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Retirement Answers: Daily Summaries Delivered
by Jacob Duke, CFP
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!
Latest Episodes
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- 2 days ago23 min
Retiring in 2027? These Are the 7 Decisions You Need to Make Right Now
If you’re planning to retire in 2027, the clock is already ticking on the decisions that matter most. In this episode, I walk through the seven things you need to figure out before the end of 2026, from pinning down what you actually spend to building your cash runway and stress testing your plan against the next market decline.Tune into this episode to find out: Why millions in savings doesn’t mean you’re ready #1 – Nail down what you’re truly spending each month Why your income is a terrible predictor of retirement spending Add a 20% buffer to your current monthly spending #2 – Factor in Social Security, pension, and fixed income #3 – Build two years of cash before you retire #4 – Decide which accounts to withdraw from first #5 – Plan your health insurance coverage before Medicare #6 – Analyze whether Roth conversions make sense for you #7 – Stress test your plan against a market decline👉 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.
- 5 days ago16 min
The Biggest Financial Mistake Retirees Make in Their First 5 Years
In this episode, Jacob explains why many retirees make an innocent financial mistake: not spending enough due to fear. He unpacks how a lifetime of saving and watching balances grow makes the psychological shift to spending difficult, and why the first 5 “go-go” years of retirement are often the most valuable for experiences and health. Jacob discusses real-life retirement spending cycles and how many plans wrongly assume spending rises steadily with inflation, and how underspending can create future tax problems through large RMDs, the widow’s tax trap, or higher taxes for heirs. He encourages listeners to change the retirement “scorecard” from portfolio balances to memories, experiences, giving, and freedom, and emphasizes building and regularly updating a real financial plan to gain confidence to spend intentionally.👉 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 In To Find Out00:00 The Mistake01:07 Saver To Spender Shift03:55 Go-Go, Slow-Go, No-Go06:31 Retirement Spending Smile08:23 Tax Trap And RMDs10:53 Change The Scorecard13:14 Permission Through Planning15:05 Mark of a Good Advisor16:28 Wrap Up
- 2 weeks ago25 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 Intro01:20 Shift From Saving02:19 Sequence Risk Explained06:01 Income Runway Buckets09:29 Tax Planning Window13:28 Roth Conversion Strategy16:17 Flexible Spending Plan19:44 Avoid Permanent Moves24:33 Final Thoughts Next Steps
- Sep 25, 202626 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 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
- Sep 17, 202615 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: The $100,000 question: what if only $30–40K of it was actually taxable? Why retirement gives you control over how your paycheck—and your taxes—are built The #1 mistake: treating withdrawals as "one account at a time" Introducing income stacking and how it reframes your withdrawal strategy Why Social Security can be taxed anywhere from 0% to 85% A real example: building $100,000 of income from four different account types How the standard deduction makes your first IRA dollars tax-free The 0% long-term capital gains bracket (and how high it actually goes) Why paying $0 in taxes isn't always the goal The smarter target: filling up the right tax brackets on purpose 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.
- Sep 8, 202617 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-numbersEmail: jacob@rivertreewealth.comWebsite: 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
- Aug 25, 202618 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-numbersEmail: jacob@rivertreewealth.comWebsite: 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
- Jul 22, 202628 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-numbersEmail: jacob@rivertreewealth.comWebsite: 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
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About Retirement Answers
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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