Ozarks Retirement Show

Hosted by Brad Pistole

Business Investing

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Episodes

167

Latest episode

Oct 2026

Language

EN-US

About the show

Brad Pistole, RICP®, and the Ozarks Retirement Group help pre-retirees and retirees turn savings into reliable monthly income. Each episode covers Social Security timing, tax-efficient withdrawals, sequence-of-returns risk, guaranteed lifetime income, Medicare/IRMAA, and the questions you must answer before you retire. Practical planning from the longest-running retirement show in the Ozarks—now The Ozarks Retirement Show. ozarksretirement.com

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60 recent

October 22, 202652 min

STOP Buying This Before Retirement

Retirement can sneak up on you fast, especially in a post-COVID work world where burnout is real and the pace of change feels nonstop. If you are within five years of retiring, the decisions you make right now can either protect your future or create payments and regrets you carry for decades. We get practical and direct about what to pause before you “pull the trigger,” even when the purchase feels earned. We walk through seven common pre-retirement spending traps: buying a brand new luxury vehicle, taking on a major home remodel you do not truly need, putting vacations and lifestyle on a credit card, and helping adult children in a way that puts your own financial independence at risk. Then we move into the risks people overlook when retirement is close, including speculative investments you do not fully understand, the hidden upkeep of a second home or vacation property, and anything that locks up your money without a clear retirement purpose. Along the way, we tie everything back to what matters most in retirement planning: creating a reliable monthly paycheck. That means coordinating your retirement income plan with Social Security, Medicare awareness, tax planning, and a real decumulation strategy so your savings can last for 20 to 40 years. If you are asking, “Can I retire now?” or “Should I buy this right before I retire?” this conversation gives you a clear framework to pressure test the math. If you found this helpful, subscribe on Apple Podcasts or Spotify, share it with a friend who is close to retirement, and leave a review so more people can find the show. What purchase are you debating right now, and what would you want a second opinion on? Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

October 16, 202650 min

Seven Signs You Can Retire NOW

Retirement is not a date on the calendar, it is a handoff from earning a paycheck to creating one. We start with the question we hear constantly right after Labor Day: “Do you think I’m ready to retire?” Then we walk through a practical seven-part checklist that helps you pressure test your plan before you turn in a resignation letter. We dig into full retirement age and the bigger issue behind it: Social Security claiming strategy. “Can I take it?” is easy. “Should I take it?” is where real retirement income planning lives, especially for married couples thinking about survivor benefits, longevity risk, and the long-term impact of filing early versus delaying. From there, we talk about replacing your income in retirement, including how pensions fit for the minority who still have them and how many families try to recreate that dependable monthly income with annuities, investments, and a coordinated withdrawal plan. Healthcare is a major swing factor, so we cover Medicare timing and why retiring before 65 can create expensive gap years. We also hit two unglamorous but decisive factors: being debt-free and keeping enough liquid cash reserves so one roof repair, storm, or hospital bill does not force you to sell investments at the wrong time. Finally, we zoom out to the human side of retirement, because even a perfect spreadsheet can fall apart if you have no plan for your time, your routines, and your sense of purpose. If you want a simple framework to decide whether to retire now or wait, hit play and follow along with the checklist. Subscribe, share this with a friend who is on the fence, and leave a review so more families can find smart retirement planning guidance. Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

October 9, 202651 min

Client Conversation #1: Paul Showalter - Semi-Retired With Purpose

The moment you retire is supposed to feel like relief, but what happens when the market drops right after you walk away from your paycheck and you realize you’ve never lived through retirement before? We sit down with our client Paul Stowalter, who retired at 59 and a half, to share the honest version of that transition: the excitement, the stress, and the decisions that made the difference once real money and real life showed up. Paul talks about leaving a decades-long career in the food industry and stepping into a working retirement built around two things he loves: running his music store and leading a homeless outreach ministry. We unpack what changes when you’re no longer tied to a rigid schedule, why that freedom can be both energizing and disorienting, and how purpose becomes the real “retirement plan” that keeps you healthy, social, and motivated. On the financial side, we break down sequence of returns risk in plain English and why a negative market early in retirement can create outsized damage if you’re withdrawing at the wrong time. We also talk through practical retirement income planning choices, including using protected strategies for stability, plus the unique challenges of retiring before Medicare at 65 when health insurance costs can hinge on earned income. We wrap with bigger-picture retirement planning issues like Medicare IRMAA and why what you earned two years ago can raise premiums today, along with tax-smart charitable giving concepts that matter later in life. If you’re asking “can I retire” or “what will I do with my time,” this conversation is a grounded place to start. Subscribe, share with a friend who’s close to retiring, and leave a review with your biggest retirement question. Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

