Retirement Answers
Business & Finance
About
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!
Episodes
- Avoid These 5 Retirement Mistakes Before It’s Too Late
This episode of Retirement Answers details five common retirement mistakes, including claiming Social Security prematurely, overly safe investments, insufficient spending, late tax planning, and managing too many accounts. The host offers…
- Why Your 401(k) Isn’t Enough - The Ideal Retirement Mix
This episode of Retirement Answers examines common issues with relying on 401(k) accounts for retirement savings. It explores potential risks associated with having all retirement savings in pre-tax accounts and how to address them.
- The Mental Trap That's Sabotaging Your Retirement
This episode of Retirement Answers explores how striving for "more" can hinder retirement satisfaction. Jacob explains how excessive money, over-optimization, increased possessions, and purposeless time can lead to negative outcomes in ret…
- Avoid These 8 Retirement Mistakes (They Look Harmless… But Aren’t)
This episode of Retirement Answers focuses on common retirement mistakes. The host outlines 8 costly errors and explains how to avoid them to prevent negative impacts on income, taxes, and financial freedom.
- 5 Reasons NOT To Claim Social Security Early
This episode of Retirement Answers explores five reasons to consider not claiming Social Security benefits early. It also covers potential hidden risks associated with early claims.
- These Are The Most Important Years of Retirement
The episode focuses on a crucial 10-year period that impacts retirement. It emphasizes the importance of correct preparation and execution for a successful retirement.
- The Roth IRA 5-Year Rule Explained (Ultimate Guide)
This Retirement Answers episode serves as a guide to the Roth IRA 5-year rules, explaining the two different rules and clarifying potential confusion. Jacob Duke, CFP, MBA, hosts the podcast and founded Rivertree Wealth.
- Most Retirement Plans Look Good on Paper, But FAIL in Reality
Jacob Duke explains on the Retirement Answers podcast that most retirement plans are not optimized correctly and will ultimately fail, though perhaps not in the ways people anticipate. He discusses the true criteria for a successful retire…
- 7 MAJOR Benefits of a Brokerage Account in Retirement
This episode of Retirement Answers explores seven key benefits of utilizing a brokerage account during retirement. Host Jacob Duke discusses advantages such as flexibility, tax-gain and tax-loss harvesting, asset location, liquidity, and e…
- 4 Reasons You Should Take Social Security at 62
This episode of Retirement Answers explores four reasons why individuals might consider taking Social Security benefits at age 62. It also discusses the drawbacks of using traditional break-even analysis for this important financial decisi…
- Don't Retire Yet - Try This Instead
This episode of Retirement Answers introduces phased retirement, a strategy for gradually reducing work hours or stress. It covers the financial and emotional advantages, offering practical advice for a less abrupt transition.
- The Big HSA Mistake Retirees Don’t Know They Are Making
This episode of Retirement Answers focuses on potential risks and mistakes individuals near or in retirement may encounter with their HSAs, particularly concerning mid-year plan changes and transitioning to Medicare.
- New 2026 Tax Brackets, Standard Deductions & More!
This episode of Retirement Answers discusses the updated federal income tax brackets for 2026, standard deductions, capital gains brackets, and retirement contribution limits. It also covers Roth and Traditional IRA rules, Medicare premium…
- MAJOR Changes To 401k Catch-Up Contributions in 2026
This episode of Retirement Answers discusses significant changes to 401k catch-up contributions effective in 2026, particularly impacting those aged 50 and over, with a focus on new regulations for high earners and strategic saving approac…
- 4 Retirement Fears to STOP Believing After You Reach 50
This episode of Retirement Answers discusses four common fears that hold people back from achieving their dream retirement after the age of 50.
