Retire Early Podcast

Sam Benson & Linwood Fraher
  • 5.0 (10)
  • Self-Improvement
  • Updated Weekly

Welcome to ”The Retire Early Podcast,” your essential guide to achieving the retirement you’ve always dreamed of—sooner rather than later! Hosted by Sam Benson and Linwood Fraher, this podcast is tailored specifically for individuals aged 50-65 who are passionate about retiring early and living their best lives. Each week, we’ll dive deep into essential retirement topics including tax-efficient strategies, smart investing, healthcare planning, income optimization, Social Security tips, estate planning, and actionable financial advice. We’ll feature expert insights, inspiring stories, and practical tools to empower you on your journey toward early retirement. Whether you’re planning to retire in 5 years or 15, ”The Retire Early Podcast” equips you with the knowledge and confidence to secure your financial future, maximize your wealth, and enjoy the retirement lifestyle you deserve. Subscribe today and join our community committed to retiring early and thriving in retirement!

  1. 6d ago

    Why Your 401(k) Feels Like a Pair of Cuffs

    A 401(k) with its complex rules and withdrawal limits can often leave early retirees feeling restricted. Managing it unprepared means navigating strict government regulations, taxes, and penalties right when you want to access your funds for retirement.   In this episode of the Retire Early Podcast, Sam Benson and Lynwood Freyer discuss why 401(k) accounts have strict rules and how early retirees can navigate them. They break down three critical questions around 401(k) access, rolling over funds, and generating retirement income to help you avoid costly mistakes and unlock your savings.   Episode Outline 00:00 — Introduction: Why a 401(k) feels like wearing handcuffs 01:47 — Why 401(k) accounts are designed to restrict early access 03:45 — Accessing funds early: The Rule of 55, loans, and hardship withdrawals 05:10 — The cost of early withdrawals: Income taxes and the 10% penalty 06:28 — Should you leave your 401(k) or roll it over to an IRA? 07:13 — Analyzing plan fees, expense ratios, and fund quality 08:27 — Why rolling over can ruin Rule of 55 access or backdoor Roth strategies 11:42 — How to convert 401(k) funds into sustainable retirement income 13:42 — Tax planning considerations and managing withdrawal strategies 14:16 — Sequence of return risk and shifting from accumulation to decumulation Learn more about working with Sam Benson and Linwood Fraher at www.martinwealth.com

  2. Sep 22

    Expecting an Inheritance? Don’t Make These Mistakes

    Receiving a large inheritance can completely change your financial picture—but it can also create new risks, tax considerations, family complications, and emotional pressure. In this episode of Retire Early, Sam Benson and Linwood Frayer discuss how to prepare for a potential inheritance before it arrives and what to do after receiving it. They explain why you shouldn’t reduce your savings or increase your spending based on an expected inheritance, how different inherited assets can carry very different tax implications, and why major financial decisions are often best postponed while you’re grieving. They also cover some of the biggest mistakes people make with inherited wealth—including treating principal like income, becoming overly conservative with the money, and becoming too generous too quickly.   Topics Discussed: 00:00 — Preparing for a potential inheritance 01:00 — The emotional side of inherited wealth 03:00 — Planning for an inheritance without depending on it 05:00 — Why emotion can lead to costly decisions 05:30 — Don't save less or spend more because an inheritance is coming 06:15 — Why an inheritance doesn't automatically mean you can retire 07:00 — How long-term care can dramatically reduce an expected inheritance 08:00 — Understanding the tax implications of inherited assets 09:00 — Inherited IRAs and distribution planning 10:00 — Modeling different inheritance scenarios 11:00 — Wills, trusts, beneficiaries, and professional relationships 12:30 — Why you should keep an inheritance private 13:15 — Having inheritance conversations with your parents 15:00 — Creating an estate and asset checklist 16:00 — What to do once the inheritance arrives 17:00 — Avoiding major financial decisions while grieving 18:00 — What needs immediate attention—and what can wait 19:00 — Understanding exactly what you've inherited 20:00 — The risks and expenses of inherited real estate 21:00 — Build the financial plan before the investment portfolio 23:00 — Mistake #1: Treating principal like income 24:00 — Mistake #2: Becoming too conservative 25:00 — Mistake #3: Becoming too generous too quickly 26:00 — Assigning specific goals to inherited money 27:00 — Updating your own estate plan and slowing down   Connect with Sam and Linwood at www.martinwealth.com

  3. Sep 15

    Should I Wait One More Year to Retire?

