Shows / The Investor Coaching Show with Paul Winkler
The Investor Coaching Show with Paul Winkler
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
- The Investor Coaching Show with Paul Winkler
Market Update, August 2026: Bond Sell-Offs, Interest Rates, and Inflation
Paul gives an update on markets in the third quarter of 2026 and explains why this month has been marked by bond sell-offs that have affected interest rates…
- The Investor Coaching Show with Paul Winkler
You’re Saving in Your 401(k) — But What Are You Actually Investing In
Today, Paul shares a common trap most investors face when investing at work: not doing the initial legwork, trusting your employer to offer good 401(k)…
- The Investor Coaching Show with Paul Winkler
Can Governments Fix Their Problems by Taxing the Wealthy?
It seems that more and more politicians are starting to believe that governments don’t have enough resources because they don’t make wealthy people pay their…
- The Investor Coaching Show with Paul Winkler
Warning: AI Recommends What It Learns From Industry Marketing Materials
At a staff meeting this week, an advisor shared that a client used AI to find a fund with optimal diversification. The problem is that AI trains on the…
- The Investor Coaching Show with Paul Winkler
You Can’t Trust the Industry To Get You Properly Diversified
Today, Paul shares two practical examples that highlight the same problem: The industry is set up to sell and provide education, diversification, and the best…
- The Investor Coaching Show with Paul Winkler
Simple Hacks To Take Control of Your Finances
Regardless of your stage of life, there are always a few good reasons not to save for retirement. Paul wants you to know that, for most people, the status quo…
- The Investor Coaching Show with Paul Winkler
Former Treasury Secretary Talks About Economic Worries
Many Americans fear that America's economy may be surpassed by China’s and that China’s use of AI may affect the future of the world’s job market and economy…
- The Investor Coaching Show with Paul Winkler
A Battery Breakthrough That Could Change More Than Technology
What if the next generation of batteries didn’t need rare earth minerals? Today, Paul shares an article about new battery technology that uses common materials…
- The Investor Coaching Show with Paul Winkler
This Explains Why We Don’t Recommend Real Estate As an Investment
Choosing whether or not to buy your primary residence is different from considering real estate as an investment. Today, Paul shares a commercial that says…
- The Investor Coaching Show with Paul Winkler
Why You Won’t Ever See a Market Forecast From Paul Winkler, Inc.
Large investment companies lead with the claim that they are fiduciaries and that they align their interests with yours, but then they turn around and market…
- The Investor Coaching Show with Paul Winkler
Ask These Questions, and You’ll Unlock the Key to Confident Investing (Part 2)
If you don’t know what questions to ask, you’ll never discover what it means to be a confident investor who can truly relax about money. Over the years, Paul…
- The Investor Coaching Show with Paul Winkler
Ask These Questions, and You’ll Unlock the Key to Confident Investing (Part 1)
If you don’t know what questions to ask, you’ll never discover what it means to be a confident investor who can truly relax about money. Over the years, Paul…
- The Investor Coaching Show with Paul Winkler
“How Do Fund Companies Hide Their Poor Performers?”
Many investors get pulled into a portfolio or fund that has performed well, only to find that they don’t ever enjoy the returns that were described. Today…
- The Investor Coaching Show with Paul Winkler
25 Years of Teaching Investors To Ignore the Sales Pitch
Paul looks back at how “The Investor Coaching Show” began 25 years ago and the people, relationships, and lessons that helped shape its mission. From the…
- The Investor Coaching Show with Paul Winkler
Risk in Investing Is Different Than Most Investors Think
Today, Evan looks at a few more questions confident investors should be able to answer: What is risk tolerance, and how much personal risk should you take in…
- The Investor Coaching Show with Paul Winkler
Is a Section 351 Exchange a Tax Loophole — or a Legitimate Planning Tool?
More investors are starting to ask about Section 351 exchanges, a little-known part of the tax code that can allow someone to move appreciated stocks into an…
- The Investor Coaching Show with Paul Winkler
If You Can Answer These Basic Market Questions, You’re Ahead of Most Investors
What is the stock market, how do investors get paid, and how should you choose which investments to own? Evan shares several questions from a list of 20 that…
- The Investor Coaching Show with Paul Winkler
AI Financial Planning - User Beware
Will AI eventually replace human financial advisors? Evan shares how a client recently used ChatGPT to learn about their financial plan and prepare for a more…
- The Investor Coaching Show with Paul Winkler
Stop Waiting To Build the Future You Want
Whether retirement is 10 years away and you are disappointed by how little you have saved, or 30 years away and you are skeptical of the entire system, it is…
- The Investor Coaching Show with Paul Winkler
Private Equity: Low Returns. No Liquidity. Still Being Hyped.
