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 / 454: How To Invest – Ten Rules of Thumb for Individual Investors

454: How To Invest – Ten Rules of Thumb for Individual Investors

November 1, 2023 by David Stein · Updated November 11, 2023

We discuss ten rules of thumb for individual investors to consider when saving and investing for and in retirement.

Abstract colors with the caption "How to Invest"

Here are the ten rules of thumb:

  1. Don’t use institutional hand-me-downs
  2. Stay close to home base
  3. Beware of dragon risk
  4. Mind your investment seasons
  5. Catch the popping corn
  6. Watch for market swarms
  7. Track the economic winds
  8. Follow the traffic lights
  9. Diversify your baskets
  10. Don’t burn your ships

Show Notes

How to Invest Money E-book

Episode Sponsors

Madison Trust Self-Directed IRA – Go here to learn more and get your $100 promo code

Monarch Money – Get an extended 30-day free trial

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.

Related Content

A Complete Guide to Mortgage REIT Investing

A Complete Guide to Equity REIT Investing

451: How Much Should You Invest in Stocks? The Art of Position Sizing in a Volatile Market

Transcript

Welcome to Money for the Rest of Us. This is a personal finance show on money, how it works, how to invest it, and how to live without worrying about it. I’m your host, David Stein. Today is episode 454. It’s titled How to Invest Money: 10 Investing Rules of Thumb.

In early 2012, right before I was going to leave my investment advisory firm, I spent a couple of weeks in Southern Mexico, in the Yucatan. I went by myself, and I spent the time taking photographs, writing, thinking. One of the things I was really focused on—putting down my investment philosophy, as it would apply to individuals. 

I had spent almost 15 years managing money for institutions, university endowments, private foundations, as well as managing the assets for individual investors, the assets of financial advisors. I hadn’t thought much about this writing—it eventually became an eBook—until this past week. 

And it turns out, I’ve touched on some of these principles in the podcast; I certainly discussed them some in my book, Money for the Rest of Us: 10 Questions to Master Successful Investing, but they are somewhat different. I thought it would be helpful to share these investing rules of thumb and expound on them a little bit and what might have changed in the past decade. Because things do change, markets evolve, economies evolve.

Tulum, where I spent a week on the beach a decade ago, in 2012, I spent about just under $200 a night for a little cabana on the beach; beautiful, beautiful beach. It was difficult to get to Tulum at that time. I rented a car, but you had to drive an hour or so from Cancun. Now, apparently, Delta has a direct flight to Tulum. And that same hotel, or cabana, where I spent less than $200 a night, last time we checked, they wanted over $1,500 a night per room. And we don’t stay there anymore; it’s just not worth it. So things evolve.

Don’t Use Institutional Hand-me-downs

Here’s investment rule number one: stop using institutional hand-me-downs. When I was growing up, I got a lot of hand-me-down clothes from my cousins. Some I loved. I had a killer pair of red bell-bottom pants that I loved to wear. But others I just sort of hid away in the drawer. 

As individual investors, we also inherit hand-me-downs. Not hand-me-down clothes, but tools and language that institutional investors such as pension plans and college endowments use to manage their portfolios. They include complicated-sounding tools such as strategic asset allocation, Monte Carlo simulation, market benchmarks. Some of the tools can be helpful, but we need to remember that we’re individual investors, we’re not pension plans, so we don’t have to invest like them, nor do we have to use the same tools that they use.

Because there’s a main difference between us and an institution, a college endowment. We die. Institutions don’t. Or usually don’t. The investment time horizon for an institutional investor is significantly longer than that of individuals. Most institutions invest for perpetuity. And given their longer time horizon, institutions can afford to make mistakes, because there’s ample time to recover from them. But as individuals, we don’t get second chances. Institutions do.

If an institution such as a pension plan or college endowment suffers devastating portfolio losses, they can go to their corporate sponsors, or their fundraising arm, to get more funds. But as individuals, if we’re approaching retirement, we don’t have that luxury.

As a Money For the Rest of Us Plus member, you are able to listen to the podcast in an ad-free format and have access to the written transcript for each week’s episode. For listeners with hearing or other impairments that would like access to transcripts please send an email to team@moneyfortherestofus.com Learn More About Plus Membership »

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: investing rules, rules of thumb

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}