    One of the most common and difficult questions anyone nearing their target retirement date faces is, “Should I wait just one more year to retire?” Retirement is a major life transition, and working an extra 12 months can profoundly affect both your financial security and your personal life.   In this episode of Retire Early, Sam Benson and Lynwood Freyer discuss the pros and cons of delaying retirement by just one year. They discuss how a final year of employment can boost your retirement savings, increase your Social Security benefits, and allow you to pay down remaining debt. On the flip side, they explore the non-financial trade-offs, explaining why spending your time on earth, avoiding workplace burnout, and enjoying your health while you still have it are compelling reasons to hang it up now.   Episode Outline 00:00 — Introduction: Should you work one more year before you retire? 01:15 — The financial pros: Maximizing your 401(k) and retirement savings 02:18 — How an extra year affects your Social Security calculations and monthly benefits 03:40 — Evaluating employer benefits: Keeping quality health insurance before Medicare 05:10 — Using a final working year to become completely debt-free 07:13 — Portfolio impacts: Reducing the timeline and size of your retirement withdrawals 09:04 — Treating your final year as a "practice year" to test your retirement budget 12:11 — The cons of working longer: Recognizing that time in retirement is finite 13:39 — Factoring in physical health, mental health, and unexpected life events 15:22 — Dealing with workplace burnout and high-stress environments 16:41 — Avoiding regrets and missed milestones with friends and family 19:53 — Final thoughts and how to weigh the data for your own retirement timeline   Connect With Martin Wealth Solutions Learn more about working with Sam Benson and Lynwood Freyer at martinwealth.com

  4. Sep 8

    How to Pay for Health Insurance If You Retire Early

    One of the biggest questions facing anyone who wants to retire before age 65 is simple: What do you do about health insurance? Leaving your job often means leaving employer-sponsored health coverage behind — but Medicare may still be years away. That gap can become one of the largest expenses in an early retirement plan. In this episode of Retire Early, Sam Benson and Linwood Fraher break down three major ways to cover healthcare before Medicare: ACA Marketplace insurance, COBRA, and employer-sponsored coverage. They discuss the tradeoffs between premiums and benefits, why your income and healthcare needs matter, and why simply choosing the cheapest option can expose your retirement plan to significant risk. Episode Outline 00:00 — The healthcare challenge when retiring before Medicare 01:00 — Why healthcare can become a major early-retirement expense 02:34 — Option #1: ACA and Marketplace health insurance 04:00 — Who Marketplace plans may work well for 05:00 — Getting professional help choosing a health plan 05:40 — Why an independent insurance broker may be preferable 07:15 — Option #2: Using COBRA after leaving your employer 08:00 — The potentially surprising cost of COBRA 09:00 — Comparing COBRA with ACA coverage 10:00 — The danger of simply choosing the cheapest plan 11:40 — Option #3: Employer-sponsored coverage 12:00 — Using transitional or part-time employment for health insurance 13:50 — Joining a working spouse’s health plan 15:00 — Planning for healthcare costs before retiring early 16:00 — Final thoughts Connect With Martin Wealth Solutions Learn more about working with Sam Benson and Lindood Fraher at martinwealth.com.

  5. Sep 1

    The 3 Worst Investment Decisions to Make Before Retirement

    The decisions you make with your investments as you approach retirement can have consequences that last for decades. In this episode of the Retire Early Podcast, Certified Financial Planners Sam Benson and Linwood Fraher discuss three of the biggest investment mistakes they see people make heading into retirement, and how planning ahead can help you avoid them. The conversation begins with the story of an investor who watched the market fall during COVID while preparing for retirement. Fear took over, and he moved his investments into CDs. Years later, he regretted the decision. Sam and Linwood explain why retirement investing isn't simply about avoiding market losses. You need a strategy for turning your portfolio into a paycheck, managing taxes, maintaining enough long-term growth to keep pace with inflation, and preparing your plan for the unexpected. Mistake #1: Retiring Without an Income Distribution Plan For decades, your employer provides a paycheck. In retirement, that responsibility shifts to you and your portfolio. Without an income distribution strategy, retirees can end up taking money from the wrong accounts at the wrong time, overspending, or unexpectedly increasing their tax bill. Sam explains how something as simple as taking a large IRA distribution for a vehicle could potentially push someone into a higher tax bracket. The goal is to understand how much you'll need, where the money will come from, and how your different accounts can work together to recreate a dependable retirement paycheck. Mistake #2: Getting Completely Out of the Market Market volatility becomes much more intimidating when retirement is close. That fear can lead investors to abandon the market entirely for CDs, Treasuries, savings accounts, and other conservative investments. While those assets can have an appropriate role in a retirement strategy, moving everything to short-term investments creates another risk: your money may fail to keep pace with inflation and your long-term spending needs. Sam and Linwood discuss investors who sold during major downturns—including the 2008 financial crisis and the COVID crash, and then remained on the sidelines during the recovery. Mistake #3: Failing to Stress-Test Your Retirement A retirement plan shouldn't only work when everything goes right. What happens if investment returns are lower than expected? Inflation runs higher? Social Security benefits change? Spending increases? A major home repair arrives? Or one spouse dies earlier than anticipated? Stress-testing a retirement plan means deliberately modeling difficult scenarios to identify its weak points before those problems actually happen. The goal isn't to predict the future. It's to build enough flexibility into the plan that unexpected events don't automatically derail your retirement. In This Episode 00:00 — A Retirement Decision He Regretted 01:00 — The 3 Biggest Investment Mistakes Near Retirement 02:00 — Mistake #1: No Retirement Paycheck Plan 03:00 — Taking Money From the Wrong Accounts 04:00 — How Much Can You Actually Spend? 05:00 — Mistake #2: Getting Out of the Market 06:00 — The Hidden Problem With "Safe" Investments 07:00 — Spend Your Retirement While You Can Enjoy It 08:00 — Recovering From Emotional Investment Decisions 10:00 — Why COVID Felt Different 11:00 — Mistake #3: Failing to Stress-Test Your Portfolio 12:00 — Preparing for Major Retirement Expenses 13:00 — What Happens When the Plan Goes Wrong? 14:00 — The 3 Mistakes to Avoid 15:00 — Where to Start

