The Investor Coaching Show with Paul Winkler

In 2025 in the U.S. alone, insurance companies and insurance salespeople sold almost half a trillion dollars of annuities. Today, Paul and Dan explain how so many people get sold on a product they don’t fully understand and offer a real breakdown of the fees and commissions of various annuity products.     Want to cut through the myths about retirement income and learn evidence-based strategies ba...

The industry is working really hard to push alternative investments right now. The pitch is that the old way is broken and that these new investments are the true path forward to building wealth. Today, Paul and Dan talk about how frustrating it is to watch well-meaning investors get sucked into these sales pitches and fail to understand how risky and misleading these products are. In all the jarg...

Today, Paul and Dan discuss how the SpaceX IPO is dominating headlines, leading investors to wonder whether they will miss out if they don’t jump in. Listen along as Paul shares some painful stories about investors taking a big gamble on single companies and why IPOs are hype machines designed to underperform. Later in the episode, Paul pushes back against the idea that AI is propping up a weak ec...

Many retirees don’t realize that suffering major portfolio losses during the first few years of retirement can dramatically increase the odds of running out of money later on. In this episode, Paul and Evan explain sequence of returns risk, why early retirement losses can be so damaging, and whether your portfolio is designed to withstand difficult market environments — or vulnerable to them.   Wa...

Paul and Evan pick up on a conversation about AI and regulation that makes an important but overlooked point: Tech leaders don’t share the same values as the average American. Listen along to hear some ideas these two advisors have that would help protect the American public around AI content and why regulation may be more of a publicity boost for AI companies than a genuine safeguard for its user...

Many investors are drawn to platforms that promise everything in one place. But when investing becomes too easy, it can also become more dangerous. Companies built to maximize engagement often push the flashiest, most speculative products — making impulsive decisions easier than thoughtful investing. In this episode, Paul and Evan break down an interview with Robinhood’s CEO about prediction marke...

Today, Paul and Evan start the show by discussing the common misconception that investing is simply learning about companies so you can pick the “right” ones. The two advisors explain that this method doesn’t even work for the brightest minds in the industry. Paul shares an interview from the news this week that claims the economy would be soft without the influence of AI. Listen along to hear how...

Paul and Jim talk about those pesky expenses that seemed good at the moment but aren’t really making your life any better. Listen along as they walk through an article that shares 10 things that aren’t really worth the money anymore, and Paul discovers he has quite a few in-app subscriptions on his phone that he didn’t realize he was still paying for.   Want to cut through the myths about retireme...

Today, Paul and Jim talk about the harsh realities of the investment industry as they walk through their professional journeys from working as salespeople at major investment firms to personal financial advising and coaching. Their biggest takeaway: The major companies groom employees to represent their own interests and sell their own products. Listen along as these two advisors talk about the di...

Today, Paul shares a pitch that was recently made on Shark Tank. It’s a business called Parrot Finance. You attach your brokerage account, you choose the portfolio of well-known rich and famous investors, and then, boom, all of a sudden you’re investing in the kinds of products and portfolios that wealthy investors have had access to all along. Listen along to hear why investing like the rich almo...

Investing is not about knowing which products to pick. It’s about finding the right process and sticking with it. Today, Paul gives you a crash course in how to spot product-based marketing and pick it apart using a recent TV ad with a football star and a real estate product that sounds better than it is. Throughout your investing journey, you’ll be tempted to reach for products like real estate,...

Paul isn’t shy about sharing his love for flying cars. Sometimes people have a hard time getting motivated to save for retirement because they lump it in with other adulting tasks like dental work or jury duty. Today, Paul shares that you should leave some space for fun and dreaming about the future, and you should find ways to stay motivated toward saving. Paul then pivots to discuss how many old...

Today, Evan brings an article that shows when people have time to plan, they make very different decisions when unexpected expenses arise. Listen along as Paul and Evan talk about how having a family changes your financial needs and priorities, and share some of the basic financial literacy tools that can help a family rise to meet their financial needs. Later in the episode, Paul shares a clip fr...

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,...

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...

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 a...

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 d...

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...

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-m...

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 s...

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 futu...

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...

“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 kno...

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...

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...