TaylorMade Retirement with Taylor Demars, CFP®

Taylor Demars, CFP®
  • 5.0 (5)
  • INVESTING

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. 10H AGO

    Why You Can't Retire (Even When the Numbers Say You Can)

    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=46139 If you've done everything right — saved, invested, stayed in when markets crashed, built the kind of number that's supposed to make retirement feel obvious — and you still can't pull the trigger, your problem probably isn't money. It's that you're stuck in a system that was never built to help you actually leave work. In this episode, Taylor breaks down the two reasons financially-ready people stay stuck in "one more year": the internal one almost no one names, and the structural one almost no advisor will tell you about. He walks through Robert's story (92% confidence, still couldn't retire), Jim's story (one extra working year for $800/month after taxes), and the Purpose-Plan-Portfolio framework we use with clients to actually answer the question a spreadsheet never can. If your retirement plan stops at the math, you're getting half a plan. 📌 TOPICS COVERED → Why a 92% retirement confidence score still leaves people stuck → The cultural script that quietly trains high achievers to keep working past "enough" → The concept the financial industry never taught you: how to recognize sufficiency → Why most advisor meetings end at the math — and what's missing after that → How "one more year" can erode 70%+ of its expected value once taxes, IRMAA, and pension quirks stack up → The asymmetric risk most retirement plans completely ignore → The Purpose → Plan → Portfolio sequence (and why most advisors run it backwards) → What permission actually feels like when retirement is built in the right order → Why 51% of retirees over 60 wish they'd retired sooner — by an average of 4 years → The window for active retirement most people don't realize is closing 00:00 The "One More Year" Trap  00:38 Robert’s Story: Overqualified but Unconfident  02:03 The Five Types of Wealth & the "Busy" Trap  04:23 Reframing "Enough": Is it enough for what?  05:07 Why the Financial Industry fails at "The Landing"  06:22 Jim’s Story: The real cost of staying one more year  08:05 The Risk of Retiring Too Late vs. Too Early  09:14 The Framework: Purpose, Plan, Portfolio  11:50 A 50-Year Family Legacy in Financial Planning  13:33 Why you should believe the math 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.

    15 min

  2. 5D AGO

    Mailbag: PTO, Vacation Pay & Social Security

    A listener question came in with a deceptively simple retirement question: Should you start Social Security right away if you don’t actually need the income yet? Taylor explains why the answer involves much more than math, touching on PTO, retirement lifestyle, flexibility, and long-term planning decisions. Before you claim a single dollar, make sure you’re not walking into a Social Security timing trap. Here’s what we discuss in today’s show: 💸 Social Security Triangle: Three ways to evaluate timing 🧠 Psychology Matters: Confidence changes spending habits 🏖 PTO Test Drive: Practice retirement before retiring 🛡️ Survivor Planning: Protect the surviving spouse 🔁 Regret Risk: Early claiming limits 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.

    11 min

  3. MAY 19

    At 60 With $1.5M? You're Beating The $5M Retirees

    Taylor has seen retirees with $5 million feel broke and retirees with $1.5 million feel free. The difference isn't their portfolio — it's five planning pitfalls that smart savers make over and over. In this episode, he walks through the 5 retirement pitfalls he sees every week as a Certified Financial Planner working with pre-retirees. If you're within 5 years of retirement and sitting on a solid nest egg, these are the blind spots that quietly decide whether the next 30 years feel abundant or anxious. He also shares the bonus pitfall most advisors never mention- the one that has nothing to do with your portfolio but determines whether retirement is the best chapter of your life or the loneliest. Watch next: How the Retirement Readiness Roadmap works https://youtu.be/iQB5tdDXuc8 0:00 Why more money doesn't always mean a better retirement 1:15 Pitfall #1: Picking tools before drawing the blueprint 2:55 Pitfall #2: "You're fine" isn't a retirement plan 4:25 Pitfall #3: The silent partner (Uncle Sam) you forgot about 7:20 Pitfall #4: The stress test most plans skip 8:45 Pitfall #5: The accumulator mindset that robs you in retirement 10:45 Bonus: The ceiling of YouTube-only planning 11:10 How the Retirement Readiness Roadmap works 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.

