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Retire With Purpose - The Retirement Podcast

574: Why Most Stocks Fail (And What Retirees Need to Know)

Retire With Purpose - The Retirement Podcast

Casey Weade

Education, Business, Self-improvement, Investing

4.7564 Ratings

🗓️ 10 July 2026

⏱️ 33 minutes

🧾️ Download transcript

Summary

Your greatest investment risk may not be missing the market, but relying on your ability to identify the small handful of stocks that become the next big winners. 

As part of our "By the Numbers" series, topics covered in this episode include: 

  • Why most individual stocks fail to outperform the market
  • What increasing market concentration means for retirees
  • Why average returns can create dangerous expectations
  • How to think about risk, diversification, and income in retirement
  • The surprising case for Treasury bills and liquidity

Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Bruce Feiler provide thoughtful insights and advice on how it applies to your unique financial situation.

Show Notes: HowardBailey.com/574

📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu 

📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB

ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

Transcript

Click on a timestamp to play from that location

0:00.0

Welcome to Retire with Purpose, where we help you make better decisions with your money,

0:05.5

your time, and your life so that you can approach retirement with even more confidence,

0:10.0

clarity, and of course, it's Retire with Purpose, so Purpose as well.

0:14.3

Like, the stock market has created an almost unbelievable amount of wealth over the last century,

0:23.3

but the surprising truth is that most individual stocks have failed to deliver. Today, we're unpacking why the biggest danger

0:28.6

for investors may not be missing the market, but building a retirement plan that depends

0:33.9

on finding the rare few winners.

0:49.0

My name's Casey Weed, and I am here with fellow certified financial planner, my good friend and co-host, Marshall Johnson.

0:51.8

Hey, buddy, we're getting into it today.

0:53.2

Hey, I love it.

0:54.0

This is a great article and really

0:55.4

makes you think about numbers, numbers, and how you invest and how you may want to invest. Yeah,

1:01.3

we're covering, I came across this article, and we included it in our weekend reading for retirees email,

1:06.1

goes out every Friday, sign up retireth purpose.com. Yeah, this is an article that caught my attention because

1:12.7

it was really data-driven. I love some good numbers. And I don't think most people realize

1:19.7

just how concentrated stock market returns are and have been. I think more people view it today

1:26.9

is, oh, yeah, stock markets really concentrated

1:28.6

in these handful of stocks. But I think you have to go back the last hundred years to really

1:33.1

see the big picture. You got to zoom out. I think this article does a great job of doing that.

1:37.9

It is written and authored by one of our past podcast guests, Larry Swedro. I found it on

1:43.9

wealth management.com.

1:45.1

It's titled A Century of Stock Market Winters and why most stocks failed to deliver.

...

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