The Pilot Money Guys

Hosted by Leading Edge Financial Planning

Business Leisure

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Episodes

100

Latest episode

Oct 2026

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About the show

The Pilot Money Guys are a group of financial planners with a passion for bringing together financial planning and the commercial airline industry. Brought to you by a team of financial planners with backgrounds flying for major US airlines and military service. If you have questions about personal finance with an interest in news and interesting stories from the airlines, then we hope you will give us a listen. https://www.leadingedgeplanning.com

Listen to episodes

60 recent

October 16, 2026Episode 14047 min

Flight #140: Why Rising Interest Rates Could Be Good News for Bond Investors

Why are bond prices falling when interest rates rise, and does that mean investors should be worried? In this episode, we break down the bond market in plain English, exploring what drives bond yields, why prices move in the opposite direction to interest rates, and how inflation, economic growth and government borrowing influence the market. We also explain why recent market movements need to be viewed in historical context rather than through alarming headlines. You can find show notes, resources and more at: https://tinyurl.com/ms9aajs8

October 2, 2026Episode 13951 min

Flight #139: Should You Change Your Investments When Markets Feel Overvalued?

When headlines are shouting about AI, market highs, and economic uncertainty, how do you know what deserves your attention and what is simply noise? In this episode, we unpack listener questions that many investors are quietly asking. Listen in as we explore whether AI is creating a bubble, why all-time market highs aren't necessarily a warning sign, what history tells us about downturns, and more. You can find show notes, resources and more at: https://tinyurl.com/5dfatzax

September 18, 2026Episode 1381 hr 4 min

Flight #138: Hope, Courage and a Different Perspective on Life with Mike Penn

What can eight months in a North Vietnamese prison camp teach you about hope, courage and putting the rest of life into perspective? Former Navy pilot and Vietnam POW Mike Penn shares the extraordinary story behind his book, Hope and Courage , from the mission that led to his capture and his time in the Hanoi Hilton to the experiences that shaped his life long after he returned home. Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resources and more at: https://tinyurl.com/2z7cp9ur

August 28, 2026Episode 1371 hr 2 min

Flight #137: Indexing 101 with DFA Rob Harvey

What if the index fund you thought was simple was actually shaped by a complex set of rules, decisions, and trade-offs? In this episode, we sit down with Rob Harvey, Co-Head of Product Specialists and Vice President at Dimensional Fund Advisors, to unpack what indexing really means. You'll learn how indexes are constructed, who actually makes the rules, how index funds are managed, and why "passive" investing may not be as passive—or straightforward—as it sounds. Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resources and more at: https://tinyurl.com/2ttsnwyn

August 14, 2026Episode 13656 min

Flight #136: How Much is Enough? with Eric Hubbard

What does it really mean to have "enough"? And how do you know when you've reached it? In this episode, we're joined by Eric Hubbard, paraplanner at Leading Edge Financial Planning, to explore the difference between reaching a financial number and finding true satisfaction in life. We also discuss how pilots can prepare for retirement, not just financially but also emotionally, by understanding what they're retiring to, not just what they're retiring from. Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resources and more at: https://tinyurl.com/4fpbawmy

July 31, 2026Episode 13555 min

Flight #135: The Truth About AI: What It Can (and Can't) Do for Your Future with Dr. Jay Jay Billings

Is artificial intelligence really replacing jobs, or is it simply changing the way we work? In this episode, Dr. Jay Jay Billings, CEO and co-founder of Band Gap, cuts through the hype surrounding AI to explain what it actually is, where it's already transforming industries, and why many of the biggest headlines miss the point. You'll learn the difference between traditional AI and today's large language models, how organizations are using AI to solve real-world problems, and why putting customer needs first—not the technology—is the key to successful innovation. Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resources and more at: https://tinyurl.com/bdsemstm

July 17, 2026Episode 13449 min

Flight #134: Cutting Through Market Noise and Investing with Confidence

How do you stay focused when the headlines are shouting one thing, but the markets are doing another? In this quarterly market update, we unpack the biggest investment stories shaping the second quarter, helping investors separate fact from fiction. You'll learn what drove one of the strongest quarters for U.S. markets in years, why diversification is making a comeback, and what the latest economic data really means for your portfolio. Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resources and more at: https://tinyurl.com/mpa9ftfp

July 3, 202653 min

Flight #133: 7 Money Moves That Can Help, Hurt, or Trap You

What if the most "sophisticated" money moves you've been hearing about online are actually the least helpful for building real wealth? In this episode, we break down seven financial strategies that sound impressive on the surface but can range from genuinely useful tools to misleading traps or outright scams . From viral currency schemes to complex products like structured notes and annuities, the conversation is all about cutting through financial noise and focusing on what actually works . Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resources and more at: https://tinyurl.com/bdehcjev

June 19, 2026Episode 13248 min

Flight #132: Blessing or Curse? How to Ensure Your Financial Gifts Help Without Hurting

How can high-income professionals and first-generation millionaires support their adult children or grandchildren without creating a sense of entitlement? When does financial help empower the next generation, and when does it accidentally hold them back? In this episode, Charlie Mattingly sits down with Amelie Riendl, an Accredited Financial Counselor (AFC), to tackle the complex emotional and financial dynamics of giving to "adult-ish" kids. Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resources and more at: https://tinyurl.com/5n8bafs3

May 29, 2026Episode 13154 min

Flight #131: Do You Really Need an LLC? Tax Myths, Red Flags, and Business Structure Explained

What do pilots often get wrong about LLCs, taxes, and starting a business? And when does structure actually start to matter? In this episode, we break down some of the most common misconceptions around business formation, tax savings, and self-employment strategies for high-income professionals. Take The Pilot Wealth Index to find out if you are on track for retirement! You can find show notes, resources and more at: https://tinyurl.com/4w4v4xbd