The Roth Guy with Jude Wilson

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 you prepare for one of retirement’s biggest financial wildcards. You’ll also learn how tax moves like Roth conversions can unexpectedly impact your Medicare premiums and why it’s crucial to factor healthcare into your overall income plan. Here’s some of what we discuss in this episode: 📈 Healthcare costs rising twice as fast as inflation 🏥 Medicare doesn’t cover everything ⚠️ Watch out for IRMAA and tax surprises 🧩 Plan early to avoid financial strain Fidelity Report: https://newsroom.fidelity.com/pressreleases/fidelity-investments--releases-2025-retiree-health-care-cost-estimate--a-timely-reminder-for-all-gen/s/3c62e988-12e2-4dc8-afb4-f44b06c6d52e Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 questions you need to ask before signing on the dotted line and why your financial goals, not someone else’s agenda, should guide the decision. Then, Jude responds to a saver who has built up a sizable 401(k) balance but admits he doesn’t know what to do next. Here’s some of what we discuss in this episode: 📝 Not all life insurance is created equal ⚖️ Making financial decisions based on your goals 💰 A large 401(k) balance isn’t enough without strategy 🪣 How the “bucket plan” can help give your money purpose 🧘 Structure brings peace of mind The Tax Bomb Calculator: https://retirementtaxbill.com/?u=Z00xeHQrK3lieGhOMlYvdnlNSUIvQT09 Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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, taxable withdrawals tomorrow 💡 Roth 401k: after-tax contributions, tax-free withdrawals later ⚖️ Why a 50/50 split isn’t always optimal 📉 The “sweet spot” strategy: maximize deductions + future tax-free income 📊 Using standard deductions wisely to avoid giving money away The Tax Bomb https://thetaxbomb.com/ Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 what we discuss in this episode: 🧩 Breaking down Medicare Parts A, B, C & D 💊 Understanding prescription drug coverage and gaps 💸 Avoiding costly enrollment mistakes 🛡️ Supplemental coverage: when and why it matters 👥 How Medicare coordinates with employer insurance Learn more about Kerwyn and Jones Insurance Solutions https://jisinsurance.com/about-us Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 to do if you make too much to contribute to a Roth IRA, and whether you should convert your entire IRA all at once. Here are the questions we discuss in this episode: 💭 What is the Roth five-year rule? 💭 What if I make too much to contribute to a Roth? 💭 Should I convert my IRA to a Roth all at once? Tax Bomb Calculator: www.thetaxbomb.com Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 opportunities for Roth conversions, long-term tax planning, and smarter retirement income strategies- if you know how to use them. Here’s some of what we discuss in this episode: 📉 Marginal tax brackets extended, but not forever 🧠 Planning windows and why every tax law is written in pencil 🧾 Higher standard deduction simplifies filing for most 💬 Why “tax-free Social Security” didn’t make it into law 💰 New senior deduction may reduce taxes on Social Security income Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 reallocating taxable retirement funds 📆 Using today’s low tax rates to your advantage The Tax Bomb Calculator: https://retirementtaxbill.com/?u=Z00xeHQrK3lieGhOMlYvdnlNSUIvQT09 Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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! Here’s some of what we discuss in this episode: 🧭 Redefining your identity without your career title 🗓️ Designing new rhythms for your daily life ❤️ Navigating relationship shifts in retirement 🎯 The danger of retiring without a plan beyond finances 🎙️ How coaching can be helpful during big life transitions Learn more about Josh: https://www.joshwbell.com/ Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 discuss in this episode: 🚫 Common planning mistakes and false beliefs 🏠 Downsizing might not free up the cash you expect 👨‍👩‍👧 Counting on your kids? Think again 💵 Social Security might not stretch far enough 🧯 Putting out fires before it’s too late Retirement Tax Bill Calculator https://thetaxbomb.com/ Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 that can become costly mistakes if left unchecked. Here’s some of what we discuss in this episode: 💸 Why “living off interest” no longer works 📉 The risk of retiring into a market downturn 📊 The myth of being in a lower tax bracket later in life 🏥 The hidden costs of long-term care 💰 Why your spending might not go down after all Retirement Tax Bill Calculator https://thetaxbomb.com/ Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 during downturns 💸 Why you should keep contributing 📵 Turn off the news and stop doomscrolling Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 – Types of annuities 6:19 – Advantages of annuities 8:34 – Disadvantages and fees 15:09 – When might an annuity be a good fit? Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 your investments are placed for maximum tax efficiency and growth. Could your Roth IRA be working harder for you? Let’s discuss what it means to rocket your Roth! Here's what we discuss in today's show: 1:21 – Peter Thiel’s backstory 2:35 – Asset location and diversification 4:41 – Reallocating assets for maximum growth 6:44 – Common mistakes and tax considerations 12:42 – What would you place in the “rocket Roth?” Resources for this episode: Tax Bomb Calculator: https://retirementtaxbill.com/?u=Z00xeHQrK3lieGhOMlYvdnlNSUIvQT09 Resources for this week's show: https://www.nbcnews.com/tech/tech-news/billionaire-investor-peter-thiel-has-5b-his-tax-free-retirement-n1272317 Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 their own. Here’s what we discuss in this episode: 0:00 – Intro 1:45 – DIY investors 4:13 – Much more than investment advice 6:11 – Two client stories 7:56 – Relationships 10:06 – Life changes 13:08 – Showing our value Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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 Medicare premiums due to IRMAA surcharges. We also discuss why paying conversion taxes from the wrong account can reduce long-term growth and how misunderstanding the five-year rule could result in penalties if funds are withdrawn too soon. Beyond these key mistakes, we’ll discuss the importance of having a well-planned tax strategy to make Roth conversions as effective as possible. Here’s some of what we discuss in this episode: 0:00 – Intro 0:53 – Converting too much in a year 4:14 – Impact on Medicare premiums 6:22 – Funding Roth conversions 7:47 – The five-year rule 8:47 – Having an overall tax strategy Resources for this episode: Tax management journey document https://drive.google.com/file/d/1SlEkVuxijRceUcTnkzdqggs2_ATNrBrZ/view?usp=sharing The Tax Bomb website https://thetaxbomb.com/ Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

