How Money Works

141 Episodes

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Is DIY Financial Planning Costing You?

2026-02-0525:28

Doing it yourself feels empowering, until the margin for error disappears. Craig and Jennifer look at why many people stick with a DIY financial approach longer than they should, and how retirement quietly changes the stakes. Small decisions start to matter more, timelines get longer, and mistakes get harder to unwind. The real question isn't can you do it yourself, it's should you? Here's some of what we discuss in this episode: 🛠️ DIY Mindset: Why people choose to manage money themselves ⚠️ Common Pitfalls: Where DIY strategies often fall short 📉 Real-Life Mistakes: How small errors become costly 🤝 Advisor's Role: What experience adds beyond investments ⏳ Living Longer: Why longevity multiplies financial risk 🧭 Planning Matters: Turning uncertainty into structure Contact Maestro Wealth: Web: https://maestrowealth.com/ Email: info@maestrowealth.com Phone: 336-448-1086

Navigating Financial Changes in 2026: Retirement, Taxes & Medicare

2026-01-1524:45

Craig and Jennifer dive into the key financial updates for 2026 and how they can affect your retirement. They discuss Social Security COLAs, Medicare premium increases, new tax deductions for seniors, and smarter ways to use Roth conversions and catch-up contributions. This episode highlights why proactive tax and income planning matters and how small decisions today can make a big difference in retirement. Here's some of what we discuss in this episode: 🏥 Healthcare Costs – Rising medical expenses in retirement 💳 Medicare Premiums – How income affects what you pay 🧾 Tax Deductions – New charitable and senior deduction rules 📈 Catch-Up Savings – Expanded contribution limits for older workers 🧠 Tax Strategy – Planning withdrawals before retirement begins 📜 Secure Act 2.0 – Roth rules changing retirement contributions Contact Maestro Wealth: Web: https://maestrowealth.com/ Email: info@maestrowealth.com Phone: 336-448-1086

Retirement Sabotage: The Mistakes That Add Up

2025-12-3126:27

Most retirement mistakes don't happen all at once; they happen quietly and over time. In this episode, Craig and Jennifer walk through the most common ways people unknowingly sabotage their retirement, and how to make sure it doesn't happen to you. Tune in to learn how small, proactive planning choices can protect confidence, income, and peace of mind over the long run. Here's some of what we discuss in this episode: ⚠️ Retirement Sabotage: Quiet mistakes that compound 📉 Market Volatility: Why reacting hurts long-term plans ⏳ Social Security: Timing decisions with lasting impact 💼 Job Assumptions: When work ends sooner than expected 🎯 Financial Strategy: Replacing hope with structure Contact Maestro Wealth: Web: https://maestrowealth.com/ Email: info@maestrowealth.com Phone: 336-448-1086

Taking Out the Financial Trash in Your Retirement Plan

2025-12-1826:26

As retirement gets closer, the small financial issues you've ignored can start to pile up fast. In this episode, Craig walks through the most common "financial trash" people carry into retirement, and how to start the process of cleaning it up. What financial clutter should you clean up before retiring? If you want a clearer, more confident path into retirement, this episode shows where to start. Here's some of what we discuss in this episode: 🧹 Cash Flow Cleanup: planning income and mortgage payments 💳 Debt & Risk: reducing financial pressure before retirement 💤 Lazy Money: cash losing ground due to inflation 🏦 Pension Choices: evaluating pension versus lump sum decisions 🏢 Life Changes: navigating company sales and job transitions Contact Maestro Wealth: Web: https://maestrowealth.com/ Email: info@maestrowealth.com Phone: 336-448-1086

Safeguard Your Legacy: Avoiding Common Errors in Estate Planning

2025-12-0425:16

It's easy to avoid thinking about the realities of aging and the challenges it can bring. But, overlooking the true costs of healthcare and assistance can leave even the best financial plans vulnerable. Jennifer is joined by her son (and financial advisor) Cameron to explore why these risks are so commonly underestimated and what it means for your future security. Are you truly prepared for the hidden costs of growing older? Tune in the find out. Here's some of what we discuss in this episode: 📛 Designations Matter: why beneficiary forms override your will 💸 Planning for Expenses: the danger of ignoring future healthcare and long-term care costs 🔄 Update Your Heirs: outdated beneficiaries that send assets to the wrong person 🏡 Don't Gift Too Soon: tax traps when transferring property while alive 🤝 Avoid Family Conflict: how communication prevents litigation Contact Maestro Wealth: Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin Phone: 336-448-1086

How Money Works: Planning, Fables, and Real-Life Finance

2025-11-2023:34

The stories we believe about money often shape our choices more than the numbers do. In this episode, Craig and Jennifer explores these "financial fables," using real-life situations to reveal how hidden beliefs influence the way people plan. The team also tackles listener questions and offers smart portfolio strategies to balance risk and reward at every life stage. Here's some of what we discuss in this episode: 📘 Financial Fables: classic stories that reveal modern money lessons 🎓 Student Loan Decisions: balancing generosity with retirement readiness 🏡 Inheritance Reality: why counting on future money is risky 😨 Market Fear: handling volatility without making emotional mistakes 📊 Smart Strategies: financial planning and investment fundamentals Contact Maestro Wealth: Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin Phone: 336-448-1086

You Made It to Retirement… Now Don't Screw It Up!

