21.FIVE - Professional Pilots Podcast
A podcast for Professional Pilots, by Professional Pilots. Join hosts Dylan and Max, both professional pilots with backgrounds in Flight Instructing, Airlines, and Business Aviation, on their quest to improve as travelers, pilots, and professionals. Expect to find interesting conversations with industry experts in a variety of aviation fields, thought-provoking discussions on hot topics, and hilarious stories from the (sometimes) wild aviation industry. Whether you’re corporate, airline, charter, or anywhere in between, you’ll love our fresh and often funny take on all things aviation. Come find us online at 21fivepodcast.com and connect with us via Insta/Facebook/Twit...
167. What Happens When the Market and Your Airline Career Both Stall?
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...
166. Why Aren’t More Pilots Talking About Healthspan?
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...
165. Should You Really Jump Ship for 15 Grand More?
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...
164. How Do You Network in Aviation If You're an Introvert?
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...
163. Should You Panic or Prep? James Onieal Breaks It Down
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...
162. Can You Really Plan for an Unplannable Career?
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...
161. Is This the Craziest Warbird Recovery Attempt Ever?
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
...
160. Want to Fly Biz Jets After Airline Retirement? Here’s the Reality
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...
159. Is Aviation Insurance Finally Getting Cheaper? w/ Tom Hauge
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...
158. What’s Going on with All These Aviation Accidents?
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...
157. What’s It Really Like Flying the 787 Internationally? w/ Ted
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...
156. Does an A&P Give You a Leg Up in Business Aviation?
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...
155. The Air National Guard: Is This the ultimate career hack for pilots?
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...
154. Could You Survive 100 Days in a Falcon 2000?
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...
153. From Garage Invention to Aviation Must-Have: The AeroTow Story
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!
...
152. 2025 Pilot Hiring: What's Happening And What Should I be Doing About It?
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...
151. From Cargo to Carry-Ons: Flying ACMI in a 747 and Building Better Bags
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...
150. Flight Advice Fiesta!
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<...
149. What’s the Buzz in BizAv? Market Update with Brooks
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!
VAERUS MEANS RIGHT, TRUE, AND REAL.Buy or sell an aircraft the right way, usin...148. Fuel Leaks, Flight Sims, and Airline Internships—Oh My!
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...
147. Can Strong Leadership Save Your Flight Department?
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...
146. Flying for the Regional vs. Flying for the Border: Which Path to Choose?
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<...
145. How Much Should You Really Be Earning? Salary Insights from the AirComp Calculator
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...
144. 707s, NDBs, and Impossible Interviews (Mailbag & Flight Advice)
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
143. Can Light Sport Training Save You Big Bucks?
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...
142. What happens when pilots strike?
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...
141. Thriving in Tough Times w/ James Onieal
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<...
140. Ever Been Stuck with a Boring Co-Pilot?
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<...
139 What Does It Take to Lead 11,000 Pilots? w/ SWAPA President Casey Murray
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...
138. Feeling Stalled Out as a CFI? Here's How to Start Learning Pro Pilot Skills
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...
137. What Should Pilots Do with Election-Year Market Jitters?
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...
136. The Misadventures of Max plus Mailbag and Flight Advice
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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Be sure to su...
135. INTL Ops Update: GPS Spoofing and New Clearance Procedures
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
Be sure to subscribe to...
134. Should I leave my comfortable job to fly the 747?
In this episode, Dylan and Max dive into the bizarre trend of passengers "raw dogging" flights and wonder what the pilot equivalent would be. Then the guys dive into Chapter 6 of Hard Landing. The Mailbag segment features listener reviews and heartfelt stories, while Flight Advice tackles a career decision about flying the 747 versus staying at a regional airline.
Show Notes
0:00 Intro & Raw Dogging Flights
10:59 Hard Landing Book Club: Chapter 6
23:50 Reviews and Comments
26:04 Mailbag & Furlough Flute Remix
41:42 Flight Advice
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Be sure to subscribe t...
133. Should You Sign an Airline Training Contract?
In this episode, Dylan and Max dive deep into the topic of airline training contracts with industry expert James Onieal from Raven Careers. They explore the pros and cons, legal considerations, and long-term career impacts of signing such agreements. Whether you're a Gen Z pilot or a seasoned aviator, this discussion will help you make an informed decision. Plus Flight Advice with James: Should a 5 year SWA pilot leave for UAL?
Get in touch with James Onieal (and tell him you heard him on the 21Five Show!)
Show Notes
4:00 Predatory Training Contracts
<...132. The Balancing Act: Parenthood and Pilot Life
Dylan and Max dive into their recent Father's Day cold plunge experience and its benefits for muscle recovery, then talk about recent trips to DC, Aspen, and Havana. They read listener emails about the best luggage for pilots. In the Flight Advice segment, they tackle the challenge of balancing a pilot career with impending fatherhood, offering tips on how to stay present in your kids' lives while working the skies. Episode Outline
[00:00:00] - Introduction
[00:00:19] - Father's Day Cold Plunge Experience
[00:03:53] - Max goes to Havana and Aspen, Dylan goes to DC
[00:19:20] - Book...
131. What is the Pilot's role in an Aircraft Transaction?
In this episode, we welcome back Brooks Pettit, an expert in aircraft transactions with Vaerus Jet Sales. Brooks shares his insights on the ongoing debate between the Challenger 350 and the G280. He provides a balanced view, discussing the advantages and disadvantages of both jets from an operational and ownership perspective. We also delve into the current state of the pre-owned business jet market, with Brooks offering valuable advice for potential buyers and sellers. Plus, hear Brooks' thoughts on pilot ego and how to manage it during aircraft transactions. Don’t miss his exciting update on the DC-3 and its up...
130. Should You Take a Once-in-a-Lifetime Flying Opportunity?
Dylan and Max delve into the unexpected challenges of flying during the Cicada Fiasco of 2024, sharing firsthand accounts and tips for dealing with these pesky insects. They then transition to a deep dive into the history and impact of airline deregulation, discussing how it has shaped the modern aviation industry and what it means for today's pilots. Listener emails spark lively discussions on pilot shirt preferences and the ongoing debate between long sleeve and short sleeve uniforms, while the luggage review series continues with a focus on the Strong Bags Helix. In the flight advice segment, Dylan and Max...
129. From Paychecks to Perks: Maximizing Pilot Compensation with Dr. Broyhill
In this episode, hosts Dylan and Max interview Dr. Chris Broyhill, the creator of the AirComp Calculator, to discuss the current state of pilot compensation in business aviation. Dr. Broyhill shares insights on market trends, noting the ongoing high demand for qualified pilots and the increasing importance of comprehensive benefits packages. The discussion highlights the advantages of business aviation roles, such as better work-life balance, despite competitive airline salaries. Dr. Broyhill also emphasizes the value of reliable compensation data for pilots and employers, provided by tools like the AirComp Calculator.
Connect with Dr. Chris Broyhill on LinkedIn<...
128. Luggage Reviews, Mailbag Revelations, and Life-Changing Flight Advice
The guys kick the show off with their latest piston engine adventures. Then they dive into the luggage review video series and discuss listeners' feedback. Hard Landing chapter 3 is discussed in the book club segment.
In the mailbag we continue the discussion on AI and how pilot shirts should fit.
We have a good one for flight advice...how do I leave my high paying job to go fly full time?
To wrap up the show Dylan goes on a Hilton vs. Marriott rant.
Show Notes
0:00 Intro & Maneuvers
<...
