The 'What's Next?' Retirement Podcast

Hosted by Craig Wear, CFP®

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Jun 2025

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About the show

Welcome to another edition of The “What’s Next?” Retirement Podcast with Craig Wear. Life is full of transitions that have a financial impact now and in your future. When finances are affected, there are always questions to ask and choices to make. As an independent Certified Financial Planner for well over thirty years, Craig has helped Americans make decisions that give them their best financial futures. The experiences with so many clients has given him a unique perspective to help with “What’s Next?” for you - as you navigate the unknowns of your own life.

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22 recent

June 13, 202536 min

The Roth Illusion: Why Most Software Gets It Wrong

Hosted by: Craig Wear Guest: Daniel Jandro, CFP®, Rothologist at Q3 Advisors 🔍 Episode Summary: In this episode, Craig Wear sits down with Daniel Jandro—aka “The Professor”—to unpack one of the biggest myths in Roth conversion planning: the belief that common financial software gets it right. If you’re using tools like eMoney, RightCapital, or even DIY spreadsheets to manage your Roth conversions, this episode is a wake-up call. Craig and Daniel walk through the limitations of major platforms, why one-size-fits-all strategies fall short for IRA millionaires, and how Q3’s proprietary methodology is helping clients avoid billions in unnecessary taxes. They also reveal why most advisors and tools fail to optimize—and why specialized planning is essential when your pre-tax retirement accounts top seven figures. Try the calculator featured in this episode: 👉 https://q3.link/rmd-calculator-podcast ⏱️ Chapter Markers: • 00:00 – Introduction & Overview • 01:20 – Who Really Needs Roth Conversions? • 03:45 – Introducing the RMD Calculator • 06:00 – Sample Case Walkthrough • 09:00 – Lifetime Tax Exposure & Heir Consequences • 10:45 – What Makes This Calculator Different • 12:00 – Paradigms That Get in the Way • 14:00 – The Experience Gap for DIYers • 16:45 – The Problem with Excel and Traditional Tools • 19:45 – Review of Major Planning Software • 24:30 – Hidden Risks in Off-the-Shelf Optimizers • 26:40 – Why Specialization Matters • 28:45 – What Mastery Looks Like • 31:00 – Q3’s Real-World Experience • 33:00 – Closing Thoughts & Invitation 📌 Key Takeaways: • Why standard financial software often miscalculates Roth conversion outcomes • The million-dollar threshold : Why IRA millionaires need a totally different strategy • How Q3’s RMD Calculator can open your eyes to tax consequences for both you and your heirs • The #1 reason smart people still get Roth conversions wrong—and how to fix it • Real-world case studies and tax savings data from 1,200+ client scenarios • The problem with software like eMoney, RightCapital, MaxiFi, and NewRetirement when it comes to advanced tax optimization • The importance of working with a Roth conversion specialist instead of a generalist 💬 Quotes: “If you’re not doing accelerated conversions and you’re an IRA millionaire, you’re leaving money on the table.” – Craig Wear “When one variable is wrong, the compounding tax impact can last generations.” – Daniel Jandro 👥 Work with Q3: Learn more about Q3’s planning services, their money-back refund offer, and how to work directly with a CFP® from their team: 🔗 Schedule a Call now

November 13, 202421 min

Maximizing Your Medicare: Essential Tips for Open Enrollment 2024 with Expert Emily Gang

