering Parenthood and the Kentucky Derby this week 🏴‍☠️⚔️🍼🐎 we're broadcasting a crossover episode of Corey's excellent podcast 'Flirting with Models' with Jason as a guest. 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.