TaylorMade Retirement with Taylor Demars, CFP®

Taylor Demars, CFP®

Welcome to TaylorMade Retirement! Featuring Taylor Demars, a 3rd-generation financial advisor and CFP®, this podcast explores what it really takes to build a retirement that works- for your money and your life.  Each episode breaks down strategies, stories, and steps to help listeners approach retirement with clarity and confidence. From cutting taxes to avoiding common retirement traps, Taylor draws on decades of family expertise to make complex financial ideas easy to understand. Because life should shape your money, not the other way around. 

  1. 13h ago

    I Retired at 61 With $3.4M. Now Where Does the Money Come From?

    If you want your own custom portfolio-to-paycheck system, book a call here: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46195 👉 Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-express Retirement income sounds simple until the paychecks stop. This couple retired with $3.4 million and a paid-off house, and three weeks in it felt like going broke, because no one had ever built the system that turns a portfolio into a monthly paycheck. This is the part of retirement almost no one prepares you for. For thirty years, the whole job is saving. Then the deposits stop, and overnight you're supposed to know how to pay yourself from a stack of accounts you spent a career filling. Most people have plenty saved. What they don't have is a plan for where each month's income actually comes from. In this episode, Taylor walks through the exact system he builds for couples in that spot, using one real example with names and details changed. You'll see: * The three-bucket approach, and why your cash "pantry" is a reserve, not your monthly income * The simple, almost boring change that makes your savings feel like a paycheck again * How to keep that paycheck coming during a market downturn without being forced to sell stocks while they're down, which is the heart of managing sequence of returns risk * Which accounts to spend from first, and how a smart withdrawal order can keep more of a six-figure lifestyle in the 12% federal tax bracket or below * The low-tax "gap years" before Social Security and required minimum distributions (RMDs) begin, and why it's one of the best tax-planning windows in retirement * Three questions to ask your spouse tonight to find out whether you have a real retirement income plan, or just a pile of accounts If you're a few years from retirement with a solid nest egg and no clear picture of how it becomes income, this one is for you. 0:00 Retired with $3.4M, and it felt like going broke 1:02 Plenty saved, but something felt off 2:08 The question that stopped them cold 2:51 When "we don't know" spreads to everything 3:31 It's not a money problem. It's a paycheck problem. 4:11 Why no one taught you how to spend it 4:44 The three buckets: pantry, bond bunker, growth 5:51 Piece 1: The pantry (how much cash to hold) 7:02 Piece 2: The 15-minute paycheck setup 8:28 "Isn't that cash just sitting there?" 9:15 Piece 3: What to sell, and when 10:54 Which account to spend from first (your tax bill) 11:53 How a six-figure retirement can pay almost no tax 13:05 The part you can't do yourself 13:52 3 questions to ask your spouse tonight 14:57 How Paul & Susan's story ended Resources: Website:  https://www.demarsfinancial.com/ Phone: (509) 536-9556 Schedule an introduction call with Taylor: https://bit.ly/demarspodcast Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

  2. Jul 14

    They Had $3.5M and a 98% Score — Here's the Catch.

    Want a retirement plan optimized for what matters most? Start here: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46186 👉 Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-express We made this couple's retirement plan better — and their Monte Carlo "success score" dropped from 95% to 88%. Here's why that's not a red flag. It's the entire point. A high "retirement success score" feels reassuring. But that number only holds if everything goes exactly to plan: your investment returns, your timeline, future tax rates, how long you and your spouse live, and how much you spend each year. The one thing it can't account for is that life never goes exactly to plan — which, ironically, is the only thing we can truly count on. Over three months and seven planning meetings, we rebuilt this couple's plan to be tax-smart and ready for real life — income, taxes, investments, healthcare, and estate planning. On paper, the score went down. In real life, the plan got far stronger. In this episode, Taylor breaks down what a Monte Carlo retirement score actually measures, why a better plan can score lower, and the three "what-ifs" the score quietly ignores: the surviving-spouse "widow's penalty," the hidden cost of never spending what you worked so hard to save, and the curveballs no spreadsheet predicts. If you're 55–65 with most of your savings in tax-deferred accounts (401(k), IRA) and you want to retire with real confidence — not just a higher number on a dashboard — this one's for you. We'll get into tax diversification, Roth conversions, and why a balanced mix of taxable, tax-deferred, and tax-free money gives you options when life changes the plan. 0:00 – The review that dropped their retirement score (95% → 88%) 0:57 – Why a higher score can be a false sense of security 2:35 – The pre-tax trap: $3.5M, RMDs & a growing tax bill 3:47 – The fix: same money, reshaped into tax-free Roth 5:10 – Why tax-deferred money ties your hands (income tax + IRMAA) 6:05 – The widow's penalty: when the survivor pays double 6:58 – Why a Monte Carlo score is never actually "right" 8:08 – The road trip: Google Maps, a snowstorm & life's curveballs 9:23 – The trips and purchases you keep putting off 10:08 – Sudden costs: illness, chronic care & getting boxed in 10:53 – 95% to 88%, explained: trade-offs & Roth conversions 12:01 – The real question: not "will it last," but "how usable?" 13:00 – Run your own numbers + book a call Resources: Website:  https://www.demarsfinancial.com/ Phone: (509) 536-9556 Schedule an introduction call with Taylor: https://bit.ly/demarspodcast Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