Summary: In this episode of What's Next in Retirement , Craig Wear welcomes Medicare expert Emily Gang to unpack the intricacies of Medicare open enrollment. Whether you’re already enrolled or gearing up for your first enrollment, Emily shares essential insights on the choices available and critical considerations for 2024. From big changes to Medicare Part D, including a new $2,000 cap on medication copays, to the nuanced pros and cons of Medicare Advantage plans, this episode is packed with practical advice to help listeners make informed decisions that align with their unique healthcare needs. Craig and Emily also discuss why it’s crucial to get Medicare right the first time to avoid costly errors down the road. Tune in as they dive into strategies to save on premiums, avoid common pitfalls, and leverage Medicare’s evolving landscape to protect your healthcare and finances in retirement. Episode Highlights: [00:01] - Introduction to Medicare open enrollment and why it matters now. [02:33] - Key updates for 2024, including the impact of the $2,000 cap on prescription copays. [03:55] - How failing to review Part D plans could leave money on the table. [08:00] - Medicare Part B premiums and expected changes for high-income earners. [11:50] - Risks associated with Medicare Advantage plans and network limitations. [16:17] - Action steps for Medicare recipients before December 7th to optimize coverage and costs. [18:30] - Importance of choosing a reliable Medicare provider to avoid future complications. [20:59] - Closing advice: Be proactive in understanding Medicare rules to make the best decisions. Links & Resources: Connect with Emily Gang, “The Medicare Coach,” for personalized Medicare consultation: https://q3adv.com/services/financial-planning/ Medicare.gov for plan comparisons and to check network status. GoodRx, SingleCare, and Cost Plus for medication coupons and additional savings. If you enjoyed this episode, please rate, follow, and share What's Next in Retirement ! Don’t forget to check the show notes for a free consultation link with Emily to explore your best Medicare options.

November 7, 202421 min

The Truth About Capital Gains and Roth Conversions – A CPA’s Take

Summary In this conversation, Craig Wear and Glenn Block discuss essential financial strategies for IRA millionaires, focusing on tax implications and the importance of financial education. They emphasize the potential tax savings and the benefits of informed financial planning, aiming to simplify the financial lives of their clients. Takeaways Understanding tax implications is crucial for IRA millionaires. Proper financial strategies can save millions in taxes. Financial education is key to making informed decisions. Simplifying financial life can lead to better outcomes. Medicare premiums can significantly impact retirement finances. Staying updated on tax code changes is important. Collaboration with financial experts can enhance knowledge. Subscribing to financial resources can provide valuable insights. Planning ahead can prevent future financial burdens. Engaging with educational content can improve financial literacy. Chapters 00:00 Navigating Capital Gains and Roth Conversions 10:58 Leveraging Charitable Contributions for Tax Benefits

November 1, 202416 min

Medicare Open Enrollment 101: Navigating Changes with Todd Morrissey and Craig Wear

Interested in talking with Todd and his team? Schedule some time with them here: https://hello.q3adv.com/todd-podcast In this episode of What's Next in Retirement , host Craig Wear and guest Todd Morrissey, President of Medicare Solutions at Advisors Excel, provide insights into the Medicare Open Enrollment period. Whether you’re already on Medicare or exploring options for the first time, this discussion covers key information about Medicare Advantage, Part D, and the changes brought on by recent legislation. Todd and Craig discuss the steps to consider during open enrollment, how to evaluate plan changes, and the impact of the Inflation Reduction Act on premiums and coverage. This episode emphasizes the importance of partnering with a knowledgeable advisor who can offer tailored guidance based on your unique healthcare needs. Chapters 00:00 Introduction to Medicare and Retirement Planning 03:27 Understanding Medicare Open Enrollment 08:11 Navigating Medicare Advantage and Supplements 13:03 Market Trends and Consumer Awareness

October 14, 202429 min

Roth Conversion Myths and Tax Pitfalls: Insights from a CPA with Glenn Block

Summary In this podcast episode, Craig Wear and Glenn Block discuss the intricacies of Roth IRA conversions from a CPA's perspective. They explore the misconceptions surrounding tax brackets, the importance of strategic planning, and the role of CPAs in guiding clients through the conversion process. The conversation highlights common pitfalls, tax strategies, and the benefits of charitable contributions in relation to Roth conversions. The episode emphasizes the need for professional guidance to navigate the complexities of tax planning and retirement strategies effectively. Takeaways Roth conversions can be beneficial even in higher tax brackets. Many CPAs discourage conversions due to misconceptions about tax implications. Using external funds to pay taxes on conversions preserves Roth IRA growth. Charitable contributions can be strategically timed to offset conversion taxes. Professional guidance is essential for effective tax planning and conversions. Understanding capital gains tax is crucial when selling investments for conversions. Donor advised funds can provide significant tax benefits when making charitable contributions. The timing of tax payments can impact overall financial strategy. Roth conversions can lead to substantial tax savings over a lifetime. It's important to have a CPA who understands the nuances of Roth conversions. Chapters 00:00 Introduction to Roth Conversions 02:11 Understanding CPA Perspectives on Roth Conversions 04:01 The Timing and Tax Implications of Roth Conversions 04:53 Understanding Roth IRA Conversions 15:25 Strategic Tax Planning for Roth Conversions 22:04 The Importance of Professional Guidance 29:50 Navigating Capital Gains and Roth Conversions 43:05 Leveraging Charitable Contributions for Tax Benefits

