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 Questions01:11 HSA Basics01:47 Contribution Limits Rules03:30 Investing Tax Benefits04:40 Everyday Medical Costs05:41 Paying Medicare Premiums07:00 LTC Insurance Premiums11:42 LTC Care Services12:50 Save Receipts Strategy14:48 Cover Family Expenses16:27 COBRA And Unemployment19:23 What Changes at 6521:40 What Use Your HSA For23:49 HSA Inheritance Rules25:52 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-numbersEmail: [email protected]: https://www.rivertreewealth.comLinkedIn: https://www.linkedin.com/in/jacobdukeJacob 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 Ourselves00:31 Hidden Tradeoffs01:39 Your Healthy Years03:14 Ease Into Retirement04:33 Savings Matters Less06:09 Missing The Tax Valley09:25 Stop Moving Goalposts12:35 What Are You Saying "No" To?14:58 Build a Real Plan16:50 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-numbersEmail: [email protected]: https://www.rivertreewealth.comLinkedIn: https://www.linkedin.com/in/jacobdukeJacob 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 Question00:47 Why Cash Matters01:35 Bucket One03:33 Bucket Two05:37 Avoid Getting Too Conservative07:42 Allocation Based on Needs09:38 How to Withdraw in Practice12:04 Income From Dividends Interest13:00 Replenishing The Buckets17:01 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-numbersEmail: [email protected]: https://www.rivertreewealth.comLinkedIn: https://www.linkedin.com/in/jacobdukeJacob 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 IRA01:24 Roth IRA Basics03:25 Conversions Five Year Rule05:34 Withdrawal Ordering Rules07:57 Roth 401k Rollover Myth10:32 Qualified vs Nonqualified13:07 Nonqualified Rollover Breakdown16:34 Qualified Rollover Treatment22:18 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-numbersEmail: [email protected]: https://www.rivertreewealth.comLinkedIn: https://www.linkedin.com/in/jacobdukeJacob 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-numbersEmail: [email protected]: https://www.rivertreewealth.comLinkedIn: https://www.linkedin.com/in/jacobdukeJacob 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-numbersEmail: [email protected]: https://www.rivertreewealth.comLinkedIn: https://www.linkedin.com/in/jacobdukeJacob 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 Frustrations00:51 When RMDs Become a Problem03:10 Gap Years Tax Planning03:33 Asset Location Strategy08:40 Roth Conversions Explained13:32 Delay Social Security Benefits18:40 QCDs for Charitable Giving21:22 Spend More Before RMDs25:40 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-numbersEmail: [email protected]: https://www.rivertreewealth.comLinkedIn: https://www.linkedin.com/in/jacobdukeJacob 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