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

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.

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.

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

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.

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

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.

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