Excess Returns

All-In on the S&P 500 Worked for 18 Years | Jared Dillian on Why It's Still Wrong

September 8, 2026·56 min
Episode Description from the Publisher

Jared Dillian joins Matt Zeigler to discuss The Awesome Portfolio, his approach to asset allocation built around 20% each in stocks, bonds, gold, cash, and real estate. They explore how diversification, annual rebalancing, and managing volatility can help investors reduce financial stress and build a portfolio they can stick with through bear markets.Jared explains his "life hedge" concept, challenges conventional wisdom about stock market drawdowns, and shares how losing half his net worth during the financial crisis shaped his investing philosophy.Buy The Awesome Portfolio Bookhttps://amzn.to/3Tf3of7Topics covered:Why Jared questions putting your entire life savings in the S&P 500How the Awesome Portfolio differs from Harry Browne's Permanent PortfolioIncluding home equity when measuring your overall asset allocationWhy volatility and frequent portfolio checking can lead to costly decisionsThe life hedge: protecting against your job and investments declining togetherWhy Jared disagrees with Charlie Munger about tolerating large drawdownsIndex concentration, changing correlations, and the limits of diversificationThe portfolio's historical backtests, including its losses in 2008 and 2022Annual rebalancing, cash reserves, inflation protection, and cryptocurrencyManaging FOMO and taking practical steps toward a less stressful retirement portfolioTimestamps:00:00 Jared Dillian's case against an all-stock portfolio06:33 The five equal allocations in the Awesome Portfolio11:07 Why "never sell" can become a behavioral trap15:26 The life hedge: when your paycheck and portfolio fall together20:38 Risk-adjusted returns and S&P 500 concentration24:49 Why rising interest rates hurt diversification in 202228:51 Backtested losses in 2008 and 202234:26 Combining home equity, retirement accounts, and savings38:58 Cryptocurrency, portfolio distractions, and FOMO44:31 The Death of Equities and lessons from past crashes48:44 How diversification could have changed Jared's financial crisis53:41 First steps toward reducing portfolio risk before retirementLearn more about the Excess Returns podcast network:https://excessreturns.coNo information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

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