Retirement Answers

Jacob Duke, CFP®

Retirement Answers is a podcast built to help you succeed in retirement. The thought of retirement can be overwhelming and downright scary for many... but it doesn't have to be!

The goal of this podcast is to provide thoughtful insights and strategies to give you the confidence you need to retire successfully. At the end of the day, my ultimate goal for my clients and podcast listeners is to live a fulfilling retirement.

Follow along as I publish a new episode each week covering everything from retirement income planning, tax planning, Social Security, insurance planning, investing, and much more.

Here's to learning everything you need to know to live out your dream retirement!

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164 episodes
Updated July 22

Episodes164

Newest first

July 22 · 28 min
Does My Roth 401k Satisfy The 5-Year Roth IRA Rule?
Have you been contributing to a Roth 401(k) for years and assumed that time counts toward the Roth IRA five-year rule when you roll it over? 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Roth 401k vs Roth IRA 01:24 Roth IRA Basics 03:25 Conversions Five Year Rule 05:34 Withdrawal Ordering Rules 07:57 Roth 401k Rollover Myth 10:32 Qualified vs Nonqualified 13:07 Nonqualified Rollover Breakdown 16:34 Qualified Rollover Treatment 22:18 Takeaways
July 15 · 11 min
Stop Saving For Retirement... (Here's Why)
Do you really need to be saving more for retirement? What if it's costing you something you can't get back? Join me in this episode to hear a different perspective on how much you should be saving for retirement. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.
July 4 · 19 min
Are You Waiting Too Long to Sell Winning Investments?
Why haven't you sold that investment that has made you a lot of money? What's stopping you? I'm hearing the question "What should I do with my big winners?" a lot more lately, so I wanted to give you some ideas on how to think about this. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2025 PDF here: https://www.rivertreewealth.com/2025-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.
June 16 · 27 min
What Are the Best Strategies for Reducing RMDs?
Are you worried that required minimum distributions (RMDs) could force unnecessary taxable income and shrink your hard-earned retirement savings? In this episode of Retirement Answers, Jacob Duke explains when RMDs become a real problem, offers a quick rule of thumb based on how much you hold in tax-deferred accounts, and walks through five ways to reduce future RMDs. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2025 PDF here: https://www.rivertreewealth.com/2025-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Retirement Rule Frustrations 00:51 When RMDs Become a Problem 03:10 Gap Years Tax Planning 03:33 Asset Location Strategy 08:40 Roth Conversions Explained 13:32 Delay Social Security Benefits 18:40 QCDs for Charitable Giving 21:22 Spend More Before RMDs 25:40 Wrap Up
May 29 · 13 min
The 4% Rule Is A Terrible Retirement Income Strategy (Here's Why)
Have you ever wondered if certain beliefs or rules of thumb about retirement could actually jeopardize your future instead of secure it? In this episode, Jacob breaks down the 4% and why it doesn't make sense in real life. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2025 PDF here: https://www.rivertreewealth.com/2025-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.
May 22 · 13 min
The Lie That's Holding You Back From Retirement
You've got the savings, the spreadsheet, maybe even the perfect retirement date circled on your calendar, so what's actually holding you back? In this episode, I get honest about the real reason so many people delay retirement, and it's not the money. I share two personal stories and the mindset shift that can help you finally step forward. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. Tune into this episode to find out: (0:00) Why are so many people delaying retirement? (0:45) Blaming finances when fear is the real issue (1:19) The comfort trap of sticking with what you know (2:21) How starting this podcast taught Jacob to begin anyway (4:44) Parenting parallels: you're never fully ready (8:32) Moving the goalposts on your retirement number (9:27) More money rarely fixes the emotional hang-up (10:33) You are what's holding yourself back, not money (11:06) Stepping into retirement unlocks real fulfillment
May 12 · 16 min
Avoid These 5 Retirement Mistakes Before It’s Too Late
