Best Pilot Retirement Plan Podcasts (2025)

1
5 Ways Wishful Thinking Can Damage Your Retirement 20:48

2d ago20:48

20:48

A little hope is good for the soul, but when it comes to retirement planning, wishful thinking can lead to serious financial mistakes. Today, Scott’s walking through five common examples of wishful thinking that can quietly damage your retirement, and how you can build a plan that protects your future instead of relying on luck. Here’s some of what…

1
Is It Bad to Leave My 401(k) Where It Is? 10:41

2d ago10:41

10:41

If you've recently changed jobs, chances are your old 401(k) is still sitting right where you left it – out of sight and out of mind – and it could potentially cost you. In this episode, Ryan answers a question from a pilot who recently made the jump to a major airline and wants to know if he should roll over his old 401(k) or leave it where it is.…

1
#112 - The Tax Strategies Every Pilot Should Know in 2025 with Thomas Castelli 47:15

4d ago47:15

47:15

In this episode, Tait Duryea and Ryan Gibson welcome CPA Thomas Castelli of Hall CPA to break down the latest tax developments affecting high-income earners. From the potential return of 100% bonus depreciation to how the real estate professional status works in practice, Tom shares key strategies to help you keep more of what you earn. Whether you…

1
What happens if I lose my medical at American Airlines 22:20

5d ago22:20

22:20

In this focused solo episode, Timothy P. Pope, CFP®, breaks down what happens if an American Airlines pilot loses their medical and becomes unable to fly. Tim reviews the employer-provided long-term disability plan, the union-sponsored POD and PMA supplements, and how pilots can combine these for up to 90% of pre-disability income. From elimination…

1
#111 - Five Investing Strategies for High-Earning Pilots 44:56

9d ago44:56

44:56

Get ready to fast-track your financial freedom. In this power-packed solo episode, Tait Duryea and Ryan Gibson share the top strategies from over 110 episodes of Passive Income Pilots. From unlocking hidden cash in your 401(k) and home equity to leveraging life insurance and short-term rentals for major tax breaks, they distill years of pilot-speci…

1
Mailbag: Market Crashes, Corrections, and Staying Calm 12:28

10d ago12:28

12:28

The market’s been shaky and pilots are wondering how the volatility impacts their retirement and investment decisions. In this special mailbag edition of the show, we’ll answer real questions from aviators facing turbulence in their retirement plans. Whether they’re near retirement, sitting on cash, or watching everything dip at once, today’s quest…

1
Why Type A Investors Should Probably Do Less 15:01

9d ago15:01

15:01

Today, we’re talking about Type A personalities. If you’re driven, competitive, and goal-oriented, then you’re part of the club that often struggles during difficult markets. When things get tough, your instinct is to work harder, push more, and fix the problem. But in investing, that instinct can sometimes backfire. In this episode, Scott breaks d…

1
Spring Cleaning for Your Finances: A Marie Kondo Approach to Money 16:47

17d ago16:47

16:47

Spring is in the air and for some, that means it’s time for spring cleaning. Marie Kondo is considered an expert in tidying and decluttering, and wrote the book, “The Life-Changing Magic of Tidying Up.” In today’s episode, Ryan brings a Marie Kondo-inspired approach to finances, helping you declutter, get organized, and let go of what no longer “sp…

1
#110 - The IRA Club Advantage: The Self-Directed IRA Strategy for Pilots with Ramez Fakhoury 54:06

18d ago54:06

54:06

In this episode, hosts Tait Duryea and Ryan Gibson welcome Ramez Fakhoury from IRA Club. This episode dives into how pilots can unlock old 401(k)s, TSPs, and HSAs for real estate and other alternative investments. Hear a detailed story of a Southwest pilot transitioning to American Airlines and learn what decisions made the biggest impact. Whether …

