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PODCAST

The Investor Coaching Show with Paul Winkler

The Investor Coaching Show

A podcast to help you get an insider’s view of the financial world and escape common investment traps. Each week, we look at the financial news of the day and help you make sense of it so you can relax about money.

business investing

All Episodes

29:00

Asset Class Investing: The Key to Avoiding...

The Investor Coaching Show with Paul Winkler ·

2026/02/06

When we discuss investing in the stock market, most people think of investing in individual stocks. Paul shares that the returns with this approach are problematic. Listen along as Paul and Arlene talk about a different approach called asset class investing and explain the difference between picking individual stocks and investing in commingled investment vehicles. Want to cut through the myths about retirement income and learn evidence-based strategies backed by over a century of data? Download

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21:45

Cash, Bonds, and Stocks: What's in Your Portfolio and...

The Investor Coaching Show with Paul Winkler ·

2026/02/05

A diversified portfolio contains a mixture of cash, bonds, and stock investments. Not knowing how these assets work together leads to some of the most common and harmful investing traps. Today, Paul invites Arlene Brown onto the show to explain how cash holdings, bonds, and stocks can work together to limit your risk of short-term market fluctuations and long-term inflation. Listen along as these advisors go into detail about the strengths and pitfalls of having investments in each category. Want

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28:39

Cash, Bonds, and Stocks: What's in Your Portfolio and...

The Investor Coaching Show with Paul Winkler ·

2026/02/04

A diversified portfolio contains a mixture of cash, bonds, and stock investments. Not knowing how these assets work together leads to some of the most common and harmful investing traps. Today, Paul invites Arlene Brown onto the show to explain how cash holdings, bonds, and stocks can work together to limit your risk of short-term market fluctuations and long-term inflation. Listen along as these advisors go into detail about the strengths and pitfalls of having investments in each category. Want

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15:55

Cathie Wood Got It Wrong in 2025, but What Does She...

The Investor Coaching Show with Paul Winkler ·

2026/01/26

Paul shares a clip this morning that shows just how low the standard is for what financial media views as “credible” investing information. Listen along to hear an interview with Cathie Wood, CEO of Ark Invest, where she discusses the mistakes she learned from in 2025, which cost investors millions, and tries to get airtime to spin the 35% drop in Bitcoin as a victory in this market. Then, Paul addresses a listener who works a very physically demanding job and is in a tricky position, where

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29:19

The Average Car Payment Is $780/month. Is That a...

The Investor Coaching Show with Paul Winkler ·

2026/01/23

When most people buy a car, they take on a substantial car payment. But how long does the high of having a nice new ride really last? Today, Paul discusses why government intervention in making cars easier to buy has historically led to chaotic markets and other economic issues. Listen along as Paul explains why it’s difficult to really meaningfully change your level of happiness through things like new car purchases and how you can start to chart a course forward where the things in your life

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21:37

What Happens if the Dollar Drops? Understanding the...

The Investor Coaching Show with Paul Winkler ·

2026/01/22

Today, Paul brings in a WSJ article that provides a list of potential events this year that could weaken the dollar against other world currencies. Paul wants confident investors to remember that you shouldn’t change your plan based on what may or may not happen in the future. Then, Paul explains why a weaker dollar isn’t always a bad thing for the U.S. economy, and why investors who follow the industry are more likely to be hurt by a weakening dollar. Later in the episode, would it be helpful for

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29:09

When Paul Says "Capturing Market Returns,” Is That...

The Investor Coaching Show with Paul Winkler ·

2026/01/21

When Paul first started this show, indexing and target-date funds were not very popular at all, as the world experienced a decade where large U.S. companies struggled to generate any returns for investors. Fast forward another decade, and indexing and target date funds are now all the rage as investors believe that “indexing” is synonymous with great returns, low fees, and wealth in retirement. Indexing may sound like diversification, but Paul explains what really happens when millions of investors

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27:44

Annuity Sales Are Dangerous. Here Is the Proof.

The Investor Coaching Show with Paul Winkler ·

2026/01/19

Paul runs into an annuity salesperson on Facebook who reveals that he made $300,000 in income in his first month and wasn’t remotely interested in helping people, but in showing off his skills to his peers. So, where does caring for clients fit into most of these sales? Paul shares the four steps people use to sell these products that you can look out for, and why it’s just not possible to trust high-commission products salespeople to look out for you when their companies are pushing them to produce

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16:22

We All Have an Expiration Date. How Can You Live With...

The Investor Coaching Show with Paul Winkler ·

2026/01/16

Evan talks about a celebration of life service he attended earlier in the day and reflects on how you never know how long life will be and how having a strong sense of purpose changes your perspective about money. Listen along as these two advisors describe why investing just to be good at investing and have a lot of wealth is what sucks you into get-rich-quick schemes and marketing trends. Want to cut through the myths about retirement income and learn evidence-based strategies backed by over a

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16:42

Your Home or Your Portfolio: Where Should Your...

The Investor Coaching Show with Paul Winkler ·

2026/01/15

Paul and Evan get into a conversation about a common question for homeowners: Is it a better investment to put extra money in my house or in my portfolio? Paul talks about why you shouldn’t view your home as an investment unless you plan on selling it and moving into a tent. Listen along as these two advisors explain the importance of paying off or improving your home without viewing it as an investing decision. Later in the episode, Paul discusses how Trump is cracking down on corporate ownership

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28:04

Jim Cramer’s Investing Club Leads To Stock Picking,...

