21.FIVE - Professional Pilots Podcast

WWII & Vietnam combat pilot Col. Richard “Dick” Bushong takes us from 155-knot B-17 climbs to Mach 2.1 in the F-4, describing 28 hairy missions, dead-reckoning nav, and sheet-metal patch art. He’s 102, still volunteers every Thursday at Tucson’s 390th Memorial Museum, and wrote My Wars to capture the stories. Grab a coffee, tighten your formation, and hear a masterclass in staying alive—plus the morale-crushing day HQ “prorated” his tour. Four engines, two out, no brakes? No problem.

Learn more about the 390th Memorial Museum in Tucson, AZ

Check out Col. Bushong's book My Wars

Show Notes<...

Dylan and Max are recording from hotel rooms across the country and catching up after some time off. They kick things off with a deep dive into aviation YouTube, comparing backcountry flying with ferrying retired Airbuses from Asia. In the mailbag, they respond to listeners with questions about juggling a corporate flying gig while working for a major airline, updates from a newly minted high school grad CFI, and a debate on whether you need to report vacating altitudes during "descend via" clearances. Flight Advice wraps the episode with tips for a low-time pilot who just landed a chief...

Dylan and Max are joined (again) by everyone’s favorite multi-hyphenate pilot, Seth Lake. This time, he walks them through the process of reinstating their expired CFI certificates—turns out it’s not as terrifying as they thought. From FOIs to ACS, Seth breaks it down like a DPE Jedi. If you've let your CFI lapse, or you're just morbidly curious, this one’s for you.

Seth's Website | 10% Off the ACE Guide

Seth's Youtube Channel

Show Notes

0:00 Intro

5:01 Keeping CFI Current

15:58 Reinstatement

31:27 Creating this Document

39...

Max shares his PM flying grind and how soft pay is easing the sting—plus a soggy New Orleans beignet run. The Mailbag is loaded this week with tales from a long-haul trucker pilot, NetJets rejection therapy, type rating dilemmas, and the dreaded training contracts making a comeback. In Flight Advice, a low-time pilot lands a dream SIC gig and asks: how do you not screw this up? Max and Dylan break down how to stand out and stay sharp as a new jet FO.

Garmin Smart Charts

100LL Video - The Hidden History of Av...

Forrest Owens, aviation attorney and private pilot, joins Dylan and Max to dive into the often murky waters of FAA enforcement, pilot liability, and what every professional and private pilot needs to know before picking up the phone. From NASA reports to ADS-B nightmares, this episode is your legal safety briefing—with a side of GoPro caution. Pilots, take notes… and maybe double-check your insurance policy.

Forrest Owens | Aviation Legal Counsel Website

Email: forrest@aviationlegalcouncil.com

Phone: 888-635-9529 (888-6-FLY-LAW)

AOPA Legal Services

Show Notes

0:00 Intro

Dylan and Max kick off with hotel room hacks and tire maintenance DIYs (bed liner on bush wheels, anyone?). In the mailbag, listeners chime in on cicadas, bar recs, AI dolls, and a heartfelt shoutout to a rockstar CFI. Flight Advice features a double header: first, whether to stick with an aviation degree or pivot, and second, a pilot blindsided by a mysterious 135 termination—and the training contract bill that followed.

North America's 50 Best Bars via Listener Vince

Show Notes

0:00 Intro

4:41 Tire Coating and Cicadas

8:48 Flying Diversions

18:02 Re...

Dylan and Max debut their slick new intro track, give a proper welcome to their AI assistant "Reginald Sage," and swap tales from off-airport landings and Vegas tire goo mysteries. The Mailbag is packed with listener feedback on etiquette videos, bird segments, and even a nighttime trucking dispatch. In Flight Advice, a 26-year-old CFI wonders if a gig flying in Dubai is a golden ticket or a trap. The guys break it down with laughs, caution, and a few hydration tips.

Kalitta Air Flight Deck Ettiquette YouTube Video

Show Notes

0:00 Intro & Reginald Sage<...

Tim Pope returns to the 21.Five cockpit with a fresh instrument rating and a new venture—360 Aviation Advisors. He breaks down Q1’s market turbulence, political biases in financial behavior, and how pilots can prep for leaner flying days. Plus, Dylan and Max dive into “Captain Lifestyle Syndrome” and how to navigate financial FOMO with some flight advice.

