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Build an Awesome Portfolio with Jared Dillian

Trader Mindset

38m
Transcript

Original podcast

Summary

Written by a model from the transcript; not yet reviewed.

This episode features a conversation between the host and his guest, Jared Dillian, centering on the release of Dillian's book, The Awesome Portfolio. The discussion explores Dillian's strategy for building a low-volatility portfolio composed of stocks, real estate, gold, cash, and bonds, designed to survive severe market drawdowns without causing the psychological stress associated with traditional index investing. They examine lessons from the 2008 financial crisis, the importance of maintaining high liquidity through cash, and the challenges of countercyclical asset allocation.

  • Maintain high liquidity with substantial cash reserves to seize unexpected market opportunities and avoid forced selling. 18:39
  • Rebalance your portfolio consistently on a memorable date such as the end of the year or your birthday. 13:27
  • Avoid emotional decision-making by prioritizing drawdown reduction over maximizing speculative returns. 3:08

Chapters

  1. 0:00
    Podcast Introduction and Host Greeting

    Michael Martin welcomes listeners and introduces his friend Jared Dillian as the guest.

  2. 1:59
    Origin of the Awesome Portfolio Concept

    Jared explains how a conversation with a client sparked the idea for a low‑volatility portfolio.

  3. 2:34
    Rebalancing and Portfolio Maintenance

    The hosts talk about the importance of annual rebalancing and how to handle real‑estate exposure.

  4. 4:39
    Historical Performance and 2008 Crash Resilience

    Jared compares the Awesome Portfolio’s performance to the S&P 500 during the 2008 financial crisis.

  5. 7:36
    Cash, Gold, and Commodity Allocation Debate

    Jared defends the 20% cash and gold allocation as optionality and a hedge against inflation.

  6. 11:29
    Real‑World Examples: Ukraine, Bitcoin, and Chipotle

    The duo discusses how the portfolio performs during geopolitical events and reflects on missed investment opportunities.

  7. 15:25
    Impact on Financial Advisors and Market Dynamics

    They explore how the Awesome Portfolio challenges traditional advisory models and could reduce reliance on advisors.

  8. 24:13
    Investor Psychology and FOMO Management

    Jared explains how the portfolio helps investors avoid fear‑of‑missing‑out and stay disciplined.

  9. 34:19
    Balancing Work, Hobbies, and Investing

    Jared shares his philosophy on limiting information intake and balancing life pursuits with investing.

  10. 37:53
    Closing Remarks and Book Promotion

    Michael wraps up the episode, encourages listeners to buy the book, and thanks Jared for his insights.

Highlights

  • 1:59

    Origins of The Awesome Portfoliostory

    The guest explains that the portfolio concept emerged from casual tinkering and email discussions with a financial advisor in Idaho while looking for a low-volatility answer.

  • 4:39

    Outperforming in 2008data

    During the 2008 crash when the S&P was down 38%, the awesome portfolio was only down 9% because of its multi-asset structure.

  • 10:35

    Universal Age Allocationinsight

    Unlike traditional strategies that require shifting bond percentages as you age, the awesome portfolio is designed as a one-size-fits-all solution for any life stage.

  • 11:40

    Choosing 1972 for Backtestingstrategy

    The backtest begins in 1972 because it marks the point when Americans could legally own gold again and the first real estate index was established.

  • 18:02

    The Optionality of Cashinsight

    Cash is defended not as a dead asset, but as an option that gives investors the liquidity to buy distressed assets or take advantage of sudden opportunities.

  • 34:19

    Work Intensity and Returnsinsight

    The guest argues there is a very low correlation between how many hours you work and your trading returns, noting that investing is about decision quality.

Quotes

  • “which has half the volatility and none of the drawdowns. Like, the drawdowns are very minimal.”
    Unnamed speaker · 2:39
  • “And also, if you take a fifty percent drawdown, you have to go up a hundred percent just to get back to the high watermark.”
    Unnamed speaker · 3:18
  • “You open with the line that volatility's purpose is to make people do stupid things, right?”
    Unnamed speaker · 4:07
  • “It's pretty much impossible. I would say the one vulnerability of the awesome portfolio is rising interest rates.”
    Unnamed speaker · 12:26
  • “And it's, you're gonna get four or five 50% drawdowns in the stock market. And it's, you're probably gonna get one of them in your 40-year investing career, right?”
    Unnamed speaker · 25:21

About this episode

Amazon Link to Awesome Portfolio https://www.amazon.com/Awesome-Portfolio-stress-free-approach-investing-ebook/dp/B0GQWLCYPN/ (Not an Affiliate Link) Watch Free Trading Webinar From Drawdown to Outsized Gains https://tradermindset.com/mini-webinar - Subscribe to our YouTube Channel https://www.youtube.com/@Trader-Mindset-IVT FREE - Download The Inner Voice of Trading Audiobook https://tradermindset.com/free-ivt-audiobook-tm Contact me for Coaching or questions https://tradermindset.com/contact

Transcript

0:00
38:09

7,747 words · 2 speakers

Topics

  • The Awesome Portfolio
  • Bitcoin
  • Lehman
  • Chipotle
  • Vanguard
  • GE
  • New York Times
  • Street Freak
  • Invesco QQQ
  • Dow

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