You've spent decades saving for retirement, but are you about to make the same mistakes thousands of retirees only spot when it's too late? In this episode, I walk through the five biggest regrets I see in my work as a retirement planner, and exactly what you can do right now to avoid them. Tune into this episode to find out: (01:14) Regret #1 – Claiming Social Security too early costs you (01:44) Early claiming locks in a permanent 30% benefit cut (02:49) How claiming early closes your Roth conversion window (04:12) Regret #2 – Playing it too safe with your investments (06:43) Using the bucket system to balance safety and growth (08:37) Regret #3 – Not spending enough early on (11:06) Regret #4 – Putting off tax planning until it's too late (12:14) How RMDs, Social Security taxes, and IRMAA blindside you (13:46) Regret #5 – Juggling too many accounts and strategies (14:30) Why simplicity leads to clarity and lasting retirement confidence 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.
May 6 · 21 min
Why Your 401(k) Isn’t Enough - The Ideal Retirement Mix
You're saving for retirement, but are you saving too much into the wrong accounts? Most retirees don't realize this common issue until it's too late. In this episode, I explain why having all of your retirement savings in pre-tax accounts is major risk and how you can begin to fix things. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 01:00 Early Retirement Access Trap 02:31 Risk One: Future Taxes 04:03 Risk Two: RMD Time Bomb 06:50 Risk Three: Income Control 09:37 Risk Four: Psychological Barriers 11:51 Risk Five: Lack of Flexibility 12:51 Tax Diversification 16:28 How To Fix The Problem 19:12 Conclusion
April 24 · 14 min
The Mental Trap That's Sabotaging Your Retirement
Have you ever wondered if chasing “more” could actually make retirement harder instead of better? In this episode of Retirement Answers, Jacob is sharing how “more is not better, better is better” applies to retirement... More money can create fear, over-optimizing can steal joy, more stuff adds complexity and decision fatigue, and more time without purpose can lead to dissatisfaction. Tune in to rethink what “enough” means for you and focus on using your money, lifestyle, and time in a better way that supports a meaningful retirement. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Welcome 00:56 More Is Not Better 01:37 Defining Enough 02:27 Money Can Add Fear 05:43 Stop Over Optimizing 08:40 More Stuff Adds Complexity 10:34 Time Needs Purpose 12:43 Final Takeaways
April 1 · 26 min
Avoid These 8 Retirement Mistakes (They Look Harmless… But Aren’t)
Some of the biggest retirement mistakes don’t show up until it’s too late to fix them. Today, I’m breaking down 8 costly mistakes I see over and over again and how to avoid them before they impact your income, taxes, and long-term freedom. A few small adjustments here can make a massive difference later. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.
March 21 · 15 min
5 Reasons NOT To Claim Social Security Early
Not sure when to take Social Security? Well, in today's episode, I am sharing 5 reasons you shouldn't take your benefits early and the hidden risks of doing so. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.
March 13 · 15 min
These Are The Most Important Years of Retirement
If you don't get things right during this important window of time, your retirement likely won't be what you hoped... This 10 year period of time will determine the trajectory of your entire retirement. Prepare correctly and you will enjoy a fulfilling life without worry. Little preparation and poor execution and you will be wishing you could get a do over... Only problem is, you get one shot at retiring right the first time. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Intro 01:40 Last 5 Years of Work 11:44 First 5 Years of Retirement 14:16 Book a Call
March 3 · 16 min
The Roth IRA 5-Year Rule Explained (Ultimate Guide)
Confused by the Roth IRA 5-year rule? Did you know there are two different 5-year rules? Well, it can get quite confusing, so this episode is meant to be your complete guide for everything around the Roth 5-year rules. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.
February 25 · 11 min
Most Retirement Plans Look Good on Paper, But FAIL in Reality
Are you sure your retirement plan is optimized for the right things? In this episode, I discuss what the true mark of a successful retirement plan is and why most people's plans will fail, just not in the way they expected. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.
February 19 · 21 min
7 MAJOR Benefits of a Brokerage Account in Retirement
Is the brokerage account the secret to a fun and tax-efficient retirement? It might be a requirement, but it definitely helps. In fact, the brokerage account is my favorite account type and in this episode, I share 7 benefits that anyone can use to their advantage in retirement. 👉 See If You're a Fit: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Welcome 00:47 How 401(k)s, Traditional IRAs, and Roth IRAs Are Taxed 03:06 What a Taxable Brokerage Account Is (and How It’s Taxed) 04:16 Flexibility 05:50 The “Bridge Account” 07:10 Tax-Gain Harvesting 11:39 Tax-Loss Harvesting 13:30 Asset Location 15:54 Liquidity 16:58 Estate Planning 19:04 How to Start Using a Brokerage Account in Your Plan 20:20 Wrap-Up