Visit Tim's website for more information or to schedule a consult.

Show Notes

0:00 Intro

6:20 Updates and Q1

15:03 Planning For The Next 6-12 Months

20:53 Airline Slowdowns

33:31 Flight Advice: Realisti...

This episode kicks off with Dylan and Max diving into pilot health: UV exposure, compression socks, and the harsh truth about retirement and quality of life. In the Mailbag, listeners share wild MU-2 stories, dream trips, and thoughts on skipping the CFI route. The Flight Advice segment checks in with a second-career pilot trying to break into corporate aviation, revealing how timing, networking, and persistence are the real flight plan to success. This one’s for anyone trying to stay in the air—and out of the ER.

Check out Aero Shield's Pilot Armor

Show Note...

Dr. Chris Broyhill is back with updates on pilot compensation, market shifts in 2025, and a sneak peek at his upcoming leadership book for bizav professionals. We dig into the real value of the AirComp Calculator, how to use salary data without tanking your next negotiation, and what separates the professionals from the job-hoppers. Plus, Dr. Broyhill drops some spicy takes on military-to-civilian leadership advice.

The AirComp Calculator™ is business aviation’s only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in s...

Dylan and Max kick things off with stories of Cub flights and musing about GLS approaches and Starlink’s newest data plans. The Mailbag’s international flair includes a heartfelt message from a UK pilot and some simmering debate on career paths and sim setups. Flight Advice dives into the looming specter of single-pilot airline operations and how to future-proof your career (hint: maybe dust off that CAD software). Plus, the guys grapple with networking challenges for introverts in aviation.

Show Notes

0:00 Updates: Cub, Starlink, GLS Approaches

21:14 Reviews & Comments

25:01 Mailbag: Networking and...

In this episode, Dylan and Max sit down with James Onieal, founder of Raven Career Development, to discuss the current state of pilot hiring and effective strategies for advancing your aviation career. James shares his journey from the cockpit to career coaching, offering invaluable insights for pilots navigating today's job market. Tune in for a candid conversation filled with practical advice and a few laughs along the way.

Book your session with James Onieal

Hide your mailing address on the FAA Database here

Show Notes

6:59 Updates: Softening Market

14:19 Expectations...

Max shares a wild story involving VFR ops in a jet and a last-minute divert to Deer Valley when Scottsdale Tower ghosted them. We cover the final chapter of Hard Landing in the book club and reflect on takeaways from the book. In the mailbag, we talk about MU-2s doing angel work, the A&P to pilot career path, and the latest 737 LRD drama. Flight Advice: Should I keep my survey job or finish my CFI? Oh, and we may have created a secret pilot Freemason society while we were at it.

More info on the...

In 1995, a team of aviation cowboys set out on a mission that sounds too crazy to be real: fly a WWII B-29 bomber out of the Arctic after 50 years of abandonment. But as guest Vernon Rich tells us, things did not go as planned. From rigging up fuel pumps with trash equipment to landing a Caribou with propane-inflated tires, this story has it all—engineering ingenuity, brutal cold, and a heartbreaking ending. Strap in for one of the wildest aircraft recovery stories ever attempted.

Watch the documentary here

Contact Vernon Rich / Rich Precision Faborication

...

Dylan and Max kick things off with a deep dive into airline wifi, airport food inflation, and Dylan’s latest experiment—testing the Starlink Mini in the cockpit. Max recounts his wild adventure ferrying a Carbon Cub across the country (spoiler: electrical gremlins strike). The mailbag is packed with listener updates and career insights, while Flight Advice gets spicy with a retired airline pilot looking to pick up business jet contract work. Spoiler: It’s not as easy as he thinks.

Show Notes

0:00 Intro & Starlink

7:48 Carbon Cub Adventure

20:00 Shoutouts

23:48 Hard L...

Aviation insurance guru Tom Hauge from Wings Insurance is back, and this time, he’s got good news! After years of skyrocketing premiums, the insurance market is finally softening—meaning lower rates and fewer headaches for pilots and operators. Tom breaks down why this is happening, how you can take advantage of it, and what mistakes to avoid when renewing your policy. We also dig into contract pilot coverage, the risks of bush planes, and which aircraft are nightmares to insure. If you own or fly an airplane, you need to hear this one!

Connect with Tom on L...

