The Roth Guy with Jude Wilson

Why More Retirees Are Becoming Business Owners with George Rosen and George St Pierre III

⭐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 booming, what makes today’s market so unique, and how to tell if buying an existing business is the right path for you. They share real success stories, walk through the due diligence process, explain common pitfalls of going solo, and break down what buyers truly need in order to thrive.
 
Here’s some of what we discuss in this episode:
💼 Why so many retirees are buying businesses
🌊 The “silver tsunami” creating business opportunities
🧩 Matching the right buyer with the right business
📝 The importance of due diligence
🚫 The pitfalls of DIY business buying
 
Contango Investments:
Website: https://contangoinvestments.com/
LinkedIn: https://www.linkedin.com/company/741644/admin/dashboard/
Facebook: https://www.facebook.com/Contangoinvestmentsinc
Instagram: https://www.instagram.com/contango_investmentinc/
X:  https://x.com/biz_broker
George Rosen:
LinkedIn: https://www.linkedin.com/in/floridabusinessvaluations/
 
CONNECT 🤝
Facebook: https://www.facebook.com/CentrusFinancialStrategies/
X: https://x.com/centrusfs?s=21
LinkedIn: https://www.linkedin.com/company/-wilson-group-financial/
 
CONTACT ☎
Centrus Website: https://centrusfs.com/podcast/
The Tax Bomb Website: https://thetaxbomb.com/
Call: 800-779-4592
Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min
Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

Taxes on Sale: Why Now Is the Time for Roth Conversions

⭐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 with a clearer understanding of how to avoid costly mistakes and make smarter year-end decisions.
 
Here’s some of what we discuss in this episode:
📅 Year-End Roth Deadlines: why December 31st matters and when to act
🇺🇸 National Debt & Tax Rates: how today’s environment shapes tomorrow’s taxes
🧠 Roth Conversion Strategy: avoiding bumps into higher brackets and using “tax bracket filling”
💸 Deductions & Tax Cuts: understanding the temporary nature of today’s tax landscape
 
CONNECT 🤝
Facebook: https://www.facebook.com/CentrusFinancialStrategies/
X: https://x.com/centrusfs?s=21
LinkedIn: https://www.linkedin.com/company/-wilson-group-financial/
 
CONTACT ☎
Centrus Website: https://centrusfs.com/podcast/
The Tax Bomb Website: https://thetaxbomb.com/
Call: 800-779-4592
Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min
Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

Why Better Questions Build Better Retirements

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 some of what we discuss in this episode:
❓ Smarter Questions: why reframing your thinking improves planning
💰 “How Much Do I Need?” Understanding income needs vs. magic numbers
🏥 Long-Term Care: replacing fear-based thinking with practical options
📆 Social Security Timing: choosing based on strategy- not rumors
📉 Cash vs. Risk: avoiding emotional market reactions
 
CONNECT 🤝
Facebook: https://www.facebook.com/CentrusFinancialStrategies/
X: https://x.com/centrusfs?s=21
LinkedIn: https://www.linkedin.com/company/-wilson-group-financial/
 
CONTACT ☎
Centrus Website: https://centrusfs.com/podcast/
The Tax Bomb Website: https://thetaxbomb.com/
Call: 800-779-4592
Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min
Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

Should You Have More Than One Financial Advisor?

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 & Cons: The advantages and drawbacks of having two advisors
⚠️ Confusion Risk: How conflicting advice can derail your financial strategy
📊 Diversification Myth: Why “advisor diversification” doesn’t equal better results
🧾 Double Fees: How having multiple advisors could quietly increase your costs
📉 Performance Tracking: Why comparing results between advisors can be misleading
🧭 One Captain Rule: Why every financial ship needs a single trusted leader
 
CONNECT 🤝
Facebook: https://www.facebook.com/CentrusFinancialStrategies/
X: https://x.com/centrusfs?s=21
LinkedIn: https://www.linkedin.com/company/-wilson-group-financial/
 
CONTACT ☎
Centrus Website: https://centrusfs.com/podcast/
The Tax Bomb Website: https://thetaxbomb.com/
Call: 800-779-4592
Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min
Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

Retirement Health Care Costs Just Jumped Again- 2025 Fidelity Update

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 🤝
Facebook: https://www.facebook.com/CentrusFinancialStrategies/
X: https://x.com/centrusfs?s=21
LinkedIn: https://www.linkedin.com/company/-wilson-group-financial/
 
CONTACT ☎
Centrus Website: https://centrusfs.com/podcast/
The Tax Bomb Website: https://thetaxbomb.com/
Call: 800-779-4592
Schedule your complimentary review with Jude: https://calendly.com/centruscalendar-/30min
Watch on YouTube: https://www.youtube.com/channel/UCOyRZhgLenTC49qNZH9mEuQ/

Life Insurance Traps and Maximizing Your 401(k): Your Questions Answered!

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/

Finding the Sweet Spot: Roth vs. Traditional 401k

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/

Medicare 101: Avoid Costly Mistakes in 2025 with expert Kerwyn Jones

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/

Roth IRA Q&A: Five-Year Rule, Income Limits & Conversion Mistakes

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/

Big Beautiful Bill: Top 3 Retirement Tax Changes Explained

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/