Retirement Answers

Hosted by Jacob Duke, CFP®

Business Investing Education

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Episodes

164

Latest episode

Jul 2026

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About the show

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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60 recent

July 22, 2026Episode 16128 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, 2026Episode 16011 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, 2026Episode 15919 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, 2026Episode 15827 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, 2026Episode 15713 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, 2026Episode 15613 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, 2026Episode 15516 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, 2026Episode 15421 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, 2026Episode 15314 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, 2026Episode 15226 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.