Podcast
TaylorMade Retirement with Taylor Demars, CFP®
Hosted by Taylor Demars, CFP® · EN
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.
20episodes
Episodes
Newest firstAll episodes
They Had $3.5M and a 98% Score — Here's the Catch.
1w ago00:14:19Tap to summarizeWant 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-expressWe 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 security2:35 – The pre-tax trap: $3.5M, RMDs & a growing tax bill3:47 – The fix: same money, reshaped into tax-free Roth5:10 – Why tax-deferred money ties your hands (income tax + IRMAA)6:05 – The widow's penalty: when the survivor pays double6:58 – Why a Monte Carlo score is never actually "right"8:08 – The road trip: Google Maps, a snowstorm & life's curveballs9:23 – The trips and purchases you keep putting off10:08 – Sudden costs: illness, chronic care & getting boxed in10:53 – 95% to 88%, explained: trade-offs & Roth conversions12:01 – The real question: not "will it last," but "how usable?"13:00 – Run your own numbers + book a callResources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →Why the Year You Retire Matters More Than How Much You Have Saved
2w ago00:19:22Tap to summarize👉 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-expressTwo 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 retirements0:57 What is sequence of returns risk?1:56 Real S&P 500 data shows the impact of one bad year4:09 Robert and Susan: a tale of two $2M retirements5:10 Why the first 5 years of retirement are the most dangerous7:14 The 3 tax buckets most retirees get wrong9:52 What a market crash actually feels like without a paycheck12:27 The Retirement Shock Absorber framework explained14:37 How a down market can become a Roth conversion opportunity15:39 Why you need to build your structure before you retire17:08 A real client story from April 2025Resources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →Why 62 Is The Most Important Age For Your Retirement
3w ago00:12:15Tap to summarizeFind out if you're working longer than you need to: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46150Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-expressAge 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📋 TIMESTAMPS0:00 The most expensive mistake at 620:58 What actually happens at 62 (the convergence most people miss)2:38 The Social Security mistake most people make4:14 The healthcare gap nobody budgets for6:18 The cost nobody measures (retiring too late)8:09 The 62 Gap Analysis: 4 questions to ask before you decide9:29 Why Michael couldn't pull the trigger (and what changed)10:31 What getting 62 right actually looks likeResources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →First-Time Grandparents: How You Can Help Build Lasting Wealth
4w ago00:08:32Tap to summarizeBecoming 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 flexibilityResources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →I'm 60 With $3.5M Saved. How Much Can I Spend in Retirement? (Full Breakdown)
4w ago00:32:35Tap to summarizeFind out if you're working longer than you need to: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46150Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-expressYou'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/7MqmdDqnWcQCHAPTERS00:00 — Why $2.5M Doesn't Always Feel Like Enough01:00 — Pitfall #1: Your Statement Balance Isn't Your Real Number05:00 — The Survivor Tax Scenario Most Plans Miss05:50 — Pitfall #2: The Healthcare Gap Before Medicare09:30 — Pitfall #3: The Two Battles Every Retiree Fights11:00 — The Bucket Income Methodology Explained12:50 — The Three Questions To Find Your Real Number13:20 — Two Ways To Take The Next StepResources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →Reacting to the Most Watched Retirement Video of the Year
Jun 1800:16:35Tap to summarizeOver 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 mostWatch the video: https://www.youtube.com/watch?v=IltvyKpy8Z4Resources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →Retire NOW If You Honestly Answer "YES" to All 5 Questions
Jun 1600:16:03Tap to summarizeDownload the free Retire Once Guide: https://www.demarsfinancial.com/retire-once-guideThe 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.⏱ TIMESTAMPS00:00 - The retirement question most people are asking wrong00:48 - The goal: retire once and get it right the first time00:56 - The Accumulator-to-Spender Crisis01:32 - YES #1: You've stopped moving the goalposts02:13 - The football field problem02:44 - Self-assessment: is your number creeping up?03:14 - YES #2: Keep more of what you saved when you start spending it03:58 - The lowest-income years of your adult life04:21 - Mark and Linda: aerospace engineer and hospital administrator05:00 - The 5-year flash sale (12% bracket vs. 22%+ later)05:41 - What happens if you miss this window06:28 - YES #3: You and your spouse are reading the same map06:51 - Tom and Janet: same plan, two different questions07:43 - Gardening vs. grinding (the asymmetry problem)08:53 - INTRO CALL: Book a no-strings call with Taylor09:18 - The next two yeses are about timing09:26 - YES #4: Retire while you still can do what you want to do09:48 - Your Wealthspan: when money, time, and health overlap10:06 - Bob and Carol: the trip to Patagonia10:38 - "You can rebuild a portfolio. You can't rebuild a decade."11:42 - YES #5: Walking toward something, not just away from work12:27 - The do-over you don't see coming13:08 - What you're retiring TO (and why it has to be specific)13:40 - The 5 yeses, put together14:39 - 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 TuesdayResources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →The IPO Buzz- What Hopeful Retirees Actually Need to Know
