TaylorMade Retirement with 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.
Things Everyone “Knows” About Money (That Might Not Be True)
Some financial advice gets repeated so often that people stop questioning whether it actually makes sense. But when it comes to retirement, could following conventional wisdom sometimes do more harm than good?
In this episode, Taylor puts 10 popular money rules to the test and challenges some familiar financial assumptions. He explains why conventional advice doesn't always work for everyone and how a personalized strategy can help you make decisions that fit your goals. Plus, stick around for a few personal updates and an introduction to the newest members of the Demars Financial Group team.
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I’m 58 With $4 Million. Can I Retire and Spend $15K a Month?
Work with Taylor: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46326
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Taylor's Newsletter: https://demars-financial-group.ck.page/0457622ab4
Can you retire at 58 with $4 million and spend $15,000 per month? In this retirement case study, Taylor breaks down whether a $4 million portfolio can support an early retirement while funding an annual lifestyle of $180,000.
Retiring at 58 creates several planning challenges that do not exist with a traditional retirement. You need to...
If You’re 55 With $3M+, Watch This BEFORE You Retire
Work with Taylor: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46320
See a $10,000 Sample Plan Here: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46253
Taylor's Newsletter: https://demars-financial-group.ck.page/0457622ab4
Today we're breaking down how to avoid costly mistakes in your retirement planning by timing your financial moves correctly as you approach age 55.
Retirement planning at 55 requires careful coordination of your assets, especially when managing employer stock vesting and Roth contributions. Making these adjustments at the wrong time or for...
Financial Moves That Aren't as Simple as They Seem
Some financial decisions look complicated and turn out to be pretty simple. Others look simple and are anything but. Today we're taking a list of common money moves and sorting them into two piles: harder than it looks, or easier than it looks. The goal is to help retirees know where a simple solution may work and where an “easy button” can create unnecessary risk.
Here’s what we discuss in today’s show:
🧭 Social Security Needs Context: The right age depends on the situation
🔄 Rollovers Can Be Simple: Bu...
The Exact Moment You No Longer Need To Save For Retirement
Work with Taylor: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46313
See a $10,000 Sample Plan Here: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46253
Taylor's Newsletter: https://demars-financial-group.ck.page/0457622ab4
Can you retire at 60 with $3 million or $4 million saved, or should you work one more year? The answer may surprise you. Working longer can add millions to your projected retirement wealth without necessarily improving the retirement lifestyle you can afford.
In this episode, Taylor walks you through a hypothetical couple...
The Tax Planning Window Is Open (But Not for Long)
Most people don't think about taxes until they're sitting down to file, and by then, most of the best opportunities are gone. The moves that actually lower your tax bill usually have to happen before December 31.
In this episode, Taylor walks through several strategies that may be worth considering before December 31. If you’re proactive now, you can avoid having to fix missed opportunities next spring.
Here’s what we discuss in today’s show:
💝 Consider Charitable Giving: Donor-advised funds may create flexibility
🧾 Check Withholding: Avoid surprises or unnecessary overpayments<...
If You Only Watch One Pre-Retirement Video, Make It This
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Get The $10,000 Sample Plan Here: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46253
What should you do before retiring? In this video, Taylor walks through the major financial decisions to review before leaving work so you can enter retirement with a clearer plan for your income, investments, taxes, healthcare, and lifestyle.
Pre-retirement planning involves more than reaching a specific savings goal. You need to understand how much you expect to spend, where...
May the Force Be With Your Financial Plan
What can a galaxy far, far away teach us about retirement planning? More than you might think! Taylor brings his love of Star Wars into the financial world, exploring how familiar lessons from Jedi Masters, the Force, and even the Death Star apply to preparing for retirement. From following through on financial goals to identifying potential weaknesses in your strategy, this episode offers a fun perspective on building a stronger plan.
Here’s what we discuss in today’s show:
🌌 Trust the Plan: Let strategy guide financial decisions
⚔️ Take Action: Good intentions r...
Why Everything Changes After $3M in Retirement Savings
Work with Taylor: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46298
Get The $10,000 Sample Plan Here: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46252
Why does retirement planning change after you reach $3 million in savings? In this video, Taylor explains how a larger retirement portfolio can shift the focus from simply accumulating more money to making better decisions about income, taxes, risk, spending, and wealth preservation.
Retiring with $3 million can provide significant flexibility, but it does not eliminate the need for a plan...
Why Your Financial Plan Shouldn't Feel Like IKEA Instructions
Almost everyone has an IKEA story, whether it's getting lost in the showroom, leaving with way more than you planned, or spending a Saturday afternoon arguing over an Allen wrench. It turns out the whole experience, from the parking lot to the living room, has a lot in common with financial planning.
Here’s what we discuss in today’s show:
🗺️ Follow the Right Planning Sequence — Start with lifestyle and goals first
💰 Watch How Costs Can Stack — Income decisions can trigger tax consequences
🔍 Understand the Hidden Incentiv...
