Best Checkrides Podcasts (2025)

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Checkride Insights Ep. 1 — Tom Guillebeau on Setting Expectations and Avoiding Pitfalls 1:01:58

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1h ago1:01:58

1:01:58

In the premiere episode of Checkride Insights, Seth sits down with Tom Guillebeau, a seasoned Designated Pilot Examiner and C-130 instructor pilot with the Arkansas Air National Guard. Tom shares his journey from mowing lawns for flying lessons to becoming a military evaluator, and gives practical advice for checkride applicants—from setting expect…

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

21h 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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EP130 - Debriefing the Debriefs: Part 2 - Instrument Checkrides 1:07:00

29d ago1:07:00

1:07:00

In the compelling conclusion to their check ride series, the Midlife Pilot crew explores instrument rating experiences drawn from their Patreon community. From developing the perfect instrument scan to battling temperamental autopilots and partial-panel approaches, this episode reveals the unique challenges—and profound rewards—of becoming an instr…

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EP134 - CAF Adventures, Heat Domes, and Shredded Tubes 1:04:34

23h ago1:04:34

1:04:34

The crew welcomes Dev Cannon, who exemplifies the CAF mission by going from aviation newcomer to Music City Wing Commander in just a few years, leading 70 volunteers in preserving warbird history. Dev explains how the CAF's 19,000 international members keep aviation heritage alive through everything from flyovers at memorial services to introducing…

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Personal Minimums, Risk Management, and 135 Checkrides: What You Need to Know 1:00:59

2d ago1:00:59

1:00:59

In this episode of the VSL Aviation Podcast, Seth dives deep into the often-misunderstood topic of personal minimums—how to build them, stick to them, and apply them on checkride day. Using FAA guidance and practical examples, he outlines real-world risk management techniques, including when to cancel a flight and how to safely mitigate marginal we…

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Decoding the ACS | Part 5 - Mastering Airspace: Private, Commercial, and CFI-Level Scenarios 1:00:55

5d ago1:00:55

1:00:55

This is Episode 5 in the Decoding the ACS series, where we break down the Airman Certification Standards one task at a time. In this episode, we cover Area of Operation I, Task E: National Airspace System. Whether you're preparing for your Private Pilot, Commercial Pilot, or CFI checkride, this session explains how this task is tested across all th…

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EP133 - Ice Bags in Your Nether Regions: Remote Field Breakdown Survival Guide 57:47

8d ago57:47

57:47

The guys tackle the inevitable reality of breaking down away from home - and yeah, "you did it to yourself by choosing to take on flying in midlife." They get real about emergency prep: "have a leatherman, have zip ties, have tape" and for the love of all that's holy, "cash is options, cash is flexibility." Brian drops wisdom about proactive mainte…

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

6d 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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#114 - Trusts, Taxes & Transfers: What Every Investor Should Know with Amanda Wynalda 59:50

15d 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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EP132 - Information Whiskey: Smart Charts and Fish Finders 1:00:23

15d ago1:00:23

1:00:23

Ben raves about Garmin Smart Charts as a potential ForeFlight killer, while the gang shares their biggest radio pet peeves - from the dreaded "with you" to "fish finder." Brian explains why his ignition wires "date back to when Jimi Hendrix was an unknown rising guitarist," and they dive into listener feedback about check ride prep (spoiler: don't …

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

22d 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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EP131 - 4% Gain to Go Pants Less - Cross Country Cockpit Organization 1:04:48

22d ago1:04:48

1:04:48

The crew tackles long cross-country cockpit organization after Ted's epic 5,400-mile journey reveals that going "pants-free" provides a "4% gain" in performance (wheel pants, people!). From the critical importance of blue shop towels to strategic snack placement and lumbar support, Ben, Brian, and Ted share hard-earned tips for setting up your cock…

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CFI Hour Myths, MEI ROI, and Avoiding Illegal Charter: Live Q&A 1:00:44

25d ago1:00:44

1:00:44

In this live Q&A edition of the VSL Aviation Podcast, host Seth Lake dives into a wide range of topics submitted by the aviation community. From the myths around required CFI ground training hours to advice on whether getting your MEI is worth the investment, Seth provides practical, experience-based insights. He also tackles how to avoid inadverte…

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

29d 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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#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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EP129 - Debriefing the Debriefs: Part 1 - Private Pilot Checkrides 1:04:40

1M ago1:04:40

1:04:40

In this first installment of their two-part check ride series, the Midlife Pilot Podcast crew mines gold from their community's private pilot exam experiences through intimate Patreon debriefs. Ben, Brian, and Ted tackle everything from the anxiety-inducing oral exam (which Ben likens to "walking into the delivery room") to those heart-stopping lan…

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

1M 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 …

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EP128 - Two Bounces and a Skip: Planning vs. Reality 1:08:00

1M ago1:08:00

1:08:00

Join the Midlife Pilot Podcast crew as they return from their epic Texas fly-in adventure with tales of triumph, near-misses, and one unfortunate set of wheel pants. Ted recounts his 28.3-hour post-fly-in journey that somehow went east instead of west ("Look, you can only chase tailwinds for so long"), while Brian shares his VFR limits revelation (…