  6. Aug 25

    Should I Work One More Year Before Retiring?

    In this episode of the Retire Early Podcast, financial advisors Sam Benson & Linwood Fraher of Martin Wealth Solutions address a common question among people approaching retirement: Should I retire now or work one more year? Sam and Linwood explain how an additional year of work could affect several parts of a retirement plan. Working longer may provide another year of income, retirement account contributions, employer benefits, and potential investment growth while also reducing the number of years your portfolio must support you. However, the decision is not purely financial. They also discuss the importance of evaluating healthcare coverage, Social Security timing, retirement income, current expenses, and whether the additional year would meaningfully improve the strength of your plan. The episode encourages listeners to weigh the financial benefits of continuing to work against their health, family priorities, personal goals, and the value of their time. For anyone standing at the edge of retirement, this conversation offers a helpful framework for determining whether one more year is necessary—or whether you may already be ready to begin the next chapter. http://retirewithmartin.com/ ← Learn about working with us www.planwellretirehappy.com   Episode Breakdown 00:00 Introduction: Should you work one more year? 00:39 Meet Sam and Linwood 01:08 The financial benefits of another year of income 02:04 Social Security and retirement income considerations 03:10 Considering the intangible benefits of working an additional year 5:00 The importance of paying off different types of debts 07:08 Reducing the number of years your savings must support 08:31 Practicing a “transitional year” from employment to retirement 09:35 Will one more year significantly improve your financial security? 10:10 Continuing to work because you simply enjoy it 11:44 Health, family, and personal priorities 14:30 Experiencing burnout at work and its effects 15:40 Preparing for unexpected changes and events 16:53 Balancing financial security with the value of time and once-in-a-lifetime moments 18:25 Key takeaways, final thoughts and closing remarks   Disclaimer Opinions expressed herein are solely those of Martin Wealth Solutions, unless otherwise specifically cited. Material presented is believed to be from reliable sources, but no representations are made by our firm as to another parties’ informational accuracy or completeness. Content provided herein is for informational purposes only and should not be used or construed as investment advice or a recommendation regarding the purchase or sale of any security. There is no guarantee that any statements, opinions or forecasts provided herein will prove to be correct. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation. Past performance may not be indicative of future results. Indices are not available for direct investment. Any investor who attempts to mimic the performance of an index would incur fees and expenses which would reduce returns. Securities investing involves risk, including the potential for loss of principal. There is no assurance that any investment plan or strategy will be successful.

  7. Aug 18

    Stop. Overpaying. Your Taxes.

