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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

26:01

Risk in Investing Is More Complex Than You Think

The Investor Coaching Show with Paul Winkler ·

2026/04/24

Most investors hear the word “risk” in investing and assume it only refers to the likelihood of losing all their money on an investment. Today, Paul explains why the concept of risk in investing is more complex, covering topics such as sequence of returns risk, benchmarking, and whether stock markets are riskier today than they were in the past. Later in the episode, Paul discusses a 20-year-old day trading rule that was recently overturned, which will likely generate more revenue for companies and

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17:04

Spring 2026 Economic Update: Is Innovation Dragging...

The Investor Coaching Show with Paul Winkler ·

2026/04/23

Today, Paul gives an update on the state of the U.S. economy and explains why the jobs and equities markets haven’t struggled the way many people predicted they would in 2025 and 2026. Listen along to hear about how the FED, technology companies, and job markets are working together to respond to AI and innovation in the workplace. Later in the episode, Paul answers a listener's question about how much of your portfolio needs to be held in bonds in order to weather downturns and still take an income

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28:31

An Investment Pays You To Borrow Your Money. It’s...

The Investor Coaching Show with Paul Winkler ·

2026/04/22

Today, Paul shares the first thing to look for when you see something that claims to be an investment: a clear cost-of-capital story. Many financial products claim to be investments, but at the end of the day, they are not paying you to borrow your capital. Listen along as Paul shares why financial products that don’t have a cost of capital can be dangerous, confusing, and come with difficult-to-measure risk. Paul also answers a listener's question about closed-end funds (CEFs). Later in the

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20:36

Could Speculative Weather Trading Improve Weather...

The Investor Coaching Show with Paul Winkler ·

2026/04/20

Today, Evan shares an interesting story about how speculative weather markets could be valuable to businesses that rely on weather forecasting to make decisions by crowdsourcing information about local weather patterns. Listen along to hear why the losers for speculative markets (a.k.a gambling) are always the traders and how these speculative markets don’t appear out of nowhere, but are usually started by companies or industries that partner with trader platforms to get information from users

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27:03

The Market Is Flooded With Smart Investors Who Set...

The Investor Coaching Show with Paul Winkler ·

2026/04/17

The news is full of headlines that sound like expert advice for concerned investors, but the reality is that most of the news is about people trying to predict the future. Today, Evan discusses two powerful ideas that can lead you away from market timing and toward a portfolio that can withstand market fluctuations: market efficiency and the humility to acknowledge that no one can predict the future. Usually, being an educated and confident investor means tuning out the news and sticking to your

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22:42

How Much Can You Gift a Family Member Before Having...

The Investor Coaching Show with Paul Winkler ·

2026/04/16

Did you know that you can now give up to $19,000 as a gift each year without needing to file a form on your tax return? Today, Evan covers some basic information about how you can help set your children and grandchildren up for financial success through gifting. Listen along as Evan covers the different kinds of accounts available and the lifetime gifting amount updates available to people in 2026.Want to cut through the myths about retirement income and learn evidence-based strategies backed by

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18:12

National Financial Literacy Month: How Is Your...

The Investor Coaching Show with Paul Winkler ·

2026/04/15

“The Investor Coaching Show” is here to help you relax about money by teaching you the fundamentals of money and investing and helping you avoid common investment traps. Today, Evan jumps into a conversation about financial literacy in light of April being National Financial Literacy Month. Few people are really given a proper financial education growing up, but financial literacy doesn’t mean knowing every financial term out there. Listen along as Evan breaks down some basic concepts we use to help

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15:45

Professional Financial Pundits Are Not Financial...

The Investor Coaching Show with Paul Winkler ·

2026/04/13

Anytime a well-known pundit or financial personality encourages you to pay to join an investing club for inside information, you should walk away. Today, Paul shares some recent financial advice from Jim Cramer, how often he has flip-flopped, and how the research has proven that people would be better off doing the exact opposite of what he has recommended. This isn’t just specific to Jim, but it is the reality of a whole industry full of pundits pretending to be your financial planner. Want to

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29:31

Investment News: SpaceX IPO, Hot ETFs, and a Timeline...

The Investor Coaching Show with Paul Winkler ·

2026/04/10

Today, Paul shares some of the most common concerns that investors are bringing to the office right now and why it’s helpful to talk to an advisor about what you’re seeing before you assume that it works with your financial plan. Listen along as Paul shares insights about the SpaceX IPO, a popular ETF with questionable returns, and Trump’s announcement regarding a timeline for the war in Iran, and helps you see some of the risks that aren’t being discussed in the news. Want to cut through the

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18:02

Most Investors Are Watching Their Retirements Shrink...

The Investor Coaching Show with Paul Winkler ·

2026/04/09

Today, Paul focuses on the vast majority of American investors who are blindly trusting the industry and are now overweighted in one of the year’s most poorly performing market segments. Listen along as Paul explains why overweighting in large U.S. companies has been an industry favorite for years, even though investment firms know this practice leaves investors vulnerable to numerous risks. Paul also explains how focusing your attention on the most well-known and profitable companies can actually

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28:51

Fear, Greed, and Loyalty: The Easiest Way To Make a...