The Investor Coaching Show with Paul Winkler ·

2026/01/14

We often discuss being a confident investor on the show, but confidence is only helpful if it’s combined with a disciplined, evidence-based approach rather than behaviors such as market timing or individual stock selection. Today, Paul shares an ad for Jim Cramer’s investing club that he saw on CNBC, where a client claims she is confident and finally “in control” of her investments. The ad reveals that Jim teaches people to “win at investing” through market timing and stock picking. Paul and Evan

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13:10

Pundit Gives “13 Funds To Own in 2025.” How Did He Do?

The Investor Coaching Show with Paul Winkler ·

2026/01/12

Paul and Jim talk about a pundit who told investors which funds to own in 2025, and those funds had a return of over 14%. Paul admits that most investors who saw this increase in their portfolio would probably think they did pretty well last year. The problem is that without benchmarking, they wouldn’t realize that the funds did worse than the S&P 500 and underperformed the market's leading sector by 35%. Listen along as these advisors break down what is wrong with these investments and why

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28:49

Robinhood Found the Best Way To Make Money on You:...

The Investor Coaching Show with Paul Winkler ·

2026/01/09

Every investment company is working to sell you on the idea that they can help you build wealth through cutting-edge technology and financial expertise, but the reality is that many of these companies, like Robinhood, are making money off you through activating your emotions and trying to cultivate a dopamine addiction around the gamification of gambling. Listen along as Paul and Jim talk about some of the strategies Robinhood uses to mislead investors and take your money while claiming to help you

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21:09

Properly Preparing to Pass Your Finances to Your...

The Investor Coaching Show with Paul Winkler ·

2026/01/08

No one likes to think about the day when they will no longer be here and their spouse or children will have to take on more responsibility in managing the family's finances. Today, Paul brings an article about the different approaches people take to preparing important information — such as your primary doctor, accountant, or attorney, as well as passwords and automated payments — as well as retirement accounts and their management. Listen along as Paul shares about PWI’s “love letter,” a document

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27:20

Big News out of Venezuela. What Does It Mean for Your...

The Investor Coaching Show with Paul Winkler ·

2026/01/07

Paul talks about the news of America's capture of the Venezuelan president, Nicolás Maduro, and how this will lead to uneducated investors making one of the most painful money mistakes. Listen along as Paul talks about why responding to the news with either fear or greed comes from the basic misconception that investing is really just gambling or that knowing what will happen in the future gives you an edge in investing. Paul dispels these investing myths and encourages you to stay the course. Later

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14:16

Most Investors Fail the Diversification Test

The Investor Coaching Show with Paul Winkler ·

2026/01/05

Today, Paul shares some research that shows over 80% of investors near retirement have portfolios that lack diversification and that most investors equate large U.S. companies and cash with safety. The problem is that portfolios like these can be very difficult to take an income from and leave you vulnerable to market fluctuations. Listen along as Paul explains why a financial advisor can help teach the academic principles behind building a portfolio and why most fund companies don’t even sell funds

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30:50

Don’t Go Into 2026 Aimlessly. SMART Goals Could Help...

The Investor Coaching Show with Paul Winkler ·

2026/01/02

A new year provides a new opportunity to change your life for the better by reflecting and setting new goals. Today, Paul talks about why understanding yourself helps you actually reach your goals, instead of setting them and getting stuck in the same old patterns. Listen along to hear how you can work with your brain to overcome old patterns and have a better year in 2026. Later in the episode, Paul shares why sharing your goals with someone you trust can open new doors, bring meaningful insight,

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16:51

Crypto Investors Got What They Wanted in 2025, but...

The Investor Coaching Show with Paul Winkler ·

2026/01/01

Last year should have been a great year for crypto investors. The digital assets received favorable treatment from a pro-crypto government, and the financial industry plugged the investment at every turn. Unfortunately, that didn’t make a positive difference in market prices. Listen along as Paul shares why this year brought more losses for people who have been swept up in the crypto craze and why it doesn’t look like the currencies will become better investments anytime soon. Later in the episode,

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33:23

The People Managing Your 401(k) Are Just Making It Up...

The Investor Coaching Show with Paul Winkler ·

2025/12/31

Today, Paul explains that fund companies that offer your 401(k) plans are choosing investments that seem safe and popular. These low-cost funds focus heavily on large U.S. companies and keep your money out of the highest-performing markets of 2025. Paul explains how these fund companies have ditched academic research, forcing them to make it up as they go along. Later in the episode, Paul discusses the disillusionment of the youngest generation of investors and what might lead them to find purpose

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14:08

A New Offering in 401(k)s That Will Hurt Your Retirement

The Investor Coaching Show with Paul Winkler ·

2025/12/29

This year, private company funds made their way into 401(k) plans around the country. While Paul doesn’t think these funds adequately pay for your risk, there is another problem that makes these products even worse. Listen along as Paul and Evan explain why many investors will get sucked into a product where companies don’t have to disclose important information about their finances, which public companies are required to disclose. Want to cut through the myths about retirement income and learn

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