Best Retirement Flight Plan Podcasts (2025)

1
The 4% Rule Just Changed—What That Means for Your Flight Plan to Retirement 12:55

14d ago12:55

12:55

The 4% rule gets talked about like gospel in retirement planning. But let’s be honest, it’s always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just got a raise, or is this just another headline that oversimplifies a complex decision? In this episode, Ry…

1
The Good Enough Job w/ Simone Stolzoff (Bestie Ep) #1007 55:05

19h ago55:05

55:05

“Work will always be work. Some people work doing what they love. Other people work so that they can do what they love when they’re not working. Neither is more noble.” This is a quote from Simone Stolzoff’s new book The Good Enough Job: Reclaiming Life From Work, that’s set to publish in a couple weeks. And regardless of where you fall on that spe…

1
Money Gears: Ordering Your Money Decisions Properly (Bestie Ep) #1006 54:10

3d ago54:10

54:10

Over 1,000 years ago, somehow, the Vikings were able to sail from Norway to Greenland. Without relying on any special instruments or any rudimentary technology, they were even able to reach as far as North America! Evidently they relied on the polarization of the sky, whales or birds they came into contact with, and the color of the ocean- quite re…

1
Financial Independence Exists on a Spectrum (Bestie Ep) #1005 50:15

6d ago50:15

50:15

Are you ‘credit card FI’ or are you ‘sabbatical FI?’ But maybe we’re getting ahead of ourselves… First, does anyone else remember the home run obsession back in 1998? In an attempt to beat the single-season record, home runs became the only metric that anyone watching baseball seemed to care about. But what’s interesting is that most MLB games aren…

1
Mailbag: Should You Sell Inherited Land to Pay Off Your Mortgage? 7:08

7d ago7:08

7:08

✈️ Retire Pilots the Right Way! 🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ In this episode, Ryan answers a thoughtful listener question from Shirley, a pilot who recently inherited a parcel of land from her uncle. With a mortgage still on her home and retirement a few years away, Shirley wonders: should she s…

1
#117 - How to Evaluate and Join Real Estate Syndications 43:12

7d ago43:12

43:12

Ever wonder what happens when you invest in a syndication? In this episode, hosts Tait Duryea and Ryan Gibson break down how real estate syndications work, from deal sourcing and underwriting to legal docs, fees, and investor returns. Learn how passive investors get access to large-scale deals, what to look for in a sponsor, and what happens after …

1
Use It Up, Wear It Out, Make It Do, or Do Without with Katy Wolk-Stanley (Bestie Ep) #1004 51:58

8d ago51:58

51:58

Everybody has heard of a consumer advocate before- someone who helps to make sure that individuals are getting the best deal possible. Or to make sure that the quality of the products is up to snuff. For instance think of Consumer Reports and the countless reporting and tests they perform on the different items we use as consumers. But you likely h…

1
Butchering Your Grocery Bill (Bestie Ep) #1003 52:22

10d ago52:22

52:22

Do you know something that we’re all currently doing? Breathing. It’s something we rarely actively think about, but it turns out that there are ways to improve our technique- by breathing through our nose instead of our mouths, or by taking deeper slower breaths. Well we’re talking about another basic subject today: buying groceries. This elementar…

1
Essential Habits For Financial Success (Bestie Ep) #1002 53:40

13d ago53:40

53:40

Close your eyes and think back to high school. No matter if those were the best years of your life or if you were more of a wallflower, you were likely told that you needed to get good grades- but why? Was it because you knew that you needed a particular GPA in order to get into a specific school? Maybe, but a lot of high schoolers just know that i…

1
5 Types of Independence Every Retiree Needs 21:30

14d ago21:30

21:30

As we celebrate the Fourth of July, this episode explores what independence truly looks like in retirement, beyond fireworks and freedom. Scott dives into five core areas of independence that every retiree (or future retiree) should be aiming for as they prepare for life after work. It's not just about having enough money, but having control, peace…

1
Control the Controllables 24:54

14d ago24:54

24:54

Markets crash. Taxes shift. Congress waffles on Social Security. You can’t control any of that. And stressing over it won’t help. What will? Focusing on the four things that actually move the needle in retirement. Important Links: Website: https://www.estesfinancial.net/ Call: 817-444-8402By Tim Estes

1
Solutions for Money Anxiety with Financial Therapist Lindsay Bryan-Podvin (Bestie Ep) #1001 57:10

15d ago57:10

57:10

There’s more to successfully handling your money than just figuring out the financial nuts and bolts. Money has emotional and psychological components to it as well, which is at the core of what our guest today focuses on. We’re happy to be joined by Lindsay Bryan-Podvin, who happens to be the first financial therapist in the state of Michigan. She…

