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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

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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28:45

Will AI Take Fund Managers’ Jobs and Ruin Market...

The Investor Coaching Show with Paul Winkler ·

2025/06/13

Today, Paul talks about the long history of technology and investing and whether or not we may see a future where AI will replace the jobs of fund managers. Paul shares an article from MarketWatch, as people are already beginning to study how AI is performing against these companies. Listen along to hear how technology is used to try to give people an edge in investing and why supercomputers and AI struggle to beat out Nobel Prize-winning investment strategies.For more information about what we

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20:36

Stock Pickers Scramble As Musk and Trump Part Ways;...

The Investor Coaching Show with Paul Winkler ·

2025/06/12

Today, Paul talks about some of the biggest headlines from last week and what he thinks they mean for investors. Listen along to hear about Musk’s departure from DOGE and AI taking Ph.D.-level jobs. Financial news companies like to use times like these to make predictions and encourage investors to make changes. Paul argues that weeks like these are a nightmare for people trying to pick the winners in the market. For more information about what we do or how we can help you, schedule a 15-minute

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31:02

After 40 Years, Japan Can’t Keep Buying Our Debt. Are...

The Investor Coaching Show with Paul Winkler ·

2025/06/11

After 40 years, Japan can no longer keep buying our debt. Should U.S. lenders be worried? Are interest rates going to spike? Europe is on pace to have a better year than the U.S. Is Europe becoming a better place for business? Should investors start selling off Large U.S. stocks and investing in other places? Today, Paul talks about two pieces of international news he thinks are designed to create fear and uncertainty in investors. Listen along as Paul answers these questions and explains why

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01:00:24

2025 Social Security Webinar

The Investor Coaching Show with Paul Winkler ·

2025/06/02

Social Security is a complex topic and can be confusing to navigate. Today’s episode of the investor coaching show is our annual Social Security Webinar. If you want to see all the visuals that go along with this presentation or watch it on our website, go to: paulwinkler.com/ss. 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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17:18

Cost of Living vs. Quality of Life: Isn’t It Worse Now?

The Investor Coaching Show with Paul Winkler ·

2025/05/30

A common question Paul hears about this younger generation is: Isn’t it worse for us now? With wage stagnation and tough housing markets, it could be very easy to assume it is harder. After all, houses were for sale for $30,000 fifty years ago. Paul and Evan expand the question by including the concept of quality of life. Was the average single-family home in 1960 the same quality as the average single-family home in 2010? Did it have the same amenities? Was it larger or smaller? Listen along to

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20:26

Wealthy Investors Can Afford To Take Risks and Lose Big

The Investor Coaching Show with Paul Winkler ·

2025/05/29

It’s easy to look at wealthier investors and think they know more about money and investing. Today, Paul and Evan explain some critical differences between wealthy investors and average-income investors and why comparing yourself to wealthy investors can lead to many investing mistakes.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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22:33

Interest Rates Change. Confident Investors Don’t...

The Investor Coaching Show with Paul Winkler ·

2025/05/28

Paul and Evan talk about a trap that educated investors don’t fall into around interest rates. Last week, we saw interest rates change, which may bring about a rise in return in fixed income assets, like bond and CD rates, and a short-term drop in stock prices. Listen along to hear these two investors explain why a diversified portfolio historically beats responding to these trends and why even 10-year returns aren’t a long enough time horizon to see what is going on in stocks.For more

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423 results

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