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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.
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.
Episodes

Thursday Apr 30, 2026
Thursday Apr 30, 2026
Today, Dan talks about his experience at an investing workshop and explains how frustrating it is when the industry knows how to make a diversified portfolio, and that those portfolios would perform better than many of the products they offer, yet most investors come into PWI offices with a portfolio that is overweighted in large U.S. companies. Listen along to hear how the industry uses ratings, short-term past performance, and other emotional sales pitches to sell you yet another large U.S. fund, and why investors get sucked into investing in your “team” instead of taking an academic approach. Later in the episode, Evan brings a WSJ article about how investors who invested in private credit funds are losing big now that these private companies are defaulting on their loans.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Wednesday Apr 29, 2026
The Industry Wants You To Trust Them As the Experts. This Is a Big Trap.
Wednesday Apr 29, 2026
Wednesday Apr 29, 2026
Today, Paul, Evan, and Dan discuss a story about an advertisement in which the company basically says, “You won’t have to worry about any of this because we’ll be worrying about it for you.” Listen along as these investors explain why you never want to hear this from a company that sells you products. Over the years, PWI has found that your concerns about money and investing go away when you learn and educate yourself, not when you blindly trust people who don’t have to live off of your retirement. Later in the episode, Evan talks about how future brides are now buying dresses that are too small and taking GLP-1s. The clothing sellers are making them sign waivers confirming that they don’t fit yet and can’t be returned. All of this is a great metaphor for how investors try to predict market futures.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Monday Apr 27, 2026
Should Economics Be a College Requirement? Paul Thinks So
Monday Apr 27, 2026
Monday Apr 27, 2026
Today, Paul talks about how many high schools have wanted to replace basic economics education with personal finance. The problem is that most high schoolers won’t use any personal finance information for a decade, and research shows that their retention of the information is low. Listen along as Paul explains why the foundational concepts of capitalism create a world where personal wealth is up and so is quality of life, but market timers and proponents of communism and socialism believe the same thing: A small group of smart people can create wealth and prosperity for everyone. The problem is that it hasn’t ever worked. Paul thinks that learning the foundations of economics can create more confident investors.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Friday Apr 24, 2026
Risk in Investing Is More Complex Than You Think
Friday Apr 24, 2026
Friday Apr 24, 2026
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 increase risk for traders.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Thursday Apr 23, 2026
Spring 2026 Economic Update: Is Innovation Dragging Down the Economy?
Thursday Apr 23, 2026
Thursday Apr 23, 2026
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 in retirement.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Wednesday Apr 22, 2026
An Investment Pays You To Borrow Your Money. It’s That Simple.
Wednesday Apr 22, 2026
Wednesday Apr 22, 2026
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 episode, Paul pushes against the growing pessimism that things are worse now than they used to be, sharing an article about how the upper middle class in the U.S. has been growing steadily over the last few years.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Monday Apr 20, 2026
Could Speculative Weather Trading Improve Weather Forecasting?
Monday Apr 20, 2026
Monday Apr 20, 2026
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. Later in the episode, Evan discusses some inventions from the last century that have revolutionized the world and how capitalism is the best source of invention and prosperity because it rewards people who take risks.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Friday Apr 17, 2026
The Market Is Flooded With Smart Investors Who Set Prices Together
Friday Apr 17, 2026
Friday Apr 17, 2026
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 plan.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Thursday Apr 16, 2026
How Much Can You Gift a Family Member Before Having To Tell the IRS?
Thursday Apr 16, 2026
Thursday Apr 16, 2026
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 over a century of data? Download our free Retirement Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.

Wednesday Apr 15, 2026
National Financial Literacy Month: How Is Your Financial Literacy?
Wednesday Apr 15, 2026
Wednesday Apr 15, 2026
“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 investors stay on track and relax about money.
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 Income Guide now at paulwinkler.com/relax and take the stress out of planning your retirement.
This material is for general educational purposes only and is not personalized investment, financial, tax, or legal advice. Past performance does not guarantee future results. Nothing here is an offer, solicitation, or recommendation for any security or strategy. All financial decisions involve risk, and you should consult qualified professionals before acting on this information.
Advisory services offered through Paul Winkler, Inc., an SEC-registered investment adviser.