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...
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 encour...
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 matt...
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...
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?
...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...
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 a...
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 ta...
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 th...
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 f...
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: [email protected]
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linke...
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: [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 R...
The Lie That's Holding You Back From Retirement
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...
Avoid These 5 Retirement Mistakes Before It’s Too Late
You've spent decades saving for retirement, but are you about to make the same mistakes thousands of retirees only spot when it's too late? In this episode, I walk through the five biggest regrets I see in my work as a retirement planner, and exactly what you can do right now to avoid them.
Tune into this episode to find out:
(01:14) Regret #1 – Claiming Social Security too early costs you
(01:44) Early claiming locks in a permanent 30% benefit cut
(02:49) How claiming early closes your Roth conversion window
(04:12) Regret #2 – Play...
Why Your 401(k) Isn’t Enough - The Ideal Retirement Mix
You're saving for retirement, but are you saving too much into the wrong accounts? Most retirees don't realize this common issue until it's too late.
In this episode, I explain why having all of your retirement savings in pre-tax accounts is major risk and how you can begin to fix things.
👉 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...
The Mental Trap That's Sabotaging Your Retirement
Have you ever wondered if chasing “more” could actually make retirement harder instead of better? In this episode of Retirement Answers, Jacob is sharing how “more is not better, better is better” applies to retirement...
More money can create fear, over-optimizing can steal joy, more stuff adds complexity and decision fatigue, and more time without purpose can lead to dissatisfaction. Tune in to rethink what “enough” means for you and focus on using your money, lifestyle, and time in a better way that supports a meaningful retirement.
👉 Work With Us: https://www.rivertreewealth.com/get-started
✅ Get your...
Avoid These 8 Retirement Mistakes (They Look Harmless… But Aren’t)
Some of the biggest retirement mistakes don’t show up until it’s too late to fix them. Today, I’m breaking down 8 costly mistakes I see over and over again and how to avoid them before they impact your income, taxes, and long-term freedom. A few small adjustments here can make a massive difference later.
👉 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...
5 Reasons NOT To Claim Social Security Early
Not sure when to take Social Security? Well, in today's episode, I am sharing 5 reasons you shouldn't take your benefits early and the hidden risks of doing so.
👉 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 ta...
These Are The Most Important Years of Retirement
If you don't get things right during this important window of time, your retirement likely won't be what you hoped... This 10 year period of time will determine the trajectory of your entire retirement. Prepare correctly and you will enjoy a fulfilling life without worry. Little preparation and poor execution and you will be wishing you could get a do over... Only problem is, you get one shot at retiring right the first time.
👉 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...
The Roth IRA 5-Year Rule Explained (Ultimate Guide)
Confused by the Roth IRA 5-year rule? Did you know there are two different 5-year rules? Well, it can get quite confusing, so this episode is meant to be your complete guide for everything around the Roth 5-year rules.
👉 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 Retir...
Most Retirement Plans Look Good on Paper, But FAIL in Reality
Are you sure your retirement plan is optimized for the right things? In this episode, I discuss what the true mark of a successful retirement plan is and why most people's plans will fail, just not in the way they expected.
👉 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 th...
7 MAJOR Benefits of a Brokerage Account in Retirement
Is the brokerage account the secret to a fun and tax-efficient retirement? It might be a requirement, but it definitely helps. In fact, the brokerage account is my favorite account type and in this episode, I share 7 benefits that anyone can use to their advantage in retirement.
👉 See If You're a Fit: 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 f...
4 Reasons You Should Take Social Security at 62
Are you still trying to decide when to take Social Security? Well, in this episode, I am deviating from my normal stance to share 4 reasons you might want to take your benefits ASAP rather than delay. And be sure to listen to the end, because I share why using a traditional break even analysis in your decision making process is not a good idea.
👉 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.river...
Don't Retire Yet - Try This Instead
Are you anxious about an abrupt transition to retirement? In this episode of Retirement Answers, I share the concept of phased retirement, where you can gradually reduce work hours or stress levels instead of stopping work entirely. I explain the financial and emotional benefits, offering practical advice for a smoother, more comfortable path to 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/jacob...
The Big HSA Mistake Retirees Don’t Know They Are Making
Have you ever wondered if your HSA contributions could cause unexpected issues as you approach retirement? In this episode, I highlight potential risks and mistakes that individuals near or in retirement might encounter with their HSAs.
Specifically around scenarios such as switching into an HSA plan mid-year, transitioning out of an HSA plan mid-year, and moving from an HSA plan to Medicare.
👉 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.rivertr...
New 2026 Tax Brackets, Standard Deductions & More!
Can you believe it's 2026 already?? Ready or not here we go! In this episode, I'm sharing the updated tax brackets, standard deductions, capital gains brackets, IRMAA brackets, provisional income brackets, and more.
👉 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.
DISCL...