1
I Went to the New York Stock Exchange - Here’s What I Learned 13:58

24d ago13:58

13:58

Ryan just got back from the New York Stock Exchange, and he’s sharing what it was like to stand on the floor during the iconic closing bell. Go behind the scenes to learn more about the modern trading environment, one that’s quieter, more high-tech, and dominated by algorithms. Ryan discusses what percentage of trades are now executed by computers,…

1
Am I Saving Too Much For Retirement? 18:44

23d ago18:44

18:44

We’ve all heard that Americans don’t save enough for retirement, but what if the opposite is true for you? Can you save too much? In this episode, Scott tackles a surprising but important question raised by a listener: “Are we over-saving at the expense of living now?” As an airline professional, it can be easy to feel like you’re doing too little,…

1
#109 - The Flight Plan for Syndications: Risk, Returns, and Real Wealth 39:19

25d ago39:19

39:19

In this episode, hosts Tait Duryea and Ryan Gibson deliver an in-depth, pilot-friendly primer on syndications and passive real estate investing. They break down the risk spectrum from core to opportunistic deals, while sharing real-world analogies and experiences from their own projects, like the Canyon City land entitlement. Learn how to properly …

1
Are We Headed Towards a Recession? How to Prepare Yourself 14:26

30d ago14:26

14:26

Recession fears are back in the headlines, but should they be back in your financial plan, too? We’re in the middle of earnings season and data is coming in, so Scott will tackle the question: Are we heading for a recession? With shrinking GDP, rising inflation, and uncertain interest rate moves by the Fed, we’ll try to decipher what the latest eco…

1
What the Greats Say About Market Crashes 15:01

1M ago15:01

15:01

When the market is crashing, it's easy to feel like you're the only one who's ever felt this anxious. But the truth is, some of the greatest investors in history have lived through chaos, and they left behind wisdom that still applies today. In this episode, Ryan responds to wisdom from experts like Warren Buffett, Benjamin Graham, and Jack Bogle t…

1
#108 - Case Study: Real Estate Professional Status That Held Up in Court with Brandon Hall 21:04

1M ago21:04

21:04

In this episode, Tait Duryea flies solo to spotlight a powerful tax strategy many high-income earners overlook: real estate professional status. Featuring Brandon Hall from Hall CPA, this episode breaks down a real tax court victory by a harbor pilot who leveraged a flexible W-2 job schedule to claim REP status and unlock massive tax savings. Disco…

1
Don't Let Market Turbulence Derail Your Financial Goals 19:49

1M ago19:49

19:49

In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP® shares practical strategies for building financial resilience in volatile times. Drawing parallels between aviation safety and financial planning, Tim explains how pilots can strengthen their financial "redundancy" to absorb unexpected challenges like airline slowdowns, downgrades, or heal…

1
April Fool’s: Beliefs That Fool Retirement Savers The Most 19:15

1M ago19:15

19:15

April Fool’s Day is all about jokes and pranks, but when it comes to retirement planning, getting fooled can cost you real money. Today, we’re uncovering the beliefs that fool retirees and pre-retirees into making bad financial moves. Ryan unpacks the financial “pranks” people may fall for—from too-good-to-be-true returns to myths about Social Secu…

1
Retirement Lessons From The Masters (Part 2) 15:14

1M ago15:14

15:14

In part two of this special Masters series, Scott takes us to the “back nine”- the final stretch of retirement planning where pressure builds and smart decisions matter most. From avoiding risky plays in your 50s and 60s to understanding how emotions can derail your strategy, Scott lays out what it really means to finish strong. Here’s some of what…

1
#107 - Take Control of Your Capital: Infinite Banking Strategy With Brent Kesler 38:43

1M ago38:43

38:43

Host Tait Duryea sits down with Brent Kesler, a seasoned life insurance strategist, to explore how pilots and high-income earners can build wealth by turning whole life insurance into a personal banking system. Brent breaks down the misunderstood "infinite banking" concept and how it can be used for real estate, debt payoff, or high-return lending—…