April 29, 202437 min

Tax Tips if You’re Headed (back) to Canada

This episode focuses on the unique challenges faced by Canadians living and working in the United States and those planning to return to Canada. The conversation covers topics such as cross-border taxation, immigration issues, and retirement planning. The guests, Jerry Scott and Craig Wear, discuss the importance of finding the right professionals to navigate these complex issues and the need for proper planning to minimize tax liabilities. They also highlight the significance of filing the necessary elections and forms to ensure tax efficiency. The episode emphasizes the value of education and seeking expert advice in managing cross-border financial matters. Find Gerry Scott Around the Web: Snowbirds US Day Tracker: www.snowbirdsusdaytracker.com Snowbirds Wealth Management: www.snowbirdswealthmanagement.com Snowbirds Ex Pat Radio Podcast: https://open.spotify.com/show/43fItjxqPBHTDbuRQdJhk3?si=9d0a9d23fe694aaf Takeaways Canadians living and working in the United States face unique challenges related to cross-border taxation and immigration issues. Proper planning and finding the right professionals are crucial in minimizing tax liabilities and ensuring tax efficiency. Filing the necessary elections and forms is essential for Canadians moving back to Canada to avoid potential tax consequences. Education and seeking expert advice are key in managing cross-border financial matters and making informed decisions. Chapters 00:00 Introduction and Unique Challenges for Canadians in the US 08:18 Jerry Scott's Business and Expertise in Cross-Border Financial Planning 27:04 Working with Canadians and Americans in Cross-Border Financial Matters 32:28 Exiting the US Properly and Avoiding Tax Issues 36:45 Conclusion and Call to Action

March 21, 202450 min

My Medicare Audit: A Personal Journey to Optimal Coverage

In this conversation, Craig discusses the questions and decisions that arise when preparing for retirement, including the important decision of choosing a Medicare plan. He introduces Emily, a Medicare consultant who helps individuals make informed decisions about Medicare. They discuss the differences between Original Medicare and Medicare Advantage, and Craig decides to stick with Original Medicare for its flexibility. They explore the various parts of Original Medicare, including Part A, Part B, and Part D. Emily provides recommendations for Medigap plans and Part D drug plans, and they discuss appealing income-related penalties. Overall, the conversation provides valuable insights into navigating the complexities of Medicare. In this conversation, Craig and Emily discuss the Part D late enrollment penalty and the considerations for delaying Part D coverage. They explore the options of keeping an existing drug plan or paying for medications out of pocket. They also discuss the risk of not having Part D coverage and the guaranteed enrollment period for joining a new Medicare Part D drug plan. They delve into the importance of selecting a stable insurance company and the factors to consider when choosing a Medicare supplement plan. They also touch on dental, vision, and hearing coverage, as well as the next steps for enrolling in Medicare. Chapters 00:00 Introduction and Retirement Questions 00:29 Introduction to Medicare 00:55 Discovering Medicare Consulting 01:24 Inviting Emily, the Medicare Coach 03:20 Introduction to Emily's Business 04:02 Emily's Personal Experience with Medicare 04:22 Choosing Between Original Medicare and Medicare Advantage 05:29 Craig's Decision to Stick with Original Medicare 07:20 Understanding the Parts of Original Medicare 08:05 Choosing a Medicare Supplement Plan 09:26 Medicare Part D and Prescription Drug Coverage 11:58 Considering Doctors and Health Issues 13:26 Appealing Income-Related Penalties 14:21 Medigap Plans and Appeals 15:36 Understanding Medicare Part A and Part B 16:24 Medicare Part B Premiums and Deductibles 21:12 Appealing Income-Related Medicare Penalties 26:03 Recommendation for Part D Drug Plan 27:25 Considering Part D Penalties 27:56 Part D Late Enrollment Penalty 28:14 Considering Existing Drug Plan 28:29 The Risk of Delaying Part D Coverage 29:00 Qualifying for Medicare Part D 29:20 Guaranteed Enrollment Period 29:38 Enrolling in a Drug Plan 30:06 Options for Coverage in Case of a Curveball 30:21 Considering the Cost of Late Enrollment Penalty 30:47 Impact of Income on Part D Penalty 31:20 Coverage for Vaccinations 31:39 High-Level Overview of Part D 32:14 Selecting a Stable Insurance Company 33:15 Importance of Long-Term Planning 34:05 Guaranteed Enrollment for Medicare Supplement Plans 35:05 Comparison of Medicare Supplement Plans 36:04 Considerations for Plan G, High Deductible G, and Plan N 37:22 Considering Future Healthcare Options 38:03 Coverage for Medical Tests and Services 38:22 Dental, Vision, and Hearing Coverage 43:51 Next Steps: Enrolling in Medicare 46:09 Final Thoughts and Takeaways