If I Started Planning For Retirement in 2026, I'd Do This
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Get The $10,000 Sample Plan Here: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46252
If Taylor were starting retirement planning in 2026, this is the process he would follow. In this video, he walks through the key steps for building a retirement plan, from estimating future expenses to creating an investment and income strategy that can adapt over time.
Planning for retirement is about more than reaching a specific savings goal. Your retirement age...
Should Real Estate Be in Your Retirement Plan?
Real estate can sound like an attractive way to generate retirement income, but is owning a rental property really worth it? In this episode, Taylor breaks down the differences between buying investment property and investing through a REIT, along with the pros, cons, costs, and risks that can come with each. He also explains why it’s important to look beyond the potential income and make sure any real estate investment actually fits into your broader retirement plan.
Here’s what we discuss in today’s show:
🏠 Rental Property — Understand the real respon...
I’m 55 With $3,000,000 Saved. Can I Retire?
Work with Taylor: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46284
Get The $10,000 Sample Plan: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46251
What could it actually look like to retire at 55 with $3 million saved? In this retirement case study, Taylor breaks down the key numbers, risks, and planning decisions that can determine whether an early retirement plan is sustainable. If you’re asking, “Can I retire at 55?” or “Is $3 million enough to retire?”, this video will help you understand what should be considered before leaving wo...
Conversation Starters: Questions Worth Asking About Your Financial Future
Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. In this episode, we share some conversation starters that can help you think beyond the numbers and focus on what you want retirement to look like. From how you’d spend your time if money were no object to the goals you’d regret putting off, these questions can reveal a lot about what your retirement plan should be built to support.
Here’s what we discuss in today’s show:
💭 Define Succ...
5 Things I Wish Every Couple Knew Before Retirement
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Retirement can change a relationship in ways most couples never expect. In this video, Taylor shares five important lessons about retirement planning for couples and the things every couple should discuss before retirement. Preparing for retirement involves more than building a portfolio. It also means preparing for changes in your routines, roles, spending, identity, and relationship.
One...
Retirement Reality Check: 2026 Version
Retirement planning in 2026 looks very different from what prior generations experienced, and some of the biggest shifts have little to do with investment returns. In this episode, Taylor gives you 5 realities you need to be aware of in 2026 to build toward a successful retirement. Retirement isn't the same finish line it used to be, and pretending otherwise makes it harder to plan for. The realities change. A good plan should be able to change with them.
Here’s what we discuss in today’s show:
🏥 Healthcare Costs: Planning for expenses that can ris...
Everyone Is Wrong About the 4% Rule
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Download a sample of our $10,000 retirement plan: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46249
The 4% rule is one of the most widely repeated ideas in retirement, but following it blindly could lead to a retirement plan that doesn't fit your actual life. Taylor breaks down what the 4% rule retirement strategy gets right, where the 4 percent rule can fall short, and why your personal retirement withdrawal strategy deserves more thought than simply multiplying your...
Picking a Retirement Date
"When can I retire?" might be the question we get asked more than any other. Some people are chasing an age. Others are chasing a number. Today, Taylor breaks down what actually determines the answer. The date on the calendar or the number in the account might feel like the finish line, but neither one tells the whole story. That's what the planning process is actually for. Taylor also explains why a better approach is to work backward from the life you want, the income you’ll need, and the goals that matter most to you.
He...
When You Retire With $2M+, Tell No One, Here’s Why
Work with Taylor: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46250
Download a sample of our $10,000 retirement plan: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46249
If you’ve built up $2 million or more for retirement, you may naturally want to share that milestone with the people closest to you. But once others know how much you have, relationships and expectations can change in ways you never anticipated. That’s why you may want to keep your retirement net worth private. Retirement privacy can matter just...
The Word "Safe" Is Doing a Lot of Work in Your Portfolio
“Safe” sounds reassuring, but in retirement planning, it can sometimes create more questions than answers. Taylor explores why people often gravitate toward certainty and what that instinct can reveal about the bigger concerns they have around retirement. He also explains how a clear financial plan can help replace vague worries with greater confidence and clarity. If you’ve ever wondered whether your money is truly positioned to help you sleep better at night, this episode offers a helpful way to think about what “safe” really means.
Here’s what we discuss in today’s show:
🛡️ Def...
Early Retirement Is Hard Until You Build Systems Like This
Work with Taylor: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46243
Download a sample of our $10,000 retirement plan: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46242
Early retirement gets much easier when you stop treating every financial decision as a one-time judgment call and start building Early Retirement Systems that tell you what to do before uncertainty hits.
Taylor breaks down How to Pull the Trigger on Retirement by creating repeatable systems for income, spending, investments, taxes, and lifestyle. Whether you're trying to...
Retiring Early Isn't Always a Choice- Here's What the Data Shows
Most people plan to retire around 65. New research shows most people actually retire around 62 and it's often not by choice. Today we're digging into why that gap exists and what it means for your plan.
