Money for The Rest of Us

Investment help and financial guidance for the rest of us.

  • Podcast
  • Guides
        • Asset Classes

        • A Complete Guide to Investing in I Bonds and TIPS (2025)
        • A Complete Guide to Equity REIT Investing
        • A Complete Guide to Mortgage REIT Investing
        • A Complete Guide to Investing in Gold
        • A Complete Guide To Investing In Convertible Bonds
        • Investing in Bitcoin, Oil, and Volatility ETFs
        • Carbon Investing and its Effect on Climate Change
        • Farmland Investing
        • The Opportunity and Risk of Frontier Markets
        • Investment Vehicles

        • A Complete Guide to Investment Vehicles
        • How to Invest in Closed-End Funds
        • What Are SPACs and Should You Invest in Them?
        • Money and Economics

        • A Complete Guide to Understanding and Protecting Against Inflation
        • Understanding Web3 Investing
        • Strategy

        • Why You Should Rebalance Your Portfolio
        • What Is Risk vs Uncertainty?
        • Tail Events and Tail Risk
  • Resources
        • General Resources

        • Topic Index
        • Glossary
        • Most Influential Books
        • Member Tools

        • Member - Getting Started Guide
        • Asset Allocation and Portfolio Tools
        • Current Investment Strategy Report
        • All Investment Conditions Reports
        • Strategic and Adaptive Model Portfolios
        • Member Tools and Downloads
        • Member Resources

        • Plus Premium Episodes
        • Submit A Question to the Plus Podcast
        • Member Forums
        • David’s Current Portfolio
        • David's Portfolio Trades
        • Courses

        • Investing in Closed-End Funds
  • Members
  • Join
  • Log In
You are here: Home / Podcast / 21: Investing Without A Map

21: Investing Without A Map

September 10, 2014 by David Stein · Updated October 28, 2020

I share my own portfolio and investment philosophy as an example of investing without a map. Plus, why I don’t use peer-to-peer lending platforms such as Lending Club and Prosper.

Photo by Brian Moore
Photo by Brian Moore

In this podcast, you’ll learn:

  1. What my asset allocation looks like over time.
  2. Why I hold so much in cash.
  3. What it means to wait for a fat pitch in investing.
  4. Examples of mistakes I have made investing.
  5. How changing your asset allocation over time is different from trying to time the market.
  6. How peer-to-peer lending platforms work and how they differ from direct lending.

Show Notes

My Historical Asset Allocation

asset allocation

Note: This asset allocation graph is for general education purposes only and should not should not be construed as investment/trading advice.

Having trouble distinguishing the colors in the above chart? Click to download data and graph

Silent Risk draft by Nassim Nicholas Taleb

Become a Better Investor With Our Investing Checklist

Become a Better Investor With Our Investing Checklist

Master successful investing with our Checklist and get expert weekly insights to help you build your wealth with confidence.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Summary Article

Focus On The Extreme, Not The Average

Last week, I shared how modern portfolio theory (“MPT”) was an inaccurate map used by many financial advisors, including myself for many years, to help clients choose “optimal” portfolio mixes (i.e., the allocation split between stocks, bonds and other asset classes).

The justification I used and others continue to use is an inaccurate map is better than no map at all. At the end of the day, if modern portfolio theory helps a client to diversify their portfolio, what harm could there be?

The harm in relying on this inaccurate map is it can lead individuals to be too highly exposed to extreme negative events.

What’s Wrong With Modern Portfolio Theory

The problem with modern portfolio theory is it assumes market returns congregate around the average expected return much more than they actually do. In other words, MPT assumes exceptionally good or bad returns are extremely rare.

MPT also assumes returns in one year do not effect returns in the next. That a given year’s return is independent from the return in the previous year.

Finally, it assumes investors are rational agents who are all alike.

The truth is exceptionally good and bad returns happen much more often than the theory predicts, and these extreme events tend to clump together rather than be spread out randomly.

A Bumpy Ride

When flying in an airplane, a jolt due to air turbulence tends to be followed by another and another until eventually a period of smoother flight ensues.

Similarly, in financial markets, one period of high market volatility tends to be followed by another, at which point markets calm for a time before getting bumpy again.

Why is this important?

Because with MPT, individuals tend to focus on the average expected return rather than their exposure to extreme events.

Benoit Mandelbrot in The Misbehavior of Markets writes “What matters is the particular, not the average.”

Nassim Nicholas Taleb explains it this way, “Risk management is less about understanding random events as what they can do to us. Risk is in the tails not in the variations .”

When updating the operating system on our computers, if we focus on the average outcome we would never back up the pictures on our hard drive. Instead, we should focus on the extreme outcome that our hard drive could be wiped out, prompting us to take action and back it up.

Likewise, we should make portfolio allocation decisions knowing stock markets can fall 40% or more in a matter of days.

Extreme Market Events

During a two-week period in October 1987, the U.S. stock market fell 23%, but it fell over 40% in Australia and Hong Kong and nearly 60% in New Zealand.

In May 2010, U.S. stocks, as measured by the Dow Jones Industrial Average, fell almost 9% in a matter of minutes.

Of course, markets eventually recovered in these examples, but what would be the impact for you if the stock market fell over 40% and the recovery took decades instead of months.

For many, these extreme market outcomes would have little long-term financial impact because their portfolio balances are small and they can look forward to many more years of employment earnings that will allow them to increase their savings.

For those who are retired or approaching retirement, extreme market events could be catastrophic.

We Already Focus On The Extreme

Most people already make some financial decisions with an eye toward extreme events.

On average your house won’t burn down or be robbed, yet you carry home owners insurance.

On average, you won’t die or be incapacitated in the prime of your life, yet you buy life and disability insurance to protect your family.

We buy insurance because the future is unknown, and we want to protect ourselves against extreme outcomes.

Why wouldn’t we do the same with our investment decisions?

For most investors, there isn’t an insurance policy to protect against market losses. Instead we rely on diversification and scale our exposure to stocks based on our ability to recover from extreme negative market outcomes.

You don’t need modern portfolio theory to know that.

Related Episodes

20: How To Allocate Your Assets

127: Investing Is Wayfinding

201: Is Your Portfolio Unbalanced?

217: Rebalancing, Overvaluation, Market Timing and Stock Splits

229: Stop Maximizing Your Returns Using Modern Portfolio Theory

Ready to get serious about your investing?

Access professional-grade portfolio tools, training, and a community to help you stay on track, tune out the noise, and grow your wealth with confidence.

Learn How

Filed Under: Podcast Tagged With: asset allocation, risk

Contact | Team | Topic Index


Darby Creek Advisors LLC
P.O. Box 68544 • Tucson, AZ • 85737

Copyright © 2025 • Disclosures, Privacy Policy, and Cookie Policy • Site by Tempora

Manage Cookie Consent

We use cookies to optimize our website, marketing, and services. 

Functional Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes. The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.
Manage options Manage services Manage {vendor_count} vendors Read more about these purposes
View preferences
{title} {title} {title}
Manage Cookie Consent
We use cookies to optimize our website, marketing, and services. We never sell users' data.
Functional Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes. The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.
Manage options Manage services Manage {vendor_count} vendors Read more about these purposes
View preferences
{title} {title} {title}