2025-11-0620:05

You've worked for decades, saved diligently, and finally reached retirement, now comes the hard part: not screwing it up. Craig and Jennifer share the most common post-retirement mistakes people make and explain why having a solid, flexible plan is far more important than a collection of accounts or hot stock tips. Once you've already won the race, don't jump back in. Here's some of what we discuss in this episode: 🏗️ Build a Strong Foundation: secure income before chasing returns 💡 New Opportunities: evaluating investments with clarity, not emotion 🧩 Comprehensive Planning: coordinating taxes, income, and estate goals 🔁 Adapting to Change: adjusting your plan as life evolves 💰 Tax Strategies: keeping more of what you've earned Contact Maestro Wealth: Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin Phone: 336-448-1086

The Retirement Road Trip: Don't Drive Without a Plan

2025-10-1625:16

Most people will spend hours planning a vacation: researching routes, mapping stops, and budgeting for the trip. But when it comes to retirement, many people set off without a roadmap. Today we'll use the great American road trip as a powerful analogy for planning the retirement journey. Craig and Jennifer break down the essentials: knowing your destination, calculating the cost of the trip, and choosing the right route to get there. Just like with travel, unexpected detours will pop up, like health issues, market downturns, or surprise expenses. With a clear plan and the right guide, you can navigate those bumps without losing sight of your goal. Here's some of what we discuss in this episode: 🗺️ Decide your retirement destination before you hit the road 💰 Know what the trip will cost and how you'll pay for it 🛣️ Map your route: income, risk, and tax planning 🚧 Be ready for roadblocks like healthcare or market surprises Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

The 10-Year Retirement Countdown: Ages 55–65

2025-10-0226:01

The decade between 55 and 65 is one of the most critical stretches in your financial life. It's the runway leading into retirement, and the choices you make in these years can set the tone for the decades that follow. In this episode, Craig and Jennifer break down the key decisions that every pre-retiree needs to think about before taking the leap. Today, you'll hear how to decide what really matters in retirement, why "knowing your numbers" is more important than ever, and how healthcare costs often surprise people who assume Medicare will cover everything. This decade is one where most people start getting serious about retirement and we want to make sure you know where to focus. We won't sugarcoat the fact that there's a lot to plan for, but we'll also offer a clear process that helps you step into retirement with confidence. Here's some of what we discuss in this episode: 🎯 Decide what matters most before you retire 📊 Know your numbers: income, expenses, and gaps 🏥 Prepare for healthcare and long-term care costs 📈 Build inflation into your plan so your lifestyle keeps up 🔄 Expect change and create flexibility in your retirement strategy Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

Harder Than It Looks: Retirement Planning's Hidden Challenges

2025-09-1823:57

Some financial decisions appear simple on the surface until you start working through the details. In this episode, Craig and Jennifer break down common areas of retirement planning that are harder than they look and explain why professional guidance makes all the difference. Each of these areas can feel overwhelming if you're going it alone, but with the right plan, they don't have to be. They start with Social Security, where the choice of when to file isn't just about picking an age, it's about understanding penalties, income limits, and how benefits fit into your larger income plan. From there, they explore the real meaning of diversification, showing why simply owning dozens of funds doesn't guarantee balance. Join us and get better prepared for the road ahead in retirement. Here's some of what we discuss in this episode: 🕰️ Social Security timing: Penalties and income rules can surprise you 📈 Real diversification: Beyond the typical pie charts 🔄 401(k) rollovers: Get them right or risk major headaches 🧩 Simple vs. complex: What looks easy can derail without a plan Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

Misconceptions That Put Business Owners at Risk

2025-09-0425:55

Owning a business can be one of the best wealth-building opportunities, but it also comes with unique challenges, especially when it's time to think about retirement. Too many business owners assume their company alone will carry them through, but as Craig and Jennifer explain, that's often a dangerous misconception. In this episode, they share common myths business owners believe and the risks of relying solely on a business for future security. They discuss why saving outside your business matters, how to think about retirement plans like SEPs and 401(k)s, and why things like HSAs and Social Security shouldn't be overlooked. Real-world stories, from clients who faced unexpected tax bills to cautionary lessons about family transitions, bring these lessons to life. If you've poured your heart into building a company, don't let misconceptions put your retirement at risk. Here's some of what we discuss in this episode: 🏢 Business ≠ retirement plan, outside savings are essential 🏦 Owners can benefit from 401(k)s, SEPs, and HSAs just like employees 📊 Not every business is sellable, so don't assume top-dollar value ⚖️ A plan balances business success with personal financial freedom Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

Are You Wealthier Than You Think?

