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

Today, Jude dives into a hot topic: a new proposal that could shake up Social Security for high earners. The plan could change how benefits are structured, and while it aims to address the program’s future, it’s raising some eyebrows. Jude breaks down what this means for your retirement planning a...

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

If you’ve managed your own money successfully over the years, you may be asking, why bring in an advisor now? After all, you’ve done the hard part: saving, investing, and growing your portfolio. But as retirement approaches, the game changes in ways most people don’t expect. Jude uncovers the key ...

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

Some retirement beliefs sound harmless, but they can quietly derail your entire financial plan. In this episode, Jude tackles five of the most common retirement myths that continue to trip people up year after year. Why do these ideas stick around, and what happens when real life doesn’t match the...

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

New tax rules for 2026 bring meaningful opportunities- but only if you understand the fine print. In this episode, Jude breaks down two of the most overlooked changes: the new senior tax deduction and updated catch-up contribution rules. We clarify who qualifies, how income phase-outs work, and wh...

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

We’re excited to be back today with George Rosen and George St Pierre III of Contango Investments, Inc., to dive deeper into what it really takes to buy or sell a business as part of a retirement strategy.

In part two of this conversation, the Georges walk through the practical X’s and O’s- from s...

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

More and more retirees and pre-retirees are looking to leave corporate life not to slow down, but to buy a business and build something of their own. In this episode, Jude sits down with George Rosen and George St Pierre III of Contango Investments, Inc. to explore why business acquisitions are bo...

⭐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 ...