The Pilot Money Guys

Is Medicare more confusing than it should be? If you're nearing retirement or thinking about leaving your job early, the healthcare piece can feel overwhelming and expensive. In this episode, we sit down with Cole Craven, co-founder of Move Health, to demystify the complexities of Medicare, healthcare costs, and early retirement planning. Listen in to learn how to time your enrollment correctly, w...

Does the phrase "long-term care" make you cringe? If so, you're not alone, but it's something we all need to think about eventually. In this episode, we sit down with Amy Arnett, VP of Insurance Solutions at DPL Financial Partners, who brings 36 years of experience in the insurance world to help us understand the evolving landscape of long-term care options. Listen in to learn why insurance isn't...

What is a Market-Based Cash Balance Plan (MBCBP), and why is it becoming the go-to retirement vehicle for pilots at major airlines like Delta? In this episode, we explain what an MBCBP actually is, how it's different from a pension or 401(k), how the investments work, and why pilots need to understand this model to make smart retirement decisions. You'll hear how funds are pooled, what kind of ret...

Can a mindset of gratitude really change your financial life? In this episode, we explore how the power of gratitude directly influences your outlook, your decisions, and ultimately, your financial success. You'll learn why slowing down to reflect on what you're thankful for can actually sharpen your focus and guide you toward a more meaningful retirement. Gratitude isn't just a feeling; it's a pr...

What if you're about to retire—and the market takes a nosedive?   For those in their 60s, looking toward retirement at 65, market volatility can feel like a punch to the gut. In this episode, we dive into how to confidently retire into a turbulent market, what lessons we've learned from past downturns, and why market dips aren't as rare—or as disastrous—as they seem. You'll learn why diversificati...

What do you do when the world feels unpredictable—and your financial future even more so? In this episode, we're diving into how pilots can mentally and financially prepare for uncertain times. From industry shake-ups to unexpected announcements from new governments, uncertainty is the only constant. But it's not the events themselves that rattle the market—it's the surprise factor. Listen in to l...

What good is wealth if you don't feel good? For busy professionals—especially pilots—maintaining health and nutrition while constantly on the go is a major challenge. In this episode, financial planner Mark Covell and his wife Adriana Covell, NBC-HWC , break down how small, intentional choices can lead to long-term health without feeling deprived. Adriana discusses the emotional connection we have...

Is direct indexing the right investment strategy for you? In this episode, Shawn Jaberzadeh, Co-Head of Enterprise Group at Dimensional Fund Advisors, breaks down how direct indexing works and when it might be a better fit than off-the-shelf investment options. We explore the key differences between standard and aggressive tax management, the role of separately managed accounts (SMAs), and how tax...

How can you teach your kids smart money habits without creating entitlement? In this episode, we dive into the essential lessons of raising financially responsible children. We explore the challenges first-generation wealth builders face, the guilt that often comes with financial success, and why many families lose their wealth by the third generation. You'll learn why discussing money early and i...

What does it take to transition from a TOPGUN fighter pilot to a bestselling author? Jack Stewart, a former U.S. Navy fighter pilot with 23 years of service, joins the show to share his fascinating journey from flying combat missions to writing gripping novels. With five books under his belt, Jack dives into how he develops his stories, navigates classified information, and handles rejection in th...

What does it take to redefine success and find joy in the journey, not just the results? In this episode, we're joined by Anthony Thompson, CEO of Thompson Consulting & Advising, a mindset and performance coach, and author of The Unhurried Life: Discovering Peace and Purpose through Faith-Filled Living.  With over 20 years of experience driving growth for Fortune 500 companies and non-profits, Ant...

Are you a young professional pilot looking to build a solid financial foundation? In this episode, we sit down with Lisa Rosenthal, COO, Nolan Clark, Associate Financial Planner, and Jon Schultz, Paraplanner, to discuss strategies tailored for young professionals aiming for long-term success. From understanding your unique financial behaviors to establishing savings priorities, you'll learn about...