2025-08-2125:53

Could you be wealthier than you think once all your accounts and assets are tallied? In this episode, Craig and Jennifer explore the surprising ways your financial standing might be stronger than you realize. But first, they kick things off with a mid-year business owner checklist, covering everything from retirement plan reviews to tax strategies, cash flow, and succession planning. Then, you'll hear real-world examples of why emergency funds matter, how saving consistently builds long-term wealth, and why even small contributions add up over time. The message? Building wealth comes from intentional, consistent habits. Along the way, Craig and Jennifer share simple shifts that can help reveal hidden strengths, avoid costly mistakes, and set you on a clearer path toward lasting financial security. Here's some of what we discuss in this episode: 📋 Mid-year checklist for business owners 💰 Retirement plan "right-sizing" strategies 🛑 Common tax pitfalls and how to avoid them 💵 Why emergency funds matter so much ⏳ The compounding effect of long-term savings Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

Redefining "Safe Money:" The Truth About Cash, CDs, and Risk

2025-08-0711:48

Everyone talks about "safe money," but what does it actually mean and how much should you have? In this episode, Craig and Jennifer unpack the overused (and often misunderstood) concept of safe money. They explain what it really means to keep your money protected from loss, why liquidity is often more important than growth, and how safe money fits into the bigger picture of your financial plan, especially in retirement. You'll hear why some clients are sitting on $300k+ in cash or CDs and not realizing how little they're actually keeping after taxes and inflation. Plus, Craig and Jennifer walk through how to reposition that "safe" money for better tax efficiency and real purpose, whether you're building an emergency fund, entering retirement, or drawing income from a portfolio. You can be too safe and still go broke. The key is striking the right balance across your financial "buckets." Here's some of what we discuss in this episode: 🧊 Why liquidity can be more important than earning a higher interest rate 🛑 What "safe money" really means and common misconceptions 💵 The tax pitfalls of CDs and traditional savings accounts 🎯 Balancing safety, growth, and income throughout different life stages 🧠 The mindset shift between accumulation and distribution phases Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

The 5 Financial Pain Points You Can't Ignore

2025-07-1721:41

When it comes to retirement, most people have a few lingering fears, but some concerns come up time and again. In this episode, Craig and Jennifer break down the biggest pain points they hear from clients and explain what you can actually do about them. From running out of money to the anxiety of market crashes, this episode explores the emotional (and very real) weight of uncertainty. Craig shares how failing to run the numbers leads to unnecessary fear, while Jennifer outlines why taxes, healthcare costs, and long-term care are often overlooked until it's too late. They also talk about a less-discussed struggle: the fear of walking away from a steady paycheck and into the unknown. And if you think simply stashing money in CDs is a safe bet, it's time to rethink your plan. Today, we unpack how certain strategies can backfire and what to do instead. Here's some of what we discuss in this episode: 💸 The #1 fear most retirees won't admit 🏥 What long-term care actually costs—and who pays for it 💀 Death, taxes, and the rollercoaster of retirement 💡 Why doing nothing is the riskiest plan of all 📉 How market crashes can drain your nest egg faster than you think Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

The Five People You Meet Before Retirement

2025-07-0314:55

In the book The Five People You Meet in Heaven, each person the main character meets help him understand his life in a new way. Today, Craig and Jennifer talk about the five people you should meet before retirement, people who can guide your next chapter and help you retire with confidence, and purpose. After all, retirement isn't just about money, it's about strategy, mindset, and having the right people in your corner. Craig and Jennifer reveal the essential allies you'll want by your side before you retire, people who can help you avoid costly missteps, protect what you've built, and design a future that fits your life. You'll also meet the "bonus sixth person," a relationship that may just bring the most lasting fulfillment of all. If you're looking to retire on your terms, don't miss this insightful episode. Here's some of what we discuss in this episode: 🧭 Why you may want a retirement income specialist 📜 Estate planning mistakes you definitely want to avoid 📋 How insurance planning prevents retirement surprises 💸 Differences between tax planning and tax preparation 🏋️‍♂️ The role a fitness instructor plays in retirement vitality Contact Maestro Wealth: Web: https://maestrowealth.com/ Email: info@maestrowealth.com Phone: 336-448-1086