1
Bracket Picks and Stock Myths 22:32

1M ago22:32

22:32

When it comes to investing, are you picking winners or just playing favorites? In this episode, Ryan breaks down how our emotional biases, gut instincts, and misplaced confidence can sabotage even the best financial intentions. Using bracket-building and sports betting as a metaphor, Ryan explores how chasing individual stocks is a lot like guessin…

1
#106 – Time Freedom and Cash Strategies with Brian Herriot 39:31

2M ago39:31

39:31

Hosts Tait Duryea and Ryan Gibson welcome financial strategist Brian Herriot for a thought-provoking conversation on redefining retirement and wealth. Explore the power of time freedom, why cash might be your most underappreciated asset, and how to build passive income streams that work for pilots and professionals alike. Brian shares practical tac…

1
Retirement Lessons From The Masters (Part 1) 12:58

2M ago12:58

12:58

The Masters is a beautiful reminder of just how much strategy, patience, and long-term focus goes into a great round of golf. Turns out, retirement works a lot like the game. Today, we’re teeing up a few key lessons from the course and how they translate into smarter planning for your financial future. Here’s some of what we discuss in this episode…

1
Tax-Savvy Investing for Pilots: A Deep Dive into Oil & Gas 54:01

2M ago54:01

54:01

Join Timothy P. Pope, CFP®, and John Engel, COO of Gulf Coast Western, as they discuss strategic investment opportunities in the oil and gas sector that could help high-earning pilots. This episode offers an insider look into tax benefits and how to leverage investments to offset high W2 incomes and to secure tax advantaged future income. Dive deep…

1
Retirement Lessons From The Masters 17:34

2M ago17:34

17:34

What does Augusta National have in common with your retirement plan? A lot more than you think. Ryan uses the game of golf—and the iconic Masters Tournament—as a powerful metaphor for achieving retirement success. We drive into key takeaways, like why consistency leads to better retirement results as opposed to risking it all for a “hole-in-one” an…

1
Market Shoots Up on 90-Day Pause on Tariffs 7:56

2M ago7:56

7:56

If there’s ever been a great example of why you stay invested and avoid trying to time the market, it would be these recent market movements from tariff news. After days of sharp declines, the announcement that there will be a 90-day pause on tariffs for 75 countries and increased pressure on China led to an instantaneous pop upwards. In this quick…

1
#105 - Buying and Building a Profitable Aviation Business with James Spearman 46:05

2M ago46:05

46:05

In this episode, Tait Duryea and Ryan Gibson are joined by James Spearman, owner of Spearman Aircraft and Iconic Rides. James walks through his journey of acquiring and scaling an aircraft maintenance business through seller financing, boosting its value through streamlined systems and strategic marketing. He shares the mindset and steps that helpe…

1
Markets Plunge on Trump Tariff News – How Should You Invest? 9:54

2M ago9:54

9:54

The news of Trump’s tariffs has caused global markets to go into a tailspin, and that means panic has started to set in for many investors. Seeing red numbers across your portfolio is never easy, but what if you saw this as an incredible opportunity rather than a time to get out of the market? Today we’ll talk about how long-term investors can use …

1
Liberation Day: Is 2025 A Bad Time To Retire? 14:26

2M ago14:26

14:26

Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and fears for the economy amidst federal layoffs and tariffs. What if you’ve had 2025 marked on the calendar for a while as the year you plan to retire? Is this a bad time to do it? Here’s some of what we discuss in this episode: 0:00 – Intro 2:08 – …

1
Is 2025 A Bad Time To Retire? 12:17

2M ago12:17

12:17

Is 2025 a bad year to retire? With headlines swirling about market volatility, federal layoffs, and a possible recession, it’s a question many pre-retirees—especially pilots—are asking. If you were targeting this year for a retirement date, let’s find out if Ryan thinks pilots should still retire or put their plans on hold. Here’s what we cover in …

1
#104 - Active vs. Passive: Storage Strategies from the Flight Deck with Michael Meylor 49:01

