Best Pilot Retirement Plan Podcasts (2025)

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

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9d 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…

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[800] This Navy Pilot Raised $150 Million Without Begging for a Dime 24:37

2d ago24:37

24:37

Every year, I record a podcast on July 4th. It’s a tradition. Because “freedom” means something different to me now than it did when I was flying helicopters over the Persian Gulf… And it probably means something different to you, too. This is the thing that drives everything I do. Freedom and money go hand-in-hand. Not because you need to be rich……

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

2d 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…

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

3d 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 …

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[799] Would You Keep Flipping After Losing $20K? 17:05

4d ago17:05

17:05

While I was mid-flight last week, Dr. Sheri Fluellen dropped a story most investors would never admit. Her worst. Flip. Ever. A $75K property on 8 acres. It seemed like the perfect first deal. Instead, she got… No septic system. FIVE layers of shingles crushing the roof. A crumbling foundation $60K ARV drop A contractor who went MIA for months. 2.5…

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5 Types of Independence Every Retiree Needs 21:30

9d 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…

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[798] She Made $250k With This 5-Minute Brain Hack 39:20

11d ago39:20

39:20

One of Dr. Shannon’s clients recorded a simple 5-minute audio. She played it every morning and every night for a week. What happened next? She brought in $250,000. Now, you might think she did it with a brand-new strategy no one talks about. Or by working harder than anyone else. Sure… strategy and hard work played a role. But what really moved the…

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

11d 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…

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What Happens If I Lose My Medical At Delta Air Lines 27:03

12d ago27:03

27:03

In this detailed solo episode of Pilot’s Portfolio, Timothy P. Pope, CFP® walks Delta pilots through everything they need to know if they lose their medical and can’t fly. From contractual long-term disability benefits and the Delta Pilots Mutual Aid (DPMA) program to ALPA’s voluntary insurance options, Tim explains how to layer your benefits, unde…

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

16d 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…

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

16d 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…

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[797] The Contractor Problem No One Talks About (But Everyone Deals With) 31:41

17d ago31:41

31:41

If you’re flipping out of state, then LISTEN UP. Here’s a tactic you won’t find on YouTube (but you WILL need eventually): Before Dr. Sheri arrived to walk her new flip, her GC sent the whole crew on a lunch break. Then sprayed Febreze all over the house. Why? Because “he didn’t want her to smell anything bad…” …or “have to meet the guys.” 🤨 The re…

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[796] She’s 17 and Plans to Retire at 30 44:32

19d ago44:32

44:32

Be honest… Put a finance workshop next to Fortnite or a TikTok trend. Which one do you think your kid is choosing? Exactly. That’s where Trinity started. Her parents signed her up for a program called Teenage Tycoon. Two Zooms a week. A book a month. Boring adult stuff. She wasn’t happy. Sat off-camera, arms crossed. Decided she was too smart for i…

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

18d 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…

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[795] This Is What Happens When You Follow Up 521 Times 39:26

24d ago39:26

39:26

Reality check: Most investors give up after hearing “not interested.” Others back off because they don’t want to feel pushy. “I already called twice… I’ll just wait.” The seller ghosts. And just like that… another lead fades out. You tell yourself: They’ll reach out if they’re serious. And that’s the end of it… But is it? Let me show you what one ‘…

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

23d 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…

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

23d 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…

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[794] The $80,000 Contractor Mistake I'll Never Make Again 34:52

25d ago34:52

34:52

What if I told you the #1 reason most “investors” NEVER buy their first property... Has nothing to do with the market? It’s not a lack of leads. Not even a bad contractor (although you’ll hear how I could’ve prevented an $80,000 mistake with mine). If you’ve even done one deal, you’re statistically ahead of a lot of people. And AI could take you th…

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

26d 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…

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Tim Shares Big News + Real Estate Market Trends with Kevin Walker 34:15

27d ago34:15

34:15

In this special episode of Pilot's Portfolio, Timothy P. Pope, CFP® sits down once again with Kevin Walker, CEO of Beacon Relocation, to break down current trends in the housing market that every pilot should be paying attention to. From shifting interest rates to buyer leverage, Tim and Kevin discuss what has changed since the last real estate con…

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[793] How Tom Bell Made Money on His First Flip (And What Almost Killed the Deal) 38:17

1M ago38:17

38:17

Most people think doing the work themselves will save money on a flip. Tom Bell thought the same thing. Until a “quick” 6-week rehab turned into 5 months of nights, weekends, and missed deals. This week on The Bottom Line, I sat down with Tom, one of our 7 Figure Runway members, who came back to real estate after COVID wiped out his rental income. …

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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: …

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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…

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[792] What Broke in Our Business (and How We Solved It) 57:17

1M ago57:17

57:17

Ever catch yourself thinking… “I’ll take action…once I know exactly what to do.” It sounds smart. Strategic. Responsible. Until you stall for months at a time waiting. This week I’m doing something different with my friend Dr. Sheri Fluellen. It’s called The Bottom Line. We’re sharing real stories. Actual numbers in our business. And answering one …

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#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…

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[791] He Started with Nothing—Now He’s Raised $400K+ Private Capital 38:58

1M ago38:58

38:58

This guy had every reason to quit. He didn’t grow up with a silver spoon. He didn’t have a network. He didn’t even have stability. Dairius Kawewehi spent most of his childhood in the foster care system. Then he joined the Navy—launching jets off aircraft carriers in one of the most high-pressure, dangerous jobs in the military. That’s where he lear…

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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…

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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.…

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[790] 90% of Millionaires Built Their Wealth THIS Way 9:46

1M ago9:46

9:46

There’s a lot of noise out there right now… You’ve probably seen the ads: Find an old guy with no website. Buy the business at a discount. Plug in an operator. Cash checks from the beach. Sounds great in theory. But 90% of millionaires built their wealth this way. One of the most overlooked and most powerful strategies in real estate right now is b…

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#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…

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What Happens If I Lose My Medical At American Airlines 20:46

1M ago20:46

20:46

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…

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[789] Breaking Down Our 13X Return On Direct Mail Marketing 52:50

1M ago52:50

52:50

Ever wonder what happens when you spend $39,000 on direct mail? Well, I’m pulling back the curtain on an ACTUAL direct mail campaign that brought in over $486,000 in revenue in Q1 alone this year at Blackjack Real Estate. We’re talking about a 1.5% response rate. That’s 3x the industry average. Plus, I brought on 7 Figure Altitude member, Sarah Car…

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

1M 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…

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

1M 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…

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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…

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[788] These Two Teenagers Flipped A House In 2 Weeks On TV 29:25

2M ago29:25

29:25

I just dropped one of my favorite podcast episodes ever. It’s with Sophia and Bella Mendez, two teenage sisters who flipped a house on camera for our new TV show, Kids Who Flip. Sophia is 18. Bella is 13. Together, they flipped a house in 2 weeks where they not only added square footage but also dealt with some serious problems like a broken furnac…

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[787] How This Power Couple Went from 0 to 8 Flips in Just 12 Months 47:30

2M ago47:30

47:30

Let me paint you a picture… A busted-up mobile home. No heat. No air. A couple with zero flipping experience (but a TON of grit) decides to take a chance and buy it anyway. And somehow they turn that NIGHTMARE property into a six-figure profit on their very first deal. Ted and Stephanie Sherrat, two awesome humans from Indiana, went from a W2 and c…