Here’s what we discuss in today’s show:
⚠️ Early Retirement: Why plans may shift unexpectedly
📉 Market Risk: Protect against poor early returns
🧾 Tax Buckets: Coordinate taxable and retirement assets
🏥 Healthcare Costs: Plan for the pre-Medicare gap
💼 Part-Time Work: Reduce pressure on savings
🔎 Tax Strategy: Use lower-income years wisely
Episode Re...
How to Fix Your Retirement Plan (Before It's Too Late)
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Get the full sample plan: https://www.demarsfinancial.com/sample-plan?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46235
A retirement plan isn't something you create once and forget. Even a well-built plan can develop hidden weaknesses over time. In this episode, Taylor walks through the most important diagnostic tests he uses to uncover problems before they become expensive mistakes.
He covers retirement plan diagnostic tests, reveals the 5 cracks in retirement plans that can quietly derail your retirement, and explains how a retirement...
The Fear of Running Out of Money in Retirement
Work with Taylor: https://taylor-demars.showrunner.one/r/7a25a8f6cb18
One of the biggest challenges in retirement isn't building wealth—it's feeling confident enough to use it. The fear of running out of money retirement is incredibly common, and it often affects people who have saved diligently for decades. Even financially secure retirees can struggle with retirement psychology, making it difficult to enjoy the lifestyle they've worked so hard to achieve.
In this episode, Taylor explains why retirement spending fear is so powerful, why so many people are too scared to spend retirement sa...
Retired, But Still Clocking In — Why?
Retirement doesn’t always mean walking away from work for good. For some people, continuing to clock in provides purpose, structure, connection, or simply a little extra confidence about what comes next. In this episode, Taylor explores why people often keep working beyond the traditional retirement age and how a well-built retirement plan can help separate the things you want to do from the things you feel you have to do.
Here’s what we discuss in today’s show:
👥 Work can provide connection, routine, and a sense of purpose
😟 Money worries can m...
My Honest Advice To Anyone Retiring With $2M+
My Honest Advice To Anyone Retiring With $2M+
Work with Taylor: https://www.demarsfinancial.com/start-here
Retiring with $2 million or more can create incredible opportunities—but it also comes with important financial decisions that can have a lasting impact on your lifestyle, taxes, and legacy. If you're thinking about retiring with 2 million or wondering how to retire with 2 million, this episode walks through the key decisions Taylor believes matter most before and after retirement.
He explains how to build a sustainable 2 million retirement strategy by creating a reliable retirement income plan and focusing on...
The 5 D's of Retirement Planning
Based on a recent article from Kiplinger, there are five keys to a retirement plan that actually holds up over time. They all happen to start with the same letter — which either means it's a great framework or someone really wanted it to work out that way. Taylor explores how these five areas provide a practical framework for evaluating the strength and sustainability of your retirement strategy. How well does your plan address all five?
Here’s what we discuss in today’s show:
🧩 Diversification: Build income across multiple tax buckets
⏳...
Just Retired at 63? It's the Most Dangerous Year of Your Financial Life - Here's Why
Get started on your retirement strategy here: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46210
📋 The Retire Once Guide (free) — find out whether you're actually ready to pull the trigger: https://www.demarsfinancial.com/retire-once-guide
Master your first year of retirement by navigating crucial financial decisions. Learn how to manage income and taxes to avoid costly mistakes.
The first year of retirement is a critical period that sets the foundation for your long-term security. This episode focuses on five major decisions that converge during this time, specifically designed for t...
The Danger of Being Well-Informed The Financial World
Having more financial information at your fingertips should make decisions easier, but often, it does the opposite. In this episode, Taylor explores why constant access to research, opinions, and advice can leave investors overwhelmed or falsely confident. You’ll also hear how to evaluate what you’re hearing and recognize when more information is no longer helping. Are you truly informed, or has all that research made it harder to move forward?
Here’s what we discuss in today’s show:
🔍 Research Overload: More information can create confusion
📰 Media Incentive...
I'm A 3rd Gen Advisor. Here's What I Tell Every Client At 62
Get started on your retirement strategy here: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46203
📋 The Retire Once Guide (free) — find out whether you're actually ready to pull the trigger: https://www.demarsfinancial.com/retire-once-guide
Most retirement advice was built to help you grow your money. Almost none of it was built to help you actually use it.
Taylor is a third-generation financial advisor, and after watching this industry change from the inside since his grandfather started his firm in 1975, here's what he's learned: the word "financial advisor" can me...
How to Plan a Guilt-Free Vacation in Retirement
Dreaming of big trips in retirement but worried they’ll derail your nest egg? Travel is one of the biggest goals people have for retirement, but actually spending the money can bring more anxiety than excitement. In this episode, Taylor explains how a thoughtful retirement plan can permit people to enjoy the experiences they have spent decades saving for. Tune in to learn how to permit yourself to travel boldly while keeping your retirement on track. It’s time to learn how to spend intentionally and enjoy retirement without constantly second-guessing every trip.
Here’s what we dis...
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 ret...
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 timeli...
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 ha...
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...
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 grow...
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...
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 ot...
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 spen...
The IPO Buzz- What Hopeful Retirees Actually Need to Know
SpaceX. 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 ret...
