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 debate. They discuss how wealth creation, incentives, and entrepreneurship have contributed to longer life expectancies and higher standards of living worldwide. They also explain why financial literacy matters more than ever and share a real-life example of a high-income earner who still struggles with debt, proving that income alone doesn't guarantee financial success.

 

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. 

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 is risky, but then claim the fix is to invest in private equity and commodities. Listen along to hear why Paul and Jim disagree with these proposed solutions that ignore the research suggesting these areas may introduce uncompensated risk to your portfolio. Later in the episode, Paul and Jim get into SpaceX, the largest IPO in history, and explain why they believe chasing IPO excitement may not serve investors well over the long term.

 

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. 

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 invest emotionally because they appeal to your desire to avoid missing out on the companies and technology of the future. Listen along as these two advisors explain why IPOs like SpaceX and OpenAI sound like incredible investments and reveal the realities of IPOs that don’t get shared by financial media outlets.

 

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. 

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 two advisors discuss whether or not to put your money in a Roth or traditional IRA and explain some of the rules around taking an income in retirement that maximizes the money that you worked so hard to earn in your earning years. Later in the episode, Paul brings an article that claims you should always have 90% of your portfolio in equities and explains why the industry is so bad at understanding the purpose of bonds. 

 

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. 

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 important, but it’s not a quick process. Paul Winkler, Inc. has worked for decades to create confident investors through education. Listen along as Paul and Evan cover a few fundamental retirement concepts and discuss predicting your income with income calculators, as well as navigating your Social Security benefits to fit your needs.

 

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. 

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 important, but it’s not a quick process. Paul Winkler, Inc. has worked for decades to create confident investors through education. Listen along as Paul and Evan cover a few fundamental retirement concepts and discuss predicting your income with income calculators, as well as navigating your Social Security benefits to fit your needs. 

 

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. 

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 to implement sweeping regulation over these digital assets. Today, Paul and Dan address a question on many crypto investors' minds: Will regulation add to the value of crypto or completely defeat its purpose? Listen along to hear why a more stable crypto scene won’t create a superior investment to a properly diversified portfolio.

 

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.

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 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 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.

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 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 jargon and marketing around alternative investments, no one is ever honest about the risks. Listen along as these two investors share some of the biggest alternative investment traps and how investments like crypto, real estate, municipal bonds, private equity, and commodities can turn long-term investors into short-term gamblers.

 

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.

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 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 economy and shares an interview that suggests we haven’t yet seen the full value this new technology can bring to companies and 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.