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EP127 - Big Texas Send Live from T82: Between Two Wheelpants 1:13:21

2M ago1:13:21

1:13:21

The Midlife Pilot Podcast hosts the Big Texas Send fly in at T82 in Fredericksburg, TX and lands with a thud (but "didn't dent the runway") at the gorgeous TAC Aero hangar. Ben, Brian, and Ted swap harrowing journey tales involving everything from Brian's "measured scud running" to Ted mysteriously ascending to 15,000 feet in a light sport ("Try a …

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

2M 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 …

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Logging Time, Checkride Tips & Pilot Questions 1:19:31

2M ago1:19:31

1:19:31

In this episode, we celebrate new pilot certifications 🎉, tackle common logbook questions 📘, explain how ForeFlight sources winds aloft 🌬, and clarify cross-country time rules 🗺. We also walk through a real listener landing scenario at KVNY 🛬, give a quick weather symbol refresher 🌦, cover what to do if ADS-B is inoperative 📡, and answer listener q…

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

2M 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…

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EP126 - Information Whiskey: "Like Oregon Trail Without Dysentery" 56:08

2M ago56:08

56:08

The Midlife Pilot crew prepares for their "Big Texas Send" fly-in at T82 while navigating spring weather challenges. Brian celebrates returning to flying after a 42-day maintenance hiatus, sharing stories of tower tours and smoke-signaling air tractors. Ted plans his epic 1800-mile cross-country journey in his LSA, which Brian dubs "Oregon Trail wi…

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Runway Excursions, Non-Standard Climb Gradients, and Weather Radar Tips 1:08:12

2M ago1:08:12

1:08:12

In this week's episode of the VSL Aviation Podcast, we dig into three real-world flying topics pilots must know: Runway Excursion Mitigation: A deep dive into Advisory Circular 91-79B, how to avoid overruns, and a real-world discussion led by Ryan Bow about common landing errors and risk factors. Non-Standard Climb Gradients: Learn how to spot non-…

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

2M 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—…

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EP125 - "What Am I Doing?": Extinguishing Helmet Fires Before They Consume You 1:04:59

2M ago1:04:59

1:04:59

When your CFI asks for your name and you respond with "standby" – you're experiencing what pilots call a helmet fire. In this episode, Ben, Brian, and Ted dive into the phenomenon of task saturation that affects pilots at every level, from Ben's instrument approach adventures where he made what sounded like "Charlie Brown's teacher" over the radio,…

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Wet vs Dry Leases, Second Opinions, and Manifold Pressure Myths 1:31:18

2M ago1:31:18

1:31:18

This week on the VSL Aviation Podcast, Seth dives into three major topics that affect pilots across the training and professional spectrum. First, he breaks down the difference between wet and dry leases — why it's critical to understand operational control, how to avoid illegal charter situations, and what lease paperwork needs to be in place. The…

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#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…

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EP124 - Parking: The Episode That Goes Nowhere 57:29

2M ago57:29

57:29

Join the Midlife Pilot Podcast crew as they tackle the surprisingly complex world of airport parking that flight schools never teach you. Between Brian's maintenance woes with Lucy, Ted's triumphant return of "the egg" from annual, and preparations for their upcoming Texas fly-in, the hosts share hilarious stories about confusing marshaling signals…

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

3M 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…

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EP123 - The Answer to All Solutions: Level Seven Hangar Living 1:03:41

3M ago1:03:41

1:03:41

In this episode, Ben, Brian, and Ted dive into the challenges of finding and maintaining hangar space, or not having one. From ratchet straps (BAD) and tornado warnings (ALSO BAD) to the joys of electricity and the sorrows of cold starts, the guys discuss how far they'd travel for a good hangar and why sometimes your plane becomes 'an outdoor pet.'…

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Accidents, Digital Avionics, and Required Equipment: What Every Pilot Should Know 1:13:09

3M ago1:13:09

1:13:09

In this episode, Seth dives into three critical areas for every pilot: what to do after an accident, how modern digital avionics like MEMS sensors work, and a practical breakdown of maintenance responsibilities and required equipment. You'll get clear, no-nonsense guidance on pilot responsibilities at the scene of an accident, how to interpret comp…

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Runway Incursions, Practical Test Tips, and Live Q&A 1:19:21

3M ago1:19:21

1:19:21

In this episode of the VSL Aviation Podcast, Seth Lake dives into runway incursion avoidance, a critical focus area for the FAA and a common checkride discussion point. He shares insights from the FAA’s From the Flight Deck initiative and explains how this content can help applicants prepare—especially for CFI-level checkrides. The second half feat…

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

3M 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…

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EP122 - "I Plan My Stops Around Food" and IFR Training: CFII Erica Gilbert 1:04:36