January 29 · 13 min
4 Reasons You Should Take Social Security at 62
Are you still trying to decide when to take Social Security? Well, in this episode, I am deviating from my normal stance to share 4 reasons you might want to take your benefits ASAP rather than delay. And be sure to listen to the end, because I share why using a traditional break even analysis in your decision making process is not a good idea. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Introduction 01:31 Reason 1 03:07 Reason 2 04:19 Reason 3 06:10 Reason 4 07:51 The Flaws of Break Even Analysis 12:28 Conclusion
January 26 · 18 min
Don't Retire Yet - Try This Instead
Are you anxious about an abrupt transition to retirement? In this episode of Retirement Answers, I share the concept of phased retirement, where you can gradually reduce work hours or stress levels instead of stopping work entirely. I explain the financial and emotional benefits, offering practical advice for a smoother, more comfortable path to retirement. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Introduction 00:48 The Anxiety of Full Retirement 01:25 Phased Retirement: A New Approach 02:37 Changes in Retirement Landscape 04:04 Practical Steps for Phased Retirement 05:17 Employer Negotiations and Alternatives 07:53 Consulting and Part-Time Work Options 11:45 Financial and Health Benefits 15:39 Finding Purpose in Retirement 17:19 Conclusion
January 8 · 20 min
The Big HSA Mistake Retirees Don’t Know They Are Making
Have you ever wondered if your HSA contributions could cause unexpected issues as you approach retirement? In this episode, I highlight potential risks and mistakes that individuals near or in retirement might encounter with their HSAs. Specifically around scenarios such as switching into an HSA plan mid-year, transitioning out of an HSA plan mid-year, and moving from an HSA plan to Medicare. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Intro 00:35 Understanding HSA Contributions and Limits 04:50 Scenario 1: Switching to an HSA Plan Mid-Year 07:42 Scenario 2: Switching Out of an HSA Plan Mid-Year 12:59 Scenario 3: Transitioning from HSA to Medicare 18:27 Key Takeaways and Final Thoughts
January 1 · 20 min
New 2026 Tax Brackets, Standard Deductions & More!
Can you believe it's 2026 already?? Ready or not here we go! In this episode, I'm sharing the updated tax brackets, standard deductions, capital gains brackets, IRMAA brackets, provisional income brackets, and more. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Introduction 01:23 Federal Income Tax Brackets for 2026 02:10 Standard Deductions and Additional Deductions 04:42 Long-Term Capital Gains Brackets 06:37 Retirement Contribution Limits 08:09 Roth IRA and Traditional IRA Rules 13:07 Medicare Premiums and IRMAA Surcharges 16:20 Social Security Taxation 19:16 Final Thoughts
Dec 30, 2025 · 17 min
MAJOR Changes To 401k Catch-Up Contributions in 2026
If you're 50+ and making catching catch-up contributions to your employer 401k plan, this episode is for you. In 2026, you might have to change how you save to your employer plan if you earn to much money. In this episode, I share what you need to know about these new rules and how you can save with intention. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Intro 00:43 Updated Contribution Limits for 2026 01:25 Special Catch-Up Contributions for Ages 60-63 02:16 IRA Contribution Limits for 2026 03:13 New Rules for High Earners 05:22 Nuances and Exceptions 11:03 Strategizing Your Contributions 15:51 Conclusion & Final Thoughts

Retirement Answers

Does My Roth 401k Satisfy The 5-Year Roth IRA Rule?

Stop Saving For Retirement... (Here's Why)

Are You Waiting Too Long to Sell Winning Investments?

What Are the Best Strategies for Reducing RMDs?

The 4% Rule Is A Terrible Retirement Income Strategy (Here's Why)

The Lie That's Holding You Back From Retirement

Avoid These 5 Retirement Mistakes Before It’s Too Late

Why Your 401(k) Isn’t Enough - The Ideal Retirement Mix

The Mental Trap That's Sabotaging Your Retirement

Avoid These 8 Retirement Mistakes (They Look Harmless… But Aren’t)

5 Reasons NOT To Claim Social Security Early

These Are The Most Important Years of Retirement

The Roth IRA 5-Year Rule Explained (Ultimate Guide)

Most Retirement Plans Look Good on Paper, But FAIL in Reality

7 MAJOR Benefits of a Brokerage Account in Retirement

4 Reasons You Should Take Social Security at 62

Don't Retire Yet - Try This Instead

The Big HSA Mistake Retirees Don’t Know They Are Making

New 2026 Tax Brackets, Standard Deductions & More!

MAJOR Changes To 401k Catch-Up Contributions in 2026