What Game Shows Teach Us About Retirement

2025-06-1913:08

Retirement planning isn't always a smooth ride, and sometimes it can feel more like spinning a wheel or picking a mystery box. In this playful but practical episode, Craig and Jennifer turn retirement planning into a game show, using iconic formats like The Price is Right and Are You Smarter Than a Fifth Grader? to unpack the real-life financial decisions people face every day. Underneath the fun lies serious wisdom. Craig and Jennifer discuss why focusing only on "the pile of money" misses the bigger picture, how the timing of your pension or Social Security benefits can make or break your plan, and why cash flow, not just account balances, is what truly matters. You'll also hear their take on simplifying your strategy so it works for you in real life, and not just on paper. Here's some of what we discuss in this episode: 🎯 Why your "magic number" might be misleading 🏦 The real cost of pre-tax retirement savings 🧮 Social Security timing tricks that boost payouts 🧠 How to simplify your plan 🧾 What game shows can teach us about income planning Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

Retirement Mythbusters: Debunking the Biggest Financial Lies

2025-06-0522:30

Retirement planning comes with no shortage of conventional wisdom, but how much of it is actually true? In this eye-opening episode, Craig and Jennifer go full-on mythbusters mode to take down some of the most common financial planning myths that could seriously derail your future. From the illusion of simplicity ("all I need is a will") to dangerous assumptions about income, inheritance, and investment strategies, they expose how outdated thinking can cost you, sometimes for generations. It's a candid look at what real planning requires, especially if you're a business owner or navigating a complex life transition. With decades of experience, Craig and Jennifer guide you through the truth behind the myths, and the smarter steps you can take now to protect your lifestyle and legacy. Here's some of what we discuss in this episode: 💼 Why most business owners don't really retire 🧾 Is a financial analysis just as good as a plan? 🛑 Why "my spouse will be fine" could be a costly assumption 🧠 Learn from others' financial mistakes, without living them yourself ⚖️ Debunking common "rules" and what to consider instead Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

What to Do When Markets Get Messy

2025-05-1517:20

When the market takes a dip—or just feels unpredictable—it's natural to want to do something. But when it comes to your retirement plan, sometimes the smartest move is actually to pause. In this episode, Craig and Jennifer share a calm, methodical approach to navigating difficult markets without panicking, overreacting, or making costly mistakes. Tune in if you've been looking at your portfolio lately and wondering, "What should I do now?" You'll learn why the duo recommends a "bucketing" strategy to separate near-term needs from long-term growth, how to think about volatility in real dollars (not just percentages), and what questions to ask if you're worried about whether your plan can hold up. Plus, Craig explains how sensitivity analysis helps you stress-test your portfolio so you can stop guessing and start planning with clarity. Here's some of what we discuss in this episode: 📉 Why the worst reaction to market drops is overreaction 🧺 How "bucketing" your money may protect your peace of mind 🧠 Why emotional investors often derail their own plans 📊 What a sensitivity analysis tells you about your portfolio 💵 The real danger of needing money from volatile investments Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

Should You Retire During a Volatile Market?

2025-05-0119:54

Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and fears for the economy right now. Retiring in a down market can feel like stepping onto a shaky bridge, but with the right structure, it doesn't have to be. In this episode, Craig and Cameron unpack strategies for financial stability and peace of mind- like smart diversification and tuning out the media noise- even when the headlines are shouting panic. They cover how to build a resilient portfolio using the "three-bucket" strategy, how to plan for consistent income even if the market drops, and why risk, volatility, and media noise don't have to define your retirement. You'll also hear a powerful real-world example of how sequence-of-return risk can derail a plan and what to do instead. Here's some of what we discuss in this episode: 📉 The real risk of retiring during a downturn 📊 Understanding the risk in your portfolio 🧠 Control what you can and ignore the noise 🛡️ Real-world strategies for building a resilient income plan Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

Don't Make These Bad Assumptions About Retirement

2025-04-1721:54

When it comes to your financial future, a few bad assumptions can lead to costly mistakes. In this episode, Craig and Jennifer break down some of the most common (and dangerous) misconceptions people have about retirement planning. We'll discuss why a Roth IRA is an account—not an investment, the truth about delaying Social Security benefits, and why assuming your pension lump sum is always the best option might not work for you. We'll also talk about the implications of tax brackets and how tax laws could shift dramatically if the Tax Cuts and Jobs Act (TCJA) expires. With more than 30 years working with clients, we can help you make more informed financial decisions and avoid bad assumptions with your retirement plan. Here's some of what we discuss in this episode: 🔍 Roth IRA Misunderstanding – It's not an investment; it's a tax wrapper 📈 Social Security Timing – Delaying isn't always the best answer 💼 Pension Decisions – Lump sum vs. lifetime payments: What's the right move? 📉 Bond Risks – Rising rates can hurt your portfolio more than you think Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/ Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

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