Dylan and Max return after a wild week filled with airline rumors, aviation history, and some sobering accident reports. They break down the bizarre (and quickly debunked) Southwest-JetBlue merger rumor and share their experience chasing the final landing of the last Martin Mars flying boat. The guys also discuss the recent streak of high-profile aviation accidents and their impact on the industry. Hard Landing Book Club Chapter 17: United searches for a new CEO. In the Flight Advice segment, a retiring police officer wants to make the jump to professional flying—what’s the best path forward?

Show Note...

Back by popular demand, our favorite widebody-wielding, sleep-deprived, jetlag-conquering airline pilot—Ted—returns! This time, we’re diving deep into the reality of long-haul flying on the Boeing 787. Ted breaks down the pros and cons of international schedules, surviving crew rest, navigating time zone chaos, and why he’s officially done making PAs. Plus, we tackle the never-ending debate: Is international flying the best move for airline pilots? Grab a Tiger beer and join us for some unfiltered Straight Talk with Ted.

Show Notes

0:00 Intro

2:26 Parenting as a Pilot

5:15 Flying Wide Body Long...

Dylan and Max kick things off with a deep dive into the real debates that matter—hotel chain allegiances and the latest pilot hangout in Dallas. Max shares the chaos of nearly missing the birth of his child, a wild Honda Jet radio exchange, and an unexpected submarine sighting. The mailbag is packed with a debate on whether international flying is actually more fatiguing than domestic, a career transition question from an A&P mechanic turned pilot, and a listener with an incredible connection to legendary pilot Harvey Watt. Flight Advice tackles the serious question of what you should do...

Ever wondered what it’s like flying for the Air National Guard? In this episode, Ben joins Dylan and Max to share his journey from high school aviation dreams to the cockpit of a KC-135. We break down the steps to becoming a Guard pilot, how to balance it with a civilian flying career, and why the Guard might be the ultimate flexible gig for pilots. Plus, insider tips on navigating deployments, training, and building a career that works for you.

Connect with Ben on LinkedIn

Show Notes

0:00 Intro

2:51 Ben’s Avia...

Dylan and Max dive into Mr. Beast's bizarre aviation challenge: could you live on a Falcon 2000 for 100 days? The mailbag is overflowing with listener emails about infrared deicing, regional bases, and crazy career pivots. We also revisit the airline consolidation saga in the Hard Landing book club segment and discuss its lasting impact on the industry. Flight Advice wraps up with an ambitious 18 year old looking for career guidance.

Show Notes

0:00 Intro

2:09 Mr. Beast’s Pilot Challenge

17:05 Hard Landing Book Club: Chapter 

30:19 Max’s Musings: Addiction to Premium

35...

We’re joined by Megan Tuttle and Jordan Thieme from AeroTow, part of Amigo Mobility International, to dive into their innovative aircraft tugs. From humble beginnings in a Wisconsin garage to creating tugs that save your back (and your time), their story is as compelling as their products. Hear how they’re redefining aircraft handling for pilots, all while keeping it in the family. Plus, Max shares how AeroTow’s T1 has already transformed his hangar life!

Learn more about AeroTow's family of aviation tugs

Use code "21five" at checkout for $100 off any AeroTow product!

...

James Onieal joins Dylan and Max to unpack the turbulent landscape of pilot hiring in 2025. From overhiring at the majors to regional pilots struggling to stand out, James offers no-nonsense advice on how to stay competitive. Whether you’re a CFI with big dreams or a seasoned military pilot planning your exit, this episode is packed with actionable insights for navigating the year ahead. Tune in for a mix of hard truths, strategies, and a few good laughs!

Get in touch with James Onieal

Show Notes

0:00 Intro

2:22 2025 Hiring Forecast

17:46 To...

In this episode, we chat with 747 captain and Paradox Aviation Luggage co-founder, Derrek Khajavi. He gives us the inside scoop on ACMI flying, what it’s like hauling everything from lithium batteries to cows, and why he’s clinging to the 747 throttles for life. Plus, we dive into his innovative luggage company and how he’s solving everyday pilot problems, one aluminum bag at a time.

Check out Paradox Aviation's Luggage

Show Notes

3:07 All About ACMI

11:41 The 747 & Getting the Position

20:54 Starting Paradox Aviation

40:37 Packing Techniques

50:45 Other F...

