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: 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.

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 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

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

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

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.

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

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

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