Jun 1100:12:18Tap to summarizeSpaceX. OpenAI. These and other names have been dominating the headlines. The IPO market is heating up, and clients are asking questions. Today we're keeping it simple. What do retirees and pre-retirees need to understand about IPOs before they get caught up in the excitement?Here’s what we discuss in today’s show:🚀 What an IPO is and why companies like SpaceX generate so much investor excitement📈 Why stock prices are driven by expectations- not just company performance⚠️ The volatility risks that often come with newly public companies🎯 How retirees should think differently about speculative investments🧩 Why diversification may be more important than finding the next market superstarResources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →$2.5M Saved. But How Much Can You Actually Spend?
Jun 900:14:20Tap to summarizeFind out if you're working longer than you need to: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46150Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-expressYou've saved $2.5 million for retirement. By every measure, you should feel ready. So why does spending it still feel terrifying?In this episode, 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 he uses 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.CHAPTERS00:00 — Why $2.5M Doesn't Always Feel Like Enough01:00 — Pitfall #1: Your Statement Balance Isn't Your Real Number05:00 — The Survivor Tax Scenario Most Plans Miss05:50 — Pitfall #2: The Healthcare Gap Before Medicare09:30 — Pitfall #3: The Two Battles Every Retiree Fights11:00 — The Bucket Income Methodology Explained12:50 — The Three Questions To Find Your Real Number13:20 — Two Ways To Take The Next StepResources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →Once You Understand This, You'll Stop Working Past 58
Jun 200:15:01Tap to summarizeFind out if you're working longer than you need to: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46147Get free access to the same professional retirement planning software we use with our clients: https://www.demarsfinancial.com/right-expressCan you retire at 58? Most 58-year-olds who keep working "just one more year" aren't making a careful decision — they're avoiding one. The math may already work. The plan may already support the life you want. But there's a different account most people never measure, and it's draining whether you track it or not.In this video, Taylor walks through the three tests that actually determine whether stopping work at 58 is possible — financial readiness, identity readiness, and Wealth Span readiness — using The WealthSpan Framework, the same process the team at Demars Financial Group uses to help clients in their late 50s and early 60s decide whether they're truly ready to retire.If you've saved well — somewhere in the range of $2 million to $5 million — and you keep telling yourself another year of work is the responsible play, this episode is for you. Taylor walks you through the five planning pillars of The Retirement Readiness Roadmap, why most retirement plans miss the most important account you have, and the one question 50 years of clients have told him they wish they'd asked sooner.🔎 THIS VIDEO IS FOR YOU IF YOU'RE ASKING:- Can I retire at 58 with $3 million?- How do I know if I'm ready to retire early?- What is the real cost of working past 58?- How do I decide between retiring now or working a few more years?- What does a real retirement readiness plan look like?- How much do I need to retire comfortably in my late 50s?⏱️ TIMESTAMPS00:00 — The silence around the retirement decision01:15 — Meet Dan and Linda (a real retirement story)03:00 — Why most 58-year-olds keep working "one more year"04:30 — Lifespan vs. health span vs. Wealth Span explained07:00 — Test #1: Financial readiness (The Retirement Readiness Roadmap)09:00 — Test #2: Identity readiness — who are you when you stop working?11:30 — Test #3: Wealth Span readiness and how to evaluate it13:00 — The retirement tradeoff that changed Dan's mind14:30 — What 50 years of retirees actually regretResources:Website: https://www.demarsfinancial.com/Phone: (509) 536-9556Schedule an introduction call with Taylor: https://bit.ly/demarspodcastCheck out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirementTaylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0eDisclaimer: 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.
Transcribe →