Paul Winkler, Inc.

06/01/2026

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 offer sweeping regulation over these digital assets.

Paul and Dan address a question on many crypto investors' minds: Will regulation add to the value of crypto or completely defeat the purpose?

Listen along to hear why a more stable crypto scene won’t create a superior investment to a properly diversified portfolio.

Click the link below to listen to the episode.

05/29/2026

In 2025 in the U.S. alone, insurance companies and insurance salespeople sold almost half a trillion dollars of annuities.

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.

Click the link below to listen to the episode.

05/28/2026

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.

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.

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05/27/2026

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.

Click the link below to listen to the episode.

05/25/2026

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.

Click the link below to listen to the episode.

05/22/2026

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 users.

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05/21/2026

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 markets and explore the difference between an “all-in-one” investing app and a financial advisor who understands your goals and wants you to understand investing.

Click the link below to listen to the episode.

05/19/2026

Why do so many people struggle to save for retirement — even when incentives exist?

In this conversation with Joan Jones, Paul Winkler breaks down the proposed “Trump IRA,” the behavioral psychology behind investing, and why automation may matter more than motivation when it comes to building wealth.

To listen to this thoughtful discussion on retirement, ownership, and the long-term power of investing, click the link in the comments below 👇

05/18/2026

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.

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05/15/2026

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 difficult nature of working for a company that will only pay you when you sell products and will take all your clients when you try to walk away.

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 t...