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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

30:56

Social Security Confusion: How To Use It and How To...

The Investor Coaching Show with Paul Winkler ·

2025/07/18

Today, Paul dives into one of the most misunderstood aspects of financial planning: Social Security. Almost no one Paul talks to fully understands how it was formed, what the problems are, and how to make the most of yours when you retire. Listen along to hear a seasoned advisor break down the most common misconceptions and give you a crash course on the most important components of this government program.For more information about what we do or how we can help you, schedule a 15-minute call

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15:41

Paul Is Back and Jumps Right Into the Big Beautiful...

The Investor Coaching Show with Paul Winkler ·

2025/07/17

Paul just happened to take the week off at the same time Congress decided to pass one of the largest pieces of tax legislation in recent history. Listen along as Paul jumps straight into this new law and why it will change the future of tax preparation and retirement planning for Americans. Paul covers topics like the standard deduction, child tax credit, bonus deductions for people over 65, new write-offs, Trump Accounts, and what happens with all the debt this bill creates.For more information

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30:56

Paul Is Back and Jumps Right Into the Big Beautiful...

The Investor Coaching Show with Paul Winkler ·

2025/07/16

Paul just happened to take the week off at the same time Congress decided to pass one of the largest pieces of tax legislation in recent history. Listen along as Paul jumps straight into this new law and why it will change the future of tax preparation and retirement planning for Americans. Paul covers topics like the standard deduction, child tax credit, bonus deductions for people over 65, new write-offs, Trump Accounts, and what happens with all the debt this bill creates.For more information

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27:01

Try To Avoid These Financial Planning Mistakes

The Investor Coaching Show with Paul Winkler ·

2025/07/15

Today, Evan, Jonathan, and James talk about some of the most common financial missteps that keep people from being able to retire when they want to or have the kind of income they need later in life. Listen along as these advisors cover topics like taking advantage of your company match, medical expenses, saving for your kids' college, and insurance. For more information about what we do or how we can help you, schedule a 15-minute call with us here: paulwinkler.com/call.

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17:57

One in Four Working Americans Will Need This...

The Investor Coaching Show with Paul Winkler ·

2025/07/14

Evan, Jonathan, and James open with a discussion about the declining rates in disability insurance. It seems that more Americans believe they will never encounter a medical situation that prevents them from working for a year or more before they retire. Evan warns that disability insurance is statistically one of the best insurances you can have and is designed to protect your income during your working years. Listen along as these advisors explain some of the nuances of this insurance, why

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17:29

Middle East at the Brink of War and Markets Go Up?

The Investor Coaching Show with Paul Winkler ·

2025/07/12

Paul shares why even if you had a crystal ball and could see future news events before they happened, it wouldn’t make market timing any easier. After a week of Israel, Iran, and the U.S. being on the verge of military conflict, markets have seen an influx of money come in from everyday investors. Paul shares a few clips from financial pundits this week who admit they would not have predicted this outcome in markets even if they had heard the news days before it happened. For more information

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21:25

AI and Financial Firms: Neither Are Looking Out for...

The Investor Coaching Show with Paul Winkler ·

2025/07/11

Paul shares a study that reveals how AI is actually causing people to turn off important critical thinking skills. What do you think this means for AI’s future? Listen along as Paul talks about similarities between AI and the way firms market: They look like experts. They tell you everything you want to hear, but there are some obvious red flags that they aren’t looking out for your interests. For more information about what we do or how we can help you, schedule a 15-minute call with us here:

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16:17

The Big Beautiful Bill is Now Law. How Are You...

The Investor Coaching Show with Paul Winkler ·

2025/07/10

With Paul out of town for the weekend, Evan, Jonathan, and James jump into the biggest piece of financial planning news the United States has seen in a while: the signing of the Big Beautiful Bill into law. Listen along as these three advisors share their first takes on this new legislation, where you might see the most dramatic changes, and why it may still take months or years to fully understand what this law means for investors. For more information about what we do or how we can help you,

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14:51

The Big Beautiful Bill Is Now Law. How Are You...

The Investor Coaching Show with Paul Winkler ·

2025/07/09

With Paul out of town for the weekend, Evan, Jonathan, and James jump into the biggest piece of financial planning news the United States has seen in a while: the signing of the Big Beautiful Bill into law. Listen along as these three advisors share their first takes on this new legislation, where you might see the most dramatic changes, and why it may still take months or years to fully understand what this law means for investors. For more information about what we do or how we can help you,

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15:19

ETFs Are Becoming the New Market Timing Tool

The Investor Coaching Show with Paul Winkler ·

2025/07/08

Paul shares the number one factor that leads to an underperforming retirement account: investor behavior. Listen along as Paul shares how the industry hides their market timing and stock picking through “diversified” investments like ETFs and indexing, and terms like “turnover ratio” and “tactical asset allocation.” Paul wants investors to watch out for these practices and shares where companies are required to disclose if they are gambling with your money. For more information about what we do

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10:32

The Unused Asset of Young Investors

The Investor Coaching Show with Paul Winkler ·

2025/07/02

Today, Paul talks about the one asset young people have that they don’t fully use to their advantage: time. Investing is a time game. It’s hard to envision or care for your older self, but many older investors are taking big risks and making big mistakes trying to play catch-up. Listen along to hear why caring for your future self and avoiding fear and greed are the foundations of confident investors.For more information about what we do or how we can help you, schedule a 15-minute call with us

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10:24

What’s in the Big Beautiful Bill?

