Have you been telling yourself you’ll “just work one more year” to make retirement feel safer? In this episode, Jacob Duke explains that the tradeoff isn’t just financial.

Jacob walks through five overlooked costs of working one more year an he encourages listeners to build a real plan to determine whether retiring sooner is already possible and to weigh what they’re giving up by delaying.

👉 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 The Lie We Tell Ourselves

00:31 Hidden Tradeoffs

01:39 Your Healthy Years

03:14 Ease Into Retirement

04:33 Savings Matters Less

06:09 Missing The Tax Valley

09:25 Stop Moving Goalposts

12:35 What Are You Saying "No" To?

14:58 Build a Real Plan

16:50 Wrap Up

How much cash should you have set aside as you enter the early years of retirement so you can weather market downturns without constant worry? In this episode of Retirement Answers, Jacob Duke explains Rivertree’s bucket strategy: keep two years of portfolio-withdrawal needs in cash (money market) and three years in short-duration fixed income to create a five-year runway, while avoiding being overly conservative and losing purchasing power to inflation. He also walks through how to take withdrawals in practice—generally pulling from what has gone up the most or down the least—and how to proactively replenish cash and bond buckets after strong market periods or following a decline.

👉 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 Big Question

00:47 Why Cash Matters

01:35 Bucket One

03:33 Bucket Two

05:37 Avoid Getting Too Conservative

07:42 Allocation Based on Needs

09:38 How to Withdraw in Practice

12:04 Income From Dividends Interest

13:00 Replenishing The Buckets

17:01 Closing

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