3M ago1:04:36

1:04:36

Join us for special guest Erica Gilbert, a CFII and TBM pilot who brings her expertise on cross-country planning and adult learning to the show. While Ben mourns his grounded "Beast" waiting on engine work, and Mark celebrates his impressive 693-nautical-mile nonstop flight in his upgraded Cherokee 235, Erica shares her refreshing approach to fligh…

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How to Become a Pilot ep. 9 59:44

3M ago59:44

59:44

Send us a text We sat down with firefighter and and new student pilot Tiffany Walls-forte, who drove straight to the studio after her discovery flight. She shares her experience, excitement, and readiness to begin flight training. Tiffany took off from Oakland airport enjoyed beautiful and unique views of the bay. If you are interested in becoming …

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

3M 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…

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EP121 - Information Whiskey: Between Patience and Numbness 1:03:48

3M ago1:03:48

1:03:48

Join Ben, Brian, and Ted for hangar talk about the joys (and pains) of annual inspections in this episode of the Midlife Pilot Podcast. The guys commiserate over their planes being simultaneously grounded, with Ben's Beast down to five cylinders and showing remarkable "patience" (or is it numbness?). Brian dishes on his new book of aviation essays …

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Don’t Log That! FAA Time-Building Mistakes and How to Avoid Them 54:38

3M ago54:38

54:38

In this week’s VSL Aviation Podcast, Seth dives deep into three critical topics for pilots and instructors alike. First, he breaks down how to get involved with the FAA Safety Team (FAASTeam) and make the most of the WINGS Program. Next, he explains the real why behind airspace design—offering a fresh approach for CFIs to improve student understand…

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

3M 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…

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EP120 - Descending from Mount Stupid: with Paul Craig 1:04:17

3M ago1:04:17

1:04:17

For this very special episode we welcome Paul Craig, author of "The Killing Zone," "Be a Better Pilot," and numerous other aviation books including his memoir "Flight Times: Stories from the Second Best Instructor." In this episode, we explore how aviation has evolved since Paul's last book edition, from the rise of electronic flight bags to the We…

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ADS-B Pitfalls, Mastering Forward Slips, and What CFIs Are Missing 49:44

3M ago49:44

49:44

Welcome back to the VSL Aviation Podcast! I'm your host, Seth Lake, a CFI and DPE here to help you navigate checkrides and general aviation topics. This weekly podcast is recorded live on Discord, with additional streaming on YouTube, Instagram, and Twitch. In this episode, we dive into three major topics before opening the floor to listener questi…

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Illegal Charters, Emergency Procedures, and Checkride Prep – VSL Aviation Podcast 1:14:40

3M ago1:14:40

1:14:40

VSL Aviation Podcast – Episode Recap In this episode of the VSL Aviation Podcast, host Seth Lake dives into key aviation topics, answers listener questions, and shares insights from real-world flying experiences. Topics Covered: Chapters: 02:30 Understanding Part 135 Operators – How to verify if an employer is legally operating under Part 135, usin…

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

4M 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…

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EP119 - The Cockpit Lies, Data Doesn't: Flysto Debrief 54:42

4M ago54:42

54:42

Join Ben, Ted, and special guest Mark (aka 1DullGeek) as they talk Flysto, the flight-tracking app that brutally reveals they're better and worse pilots than they thought. Geek out over landing scores, wind data, and traffic playback that "takes the emotional component out of the debrief" – perfect for analyzing that crosswind landing you swore was…

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Avoid These Pilot Errors! | 2025 FAR Changes, CFI Privileges & TEM Explained 1:09:15

4M ago1:09:15

1:09:15

In this episode of the VSL Aviation Podcast, Seth Lake covers a variety of key aviation topics and answers listener questions. We kick things off with Threat and Error Management (TEM) and how to apply it in your daily flying. Then we dive into clarifying CFI responsibilities, discuss updates to the 2025 FAR/AIM, and wrap up with insights on CFI pr…

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From Childhood Dreams to Checkride: Ali’s PPL Journey | ep. 8 56:24

4M ago56:24

56:24

Send us a text In this episode of the Fly Media podcast, we interview student pilot Ali Chokr, who shares his journey from childhood fascination with aviation to preparing for his checkride. They discuss the challenges of flight training, the importance of choosing the right flight school, and flight instructor. Ali shares his experiences flying in…

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

4M 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…

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EP118 - All Aboard the Pain Train: The Trials of Aircraft Ownership 49:21

4M ago49:21

49:21

"Freedom to go broke." The guys dive deep into the bittersweet reality of aircraft ownership—from the freedom it provides to the unique challenges it presents. Brian compares airplane ownership to marriage, Ted discusses his aversion to suction cups, and Ben reveals he's "fully funded on my pro rata share" of an eventual engine overhaul. They discu…

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A Lifetime in the Sky: American Eagle Captain Sue Clark | ep.7 45:32

4M ago45:32

45:32

Send us a text Get ready for an inspiring episode featuring aviation legend Sue Clark—a retired American Eagle Airlines captain, one of the first female Designated Pilot Examiners (DPEs), and the founder of RV to the Rescue, a nonprofit that saves animals through aviation. Sue shares her incredible journey, from breaking barriers as a female pilot …