The Investor Coaching Show with Paul Winkler ·

2026/04/08

Paul started his financial career the way most people do: learning about financial products from insurance companies and brokerages, then trying to sell those products to investors for a commission. Listen along as the Investor Coach shares some inside industry information to help you understand that the whole industry is designed to appeal to your fear, greed, or loyalty to sell you solutions to problems that the industry has invented. Paul explains how to spot these sales tactics and what you need

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14:43

How Do You Know an Investment Firm Is Right for You?

The Investor Coaching Show with Paul Winkler ·

2026/04/06

Unfortunately, it is not difficult to get into the investment industry as a financial planner with no experience and very little education. However, each firm aggressively markets itself as the most qualified and most sophisticated fiduciary to help you manage your wealth and meet your goals. Today, a listener asks Paul: In an environment like this, how can you know that an investment firm is really right for you? Listen along as Paul explains that looking at an advisor’s planning process and

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29:08

Diversify and Hold: The Confident Investor’s Strategy

The Investor Coaching Show with Paul Winkler ·

2026/04/03

Investors who responded to the war in Iraq are now faced with a dilemma: Is it time to get back in the market? Are the U.S. and Iraq in talks that could move markets up, or is this just the beginning of a long slump in equity markets? Today, Paul explains why market timing is impossible to master. Listen along to hear why confident investors don’t rely on headlines and luck, but on a strategy that helps them reach their financial goals in the long term. Later in the episode, Paul explains why

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25:24

Why Do We Invest in Bonds? Why Not Buy an Annuity...

The Investor Coaching Show with Paul Winkler ·

2026/04/02

It’s very common for financial professionals to convince investors that stocks are too risky and bonds won’t perform well enough to provide an income from your portfolio. Their solution almost always involves selling you confusing, high-commission annuity products. Listen along as Paul shares why annuities are a very bad replacement for bonds and why the people who don’t understand why they own bonds are the most likely to fall for this trap. Want to cut through the myths about retirement income

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19:52

Annuities, Bonds, Stocks, Commodities, Real Estate:...

The Investor Coaching Show with Paul Winkler ·

2026/04/01

Only a few things are truly considered investments. There’s a good chance that you’ve heard of investment options recommended from an advisor or family or friends that don’t meet the criteria to be called an investment. Today, Paul walks through some of the most popular options people turn to when they want to invest and explains how confident investors can distinguish between investments and financial products. Want to cut through the myths about retirement income and learn evidence-based

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20:41

Is Owning the S&P 500 Enough for Retirement?

The Investor Coaching Show with Paul Winkler ·

2026/03/30

Paul and Jim tackle the overconfidence that many investors have in large U.S. stocks and explain why owning the S&P 500 alone doesn’t lead to confident investing, but to sequence of returns risk, lack of diversification, and worry over the health of U.S. companies and markets. Listen along as these two advisors share why you need to move from a product approach to a process approach to your investing. Later in the episode, Jim covers some new information the industry has about the strategies

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24:31

Texas Court Tosses Fiduciary Rules: A Big Win for...

The Investor Coaching Show with Paul Winkler ·

2026/03/27

Texas throws out a Biden-era fiduciary rule giving insurance companies more license to sell bad products to people who don’t fully understand them. Today, Paul and Jim talk about how the industry uses the term “fiduciary” to build trust, but can just as easily push you toward products that are in the agent's best interest as well. Listen along to hear why fiduciary rules don’t fix the industry, but why removing them gives big insurance companies a lot of confidence to be misleading.Want to cut

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19:02

The Investor Coach Answers: Should I Use My Age As My...

The Investor Coaching Show with Paul Winkler ·

2026/03/26

Paul answers a few popular questions directly from listeners of the show. Listen along as Paul responds to an investor who wants to know if the common strategy of using your age to determine your bond allocation is a reliable way to keep your portfolio healthy through retirement. Later in the episode, a listener wants to know how you monitor and manage the hidden trading costs inside a portfolio. Paul answers his question and explains how the industry uses “low-cost” to sell funds and where expenses

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27:56

The Investor Coach Answers: How Will the War Affect...

The Investor Coaching Show with Paul Winkler ·

2026/03/25

Today, Paul answers a few popular questions directly from listeners of the show. Listen along as Paul starts with a burning question for most investors: How will the war in the Middle East affect markets and investors saving for retirement? Later in the show, Paul addresses a listener's question about whether he has changed his position on owning precious metals, such as silver, given their widespread use in technology.Want to cut through the myths about retirement income and learn evidence-based

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15:24

The Design of Your Portfolio Determines Its Performance

The Investor Coaching Show with Paul Winkler ·

2026/03/23

Everyone wants to fly in an airplane that has been carefully designed and constructed. The design of the airplane determines its performance. Today, Evan explains that the same principles apply to the design of an investment portfolio and can be the difference between reaching your destination and having to bail out in an emergency landing. Want to cut through the myths about retirement income and learn evidence-based strategies backed by over a century of data? Download our free Retirement

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