2M ago49:01

49:01

In this episode, Tait Duryea and Ryan Gibson sit down with Michael Meylor, a seasoned pilot and self-storage investor who has built an impressive portfolio without raising outside capital. Michael shares how he transitioned from military to commercial flying, how he and his wife started investing in single-family rentals, and why they pivoted to co…

1
Flying West: Preparing Your Estate as a Pilot 21:29

2M ago21:29

21:29

Join Timothy P. Pope, CFP®, in a profoundly important episode of Pilot's Portfolio, where he tackles the uncomfortable yet crucial topic of estate and financial planning for pilots. With a recent tragic aviation incident as a backdrop, Tim highlights the necessity of being prepared for unforeseen events. This discussion is not just about planning f…

1
#103 - Multifamily Mastery: Building Cashflow and Legacy with Gino Barbaro 45:35

2M ago45:35

45:35

In this episode, Tait Duryea welcomes Gino Barbaro of Jake & Gino to unpack the mindset and mechanics behind building lasting wealth through multifamily real estate. Gino shares his journey from running a family restaurant to becoming a real estate investor with over 1,800 units. They explore topics like values-based decision-making, creating "happ…

1
Infinite Banking: The Smarter Way to Build Wealth 52:49

2M ago52:49

52:49

What if you could become your own banker and take control of the way you finance your life? Today we’re excited to welcome on Brian Moody and Hans Tooey of Remnant Finance to explore the Infinite Banking Concept- a financial strategy designed to help you protect, save, and grow your wealth without relying on traditional banks. Here’s some of what w…

1
#102 - Creating True Passive Income Through Note Investing with Tom Force 49:39

2M ago49:39

49:39

In this episode, Tait Duryea and Ryan Gibson sit down with retired airline captain and seasoned investor Tom Force to discuss a real estate strategy many overlook—note investing. They cover tax strategies, risk management, and how to get started in note investing. If you’re tired of tenant headaches and want to invest like a bank, this episode is f…

1
Pilot in Command: Navigating Market Turbulence

3M ago

—

In this insightful solo episode, Timothy P. Pope, CFP®, explores how pilots can maintain command over their personal finances amidst market turbulence and external economic factors. Tim emphasizes the importance of focusing on what pilots can control in their financial planning, from responding to market conditions to proactive financial strategies…

1
Market Corrections: Panic or Opportunity? 8:21

3M ago8:21

8:21

With markets off to a volatile start in 2025, many investors are feeling uneasy. But should you be worried? Ryan took a break during a recent trip to an advisor conference to share some thoughts on the recent market pullback, explaining why it’s normal, healthy, and even an opportunity for long-term investors. If you’re concerned about the latest m…

1
How Side Gigs Impact Your Retirement Portfolio 11:24

3M ago11:24

11:24

Thinking about starting a side gig? Many pilots explore side hustles like real estate or passion projects, but how do these extra income streams impact retirement planning? Are there tax advantages you should be taking advantage of? And how can you ensure your side hustle is working for you, not creating extra stress? In this episode, Scott breaks …

1
#101 - Airbnb for Aircraft: Hangar Investing & Aviation Real Estate with Trenton Ray 41:21

3M ago41:21

41:21

Hangar space is in short supply, but Trenton Ray is changing that. In this episode, Tait Duryea and Ryan Gibson chat with Trenton about Hangar Direct, his platform that’s like Airbnb for hangars—making it easier for pilots to find and rent space. They dive into the supply shortage, investment potential, and what to know about leasing, financing, or…

1
Should You Stay in Cash or Keep Investing in Your 401k? 11:39

3M ago11:39

11:39

The thought of a market crash will often make investors rethink their portfolio and move into cash. That’s what one American Airlines pilot reached out to us about recently. He has concerns about the market so half of his 401K is in cash, but now he wants to know when he should start investing it again. Today we’re going to answer that question and…

1
Do Smart Investors Need a Financial Advisor? 13:43

3M ago13:43

13:43

If you’ve spent years successfully managing your own investments, do you really need a financial advisor? Scott works with a lot of highly skilled, intelligent professionals. So, for someone like this, is working with an advisor just an extra expense, or could it actually add real value? In this episode, we break down when and why even experienced …

