Retirement Answers

Hosted by Jacob Duke, CFP®

Business Investing Education

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Episodes

169

Latest episode

Oct 2026

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About the show

Retirement Answers is a podcast built to help you succeed in retirement. The thought of retirement can be overwhelming and downright scary for many... but it doesn't have to be! The goal of this podcast is to provide thoughtful insights and strategies to give you the confidence you need to retire successfully. At the end of the day, my ultimate goal for my clients and podcast listeners is to live a fulfilling retirement. Follow along as I publish a new episode each week covering everything from retirement income planning, tax planning, Social Security, insurance planning, investing, and much more. Here's to learning everything you need to know to live out your dream retirement!

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October 16, 2026Episode 16625 min

The First 5 Years of Retirement Matter More Than You Think

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: 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 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

September 25, 2026Episode 16526 min

9 Things You Can Do With Your HSA in Retirement (And What You Can’t)

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: 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 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

September 17, 2026Episode 16415 min

Most Retirees Don’t Realize They Can Pay No Taxes Using This Strategy

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: 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.

September 8, 2026Episode 16317 min

Working One More Year is Costing You More Than You Realize

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

August 25, 2026Episode 16218 min

How Much Cash Should You Hold in Retirement? (2026 Update)

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

July 22, 2026Episode 16128 min

Does My Roth 401k Satisfy The 5-Year Roth IRA Rule?

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

July 15, 2026Episode 16011 min

Stop Saving For Retirement... (Here's Why)

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.

July 4, 2026Episode 15919 min

Are You Waiting Too Long to Sell Winning Investments?

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.

June 16, 2026Episode 15827 min

What Are the Best Strategies for Reducing RMDs?

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

May 29, 2026Episode 15713 min

The 4% Rule Is A Terrible Retirement Income Strategy (Here's Why)

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.

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