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

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.
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Topics covered:
• Why Jared questions putting your entire life savings in the S&P 500

• How the Awesome Portfolio differs from Harry Browne's Permanent Portfolio

• Including home equity when measuring your overall asset allocation

• Why volatility and frequent portfolio checking can lead to costly decisions

• The life hedge: protecting against your job and investments declining together

• Why Jared disagrees with Charlie Munger about tolerating large drawdowns

• Index concentration, changing correlations, and the limits of diversification

• The portfolio's historical backtests, including its losses in 2008 and 2022

• Annual rebalancing, cash reserves, inflation protection, and cryptocurrency

• Managing FOMO and taking practical steps toward a less stressful retirement portfolio

Timestamps:
00:00 Jared Dillian's case against an all-stock portfolio
06:33 The five equal allocations in the Awesome Portfolio
11:07 Why "never sell" can become a behavioral trap
15:26 The life hedge: when your paycheck and portfolio fall together
20:38 Risk-adjusted returns and S&P 500 concentration
24:49 Why rising interest rates hurt diversification in 2022
28:51 Backtested losses in 2008 and 2022
34:26 Combining home equity, retirement accounts, and savings
38:58 Cryptocurrency, portfolio distractions, and FOMO
44:31 The Death of Equities and lessons from past crashes
48:44 How diversification could have changed Jared's financial crisis
53:41 First steps toward reducing portfolio risk before retirement
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No 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.