October 1, 202650 min

10 Things That Cost You Years Of Retirement

One forgotten subscription here, a “free” upgrade there, a couple food deliveries every week, and a payment that feels manageable on paper can quietly turn into the reason you’re still working years longer than you planned. We lay out the real retirement math behind the everyday habits that pre-retirees often ignore, and we do it in plain language you can actually act on. We count down the biggest “money leaks” we see: status spending that tries to impress other people, lifestyle inflation that grows right alongside your income, and convenience spending that becomes automatic. We also dig into the hidden price of buying a new car too soon, shopping because something is on sale, and buy now pay later plans that make big purchases feel small until the monthly obligations pile up. Along the way, we talk insurance planning mistakes, why tracking a year of delivery fees can be shocking, and how to pressure-test your budget before you claim you’re ready to retire. Then we hit the hard truth items: subscriptions you do not even remember you have, the compounding damage of credit card interest, and the “plus one” that can dwarf every other financial mistake, divorce, including graying divorce after age 55. You’ll leave with a clear weekly challenge to review your statements and ask one question about every recurring charge: is this helping your retirement goals or stealing from them? Subscribe to the Ozarks Retirement Show, share this with a friend who’s close to retirement, and leave a review so more families can find practical retirement planning guidance. What’s the first expense you’re cutting this week? Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

September 28, 202652 min

The Real Reasons People Roll 401(k)s Into IRAs

Your 401(k) feels familiar until the day you realize you might be one rollover away from changing your retirement forever. We walk through the real-world tradeoffs behind 401(k) vs IRA decisions, including why IRAs now hold trillions more than 401(k) plans and why most of that growth comes from rollovers, not direct IRA contributions. If you’re nearing retirement, changing jobs, considering an in-service withdrawal at 59½, or navigating a divorce settlement, this conversation is designed to help you slow down and choose deliberately. We also get blunt about incentives. Not everyone who says “fiduciary” is operating under a true fiduciary standard, and rollover advice is where the conflicts show up fast. We share what to ask for in writing, why employers have fiduciary obligations inside the 401(k), and how sales-driven rollover pitches can lead to higher fees or the wrong product. Along the way, we reference insights from retirement research voices like Dr. David Blanchett and Social Security expert Dr. Jason Fickner to ground the discussion in more than hype. Then we tackle the mistakes that sting later: rolling money into an IRA too early and triggering penalties, missing the Rule of 55 exception, and letting “keeping up with the Joneses” distort your retirement readiness. We compare the 4% rule math to guaranteed lifetime income concepts so you can think in monthly paycheck terms, not just account balances. Subscribe, share this with a friend facing a rollover, and leave a review so more families can plan smarter and live better. Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

September 10, 202639 min

The Forever Paycheck with Jean Chatzky

You can do everything “right” for decades, max out your 401(k), build a solid IRA, and still hit retirement with a knot in your stomach. The paycheck that’s always been there is about to disappear and suddenly your life savings feels less like freedom and more like a fragile pile you’re afraid to touch. That fear shows up everywhere, from 30-somethings to boomers, and it’s one of the biggest reasons people either overreact to market dips or underspend and leave joy on the table. We talk with personal finance powerhouse Jean Chatzky about The Forever Paycheck and the shift from accumulation to retirement income planning. We dig into why retirees often refuse to spend principal, how the “no more do-overs” reality changes risk, and why classic rules of thumb like the 4% rule can feel shaky when sequence of returns risk, inflation, and interest rates don’t cooperate. Then we get practical: separating needs, wants, and wishes, figuring out real spending (not guesses), and designing an income floor you can count on. We also get specific about guaranteed lifetime income and annuities as tools, not magic. Jean shares how her views evolved, how guarantees can reduce stress for couples and surviving spouses, and why insuring part of your income can free you to invest the rest with a longer time horizon and more flexibility. If you want a retirement strategy built around confidence, clarity, and a paycheck you can’t outlive, this conversation will help. Subscribe for more retirement planning and personal finance conversations, share this with someone who worries about retirement income, and leave a review so more listeners can find the show. Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

