The Roth Guy with Jude Wilson

Jude Wilson
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Welcome to The Roth Guy with Jude Wilson, your go-to podcast for all things tax, finance and retirement, hosted on YouTube and available on your favorite podcasting platforms! Each episode, join Jude Wilson as we explore the essential world of retirement planning, tax strategies, and overcoming financial hurdles. Imagine your financial journey as an epic superhero tale—filled with challenges like taxes, inflation, and market risks. But don’t worry, with Jude’s guidance, you can master your financial destiny and emerge as the hero of your own story. From practical advice on navigating taxes efficiently to strategies for securing your financial future, this podcast is both educational and entertaining. Tune in to The Roth Guy with Jude Wilson and start your journey toward financial freedom with insights, tips, and resources designed to empower you. Ready to transform your approach to finance? Let’s make your financial story a heroic one!

  1. 5D AGO

    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/

    22 min

  2. DEC 4

    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/

    14 min

  3. NOV 20

    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/

    16 min

  4. NOV 6

    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/

    16 min

  5. OCT 23

    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/

    15 min

  6. SEP 25

    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/

    13 min

  7. SEP 11

    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/

    21 min

  8. AUG 28

    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/

    24 min
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5
out of 5
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About

Welcome to The Roth Guy with Jude Wilson, your go-to podcast for all things tax, finance and retirement, hosted on YouTube and available on your favorite podcasting platforms! Each episode, join Jude Wilson as we explore the essential world of retirement planning, tax strategies, and overcoming financial hurdles. Imagine your financial journey as an epic superhero tale—filled with challenges like taxes, inflation, and market risks. But don’t worry, with Jude’s guidance, you can master your financial destiny and emerge as the hero of your own story. From practical advice on navigating taxes efficiently to strategies for securing your financial future, this podcast is both educational and entertaining. Tune in to The Roth Guy with Jude Wilson and start your journey toward financial freedom with insights, tips, and resources designed to empower you. Ready to transform your approach to finance? Let’s make your financial story a heroic one!

Information

  • Creator
    Jude Wilson
  • Years Active
    2018 - 2025
  • Episodes
    148
  • Rating
    Clean
  • Copyright
    © Copyright 2024 Jude Wilson
  • Show Website
    The Roth Guy with Jude Wilson

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