March 7, 202430 min

Unlocking Your Retirement Goldmine: How to Legally Tap into Your 401K and Pension Now

Summary This episode discusses accessing retirement funds while still working. Marcus Foote, an attorney, shares his discovery of a way to access qualified funds such as 401ks and pension plans. The most common reasons for accessing these funds include diversifying investment options, investing in alternative investments, and rolling funds down to a younger spouse. Marcus explains the process of using in-marriage quadros to transfer funds legally. He also addresses limitations and considerations, such as the type of plan and state-specific laws. The episode concludes with information on how to contact Marcus and schedule a consultation. Takeaways There is a way to access retirement funds while still working, such as 401ks and pension plans. Common reasons for accessing these funds include diversifying investment options and investing in alternative investments. In-marriage quadros can be used to transfer funds legally. Considerations include the type of plan and state-specific laws. Chapters 00:00 Introduction 00:30 Accessing Retirement Funds While Still Working 01:24 Introducing Marcus Foote 04:27 Common Reasons for Accessing Retirement Funds 06:11 Benefits of Rolling Funds Down to a Younger Spouse 07:40 Using Quadros to Avoid Early Withdrawal Penalties 09:24 Limitations and Considerations 11:16 Process Overview Want to Learn More? To discuss how the ideas presented here may fit into your future, simply email cw@craigwear.com to schedule a complimentary consultation with one of our CFPs. For more information or to schedule a time to talk to Marcus Foote, please email JDear@InMarriageQDRO.com

February 27, 202418 min

Supercharge Roth Conversions Through DAFs

Summary In this episode, Craig Wear discusses how to supercharge your Roth conversion strategy by using donations. He introduces the concept of Qualified Charitable Donations (QCDs) and explains how they can be used to offset taxable minimum distributions. Craig then dives into the benefits and workings of Donor Advised Funds (DAFs), which act as charitable giving accounts. He highlights the tax advantages of DAFs, including immediate tax deductions and the elimination of capital gains tax. Craig concludes with an example demonstrating the combination of Roth conversion and DAFs, and offers recommendations for a coordinated approach. Takeaways Qualified Charitable Donations (QCDs) can be used to offset taxable minimum distributions from IRAs. Donor Advised Funds (DAFs) are flexible charitable giving accounts that offer immediate tax deductions and tax-free growth. Combining Roth conversions with DAFs can result in significant tax savings. Coordinating with a Roth specialist, investment advisor, and CPA is recommended for an effective strategy. Chapters 00:00 Introduction and Setting the Stage 01:25 Using Qualified Charitable Donations (QCDs) 04:37 Donor Advised Funds (DAFs) 09:08 Tax Benefits of Donor Advised Funds 12:28 Example: Combining Roth Conversion and Donor Advised Funds 15:15 Considerations and Recommendations

November 16, 202339 min

Recession proof your investments with this...

Join in to listen to Craig and Matt Blackwell discuss how to recession proof your investments. Special Guest: Matt Blackwell Schedule a call to learn more www.reliant-mgmt.com mblackwell@reliant-mgmt.com Check out my books here .