Retirement Answers

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

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

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

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.

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.

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

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.

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.

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

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

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

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