    12 min

  4. MAY 14

    If Financial Tools Had Yearbook Awards

    Graduation season is here, and we’re handing out “class superlatives” to popular retirement tools and strategies. Taylor hands out “yearbook awards” to some of the most talked-about financial tools and strategies and breaks down where common financial advice can fall short. Tune in to learn which strategies deserve a spot in your retirement yearbook, and which ones might be holding you back. Here’s what we discuss in today’s show:  🎓 HSAs Deserve More Love: Triple tax advantages make them incredibly powerful 💸 Dividend Chasing Has Tradeoffs: Higher payouts can create tax and growth issues 📄 Fine Print Matters: Variable annuities often come with hidden complexity and costs 🛑 Cash Isn’t Free: Sitting on too much idle money can quietly drag down returns 🧾 Taxes Confuse Everyone: Most people misunderstand how tax brackets actually work 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.

    14 min

  5. MAY 12

    $4 Million Saved, Here's How He Retired 5 Years Earlier

    A client came to us with $4 million saved, convinced he had to work until 63. His advisor of 12 years said he was on track. But when we rebuilt his plan from the ground up, we found three assumptions that were costing him five of his healthiest retirement years. In this episode, Taylor walks through the three specific changes we made to his plan, without adding a dollar to his savings or increasing his risk, that moved his retirement date from 63 to 58. If your plan uses flat spending projections, a default investment allocation, and no Roth conversion strategy, this video will show you what you might be missing. Watch next: The Truth About Retiring at 55 Versus 65 https://www.youtube.com/watch?v=7MqmdDqnWcQ&t=5s  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.

    19 min

  6. MAY 7

    My Investments Underperformed the Market - Should I Fire My Advisor?

    It’s one of the most common (and emotional) questions investors ask: If my portfolio isn’t keeping up with the market, is my advisor doing their job? On the surface, it feels like a simple comparison, but there’s usually a lot more going on beneath it. Taylor walks through how to think about performance the right way, why comparing your portfolio to “the market” can be misleading, and what actually matters when evaluating your advisor.  Here’s what we discuss in today’s show: 📊 Wrong Comparison: Portfolios ≠ the S&P 500 🎯 Goal Alignment: Strategy should match your needs ⏳ Long-Term Lens: One year doesn’t tell the story 🔍 Know What You Own: Simplicity builds confidence ⚖️ Second Opinion: Clarity beats guesswork 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.

    13 min

  7. MAY 5

    Pension Payout Decision: The Break-Even Analysis Most People Miss

    Should you take the pension lump sum or monthly payments? It's one of the most important — and most permanent — financial decisions you'll make in retirement. And most of the advice out there starts and ends with the math. Today, Taylor walks you through The Pension Clarity Test: three questions that go beyond the spreadsheet and help you make the pension decision you won't second-guess at 80. We'll cover how to evaluate a pension lump sum vs. monthly payments, the break-even math most people miss, the survivorship question every married couple needs to have, and the long-term reality of managing a lump sum through 30 years of market cycles. Whether you're sitting on a pension buyout offer, weighing a defined benefit plan payout, or just trying to figure out the right pension payout option before retirement, this episode gives you a framework that works for your life — not just your spreadsheet. WATCH NEXT 4 Mistakes To Avoid If You Have a Pension → https://www.youtube.com/watch?v=-tZ-CMku0CA 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.

    15 min

  8. APR 30

    Volunteering: The Best Investment You Might Make In Retirement

    Retirement isn’t just about stepping away from work. It’s about stepping into something meaningful. While most people focus on finances, the happiest retirees often find something deeper: purpose, connection, and a reason to get out of bed each morning. Today, Taylor explores how volunteering can transform retirement through your time, talents, and financial resources. You’ll hear real-life examples of why giving back might deliver the greatest return you’ll ever experience. Here’s what we discuss in today’s show: 🤝 Meaningful Connection: Build purpose and community ⏰ Time Well Spent: Turn hobbies into service 🧠 Use Your Skills: Impact others with experience 💰 Smart Giving: Maximize tax-efficient strategies 🎓 Lasting Impact: Create life-changing opportunities 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.

    13 min
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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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