- Don't Retire Early Without Understanding THIS Tax Strategy First
This episode of Retirement Answers explains strategies for early retirement, using a case study of a client named Joe who retired at 55. It covers the Rule of 55 for accessing retirement funds, tax strategies, and health insurance subsidie…
- 5 Misleading Retirement Beliefs That Can Sabotage Your Future
This episode of the Retirement Answers Podcast, hosted by Jacob Duke, CFP, identifies five common retirement beliefs that could negatively impact your financial future. Duke explores myths about a "magic number," spending habits, the neces…
- 5 Questions You MUST Answer If Retiring Before 65
Jacob Duke discusses five crucial questions individuals must answer when planning to retire before the age of 65. The episode aims to provide educational guidance for early retirement planning.
- This Is The Roth Conversion SWEET SPOT
This episode of Retirement Answers defines the Roth conversion sweet spot, explaining what constitutes the most optimal time for Roth conversions.
- Every Retiree Needs To Hear This... (What I've Learned After Helping 100 Clients Retire)
Jacob Duke, founder of Rivertree Wealth and host of Retirement Answers, shares a crucial lesson learned from helping over 100 clients retire. This insight is valuable for anyone planning their retirement.
- The Roth Conversion MISTAKE Every Retiree Should Avoid
This episode discusses Roth conversions and explains the tax efficiency of holding Traditional IRA assets in retirement. It warns against common Roth conversion errors and highlights the benefits of a diversified retirement savings approac…
- The 2026 Social Security COLA + Who It Applies To
The 2026 Social Security COLA has been announced. This episode of Retirement Answers explains the COLA amount, who it applies to, the calculation method, and how claiming strategies affect future COLAs.
- Social Security REGRETS: The Top 5 Mistakes Retirees Make
This episode of Retirement Answers discusses five frequent errors individuals make when claiming Social Security benefits. It aims to help listeners identify and avoid these mistakes to make better decisions about their retirement income.
- Why Retirees with $1M Actually End Up With TOO MUCH
This episode of Retirement Answers discusses the underspending epidemic among retirees, a mistake that can lead to having excess funds later in life. The host explains the causes of this issue.
- Are You Optimizing Social Security For The WRONG Thing?
This episode of Retirement Answers questions the conventional methods of optimizing Social Security benefits, such as break-even analysis or aiming for maximum lifetime benefits. Host Jacob Duke introduces a different perspective on Social…
- Roth Conversions Just Got More Complicated (OBBBA Update)
The Retirement Answers podcast discusses how the July 2025 OBBBA update has made Roth conversions more confusing for retirees. New senior deductions may help some, but those planning Roth conversions face difficult choices.
- Can Capital Gains Push Me Into a Higher Tax Bracket?
This episode explains the interaction between capital gains and normal income, detailing how capital gains impact other income and the concept of "income stacking." It also highlights unintentional drawbacks associated with capital gains.
- Retiring Early? Use the Rule of 55 To Unlock Retirement Freedom
This episode explains the IRS Rule of 55, a strategy that may permit penalty-free withdrawals from an employer retirement plan for those retiring in or after the year they turn 55. It covers the rule's conditions, importance, and potential…
- Are You Over-Saving For Retirement? Here's How You Could Be Sabotaging Yourself
This episode of Retirement Answers discusses the potential pitfalls of over-saving for retirement, explaining how it can be a problem and offering advice on how to prevent this risk.
- How To Create Tax-Free Income In Retirement WITHOUT A Roth IRA
This episode explains how to create tax-free income in retirement without a Roth IRA, using a couple with $1.2m as an example. The host suggests that a well-crafted income plan can eliminate the need for Roth IRAs.
- These 5 Tax Mistakes Will Waste Your Retirement Savings
This episode of Retirement Answers discusses five common tax planning mistakes that can cost retirees substantial amounts of money. Proper tax planning is crucial for preserving retirement savings.
- Retirement Tax Planning: What It Is (Actually) + Why It Matters
This episode of Retirement Answers, hosted by Jacob Duke, explains the core components of retirement tax planning and emphasizes its importance in developing a comprehensive retirement strategy. The discussion goes beyond just Roth convers…
- The Widow's Tax Trap: What Is It & How To Avoid It
This episode of Retirement Answers discusses the Widow's Tax Trap, a financial risk that can affect retired couples. The host explains what the trap is and provides advice on how to avoid it.