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: 0:00 – Intro 3:24 – The rate of inflation to account for 6:43 – Planning for inflation and market downturns 10:47 – Factoring in taxes when planning for retirement Resources for this episode: Check out the Bucket Plan & Tax Funnels Diagrams mentioned in today’s show: https://centrusfs.com/resources/#downloads-resources S&P 500 Average Returns and Historical Performance for the 2000s: https://www.investopedia.com/ask/answers/042415/what-average-annual-return-sp-500.asp Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

Welcome to 2025! In this episode of The Roth Guy, Jude and Marc kick off the new year with an essential financial checklist to help you start the year on the right foot. They discuss strategies to stay proactive, avoid costly mistakes, and make the most of your financial planning opportunities. With insights on everything from reviewing your investment portfolios to navigating the latest contribution limit updates, they’ll help you stay ahead of the curve. Happy New Year! Here’s some of what we discuss in this episode: 0:00 – Intro 1:03 – Recap of last year’s market performance 2:45 – Proactive financial planning for 2025 5:04 – Investment portfolios and tax efficiency 7:41 – New Year contribution limits and savings opportunities 10:10 – Balancing retirement contributions and tax deductions 12:10 – HSAs and their benefits 13:19 – Insurance and estate planning reviews 14:25 – Creating a financial action plan for 2025 Important Tax Numbers 2025 PDF https://thetaxbomb.com/wp-content/uploads/2025/01/Important-Tax-Numbers-2025.pdf Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

Social Security is the backbone of retirement for millions of Americans, but big changes may be coming. In this episode, we dive into the recently released proposal to raise the full retirement age to 69 and what it means for your benefits, your future, and your financial security. Here’s some of what we discuss in this episode: 0:00 – Intro 0:52 – The proposed change and potential impacts 4:30 – The potential 40% reduction in benefits 6:32 – Proactive planning and the need for change 12:46 – Talking to a professional who understands Social Security Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

As the end of November approaches, it’s a great time to take a closer look at your financial plans and make any necessary tweaks to prepare for the year ahead. That’s why this week, Jude and Marc are sharing some financial items that you should be thinking about as the year winds down. Whether it’s reviewing your retirement contributions, exploring tax-saving strategies like QCDs, or tax-loss harvesting, let's make sure you're finishing the year on a high note. Here’s some of what we discuss in this episode: 0:00 – Intro 0:48 – The importance of tax loss harvesting 4:55 – Maximizing retirement contributions 8:23 – Optimizing tax brackets 10:29 – Charitable contributions and QCDs 12:41 – End of year savings and HSAs 16:02 – Bunching deductions Get the "What Issues Should I Consider Before The End Of The Year?" Guide here: https://drive.google.com/file/d/1-uGZpXb4KdavKB2JEjolQot5xYIdZ7EM/view?usp=sharing Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

We talk about the ticking tax time bomb a lot on this show regarding the national deficit. It’s a reality we are faced with, and while it sounds scary, there are action steps that you can take to minimize the impact of potential future tax increases on you. In this episode, Jude and Marc explore how tax efficiency funnels can be utilized to optimize your financial strategy and mitigate the risks associated with these rising taxes. Jude breaks down the three tax funnels- the pre-tax funnel, the post-tax funnel, and the tax-advantaged funnel- and discusses the benefits and drawbacks of each. With the Tax Cut and Jobs Act set to expire in 2025, the window for taking advantage of current low tax rates may be closing. It’s important to strategize now and prepare for the potential changes ahead. Here’s some of what we discuss in this episode: 0:00 – Intro 5:06 – The pre-tax funnel 7:05 – The post-tax funnel 8:37 – The tax-advantaged funnel 9:01 – Real-world example 13:24 – Potential expiry of the Tax Cut and Jobs Act 15:17 – Action steps you can take Connect: Website: https://centrusfs.com/podcast/ Call: 800-779-4592 Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/