  3. Jul 7

    Why the Year You Retire Matters More Than How Much You Have Saved

    👉 Find out if your portfolio is ready for retirement: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46175 👉 Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-express Two retirees. Same $2M portfolio. Same market crash in year one. Completely different retirements. In this episode, Taylor breaks down sequence of returns risk, why it's one of the biggest threats to a multi-million dollar retirement, and the withdrawal structure that separates the retirees who thrive from the ones who don't. If you have $2M or more saved for retirement, this is the risk most plans never address. Watch Next: A full retirement case study: https://youtu.be/uYTiLWqM9gA 📌 CHAPTERS: 0:00 Same $2M, same market crash, different retirements 0:57 What is sequence of returns risk? 1:56 Real S&P 500 data shows the impact of one bad year 4:09 Robert and Susan: a tale of two $2M retirements 5:10 Why the first 5 years of retirement are the most dangerous 7:14 The 3 tax buckets most retirees get wrong 9:52 What a market crash actually feels like without a paycheck 12:27 The Retirement Shock Absorber framework explained 14:37 How a down market can become a Roth conversion opportunity 15:39 Why you need to build your structure before you retire 17:08 A real client story from April 2025 Resources: Website:  https://www.demarsfinancial.com/ Phone: (509) 536-9556 Schedule an introduction call with Taylor: https://bit.ly/demarspodcast Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

  4. Jun 30

    Why 62 Is The Most Important Age For Your Retirement

    Find out if you're working longer than you need to: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46150 Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-express Age 62 isn't just when Social Security becomes available. It's the first point where Social Security, portfolio withdrawals, taxes, and healthcare before Medicare all start affecting each other at the same time. Most people only plan for one of those decisions. This episode walks you through what happens when you plan for all of them together. Taylor breaks down the real cost of claiming Social Security early vs. late (it's not just a breakeven chart), why the healthcare gap before Medicare is more expensive than most people budget for, and the one cost the financial industry almost never measures: the cost of waiting too long to retire. He also walks through what he calls the 62 Gap Analysis — four questions he asks every client before they make any major decision at this age. 📺 Watch next: Why the Math Says Yes, But You Still Can't Pull the Trigger https://youtu.be/agz5kbJLFMM 📋 TIMESTAMPS 0:00 The most expensive mistake at 62 0:58 What actually happens at 62 (the convergence most people miss) 2:38 The Social Security mistake most people make 4:14 The healthcare gap nobody budgets for 6:18 The cost nobody measures (retiring too late) 8:09 The 62 Gap Analysis: 4 questions to ask before you decide 9:29 Why Michael couldn't pull the trigger (and what changed) 10:31 What getting 62 right actually looks like Resources: Website:  https://www.demarsfinancial.com/ Phone: (509) 536-9556 Schedule an introduction call with Taylor: https://bit.ly/demarspodcast Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

  5. Jun 25

    First-Time Grandparents: How You Can Help Build Lasting Wealth

    Becoming a grandparent often brings a new question: how can you help create opportunities for the next generation? In this episode, Taylor explores several ways grandparents can support their grandchildren financially while maintaining flexibility and control. He discusses how different strategies can align with different goals, whether you're thinking about education, retirement, or creating a lasting family legacy. Here’s what we discuss in today’s show: 🎁 Grandparent Goals: Helping grandkids for life 🎓 529 Power: Flexible long-term planning tool 📈 Roth Head Start: Decades of tax-free growth 💰 Super Funding: Front-load future opportunities 🏛️ Legacy Planning: Align gifts with your goals ⚖️ Control Matters: Ownership affects flexibility Resources: Website:  https://www.demarsfinancial.com/ Phone: (509) 536-9556 Schedule an introduction call with Taylor: https://bit.ly/demarspodcast Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

  6. Jun 23

    I'm 60 With $3.5M Saved. How Much Can I Spend in Retirement? (Full Breakdown)

    Find out if you're working longer than you need to: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46150 Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-express You've saved $2.5 million for retirement. By every measure, you should feel ready. So why does spending it still feel terrifying? In this video, Taylor walks through three retirement pitfalls he'd want addressed before telling a 60-year-old with $2.5 million, "Yes, you can retire." These aren't problems you can solve from a statement balance — they're the gaps that turn a healthy portfolio into a plan that quietly underperforms in the years that matter most. He'll show you why your account balance isn't your spendable retirement money, what the bridge to Medicare actually costs (and why most plans bury it in the wrong place), and the bucket income methodology we use to make sure the right dollars are doing the right jobs over a 30-year retirement. By the end, you'll know what questions to ask, what numbers to start gathering, and how to find your real retirement number — not just your statement balance. WATCH NEXT — The truth about retiring at 55 vs 65: https://youtu.be/7MqmdDqnWcQ CHAPTERS 00:00 — Why $2.5M Doesn't Always Feel Like Enough 01:00 — Pitfall #1: Your Statement Balance Isn't Your Real Number 05:00 — The Survivor Tax Scenario Most Plans Miss 05:50 — Pitfall #2: The Healthcare Gap Before Medicare 09:30 — Pitfall #3: The Two Battles Every Retiree Fights 11:00 — The Bucket Income Methodology Explained 12:50 — The Three Questions To Find Your Real Number 13:20 — Two Ways To Take The Next Step Resources: Website:  https://www.demarsfinancial.com/ Phone: (509) 536-9556 Schedule an introduction call with Taylor: https://bit.ly/demarspodcast Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