1
#116 - Medical Checkride: Medical Myths, Truths, and Tips with Dan Monlux 55:19

16d ago55:19

55:19

What could cost you your flying career? Not being prepared for your medical. Hosts Tait Duryea and Ryan Gibson welcome back Dan Monlux of Wingman Med to discuss how pilots can protect their FAA medical certificates. Dan breaks down what happens during a medical exam, the importance of primary care, and why early detection matters. This is a must-li…

1
Ask HTM Anything! #1000 1:05:49

17d ago1:05:49

1:05:49

Join us as we celebrate our 1000th episode with an AMA!!! We are incredibly thankful and fortunate that we’re able to create a podcast for listeners who are looking to better their lives by improving how they handle their money. Of course at the core of the show are ways to earn, save, spend, and invest more effectively… all with a little bit of Jo…

1
We're (mini) Retiring! w/ Jillian Johnsrud #999 58:51

20d ago58:51

58:51

*Special Episode Alert*... take a peek behind the curtain as we have an intimate, candid chat with our friend Jillian Johnsrud, a master of intentional career breaks and author of the upcoming book Retire Often (out in September). As we take a summer hiatus from new podcast episodes, we dive deep with Jillian into the art of stepping away from work…

1
War, Rates & Real Estate—Plus Smart Money Moves for New Grads 18:40

21d ago18:40

18:40

In this episode, Ryan delivers a “pilot report,” offering a timely look at today’s economic turbulence. From global conflict and rising interest rates to inflation pressure and a shifting housing market, Ryan explains how these forces are shaping your financial flight path, and what adjustments you might need to stay on course. Ryan also shares pra…

1
Smarter Estate Planning: Why You Need a Plan Now 20:55

21d ago20:55

20:55

Estate planning is something we all know we should do, but it’s often pushed to the bottom of the list. In this episode, Scott shares a heartbreaking real-life story: a close friend’s brother died suddenly at 42. Recently divorced, with two young sons and no estate plan in place, the aftermath was a painful legal tangle. It’s a tragic example of wh…

1
From Monk to Money Manager w/ Doug Lynam #998 51:15

22d ago51:15

51:15

Today’s guest, Doug Lynam, has lived an extraordinary life! From overcoming bankruptcy to achieving financial security, taking vows of poverty as a Benedictine monk to managing over $250 million in assets as a wealth advisor, and graduating top of his class as a Marine to spending 20 years in monastic life, Doug’s journey is as diverse as it is ins…

1
#115 - Inside Self-Storage: A Hidden Powerhouse for Investors 50:47

23d ago50:47

50:47

Get ready to uncover the secrets of one of commercial real estate’s most resilient and misunderstood asset classes: self-storage. In this in-depth episode, Tait Duryea and Ryan Gibson explore why self-storage continues to outperform in uncertain times, how millennials are transforming storage use, and what makes it such a powerful wealth vehicle fo…

1
Ask HTM - Road Trips with Old Cars, Steps to Combining Finances, & When to Drop Escrow #997 51:31

24d ago51:31

51:31

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
Friday Flight - Dumpster Diving, Insurance Dodging, & Pudgy Penguins #996 40:48

27d ago40:48

40:48

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

1
A Market Strategy for Pilots With Type A Personalities 16:26

28d ago16:26

16:26

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, Ryan explains wh…

1
Retirement Breaking News: The 4% Rule Gets a Makeover? 19:39

28d ago19:39

19:39

The 4% rule gets talked about like gospel in retirement planning. But let’s be honest, it’s always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just got a raise, or is this just another headline that oversimplifies a complex decision? Here’s some of what…

1
The Power of Cash w/ Jay Zagorsky #995 51:27

29d ago51:27

51:27

Will our guest today convince us to ditch digital payments?! Listen to find out! Because here’s something that we hear all the time: “You can just Zelle me” or “Venmo me!”. It’s sort of like “I’ll just Uber to the airport” – once a company name has become a verb, is it possible to decouple it from culture? And of course the fact that they’re incred…

1
#114 - Trusts, Taxes & Transfers: What Every Investor Should Know with Amanda Wynalda 59:50

30d ago59:50

59:50

In this episode, hosts Tait Duryea and Ryan Gibson sit down with attorney Amanda Wynalda from Anderson Advisors to unpack everything pilots and high-income earners need to know about trusts, wills, and asset protection. From revocable vs. irrevocable trusts to layering LLCs and avoiding the due-on-sale clause, this episode is a blueprint for protec…

1
Ask HTM - Teenage Homebuyers, Best Type of Life Insurance, & Making Easy Money with Securities Lending #994 51:41

1M ago51:41

51:41

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
Friday Flight - Unemployment Uptick, Ridiculous Returns & The 4% Rule Debunked #993 38:22

