HeyJaredThe Pilot Money Guys
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.
- Indexed episodes, last 90 days
- 6
- Latest publication
- Sep 18, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 3, 2026
Latest episodes
Flight #138: Hope, Courage and a Different Perspective on Life with Mike Penn (opens the original)
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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 an
Flight #137: Indexing 101 with DFA Rob Harvey (opens the original)
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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 f
Flight #136: How Much is Enough? with Eric Hubbard (opens the original)
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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
Flight #135: The Truth About AI: What It Can (and Can't) Do for Your Future with Dr. Jay Jay Billings (opens the original)
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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 custome
Flight #134: Cutting Through Market Noise and Investing with Confidence (opens the original)
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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
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