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The Pilot Money Guys

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Rating
★★★★★
4.8
from
49 reviews
This podcast has
100 episodes
Language
English
Date created
2021/03/08
Latest episode
2026/10/02
Average duration
55 min.
Release period
15 days

Description

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

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Podcast episodes

Check latest episodes from The Pilot Money Guys podcast


Flight #139: Should You Change Your Investments When Markets Feel Overvalued?
2026/10/02
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
Flight #138: Hope, Courage and a Different Perspective on Life with Mike Penn
2026/09/18
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
Flight #137: Indexing 101 with DFA Rob Harvey
2026/08/28
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
Flight #136: How Much is Enough? with Eric Hubbard
2026/08/14
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
Flight #135: The Truth About AI: What It Can (and Can't) Do for Your Future with Dr. Jay Jay Billings
2026/07/31
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
Flight #134: Cutting Through Market Noise and Investing with Confidence
2026/07/17
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
Flight #133: 7 Money Moves That Can Help, Hurt, or Trap You
2026/07/03
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
Flight #132: Blessing or Curse? How to Ensure Your Financial Gifts Help Without Hurting
2026/06/19
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
Flight #131: Do You Really Need an LLC? Tax Myths, Red Flags, and Business Structure Explained
2026/05/29
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
Flight #130: Help Looks Different for Everyone with Danielle Lewis
2026/05/15
What happens when you stop judging people by their circumstances and start seeing them as human beings first? In this powerful episode, Danielle Lewis shares her journey from her own upbringing to becoming the founder of Village Hope, serving the unhoused community in downtown Atlanta. Danielle opens up about the moment she realized she wanted to dedicate her life to helping people struggling with homelessness, addiction, and poverty, and why compassion often matters more than having all the answers. 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/4h5ysth2
Flight #129: What's Really Moving the Markets Right Now
2026/05/01
What's really driving the market right now, and are you paying attention to the right signals? In this episode, we break down what happened in the first quarter and unpack some of the global events quietly shaping investor sentiment, including the situation in Iran and how geopolitical tensions can influence market opportunities and risks.  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/msjck2fp
Flight #128: Master Your Money Mindset for Long-Term Wealth with Jason Moore
2026/04/17
What does it really take to be successful with money? And why do even high-income professionals still struggle? In this episode, you'll learn why financial success has far less to do with knowledge and far more to do with behavior. Jason Moore, Certified Financial Therapist, breaks down the hidden patterns, biases, and emotional triggers that influence how we earn, spend, and invest, as well as how these can quietly derail even the most capable individuals.  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/4k6k56nd
Flight #127: Cutting Through the Financial Noise: Inflation, Energy, Bitcoin, and the Global Economy with James Angel
2026/04/04
There is a lot of financial noise right now, but what actually matters? In this episode, James Angel joins the show to cut through the headlines and explain what's really happening with inflation, the strength of the U.S. dollar, global conflict, China's economic impact, Bitcoin, stablecoins, and the future of the global economy. Listen in to learn why energy is the foundation of the entire economy, how money printing leads to inflation, why the global economy is more connected than ever, and what makes today's economic environment different from past recessions. 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/yd5ch94t
Flight #126: The Art and Science of Early Retirement for Pilots
2026/03/20
What does it really take to retire early as a pilot—and are you truly prepared for what comes next? In this episode, we break down both the financial strategies and emotional realities behind early retirement, specifically for those in aviation careers. You'll learn the essential "science" of early retirement, including how to estimate your true spending needs, manage portfolio risk, plan distributions, and prepare for major costs like healthcare. 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/deuraj9n
Flight #125: What the Mind the Gap Study Reveals
2026/03/06
If you bought and held a mutual fund or ETF, what return should you earn—and why do some investors earn less? In this episode, we unpack the fascinating findings from Morningstar's Mind the Gap study and explore the difference between total returns and actual investor returns. You'll learn what the "investor return gap" is, why it exists, and how timing decisions, emotional reactions, and behavioral biases quietly erode performance over time. 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/bdd2tz84

Podcast reviews

Read The Pilot Money Guys podcast reviews


4.8 out of 5
49 reviews
★★★★★
AAirborn 2026/06/19
Good overall advice
I listen to several podcasts on finance and money advice and this podcast has a balance approach with action steps and things to consider for your sit...
★★★★★
Ginathisnicknamenottaken 2026/04/24
Honest company
I enjoy their information and find it to be specific to pilot concerns. They’re very responsive to questions, and I was impressed when I approached th...
★★★★★
Cosmo457 2026/04/24
Outstanding
Trusted these folks for years with my money. They understand the pilot financial situation with-respect-to contract, benefits, insurance, etc. It’s be...
★★★★★
J Stouffer 2023/07/10
Entertaining and meaningful perspectives
I’m definitely enjoying the airline and military pilot perspective on the financial landscape. As the major airlines and cargo carriers are achieving...
★☆☆☆☆
Chris - DFW International 2023/05/09
1 & Done… These guys, they’re a JOKE!
Just listened to my 1st episode. It’ll be my last. These guys share little to no financial knowledge or insight. They have obviously done little to no...
★★★★★
me73p 2023/01/06
Over all podcast review.
What a great source of easily digestible financial information. I have been listening for over a year and thoroughly enjoy this pod cast. The guest sp...
★★★★★
KyColonel13 2022/10/05
Great info for new pilots
As a regional pilot that is relatively new in the industry this podcast offers some great info! I’d highly recommend this to anyone looking to find th...
★★★★★
Can I get a third? 2022/09/17
Great information and fun atmosphere!
Rob, Charlie and gang always bring a fun atmosphere with some light-hearted advice on serious financial topics. Great work tying together finance and ...
★★★★★
anonoymous-51 2021/10/09
Great information
Extremely relevant and follows current topics. I love the laid back discussion, it feels like I’m sitting around with my buddies.
★★★★★
Nikki667667777 2021/08/12
I'm a FAN!
Lots of fabulous and useful advice! A must listen to for all. The pilot money guys for the WIN!!!
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