1M ago38:22

38:22

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

1
Why The Psychology of Money Says Your Emotions Matter More Than Math 21:44

1M ago21:44

21:44

Today, Ryan’s taking us through some of the key concepts of The Psychology of Money by Morgan Housel. This book isn’t just about money strategies. It’s about why we make the choices we make, even when they don’t seem to make sense. You might find that your mindset is a bigger advantage than any investment tip. Here’s what we cover in this episode: …

1
The Lazy Way to Retire? Let’s Talk Target-Date Funds 17:24

1M ago17:24

17:24

Target-date funds just passed $4 trillion in assets. They’re now the default investment in many 401(k)s, and millions of Americans are using them without really understanding how they work. So, are they a smart choice… or just the easiest one? Here’s some of what we discuss in this episode: 🧭 Why defaulting to a target-date fund could misalign with…

1
No New Things w/ Ashlee Piper #992 56:26

1M ago56:26

56:26

I’m pretty sure everyone listening will want to either get out of debt, reduce the amount of clutter in their life, crush other financial goals, become healthier and happier… OR, why even choose? Why not select: d - all of the above?! That’s because that was the outcome of our guest today, Ashlee Piper, who documented her journey in her new book No…

1
#113 - The Fed, The Treasury, and Your Portfolio with Dr. Peter Linneman 53:42

1M ago53:42

53:42

In this episode, hosts Tait Duryea and Ryan Gibson talk with chief economist Dr. Peter Linneman to demystify interest rates, the national deficit, and how it all affects pilots, real estate investors, and entrepreneurs. Discover why U.S. debt may not be the threat it’s made out to be, how capital flows drive values, and what most people get wrong a…

1
Ask HTM - Early Retirement Target Date Funds, Frugal Personal Hygiene, & Coercive House Painting #991 51:27

1M ago51:27

51:27

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
Friday Flight - TACO Trading, Pointless Points, & Millionaire Renters #990 34:17

1M ago34:17

34:17

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

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

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

1M 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
Tactile Management vs Passive Management: What's Right for You? 15:06

1M ago15:06

15:06

If you’ve ever felt uncertain about what your investment strategy should look like, especially in today’s rapidly changing economic landscape, you are absolutely not alone. One of the most common questions Brie hears from clients is: “Should I just invest in index funds and ride it out?” or “Should someone be adjusting my portfolio as the market sh…

1
Pharmacist to Full Time Real Estate Investor w/ Ryan Chaw #989 55:51

1M ago55:51

55:51

Newer listeners may not realize how OBSESSED with investing in real estate we were back in the day. In fact, when we were batting around ideas for a podcast, we initially thought it might be focused only on real estate... Luckily we zoomed out enough to cover personal finance more broadly. And it’s not that we’re not excited about rentals anymore, …

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

1M 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
Ask HTM - Buying a Used Mattress, Best Use of an Inheritance, & Disqualified from a Roth #988 50:36

1M ago50:36

50:36

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
Friday Flight - Credit Crunch, MAGA Money, & Gas Gouging #987 36:13

2M ago36:13

36:13

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

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

2M 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

2M 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

2M 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
Impoverished Upbringing to Money Monster w/ Listener Nick Gangwer #986 53:10

2M ago53:10

53:10

We’re trying something completely new for our episode today: we’re hearing from a listener. Not in the form of a question submitted via voice memo, but we’re actually sitting down and having a ‘real money’ conversation, with Nick Gangwer. We met Nick at a listener hang about a year ago and his personal story and the proactive steps that he had take…

1
Ask HTM - Special Roth Accounts, Investing During A Sabbatical, & Reverse Mortgages #985 51:28

2M ago51:28

51:28

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

1
Friday Flight - Streaming Sports, Trade-In Tradeoffs & AI Lies #984 36:53

2M ago36:53

36:53

Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and help…

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

2M 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
Practical AND Beautiful Investing Advice w/ Callie Cox #983 56:40

2M ago56:40

56:40

What it means to have a practical and beautiful portfolio. How recent policy decisions have roiled the stock market. Right-sizing your risk tolerance… These are just a few of the topics we discuss with our guest Callie Cox who is a part of the Ritholtz Wealth Management team. She is also the author of OptimistiCallie, her newsletter where she seeks…

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

2M 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
Ask HTM - Unnecessary Credit Cards, Creatively Funding Grad School, & Dropping Car Insurance To Save #982 52:42

2M ago52:42

52:42

Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you …

Podcasts Worth a Listen

Retirement Flight Plan Podcasts

Podcasts Worth a Listen

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