1
#100 - Getting to Know Tait & Ryan 51:12

3M ago51:12

51:12

In this special 100th episode of Passive Income Pilots, Tait Duryea and Ryan Gibson take listeners behind the scenes of the podcast, sharing how it all started and what goes into creating each episode. They also dive into their personal journeys in aviation, investing, and entrepreneurship. From buying their first rental properties to scaling multi…

1
Maximizing Real Estate Savings: A Pilot's Guide with Kevin Walker 30:00

3M ago30:00

30:00

Join Timothy P. Pope, CFP®, and Kevin Walker, CEO of Beacon Relocation as they discuss real estate benefits specifically tailored for pilots and air traffic controllers. Recorded shortly after the PSA and army helicopter crash, this episode acknowledges the recent tragedy. This episode focuses on financial savings in real estate transactions for pi…

1
What Do Proposed Tariffs Mean For Your Portfolio? 10:19

3M ago10:19

10:19

The day President Trump took office, he announced plans to implement a 25 percent tariff on goods from Mexico and Canada. Additional tariff conversations have exploded since that day. How might this impact your personal finances and the economy? In this episode, we’ll take a closer look at the backstory of tariffs- what they are, why governments im…

1
Financial Lessons from the Past 6 Months & Early 2025 11:42

3M ago11:42

11:42

We haven’t lacking headlines over the past six months but the craziness can provide some valuable lessons for investors. In this episode, we take a closer look at the recent fluctuations in the financial markets and the emotional responses of investors during turbulent times. Understanding the purpose of your investments is crucial. Many investors …

1
#99 - Turnkey Real Estate: Passive or Problematic? A Deep Dive with Zach Lemaster 52:24

3M ago52:24

52:24

In this episode, Tait Duryea and Ryan Gibson connect with Zach Lemaster to explore the world of turnkey real estate and build-to-rent properties. They discuss the benefits and challenges of owning physical real estate, the tax advantages of rental properties, and how busy professionals can invest without becoming full-time landlords. Zach shares in…

1
America Has a Major Retirement Savings Problem 13:05

3M ago13:05

13:05

In an era where retirement depends on an individual’s ability to save, the statistics tell us that America has a real problem. Ryan saw a few stats on tv recently that raised some major concerns, and it’s time to address the root of the issues. Today we’ll share the numbers that caught our attention and talk about the steps pilots need to be taking…

1
Money Questions Every Couple Needs To Discuss 14:15

3M ago14:15

14:15

Valentine’s season is all about love, but let’s be honest, money plays a huge role in any relationship. Whether you’ve been together for decades or are just starting out, financial stress can put a strain on even the strongest partnerships. So, how do you talk about money without killing the romance? In today’s episode, we’re looking at the questio…

1
#98 - The Right Coverage: Property Insurance Strategies with Valerie Cusano 49:46

3M ago49:46

49:46

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with Valerie Cusano, an insurance expert with a background in law and decades of experience in commercial and residential insurance. Val dives deep into the critical aspects of real estate insurance, particularly for condo and rental property owners. She explains the dif…

1
2025 Retirement Update: What Pilots Need to Know 19:03

3M ago19:03

19:03

Join Timothy P. Pope, CFP®, in this informative episode of Pilot's Portfolio as he discusses the latest updates and changes in retirement contributions for pilots. Tim discusses the implications of increased contribution limits and how these adjustments can impact your financial planning. Additionally, he shares an IRS provision that bugs him conce…

1
Retirement Lessons from Andy Reid: Super Bowl-Worthy Financial Strategies 13:01

4M ago13:01

13:01

Fresh off another Super Bowl appearance, Andy Reid is a legendary head coach known for his strategic brilliance and leadership in the NFL. But what if we told you that his insights could also apply to financial planning and retirement strategies? In our latest podcast episode, we’ll share four bits of wisdom from Andy Reid draw parallels between hi…

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