How Money Works

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...

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 r...

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 disc...

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....

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 hi...

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...

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 discus...

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 c...

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 matt...

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 st...

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...

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...

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, es...

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 share...

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 rig...

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...

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 inve...

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 la...

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 th...

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 be...

Ever wonder what other people talk about with their financial advisors? A new survey of nearly 400 experienced advisors reveals the biggest concerns, challenges, and financial goals their clients are facing today. In this episode, Craig and Jennifer Moser break down the results and compare the findings to what we see at Maestro Wealth Advisors. We'll unpack insights on why 52% of clients are prima...

There are a lot of things to consider when it comes to investing in real estate, especially if you're buying a rental property. Not only are there tax implications that come with buying and selling real estate, but there is also the labor element that comes with being a landlord if you choose to buy a rental property.   In this episode, Craig and Jennifer will dive into the realities of real estat...

When you think of retirement planning, saving and investing are two of the things that likely come to mind first. That's why many people are unprepared for the next phase of the plan, which is the shift to distribution. Knowing how much income you'll need and where that money is pulled from is incredibly important for retirement success so today we're talking all about this essential component of...

Kids and grandkids often play a big role in financial plans. Let's talk about some of the common scenarios we see where the future generations somehow come into play during the retirement planning process. Find out how Maestro Wealth typically advises people in these situations. This episode will explore challenges like supporting adult children as you approach retirement, preparing for future hea...

It's been an incredibly busy week since the Trump administration took office and investors are wondering how the current economic landscape might be changing.   As we navigate through an era of volatility, understanding what changes are happening is crucial for making informed financial decisions. Most of the focus is on the recent changes in government policies and their implications on the econo...