The Roth Guy with Jude Wilson

⭐Let’s make your financial story a heroic one! Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min

As the year wraps up, many investors are scrambling to decide whether a Roth conversion makes sense before December 31st. In this episode, Jude breaks down the logic behind “taxes on sale” and why strategic conversions can become a powerful long-term tool when done correctly. You’ll walk away wi...

Many people think they’re asking the right questions about retirement- but the way those questions are framed often leads to incomplete or even misleading answers. In this episode, Jude breaks down the most common questions he hears and shows how a simple reframing can uncover clearer strategies and more confident retirement decisions. Better questions lead to better answers… and better answers build better retirements.

Here’s so...

Some people believe having two financial advisors means double the wisdom. But does it really equal double the problems? Today, Jude tackles a listener’s question about this very dilemma. At the end of the day, having two advisors usually creates more confusion than confidence. What most people really need isn’t more voices in the mix; it’s one clear, coordinated plan.

Here’s some of what we discuss in this episode:

⚖️ Pros & C...

Healthcare costs in retirement just keep climbing- and the newest Fidelity study shows how serious the challenge has become. In this episode, Jude breaks down what retirees can expect to pay for medical expenses, why those costs are outpacing inflation, and the most overlooked ways to plan ahead.

From the hidden expenses Medicare doesn’t cover to how an HSA can serve as a “stealth Roth,” Jude shares actionable strategies to help yo...

In this episode, Jude tackles two listener questions from the mailbag, focusing on two of the most common retirement concerns: life insurance and investing. First up, what should you do if someone is pitching you a life insurance policy as an “investment”? Jude explains the pros, cons, and the middle ground between the extremes of “buy it all” and “avoid it completely.”

Jude also lays out the key questi...

Choosing between a traditional 401k and a Roth 401k is one of the most common questions workers face today. With more employers now offering both options, many people default to a 50/50 split simply because they don’t know what else to do. But is that really the best strategy? And how do you figure out the right mix for your situation?

Here’s some of what we discuss in this episode:

🏦 Traditional 401k: tax deduction today, taxab...

For many retirees, Medicare feels like a maze of rules, parts, and choices that only get more confusing the closer you get to age 65. In this episode, Jude is joined by Medicare specialist Kerwyn Jones to bring clarity to one of the most misunderstood pieces of retirement planning. Kerwyn explains the different parts of Medicare- what they cover, what they don’t, and the common pitfalls people make when signing up.

Here’s some of w...

This week on the show, Jude answers some of the most common Roth IRA questions! First up: the Five-Year Rule. What does it really mean, how does it apply to contributions versus earnings, and why should you start the clock as soon as possible? Jude breaks it down in plain language with a reminder that waiting too long could delay your tax-free income in retirement. Next, Jude tackles two questions that often go hand in hand: what t...

The Big Beautiful Bill (BBB) passed on July 4th, bringing major changes that retirees and pre-retirees need to understand. In this episode, Jude breaks down the top 3 provisions most relevant to his clients and listeners: the permanent extension of marginal tax brackets, the increased standard deduction, and a new senior citizen deduction that could reduce taxes on Social Security for millions of retirees. These updates offer new o...

Is your retirement account a ticking tax time bomb? In this episode, Jude gives a hands-on demo of his Tax Bomb Calculator- a powerful tool at thetaxbomb.com- that helps you estimate how much of your 401(k) or IRA could be lost to taxes.

Here’s some of what we discuss in this episode:

💣What is the tax time bomb?

📊 Understanding your future tax liability

🧠 “Mandatory” vs. “optional” taxes in retirement

🔄 The power of realloca...

The transition into retirement isn’t just a financial shift- it’s a psychological one. We’re excited to have a special guest on the show this week. Josh Bell, coach and consultant at The Josh Bell Company, is joining us to explore what it really means to leave your job title behind and step into the unknown.

Tune into this great conversation on building a retirement life filled with clarity, purpose, and healthy relationships!

He...

Wishful thinking feels comforting, but in retirement planning, it can quietly sabotage your future. In this second installment, Jude breaks down five more dangerous assumptions people make when planning for their golden years. From relying too much on Social Security to assuming Medicare will handle long-term care, this episode challenges listeners to face financial realities with clarity and strategy.

Here’s some of what we discus...

A little hope is good for the soul, but when it comes to retirement planning, wishful thinking can lead to serious financial mistakes. Today, we’re walking through 5 common examples of wishful thinking that can quietly damage your retirement and how you can build a plan that protects your future instead of relying on luck. From relying on outdated rules of thumb to underestimating healthcare costs, these are the “harmless” beliefs ...

When the headlines scream and markets tumble, your instinct might be to do something. But what should you actually do when the market drops? In this episode, Jude walks through 4 key things to consider when your portfolio takes a hit.

Here’s some of what we discuss in this episode:

🧠 Gut check: You may not be down as much as you think

⚖️ How diversification can help when the market takes a hit

🔁 Rebalancing & Roth conversions...

Annuities are often misunderstood- some see them as a financial nightmare, while others consider them a key part of a well-rounded portfolio. So, what exactly are they? And can they offer any tax advantages?

Jude is here to break it all down- how annuities work, their tax implications, and when they might fit into a retirement strategy.

Here’s some of what we discuss in this episode:

0:00 – Intro

2:07 – What is an annuity?

3:40 – T...

Peter Thiel, co-founder of PayPal and early investor in Facebook, reportedly grew his Roth IRA to a jaw-dropping $5 billion- completely tax-free. But how did he do it? And more importantly, can everyday investors use similar strategies to maximize their own retirement savings?

In this episode, Jude Wilson and Marc Killian break down the "Rocket Roth" strategy- an approach that goes beyond basic diversification to optimize where you...

If you’ve spent years successfully managing your own investments, do you really need a financial advisor? That’s the question one of our listeners sent in after years of handling his portfolio solo. So, is working with an advisor just an extra expense, or could it actually add real value?

In this episode, we break down when and why even experienced investors might benefit from professional guidance and when they’re probably fine on...

In this episode of The Roth Guy, Jude breaks down five crucial Roth conversion mistakes that could derail your retirement strategy. For example, many investors rush into conversions without considering the tax implications, often converting too much in a single year and inadvertently pushing themselves into a higher tax bracket. Jude explains how this mistake can trigger a "domino effect," leading to unexpected costs like increased...

Inflation has been a hot topic for years, and it's still a major concern as we move through 2025. While some reports suggest that inflation rates are decreasing, many consumers continue to feel the financial pinch. Because of this, inflation’s impact on retirement planning could be bigger than ever. In this episode, we’ll explore how to adjust your retirement strategy to stay ahead. 

Here’s some of what we discuss in this episode...