Retirement Answers

By Jacob Duke, CFP®Business Education Investing

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Typical duration
17 min
per episode

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Retirement Answers episodes

November 03 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:
(00:00) Why millions in savings doesn’t mean you’re ready
(00:40) #1 – Nail down what you’re truly spending each month
(03:00) Why your income is a terrible predictor of retirement spending
(04:00) Add a 20% buffer to your current monthly spending
(06:15) #2 – Factor in Social Security, pension, and fixed income
(07:40) #3 – Build two years of cash before you retire
(09:35) #4 – Decide which accounts to withdraw from first
(13:30) #5 – Plan your health insurance coverage before Medicare
(16:30) #6 – Analyze whether Roth conversions make sense for you
(19:20) #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: [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.
24 min
October 31 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: [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 In To Find Out
00:00 The Mistake
01:07 Saver To Spender Shift
03:55 Go-Go, Slow-Go, No-Go
06:31 Retirement Spending Smile
08:23 Tax Trap And RMDs
10:53 Change The Scorecard
13:14 Permission Through Planning
15:05 Mark of a Good Advisor
16:28 Wrap Up

17 min
October 16 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: [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
26 min
September 25 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: [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
27 min
September 17 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: [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.

16 min
September 08 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: [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.
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
18 min
August 25 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: [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.
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
19 min
July 22 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: [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.
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
29 min
July 15 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: [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.
12 min
July 04 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: [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.
20 min

About Retirement Answers

From the publisher's feed

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!