In this episode, Dylan and Max dive into the world of pilot tech toys, debating the merits of the Meta Smart Glasses for aviation and everyday life. The mailbag overflows with emails about flying for passion versus practicality, dealing with unexpected VIP TFRs, and updates from listeners taking unique paths in their aviation careers. Finally, the Flight Advice Fiesta tackles navigating military-to-bizav transitions and making career decisions that align with long-term goals.

Show Notes

0:00 Meta Glasses

11:26 Microsoft Flight Simulator

18:18 Plane Updates, Snow Broom, and Giant Microwaves

27:04 Reviews & Pilot Podcasts<...

Q4 is crunch time in the business aviation world, and Brooks from Vaerus Jet Sales is back to explain why. From analyzing tax incentives like bonus depreciation to discussing market trends on popular airframes, Brooks shares his insights on what’s hot (and not) in bizjet sales. He even gives us a peek into his DC-3 adventures and drops some hard truths about insurance and personal use compliance. If you're a pro pilot or a bizav enthusiast, you don't want to miss this one!

This week, Dylan and Max tackle the highs and lows of aviation life, from Max’s fuel leak woes to a surprising guest appearance reviewing the new Microsoft Flight Simulator. In the Mailbag, listeners share experiences from the world of air ambulance flying and tips for mastering cockpit emergencies. Flight Advice takes on a big question for aspiring airline pilots: should you intern with a major airline or focus on building hours?

Show Notes

0:00 Realistic Day in the Life

8:14 Microsoft Flight Sim 2024

12:53 Hard Landing Book Club: Chapter 13

20:50 Aviation is a...

In this episode, Dylan and Max sit down with Jim Lara of Gray Stone Advisors and Jenny Showalter of Showalter Business Aviation Career Coaching to explore the critical role of leadership in business aviation. They unpack why many flight departments are at risk and how strong leadership can be the difference between thriving or shutting down. From empowering the next generation to navigating small flight departments, Jim and Jenny offer actionable insights for pilots and aviation pros alike.

Jenny Showalter | Showalter Business Aviation Career Coaching | Follow on LinkedIn

Jim Lara | Gray Stone Advisors | Follow on L...

Dylan and Max jump right into Max’s “notes,” sharing stories of unique ATC run-ins, surprising speed regulations, and the challenges of keeping a safe cockpit. In the mailbag, listeners chime in on airline pilot influencers and the unique journey of buying an airplane for time-building. Finally, the Flight Advice segment tackles a tough choice: a new regional pilot gig versus a unique CBP opportunity. Plus, some updates from our aviation-themed book club and tips for maintaining CRM in small flight departments!

Briggs and Riley SmartLink strap / J Hook replacement

Show Notes

2:09 Max’s Notes<...

Dr. Broyhill joins us for an in-depth look at the latest pilot compensation data and the shifting landscape of aviation salaries. From surprising increases in maintenance roles to the impacts of training backlogs, we dig into what’s driving today’s pay rates. Plus, we discuss retention tactics, leadership lessons, and how to assess a job offer beyond just the dollar signs. A must-listen for any pilot navigating today’s job market! Employee Compensation Software That Answers "What's the Going Rate?"

The AirComp Calculator™ is business aviation’s only online compensation analysis system. It can provide precise compensation ranges for 14 bus...

In this episode, Dylan and Max reminisce about the grueling interview days at American Eagle, where 500 hours landed you in the 707 sim. They compare corporate and airline training styles, from smoke-filled cockpit drills to NDB approaches and trust falls. Mailbag: Reserve Flying, Setting the record straight on the United 570, and more on the Delta sidestep. Flight Advice: A tense relationship with a chief pilot after securing a better compensation package.

Show Notes

0:00 Intro & Hot Air Balloons

3:33 Smoke Training & Other Thoughts

24:51 Descend Via Clearance Response

29:34 Ass Pad, 787 Book, NOTAM System

In this episode, Dylan and Max sit down with Kaity (aka Pilot Kaity) to explore her unconventional journey through light sport flight training. Kaity shares how she found a unique path that kept her out of debt and got her into the cockpit faster than most. Plus, Kaity drops some career advice on balancing cost-saving hacks with quality training.

Follow Kaity on Instagram | YouTube

Show Notes

0:00 Intro

6:30 Kaity’s Background

16:01 Instructing Light Sport

22:32 Pilot Path Plans

37:46 Transition to PC-12 & Social Media

47:23 Kaity’s Air...