In this episode, Paul breaks down an interview that promotes private equity while also admitting that individual investors may be better off avoiding it. With…
- The Investor Coaching Show with Paul Winkler
Could the Federal Deficit Hurt the Stock Market?
For decades, financial pundits and economists have warned that a large U.S. budget deficit could hurt the market and cause pain for investors. Today, Paul…
- The Investor Coaching Show with Paul Winkler
Private Equity Is the Latest Distraction Keeping Investors From Market Returns
Private equity is the product being pushed right now. Investors are constantly told that the next strategy, product, or private-market opportunity could…
- The Investor Coaching Show with Paul Winkler
Confident Investors Know How To Spot Bad Financial Information
One of the strongest skills confident investors develop is learning how to recognize information that is incomplete, misleading, or designed to sell something…
- The Investor Coaching Show with Paul Winkler
Trump Account vs. 529. What Do You Pick When Investing for Children?
On July 4, Trump Accounts were signed into law and are now available as an option to invest in your kid’s future. Many investors are curious about the $1,000…
- The Investor Coaching Show with Paul Winkler
Index Funds Bought SpaceX. So Why Didn’t the Stock Go Up?
Many investors expected SpaceX’s addition to major indexes to create a surge in demand and push its stock price higher. Instead, the price fell. So what did…
- The Investor Coaching Show with Paul Winkler
Fidelity Predicts Low Large U.S. Returns — so Why Is So Much Client Money Still There?
Fidelity is forecasting relatively weak returns for large U.S. stocks over the next 10 years. Yet, much of the money it manages remains heavily invested in…
- The Investor Coaching Show with Paul Winkler
When You Hear “The Market Is Down,” You’re Not Hearing the Whole Story
When people say “the market is down,” they may not be telling the whole story. In reality, there isn’t just one market, and the way your portfolio is…
- The Investor Coaching Show with Paul Winkler
5 Reasons You Might Not Convert to a Roth IRA
A client calls Paul unsophisticated because he doesn't actively use a specific Social Security analysis software or push clients to do Roth conversions. The…
- The Investor Coaching Show with Paul Winkler
Watch This "Legendary" Market Timer Get Called Out on National Television
It’s a common misconception in the investing industry that bigger is always better. If someone manages $85 billion in investments, shouldn’t they be a pro?…
- The Investor Coaching Show with Paul Winkler
How to Become Financially Independent: 6 Habits That Matter Most
You go through two different phases with money in life. In the first phase, you work for money. In the second, your money begins working for you. No one wants…
- The Investor Coaching Show with Paul Winkler
Does Your Adviser Believe It’s Their Job To Market Time for You?
Does your adviser believe that it’s their job to make sure you’re in the “right” part of the market at the right time? Today, Paul and Jim talk about why it’s…
- The Investor Coaching Show with Paul Winkler
Free Dinner Workshops Are a Cash Cow for the Industry
There is an entire side industry in the investing world that teaches advisers how to give free dinner workshops and presentations to make sales. Paul and Jim…
- The Investor Coaching Show with Paul Winkler
SpaceX Isn’t Invincible: Don’t Break Market Timing Rules for Any Company
After all the hype over SpaceX in the last few months, some investors were convinced they should break a basic investing rule and try to time the market…
- The Investor Coaching Show with Paul Winkler
Financial Freedom or Financial Trap? Why the FIRE Movement Is Dangerous for Most
An investor works really hard to live off a side hustle, maximize saving, minimize spending, and retire by 25. Sounds great, right? Today, Paul and Jim…
- The Investor Coaching Show with Paul Winkler
Why Your First House Feels Out of Reach
Today, Paul shares a lot of rhetoric around why first-time homebuyers can’t get into a home. Most people think that housing regulations or lifestyle are to…
- The Investor Coaching Show with Paul Winkler
Life Insurance “Investment” Sales Pitches Are Convincing. Let’s Walk Through One.
Paul opens the show by talking about his experience in insurance sales at the beginning of his career. In these companies, advisors are taught to “smile and…
- The Investor Coaching Show with Paul Winkler
Social Security Could Run Out by 2032? Here's What That Really Means.