MAJOR Changes To 401k Catch-Up Contributions in 2026
If you're 50+ and making catching catch-up contributions to your employer 401k plan, this episode is for you. In 2026, you might have to change how you save to your employer plan if you earn to much money. In this episode, I share what you need to know about these new rules and how you can save with intention.
👉 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/i...
4 Retirement Fears to STOP Believing After You Reach 50
Have you ever wondered why so many people dream of early retirement but never actually do it? In this episode, I dive into the most common fears that hold people back from their dream 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 podca...
Don't Retire Early Without Understanding THIS Tax Strategy First
What if you could retire earlier than expected, access your savings without penalties, get health insurance subsidies, and pay no taxes for the first few years? Would you believe that's possible?
In this episode of Retirement Answers, I explain how it can be done using a case study of a client named Joe where I break down the strategies and financial maneuvers used to help him retire at 55.
👉 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@rivert...
5 Misleading Retirement Beliefs That Can Sabotage Your Future
Have you ever wondered if certain beliefs about retirement could actually jeopardize your future instead of securing it? In this episode of the Retirement Answers Podcast, Jacob Duke, a certified financial planner, delves into common assumptions that may seem harmless but can quietly derail your retirement plans. Tune in to learn how to identify and overcome these misconceptions for a secure and fulfilling retirement journey.
👉 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.r...
5 Questions You MUST Answer If Retiring Before 65
Get the FREE Checklist Here: https://www.rivertreewealth.com/pre-65-retirement-checklist
👉 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.
This Is The Roth Conversion SWEET SPOT
What ingredients make for the most optimal Roth conversions? In this episode, I explain what the Roth conversion sweet spot is and why this period of time is the best time to do conversions.
📋 Get Your FREE Checklist here: https://www.rivertreewealth.com/roth-conversion-sweet-spot-checklist
👉 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...
Every Retiree Needs To Hear This... (What I've Learned After Helping 100 Clients Retire)
You ever have something not be what expected it to be? Well, as a retirement planner who is helped over 100 clients, I have learned an important lesson that I think anyone who is preparing for retirement needs to understand.
👉 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 th...
The Roth Conversion MISTAKE Every Retiree Should Avoid
Roth conversions might help you save on taxes in retirement, but that doesn't mean you only need Roth IRAs... In this episode, I share why it's actually tax-efficient to have money in a Traditional IRA.
👉 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 podca...
The 2026 Social Security COLA + Who It Applies To
The 2026 Social Security COLA has been announced! I will share what it is, who it applies to, how it's calculated, and why your Social Security claiming strategy impacts your future COLAs.
👉 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...
Social Security REGRETS: The Top 5 Mistakes Retirees Make
Are you sure you are taking Social Security at the right time? Well, in this episode, I share 5 common mistakes retirees make when claiming Social Security and what you should look out for.
👉 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.
DIS...
Why Retirees with $1M Actually End Up With TOO MUCH
Are you making the same mistake many other retirees make? If so, you could end up missing out on a lot right now, and have more money that you ever need later in life. In this episode, I talk about the underspending epidemic among retirees and what causes it.
👉 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 i...
Are You Optimizing Social Security For The WRONG Thing?
Is a break even analysis or trying to get the maximum lifetime benefits from Social Security the wrong way to optimize your benefits? In this episode I share an different idea with you about your Social Security claiming strategy.
👉 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
Other episodes mentioned: https://open.spotify.com/episode/1lGNMCcz8U7wyWSdNS0kNA?si=8fcecfdd482445cd
Submit your question to have it answered on the podcast: https://www.rivertreewealth.com/questions
Ema...
Roth Conversions Just Got More Complicated (OBBBA Update)
The OBBBA was passed back in July 2025, but now Roth conversions are more confusing for retirees. The new senior deductions might be helpful for some, but for those who were planning to do Roth conversions could have some tough decisions to make.
👉 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
Other episodes mentioned: https://open.spotify.com/episode/1lGNMCcz8U7wyWSdNS0kNA?si=8fcecfdd482445cd
Submit your question to have it answered on the podcast: https://www.rivertreewealth.com/q...
Can Capital Gains Push Me Into a Higher Tax Bracket?
The interaction between capital gains and normal income is often misunderstood, so in this episode, I share how capital gains affect your other income and how "income stacking" works.
I also share some unintentional drawbacks of capital gains that you have to watch out for.
👉 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
Other episodes mentioned: https://open.spotify.com/episode/1lGNMCcz8U7wyWSdNS0kNA?si=8fcecfdd482445cd
Submit your question to have it answered on the p...
Retiring Early? Use the Rule of 55 To Unlock Retirement Freedom
Trying to retire before 60? Creating income for yourself can be tough and can cause penalties if you aren't careful... That's where the Rule of 55 can be helpful and allow you to take money from your employer retirement plan without early distribution penalties, if you satisfy all of the rules.
In this episode, I share what the Rule of 55 is, why it matters, the rules you need to know, and some alternatives.
👉 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
Subm...