In this episode, Dylan shares his recent experience flying Southwest and reflects on the airline’s unique in-flight culture. The guys also discuss the lessons from United’s pilot strike and its impact on the industry as recounted in Hard Landing. The Mailbag includes a listener’s take on sidestep maneuvers and the challenges of operational compliance. For Flight Advice, a listener asks whether it’s better to go Fractional, Regional, or ULCC after flight instructing. 

0:00 Intro

2:48 Southwest Shananigans

5:27 Max’s Airplane Mission

11:42 Getting Random-ed

15:37 24-Hour B2 Sim

16:51 Woo...

In this episode, Dylan and Max welcome back career expert James Onieal from Raven Career Development to discuss the state of the aviation industry and how pilots can navigate these turbulent times. From ULCC pilots feeling stuck to legacies that aren’t hiring as quickly, James dives deep into how pilots can strategize their next move. If you’re wondering whether it’s time to jump ship or stay put, this episode is for you.

Get in touch with James Onieal (and tell him you heard him on the 21Five Show!)

Show Notes

0:00 Intro<...

Dylan and Max reflect on the surprising amount of time pilots spend together, from shared meals to long-haul convos in the cockpit. We cover Chapter 9 of Hard Landing in the book club. A listener writes in about a vibrating seat mystery on a recent 787 flight. And in Flight Advice, the hosts help a commuting pilot navigate the unwritten rules of jump seat etiquette, offering tips on how to avoid awkward situations while traveling in uniform.

Show Notes

0:00 Intro

8:03 Story Time with Max

22:34 Hard Landing Book Club: Chapter 9

37:50 Listener Reviews<...

In this episode, Dylan and Max sit down with Casey Murray, President of the Southwest Airlines Pilots Association (SWAPA), to discuss the challenges and triumphs of leading 10,000 pilots. From contract negotiations to managing pilot expectations, Casey sheds light on what it takes to keep a union strong and independent. Plus, we dive into the flexibility pilots enjoy at Southwest and what’s next for the airline.

Show Notes

0:00 Intro

2:12 Union Basics

10:26 Professional Standards & Negotiations

26:56 Contract Cycle & Ending Negotiations

41:05 Pilot Flexibility & Looking Ahead

54:58 Unpredictability and Industry Ad...

In this episode, Dylan and Max dive into the surprising results from the 2024 AIN product survey, revealing a major shake-up in aircraft rankings—Bombardier is on top, while Gulfstream slips. The mailbag features a listener sharing their experiences with tricky aircraft maintenance, sparking a hilarious yet insightful discussion on handling service centers. 

In the Flight Advice segment, Dylan and Max advise a low-time CFI feeling overwhelmed by professional pilot knowledge. They suggest starting with basics like turbine engine systems and crew resource management, reassuring them that it's normal to feel this way early in their career.

E...

In this episode, Dylan and Max sit down with financial guru Timothy P. Pope to navigate the complexities of financial planning for pilots. From managing retirement funds during an election year to deciding whether to pay back a hefty retention bonus, Tim offers sage advice tailored to the unique needs of aviation professionals. If you've ever wondered how to make the most of your airline's financial programs or whether to stay the course in a volatile market, this episode is a must-listen.

Show Notes

0:00 Intro

3:08 Handling Election Years

9:17 Unexpected Stalls & Other...

They guys catch up on their latest adventures. Book Club: Hard Landing Chapter 7. In this episode’s mailbag, they discuss listener feedback on braking roll-aboards and tough non-rev adventures. Finally, in Flight Advice, they dig into the dilemma of choosing between a tough commute at a struggling ULCC or trying out the cargo life, all while aiming for that elusive legacy carrier job.

Show Notes

0:00 Intro & Story Time with Max

16:29 Hard Landing Book Club: Chapter 7

27:10 Reviews

29:45 Mailbag

41:16 Flight Advice

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In this episode, Dylan and Max are joined by Greg from Advanced Air Crew Academy to discuss the latest updates in international operations. They dive into changes in oceanic clearance procedures, the impact of GPS spoofing, and essential tips for flying internationally.

Check out Advanced Aircrew Academy's International Training Modules.

OpsGroup GPS Spoofing Working Group

Show Notes

0:00 Intro

3:46 International Clearance Procedures

11:51 GPS Spoofing

20:27 Electronic Plotting & SAFA Inspections

28:59 Mexico, Canada, and More

37:47 Greg’s Funny Story

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