Is the market overvalued and on the brink of an implosion? Join us as we dive into the intricacies of market valuation and investment strategies. In this replay episode, we're tackling some of the pressing questions about whether the market is currently overvalued, what market valuation metrics mean, and how investors can navigate these uncertain times. Take The Pilot Wealth Index to find out if y...

Are you contemplating whether to enlist the expertise of a financial advisor as your income rises? In this replay episode, we dive into the pivotal question: Should you hire a financial advisor? We discuss how to evaluate and question potential advisors, shedding light on the crucial questions you must ask before making a decision.  Take The Pilot Wealth Index to find out if you are on track for r...

What truly makes for a fulfilling and happy retirement? In this episode, we explore the key pillars of health, relationships, and finances to help you create a retirement plan that aligns with your values. From understanding how deliberate planning impacts retirement satisfaction to practical tips on managing health, maintaining relationships, and navigating retirement finances, this discussion of...

Have you received an inheritance recently? Or have you been thinking about how to leave one? In this episode, Kevin and Charlie tackle key questions about inheritance, covering everything you need to know—whether you're inheriting or passing on assets. From new legislation to strategies that help both you and your beneficiaries maximize your wealth, this episode will give you a powerful roadmap fo...

Curious about strategies pilots can use to maximize tax efficiency? In this episode, we're tackling hard-hitting tax numbers, future-focused savings strategies, and essential tax changes on the horizon, especially for those over 60. You'll learn the ins and outs of tax deductions, even on W-2 income, and tips for maximizing tax-efficient retirement income. We'll also cover the benefits of backdoor...

Should you get into real estate investing? In this episode, we sit down with former Top Gun Navy and Air Force fighter pilot—and current UPS pilot—Micah Porter, aka Peachez. He joins us today to discuss his transition into real estate investing, sharing his motivation for entering the real estate market and why real estate became his side gig. Take The Pilot Wealth Index to find out if you are on...

What does it really take to be successful with money? In this episode, we dive into key insights from The Psychology of Money  by Morgan Housel, discussing principles that can help transform your relationship with money. Whether you're preparing for retirement or simply trying to make smarter financial decisions, these lessons apply to everyone. You'll learn why discipline is crucial, how to face...

How much influence does a president truly have over the stock market? In this episode, we dive deep into the relationship between presidential powers and market performance, examining how different administrations impact the economy. While many believe the president has significant control over the markets, we explore whether the data backs that up, and how much external factors really shape the f...

How does the Federal Reserve shape the economy, and what should you really know about its role? In this episode, Seema Sheth, Senior Vice President and Regional Executive of the Federal Reserve Bank of St. Louis, joins the conversation to share insights on how the Fed looks beyond the data to understand the bigger picture. She discusses her unique path to success and the importance of focusing on...

How can you become the multi-millionaire pilot next door? In this episode, we   discuss the principles of wealth building, inspired by the timeless lessons from the book The Millionaire Next Door . We'll explore how pilots, with our unique income trajectories and financial challenges, can apply these principles to build substantial wealth over time. You can find show notes, resources and more at:...

Is the market overvalued and on the brink of an implosion? Join us as we dive into the intricacies of market valuation and investment strategies. In this episode, we're tackling some of the pressing questions about whether the market is currently overvalued, what market valuation metrics mean, and how investors can navigate these uncertain times. You can find show notes, resources and more at: htt...

As the sun sets on the Tax Cuts and Jobs Act, the financial landscape for many, including our pilot community, is poised for significant changes. Join us as we dive into the upcoming tax reforms set for 2026 and how they may impact your finances.   You can find show notes, resources and more at: https://tinyurl.com/5bd9ndjm

What exactly is an activist investor, and how do they influence the companies they invest in? In this episode, we are joined by Andy Christopher, CFA, Lead Financial Planner, to explore the world of activist investors. You'll learn about their roles, the impact they have on companies, and whether they typically boost returns or create concerns.  You can find show notes, resources and more at: http...