    In this episode of the Retire Early Podcast, financial advisors Sam Benson & Linwood Fraher of Martin Wealth Solutions discuss why many early retirees end up paying more in taxes than necessary—and what they can do to avoid it. Sam and Linwood explain that retirement creates unique tax planning opportunities, but without a strategy, retirees can unknowingly increase their tax bill. They discuss how different account types are taxed, why withdrawal sequencing matters, and how careful income planning can help reduce lifetime taxes. They also cover common mistakes involving Social Security, Required Minimum Distributions (RMDs), Roth conversions, and Medicare premium surcharges, showing listeners how proactive planning can keep more money working for them instead of going to the IRS. Whether you're planning to retire early or are already enjoying retirement, this episode highlights practical tax strategies that could make a meaningful difference over the long term. http://retirewithmartin.com/ ← Learn about working with us www.planwellretirehappy.com   Episode Breakdown 00:00 Introduction to today's topic 00:52 Meet the hosts 02:05 Avoiding unexpected surprises with your taxes 03:57 Why withdrawal order matters 06:37 The importance of tax diversification 08:35 What to lookout for with Roth conversion opportunities 10:38 Social Security taxation and hidden tax costs 11:50 Coordinating investments with tax strategy 12:36 What to do with Employer stock 14:29 Retirement planning and buyer's remorse 16:15 Common tax mistakes retirees make 16:53 Action steps to improve tax efficiency  17:35 Final thoughts and closing remarks   Disclaimer Opinions expressed herein are solely those of Martin Wealth Solutions, unless otherwise specifically cited. Material presented is believed to be from reliable sources, but no representations are made by our firm as to another parties' informational accuracy or completeness. Content provided herein is for informational purposes only and should not be used or construed as investment advice or a recommendation regarding the purchase or sale of any security. There is no guarantee that any statements, opinions or forecasts provided herein will prove to be correct. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation. Past performance may not be indicative of future results. Indices are not available for direct investment. Any investor who attempts to mimic the performance of an index would incur fees and expenses which would reduce returns. Securities investing involves risk, including the potential for loss of principal. There is no assurance that any investment plan or strategy will be successful.

  8. Aug 11

    7 Red Flags That Mean You Shouldn't Retire Just Yet

    In this episode of the Retire Early podcast, financial advisors Sam Benson & Linwood Fraher of Martin Wealth Solutions discuss the warning signs that may indicate you are not quite ready to retire. Retirement readiness involves more than reaching a certain age or account balance. Sam and Linwood explain why retirees also need a dependable income plan, a clear understanding of their expenses, a strategy for healthcare, and a plan for how they will spend their time after leaving work. They also address the risks of carrying too much debt, relying on unrealistic investment returns, or making a retirement decision before both spouses are on the same page. The episode encourages listeners to identify potential gaps before submitting their retirement notice. With proper planning, many of these warning signs can be addressed, helping you approach retirement with greater clarity, confidence, and flexibility. http://retirewithmartin.com/ ← Learn about working with us www.planwellretirehappy.com   Episode Breakdown 00:00 Introduction: Are you truly ready to retire? 00:46 Meet the hosts 01:44 Retirement readiness is about more than your savings 02:26 Sign #1: You don’t understand your retirement expenses 05:01 Sign #2: You haven’t built a dependable income plan 10:41 Sign #3: You haven’t planned for healthcare costs 13:19 Sign #4: You’re carrying too much debt 15:51 Sign #5: You don't have any emergency reserves 18:50 Sign #6: You don't have a strategy for your taxes  22:41 Sign #7: You haven't created a plan with your spouse 23:56 Planning for purpose, routine, and social connection 26:07 Stress-testing your retirement strategy 26:25 Final thoughts and closing remarks   Disclaimer Opinions expressed herein are solely those of Martin Wealth Solutions, unless otherwise specifically cited. Material presented is believed to be from reliable sources, but no representations are made by our firm as to another parties’ informational accuracy or completeness. Content provided herein is for informational purposes only and should not be used or construed as investment advice or a recommendation regarding the purchase or sale of any security. There is no guarantee that any statements, opinions or forecasts provided herein will prove to be correct. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation. Past performance may not be indicative of future results. Indices are not available for direct investment. Any investor who attempts to mimic the performance of an index would incur fees and expenses which would reduce returns. Securities investing involves risk, including the potential for loss of principal. There is no assurance that any investment plan or strategy will be successful.

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About

Welcome to ”The Retire Early Podcast,” your essential guide to achieving the retirement you’ve always dreamed of—sooner rather than later! Hosted by Sam Benson and Linwood Fraher, this podcast is tailored specifically for individuals aged 50-65 who are passionate about retiring early and living their best lives. Each week, we’ll dive deep into essential retirement topics including tax-efficient strategies, smart investing, healthcare planning, income optimization, Social Security tips, estate planning, and actionable financial advice. We’ll feature expert insights, inspiring stories, and practical tools to empower you on your journey toward early retirement. Whether you’re planning to retire in 5 years or 15, ”The Retire Early Podcast” equips you with the knowledge and confidence to secure your financial future, maximize your wealth, and enjoy the retirement lifestyle you deserve. Subscribe today and join our community committed to retiring early and thriving in retirement!

Information

  • Creator
    Sam Benson & Linwood Fraher
  • Years Active
    2025 - 2026
  • Episodes
    82
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Retire Early Podcast

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