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The Pilot Money Guys

The Pilot Money Guys

Leading Edge Financial Planning · Charlie Mattingly

109 episodesEN

Show overview

The Pilot Money Guys has been publishing since 2022, and across the 4 years since has built a catalogue of 109 episodes. That works out to roughly 90 hours of audio in total. Releases follow a fortnightly cadence.

Episodes typically run thirty-five to sixty minutes — most land between 42 min and 55 min — and the run-time is fairly consistent across the catalogue. None of the episodes are flagged explicit by the publisher. It is catalogued as a EN-language Business show.

The show is actively publishing — the most recent episode landed 1 weeks ago, with 16 episodes already out so far this year. Published by Charlie Mattingly.

Episodes
109
Running
2022–2026 · 4y
Median length
48 min
Cadence
Fortnightly

From the publisher

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

Latest Episodes

View all 109 episodes

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

Aug 14, 202656 min

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

Jul 31, 202655 min

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

Jul 17, 202649 min

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

Jul 3, 202653 min

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

Jun 19, 202648 min

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

May 29, 202654 min

Flight #130: Help Looks Different for Everyone with Danielle Lewis

May 15, 202659 min

Flight #129: What's Really Moving the Markets Right Now

May 1, 202639 min

Flight #128: Master Your Money Mindset for Long-Term Wealth with Jason Moore

Apr 17, 202651 min

Ep 127Flight #127: Cutting Through the Financial Noise: Inflation, Energy, Bitcoin, and the Global Economy with James Angel

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

Apr 4, 20261h 1m

Flight #126: The Art and Science of Early Retirement for Pilots

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

Mar 20, 202659 min

Flight #125: What the Mind the Gap Study Reveals

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

Mar 6, 202647 min

Flight #124: Advanced Roth Strategies and New Changes

Are you missing opportunities to build tax-free retirement income? In Part 2 of this Roth series, we break down the latest changes and advanced strategies that could significantly impact your retirement plan. You'll learn how the new Roth catch-up rules affect those 50 and over, what the Roth NEC means for high earners, and how the mega backdoor Roth works in practice. 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/3hr2psac

Feb 20, 202643 min

Flight #123: Roth Catch-Ups, NECs, and Smarter Airline Retirement Planning

Recent changes to airline 401(k) plans—especially the Roth Nonelective Contribution (NEC) option—have created new opportunities and new confusion for pilots and airline professionals. In this episode, we break down what the Roth NEC actually is, how it works at airlines like Southwest, and why simply ignoring your elections could mean missing out on valuable catch-up contributions. 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/y7bncn35

Feb 6, 202645 min

Flight #122: 2025 Market Review and Lessons Learned

What can last year's markets actually teach us beyond the headlines and noise? In this episode, we look back at the market lessons from the past year to better understand how markets behave and why short-term movements can be so misleading. Rather than trying to predict what comes next, this conversation focuses on learning from what already happened and why diversification remains one of the most powerful tools for managing risk. 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/38ftvryn

Jan 23, 202643 min

Flight #121: The Biggest Lessons We Learned in 2025

What if the lessons from 2025 could completely change how you approach the year ahead? In this episode, we reflect on the biggest epiphanies, revelations, and insights gained from our clients, our work, and our own lives last year. You'll learn practical techniques to prioritize what matters most, avoid burnout, and separate your identity from your job. From generosity and communication to asking better questions, this conversation sets the tone for building a meaningful, balanced, and intentional life in 2026. 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/y9r6jf2u

Jan 9, 202646 min

S1 Ep 120Flight #120: Why Stock Picking Is Harder Than You Think with Hank Bessembinder

What if most individual stocks actually don't outperform and a small handful of massive winners are doing all the heavy lifting? In this episode, renowned finance professor Hank Bessembinder joins the show to break down decades of research on market returns, stock picking, and why diversification matters far more than most investors realize. We unpack his groundbreaking findings on market skewness and explain why identifying winning stocks is far harder than social media and headlines suggest. 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/3kef3pdx

Dec 26, 202559 min

Flight #119: Investing Through Peaks, Bubbles & Uncertainty with Nolan Clark and Andy Christopher

What if we're asking the wrong question about market peaks, bubbles, and crashes? Everyone wants to know what happens next, but this episode shifts the focus to what you can actually control: risk, timing, and smart decision-making. Today's conversation breaks down the most common fears investors face — from AI bubbles to gold hype to stock market pullbacks — and gives you a grounded lens for evaluating what's real versus what's noise. 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/2d3z463u

Dec 12, 202547 min

Flight #118: Redefining Success, Struggle, and Purpose with Ryan Watson

What happens when success, identity, and purpose collide with some of the hardest battles a person can face? In this powerful conversation with Ryan Watson, we explore the realities many pilots and high-performing professionals quietly carry: addiction, mental health struggles and the pressure to appear "perfect" in an industry where vulnerability can feel dangerous. Ryan opens up about the challenges he faced, the misconceptions around struggle, and the hidden cultural stigma that keeps so many silent. 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/4ahwrx8w

Nov 21, 202539 min

S1 Ep 117Flight #117: Public vs Private: Where Should You Really Be Investing?

Are private equity and alternative investments really the secret weapon of the wealthy or are public markets still your best bet? In this episode, we tackle one of the most common questions we hear: should you look beyond the stock market? We'll break down what private equity really is, who it's for, and why some companies stay private instead of going public. You'll learn how these investments work, why they're not always the golden ticket they appear to be, and how to think critically about diversifying 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/2eyuv9n8

Nov 7, 202548 min