A recent headline claims Social Security could deplete its trust fund as early as 2032, leaving many retirees wondering if their benefits are at risk. In this…
- The Investor Coaching Show with Paul Winkler
SpaceX Is Now Public: You Didn't Miss Out
SpaceX finally went public, and investors everywhere are wondering the same thing: "Should I have invested in the IPO?" If you didn’t get in on SpaceX (SPCX)…
- The Investor Coaching Show with Paul Winkler
Can One Influencer Move Bitcoin? Commodities Don’t Work Like Stocks.
What happens when an asset's value depends entirely on what someone else is willing to pay? In this episode, Paul breaks down the key differences between…
- The Investor Coaching Show with Paul Winkler
The “Golden Grind”: How Many People Are Still Working After 65?
Most people picture retirement as something they'll choose on their own terms. But what if life has other plans? In this episode, Paul examines why many people…
- The Investor Coaching Show with Paul Winkler
SpaceX IPO: Who Will Actually Make All the IPO Money?
The SpaceX IPO is already upside down. SpaceX's valuation would place it among the largest companies in the S&P 500, yet its revenue tells a very different…
- The Investor Coaching Show with Paul Winkler
Why Everyone Needs an Investing Coach in Their Corner
Not all financial planners provide advice that aligns with your goals. In this episode, Paul shares lessons from 30 years in the gym and explains how the right…
- The Investor Coaching Show with Paul Winkler
Robinhood Lets You Use AI To Make Trades for You
Robinhood has made a fortune from selling the idea of day trading and gambling to investors. Today, Paul and Jim talk about the most recent move Robinhood has…
- The Investor Coaching Show with Paul Winkler
If Timing the Market Works, Why Doesn't Anyone Agree on the Timing?
If timing the market truly works, then why doesn’t anyone agree on when you should get in or get out? Today, Paul brings a blatant example of market timing…
- The Investor Coaching Show with Paul Winkler
The Billionaire Debate Is Missing the Bigger Picture
Why are billionaires becoming the centerpiece of so many political conversations? In this episode, Paul and Jim explore the economic ideas often left out of…
- The Investor Coaching Show with Paul Winkler
Big Tech Concentration: The Media Got the Problem Right — But the Solution Wrong
Today, Paul and Jim break down an interview in which two financial media pundits correctly inform investors that having too much in large U.S. tech companies…
- The Investor Coaching Show with Paul Winkler
IPOs Look Exciting — Here’s the Catch
From SpaceX to OpenAI, IPOs are dominating the news cycle right now. Today, Paul and Evan share why IPOs look so exciting and how they entice investors to…
- The Investor Coaching Show with Paul Winkler
Roth vs. Traditional and How To Take an Income in Retirement
Today, Paul and Evan continue their conversation about getting educated and understanding how to be a confident investor in retirement. Listen along as these…
- The Investor Coaching Show with Paul Winkler
Becoming Educated for Retirement. Paul Breaks Down 30 Years of Lessons (Part 2)
This week, Paul watched a video from another advisor in which he attempts to condense 30 years of investing lessons into 20 minutes. Getting educated is…
- The Investor Coaching Show with Paul Winkler
Becoming Educated for Retirement. Paul Breaks Down 30 Years of Lessons (Part 1)
This week, Paul watched a video from another advisor in which he attempts to condense 30 years of investing lessons into 20 minutes. Getting educated is…
- The Investor Coaching Show with Paul Winkler
Crypto Faces a Regulatory Turning Point in the U.S. Will This Deflate Its Value?
The draw for many crypto investors has been owning something that isn’t tied down to any specific government or bank. Now in 2026, the U.S. moves aggressively…
- The Investor Coaching Show with Paul Winkler
These Fees Are Crazy: A Full Breakdown of the Expenses of Annuities
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…
- The Investor Coaching Show with Paul Winkler
Alternative Investments Can Turn Long-Term Investors Into Short-Term Gamblers
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…
- The Investor Coaching Show with Paul Winkler
Excitement Around the SpaceX IPO Is Peaking. Should You Invest?
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…
- The Investor Coaching Show with Paul Winkler
This One Stat Makes You Most Likely To Run Out in Retirement
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…
- The Investor Coaching Show with Paul Winkler
Why AI Needs Regulation: Tech Leaders Don’t Share Everyone’s Values
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…
- The Investor Coaching Show with Paul Winkler
Robinhood Made Investing Simple — But at What Cost?
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…
- The Investor Coaching Show with Paul Winkler
Is AI Propping Up the Economy? This Is Why We Diversify
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 Investor Coaching Show with Paul Winkler
10 Sneaky Expenses Draining Your Bank Account
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…
- The Investor Coaching Show with Paul Winkler
Paul & Jim: The Industry’s Other Side — Advisors Represent Firms, Not Clients
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…