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'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

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 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

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

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

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

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