The Investor Coaching Show with Paul Winkler ·

2025/06/30

For a few months, Congress has been working to pass the flagship legislation of Trump’s second presidency, but what is in the Big Beautiful Bill? Listen along as Paul, Evan, and Dan talk about the most likely provisions around taxes, tax dedication, and social security that are likely to pass and how they affect the financial planning world. For more information about what we do or how we can help you, schedule a 15-minute call with us here: paulwinkler.com/call.

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18:45

Kidnapped Over Crypto/Do You Know What an Income...

The Investor Coaching Show with Paul Winkler ·

2025/06/27

Today, Paul, Dan, and Evan discuss two problems with two very popular investments right now. Both crypto and annuities are sold as advanced investment options with features that old-fashioned diversified portfolios don’t have. Listen along to hear seasoned advisors talk about these options and some basic red flags that keep them from being superior to academic investing. For more information about what we do or how we can help you, schedule a 15-minute call with us here:

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19:33

Chasing Returns and Headlines: Two-Sided Trap of the...

The Investor Coaching Show with Paul Winkler ·

2025/06/26

Paul and Evan chat about two common traps the industry wants you to fall into to keep you buying and selling products and listening to their advice. Listen along as these two advisors explain how ubiquitous chasing returns has become and why it goes against the basic tenets of investing. Later, they explain why financial news media twists headlines into a story about when to buy and sell instead of a story about market efficiency.For more information about what we do or how we can help you,

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26:00

Senate Moves to Regulate Stablecoin. Does This Change...

The Investor Coaching Show with Paul Winkler ·

2025/06/25

Today, Paul talks with Evan and Dan about the federal regulation of stablecoin, affecting cryptocurrencies and other digital assets. Listen along as these advisors explain the pros and cons of the new digital currencies and assets, and whether Congress's interest in these makes them more legitimate. Paul shares his opinion about the trading markets of these assets and where this news could change his position on cryptocurrencies.For more information about what we do or how we can help you,

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22:33

Tax Changes in 2025: Big Beautiful Bills and Capital...

The Investor Coaching Show with Paul Winkler ·

2025/06/23

Today, Evan shares his perspective on the changes happening to the tax code in 2025. Evan and Paul talk about how tax policy could affect regular investors and the changes you might see in your tax situation this year or the next. For more information about what we do or how we can help you, schedule a 15-minute call with us here: paulwinkler.com/call.

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11:05

AI Companion for the Elderly: Is There Something off...

The Investor Coaching Show with Paul Winkler ·

2025/06/20

Paul and Evan both find the same story about a company creating an AI companion for elderly people to chat with. Could this be a helpful tool, or is it just creepy? Listen along as the two advisors talk about some psychological implications and how this AI bot is trained not to give certain kinds of financial advice to the people who use it. For more information about what we do or how we can help you, schedule a 15-minute call with us here: paulwinkler.com/call.

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16:26

Watch This Stock “Expert” Flip on Tesla Stock in...

The Investor Coaching Show with Paul Winkler ·

2025/06/19

Today, Paul brings some clips from a popular financial “news” show where a pundit is caught telling people they would be foolish to buy the stock and then foolish not to own it, all in the course of a week. Listen along to hear what happens when he is called out on his take and how getting emotionally wrapped up in a company or the news is a fast-track way to make the most common investing mistakes.For more information about what we do or how we can help you, schedule a 15-minute call with us

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30:57

Market Update June 2025: When Should You Get Worried?

The Investor Coaching Show with Paul Winkler ·

2025/06/18

Today, Paul and Evan talk about a heavy week in the news with market drops, oil price moves, and tension in the Middle East. With all of this bad news, you would think that investors would have the right to be a little panicked. Listen along as these two advisors explain how the news twists stories to make you believe we are living in unprecedented times and share an approach to investing that allows you to engage the news as a citizen without engaging it as an investor.For more information about

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21:40

Watch Out for “The Rules Won’t Apply Anymore”...

The Investor Coaching Show with Paul Winkler ·

2025/06/16

Today, Paul finds an article that is trying to convince investors that the aging U.S. population is a danger to both stock markets and their retirements. Listen along as Paul debunks the claims of the article and encourages all investors to be wary of any news that pushes them into fear and making transactions for the financial industry. For more information about what we do or how we can help you, schedule a 15-minute call with us here: paulwinkler.com/call.

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390 results

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