September 3, 202625 min

Why Safe Money Radio Became The Ozarks Retirement Show

The name you’ve trusted for years just changed and the reason isn’t marketing. It’s protection. After nearly two decades on the air, we’re retiring the Safe Money Radio name and stepping forward as The Ozarks Retirement Show so listeners can instantly tell who they’re hearing and where to find us online without confusing copycats. We take you back to 2009, when the country was still limping out of the 2008 financial crisis and Safe Money Radio was born as a brand-new idea. I share what it was like starting a financial services business in 2008 with no finance degree, no formal background, and plenty of pressure just to survive. You’ll hear how the show grew from humble beginnings into a national presence, largely because we stayed real, told client stories with care, and focused on clear retirement planning education instead of hype. We also talk candidly about the messy parts: the early days of scripted radio that didn’t sound like me, the criticism around annuities and being labelled “just a salesman,” and what happens when success attracts competitors who copy what works. Then COVID hits, the national network shrinks from dozens of hosts down to one, and the Safe Money Radio name gets sold, leading to a situation where someone else can host a “Safe Money Radio podcast” and claim the spotlight. Nothing changes for you except the name. Same stations, same weekly rhythm, and the same commitment to retirement income planning, market risk clarity, and top-tier guests. If you value straight talk and practical guidance, subscribe, share the show with a friend, and leave a review so more people can find The Ozarks Retirement Show. Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

August 27, 202654 min

Tax Preparation Vs Tax Planning For Retirement with Gary Wood

A big tax refund feels like a win, but it can be the clearest sign you played the wrong game all year. Brad sits down with his longtime CPA, Gary Wood, to talk about what actually drives results for retirees and near-retirees: proactive tax planning that lowers your lifetime tax bill, not just a tax return that documents last year. We get practical about the difference between tax preparation and tax planning, why most people only see their CPA when everyone is busiest, and how a year-round planning relationship creates better decisions around income, deductions, and timing. Gary shares how raising four kids changed his perspective on tax deferral and liquidity, and why “life optimization planning” can matter as much as portfolio math, especially if you expect to work part time in retirement. We also unpack the real-world tax issues that show up after you retire: Social Security taxation, Medicare IRMAA, RMDs, and how filing status can shift if you lose a spouse. Then we move into the nuts and bolts: marginal tax brackets, bracket harvesting, and why Roth IRA contributions and Roth conversions can be a smart “now, later, never” strategy when you coordinate them with deductions. We also call out the noise of viral “tax hacks” and explain why small, repeatable moves often beat flashy one-time plays. If you want clearer next steps and fewer surprises, subscribe, share this with a friend who hates tax season, and leave a review with the one tax question you want answered next. Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

August 20, 202654 min

You Are Not Ready To Retire Until You Can Answer These Three Questions

Retirement decisions get dangerous when they are driven by exhaustion instead of numbers. We start with a simple challenge: can you say, out loud, the exact monthly income you need after your paycheck stops, and can you prove it with a retirement budget you trust? If you cannot, you are not alone, and you are exactly who this conversation is for. We break retirement income planning into three must-answer questions. First, we nail down your baseline monthly expenses so you are not guessing. Second, we separate real income from “if come” by looking at what is contractually guaranteed for life versus what depends on markets, tenants, or timing. Along the way, we unpack why down years like 2022 can crush retirees who are withdrawing from traditional portfolios, and we explain the “quadruple whammy” of taking distributions during losses while still paying fees and taxes. Then we move to the part too many plans skip: risk removal. We talk survivor planning when one spouse dies and a Social Security check goes away, pension elections that can cut income, and the hard truth about healthcare and long-term care costs that can spike fast. These are not abstract risks, they are real stories and real numbers, and they are exactly why guaranteed lifetime income and smart tax planning can bring peace of mind. Subscribe for more practical retirement guidance, share this with someone within three years of retirement, and leave a review so more families can find the show. What is the one “what if” you want your retirement plan to handle? Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

August 13, 202656 min

When Your Spouse Dies: A Widow’s Story on Money, Social Security & Surviving the Shock

Your spouse dies and suddenly the questions are nonstop, and some of them are terrifyingly practical: Where are the accounts? What were the passwords? Which check is still coming next month? I sit down with my 79-year-old mom, Peggy Sue Pistole, for a raw, in-person conversation about becoming a widow and learning how to live again after losing her best friend and marriage partner, my dad, Joe “Hilliard” Pistol. We walk through the night he passed, the shock of an unexpected medical emergency, and what happens after the funeral when the paperwork and money decisions hit all at once. We talk about the things families rarely plan for: how long it can take to gain access to a computer and records, how hard it can be to even find a life insurance policy, and why Social Security survivor benefits can still bring a surprise when a deposit gets pulled back after a death. Then we get practical about retirement income planning. We explain why sequence of returns risk matters, why an “income floor” can protect a surviving spouse from panic, and how guaranteed lifetime income from annuities can create steady monthly cash flow through direct deposit even when markets feel uncertain. We also touch on Roth conversion planning and why tax free money can be a lifeline when life happens fast. If you want a retirement plan your family can run without you, listen, take notes, and share this with someone you love. Subscribe to the podcast, leave a review, and tell us what part of your plan you want to simplify next. Send us Fan Mail To learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com

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