  7. Jun 18

    Reacting to the Most Watched Retirement Video of the Year

    Over the past year, one retirement video on YouTube pulled in 3.7 million views. The title: "Sell These 5 Things Before You Retire." We thought it was worth a conversation — not to tear it apart, but to react honestly. Do we agree? How often do we actually see this play out with real clients? Let's get into it. Here’s what we discuss in today’s show: 🏡 Why downsizing is often more about lifestyle than saving money 👨‍👩‍👧‍👦 The delicate balance between helping adult children and protecting your retirement 🚐 How to decide if hobbies, RVs, boats, and other “toys” belong in your retirement plan 🚗 Do retirees really need two vehicles? The practical considerations most people overlook 🧠 Why letting go of your work identity may be one of retirement’s biggest challenges 📈 How intentional planning helps align your resources with what matters most Watch the video: https://www.youtube.com/watch?v=IltvyKpy8Z4 Resources: Website:  https://www.demarsfinancial.com/ Phone: (509) 536-9556 Schedule an introduction call with Taylor: https://bit.ly/demarspodcast Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

  8. Jun 16

    Retire NOW If You Honestly Answer "YES" to All 5 Questions

    Download the free Retire Once Guide: https://www.demarsfinancial.com/retire-once-guide The 5 yeses in this episode help you decide if you're ready to retire. The next 5—available only in the guide- help you protect that decision once you're there. Most people think the retirement question is, "Can I retire?" But after working with hundreds of retirees, Taylor thinks the better question is, "Can you retire ONCE?"—without spending the next two years rethinking the decision. He's seen both versions. Some people retire and never look back. Others retire on paper, only to spend the next year or two second-guessing the timing, reworking the plan, or realizing the retirement they stepped into wasn't the one they actually wanted. The difference between those two outcomes is rarely just the portfolio. In this episode, he's walking through the 5 yeses he looks for before he believes someone is truly ready to retire—the financial ones, the relational ones, and the one that's usually the real reason someone with enough money still can't quite leave work. By the end, you'll have a clearer way to tell whether your hesitation is actually about the money, or whether it's coming from one of the hidden places these decisions tend to break after the spreadsheet already says yes. ⏱ TIMESTAMPS 00:00 - The retirement question most people are asking wrong 00:48 - The goal: retire once and get it right the first time 00:56 - The Accumulator-to-Spender Crisis 01:32 - YES #1: You've stopped moving the goalposts 02:13 - The football field problem 02:44 - Self-assessment: is your number creeping up? 03:14 - YES #2: Keep more of what you saved when you start spending it 03:58 - The lowest-income years of your adult life 04:21 - Mark and Linda: aerospace engineer and hospital administrator 05:00 - The 5-year flash sale (12% bracket vs. 22%+ later) 05:41 - What happens if you miss this window 06:28 - YES #3: You and your spouse are reading the same map 06:51 - Tom and Janet: same plan, two different questions 07:43 - Gardening vs. grinding (the asymmetry problem) 08:53 - INTRO CALL: Book a no-strings call with Taylor 09:18 - The next two yeses are about timing 09:26 - YES #4: Retire while you still can do what you want to do 09:48 - Your Wealthspan: when money, time, and health overlap 10:06 - Bob and Carol: the trip to Patagonia 10:38 - "You can rebuild a portfolio. You can't rebuild a decade." 11:42 - YES #5: Walking toward something, not just away from work 12:27 - The do-over you don't see coming 13:08 - What you're retiring TO (and why it has to be specific) 13:40 - The 5 yeses, put together 14:39 - Retiring is one decision. Retiring once is a different one. 14:46 - FREE GUIDE: The Retire Once Guide (the next 5 yeses) 15:11 - The yes keeping you up at 11 p.m. on a Tuesday Resources: Website:  https://www.demarsfinancial.com/ Phone: (509) 536-9556 Schedule an introduction call with Taylor: https://bit.ly/demarspodcast Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

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About

Welcome to TaylorMade Retirement! Featuring Taylor Demars, a 3rd-generation financial advisor and CFP®, this podcast explores what it really takes to build a retirement that works- for your money and your life.  Each episode breaks down strategies, stories, and steps to help listeners approach retirement with clarity and confidence. From cutting taxes to avoiding common retirement traps, Taylor draws on decades of family expertise to make complex financial ideas easy to understand. Because life should shape your money, not the other way around. 

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