Advertise on podcast: Retirement Answers

The first five years after you stop working can make or break your retirement—not because of how much you saved, but because of how you start spending it. Listen in as Jacob breaks down the big shifts that hit early retirees: your investments now need to fund income (and sequence-of-return risk matters), you need a clear income plan with a five-year runway, and this may be the best tax-planning window you’ll ever get before Social Security and RMDs show up. He also explains why spending is often higher than expected early on and why flexibility matters. Finally, he warns against making permanent moves—investment, lifestyle, or relationship decisions—based on temporary market conditions or the emotional adjustment of 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: [email protected]  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 to find out: 00:00 Intro 01:20 Shift From Saving 02:19 Sequence Risk Explained 06:01 Income Runway Buckets 09:29 Tax Planning Window 13:28 Roth Conversion Strategy 16:17 Flexible Spending Plan 19:44 Avoid Permanent Moves 24:33 Final Thoughts Next Steps

So you have a large HSA in retirement, but what can you really do with it? HSAs are perhaps the most tax-advantaged account out of them all... Better than IRAs and Roth IRAs because an HSA is triple-tax advantaged. You get to deduct contributions from your income, the account grows tax-free, and you can take money from the account tax-free for qualified medical expenses. But in retirement, there are a few other things that you can use an HSA for and that's what I cover in this episode. 👉 Work With Us: https://www.rivertreewealth.com/get-started  ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers  Email: [email protected]  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 to find out: 00:00 HSA Questions 01:11 HSA Basics 01:47 Contribution Limits Rules 03:30 Investing Tax Benefits 04:40 Everyday Medical Costs 05:41 Paying Medicare Premiums 07:00 LTC Insurance Premiums 11:42 LTC Care Services 12:50 Save Receipts Strategy 14:48 Cover Family Expenses 16:27 COBRA And Unemployment 19:23 What Changes at 65 21:40 What Use Your HSA For 23:49 HSA Inheritance Rules 25:52 Wrap Up

What if you could pull $100,000 from your portfolio this year to live on, but only $30,000 or $40,000 of it actually counted as taxable income? It sounds too good to be true, but for a lot of retirees, it's completely possible. In this episode, I break down a strategy called income stacking, how to pull from cash, brokerage, IRA, and Roth accounts in the right combination, and why paying $0 in taxes isn't always the smartest move. Tune into this episode to find out: (00:18) The $100,000 question: what if only $30–40K of it was actually taxable? (00:42) Why retirement gives you control over how your paycheck—and your taxes—are built (01:03) The #1 mistake: treating withdrawals as "one account at a time" (02:18) Introducing income stacking and how it reframes your withdrawal strategy (03:03) Why Social Security can be taxed anywhere from 0% to 85% (03:36) A real example: building $100,000 of income from four different account types (05:39) How the standard deduction makes your first IRA dollars tax-free (06:21) The 0% long-term capital gains bracket (and how high it actually goes) (08:48) Why paying $0 in taxes isn't always the goal (09:36) The smarter target: filling up the right tax brackets on purpose (11:39) How managing your IRA today can reduce tomorrow's Social Security taxes 👉 Work With Us: https://www.rivertreewealth.com/get-started  ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers  Email: [email protected]  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.

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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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: [email protected]  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: [email protected]  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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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 Welcome00:56 More Is Not Better01:37 Defining Enough02:27 Money Can Add Fear05:43 Stop Over Optimizing08:40 More Stuff Adds Complexity10:34 Time Needs Purpose12:43 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: [email protected]: https://www.rivertreewealth.comLinkedIn: 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.