- 8 Important (But Little-Known) Rules To Know Before You Retire
Jacob Duke shares 8 important rules to know before entering retirement. This episode of Retirement Answers focuses on essential details for those planning their retirement. Information provided is for educational purposes and not tax, lega…
- 5 Things to STOP Doing Before You Retire (And What To Do Instead)
Jacob Duke of Rivertree Wealth discusses five common mistakes people make as they approach retirement and offers alternative actions to take instead. This episode provides guidance for those nearing retirement.
- 18 Signs You Are Better Prepared for Retirement Than Most People
This episode of Retirement Answers identifies 18 signs to help listeners determine if they are better prepared for retirement than the average person, addressing common concerns about falling behind in retirement planning.
- Retire NOW If You Answer YES to These 5 Questions
This episode of Retirement Answers focuses on determining the optimal time to retire by presenting five crucial questions. Answering yes to these questions may indicate that it is time to consider retirement.
- Why This Account Changes Everything in Retirement
This episode discusses a special retirement account that provides significant flexibility for income and tax planning, differing from a Roth IRA. Host Jacob Duke explains its benefits for retirement.
- Why Converting Everything to Roth is a MISTAKE
This episode of Retirement Answers discusses a common mistake with Roth conversions, explaining why maintaining some funds in a Traditional IRA could lead to significant tax savings. Jacob Duke, CFP, MBA, hosts.
- What Most Retirees Don't Know About Social Security Survivor Benefits
This episode of Retirement Answers focuses on Social Security survivor benefits, aiming to clarify common confusion. Host Jacob Duke breaks down the essential information to assist listeners in making more informed decisions.
- Social Security Spousal Benefits - Avoid These Common Mistakes
This episode of Retirement Answers discusses Social Security spousal benefits, clarifying common misconceptions and explaining the rules. Host Jacob Duke details how claiming decisions impact spousal benefits and advises on avoiding potent…
- What You Can Do To Avoid The IRA Pro-Rata Rule
This episode of Retirement Answers addresses the IRA Pro-Rata rule, explaining how after-tax money in a Traditional IRA can lead to higher taxes on distributions or Roth conversions and offering solutions to prevent this issue.
- What The Top 1% of Retirees Do Differently From Everyone Else
This episode discusses how top retirees differ from others by adopting an abundance mindset and living intentionally. The host, Jacob Duke, CFP, MBA, shares these insights.
- Why Your Roth Conversion Could Trigger Unexpected Tax Penalties
This Retirement Answers episode discusses the risks of unexpected tax penalties associated with Roth conversions, highlighting the importance of understanding tax implications for retirees. It also covers dividend taxation across account t…
- 10 Retirement Hacks That Will Save You Money
This episode of Retirement Answers details 10 practical hacks designed to help individuals save money during retirement. Host Jacob Duke explains strategies that can reduce expenses and lower taxes, enabling listeners to retain more of the…
- Recession-Proof Your Portfolio By Doing THIS
This Retirement Answers podcast episode addresses listener Carolina's question about preparing a retirement portfolio for market downturns. The host explains how to build recession-proof portfolios, offering strategies for potential 'what-…
- Why You Should STOP Doing Roth Conversions
This episode of Retirement Answers explains that Roth conversions can sometimes lead to higher taxes than not converting at all. Host Jacob Duke discusses how Required Minimum Distributions (RMDs) and future tax rates might be lower than t…
- Planning for Travel Expenses in Retirement? Ask Yourself These Questions
Jacob Duke addresses how to plan for travel expenses in retirement on this episode of Retirement Answers. He provides considerations for determining your retirement travel budget. This is for educational purposes only.
- This is the BEST Way To Do Roth Conversions
This episode of Retirement Answers explores a strategy for conducting Roth conversions without incurring taxes by utilizing charitable gifting. Host Jacob Duke explains how this method works.
- How To Plan For Long-Term Care in Retirement
This episode of Retirement Answers features host Jacob Duke addressing a listener's question about long-term care planning. He discusses different approaches like self-insuring versus purchasing insurance and shares his perspective.