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PODCAST

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,

leisure aviation

All Episodes

01:29:20

191. Should You Sign a $75K Contract Just to Chase...

21.FIVE - Professional Pilots Podcast ·

2025/11/18

Dylan recaps his brutal post-“ATC meltdown” commute and rants about the GA ban at 12 major airports while Max counters with cub flying and Chicago layover tips (including a dangerously spicy El Chingón). In the mailbag, listeners call the guys out for drifting toward aspiring-pilot advice, recommend MU-2 and airline YouTube channels, drop a credit-card points hack for flight training, and share how they commute to FedEx in their own airplane. Flight Advice closes the show with a regional FO at a

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58:21

190. What’s Next for BizAv Pilot Compensation?

21.FIVE - Professional Pilots Podcast ·

2025/11/11

Dr. Chris Broyhill returns to break down the latest Air Comp Calculator data and what it means for 2025 pilot compensation. Dylan and Max dig into the trends, the slowdown in wage growth, and how bizav departments are navigating post-COVID market corrections. They also talk negotiation strategy, job titles that actually matter, and Broyhill’s new 600-page industry textbook, The Business Aviation Book: Leading Operational Excellence. Finally, they wrap up the episode with a discussion on the Go/No Go

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01:51:18

189. Can You Survive 900 Hours a Year on a One-Hour...

21.FIVE - Professional Pilots Podcast ·

2025/11/04

Max kicks off his annual training rant—breaking down the highs, lows, and downright absurd moments of recurrent at “the training center.” Dylan adds perspective on flight training efficiency and why a great instructor makes all the difference. The mailbag delivers everything from a new layover guide in Portsmouth to a 14-year-old aircraft dealer to a Marine pilot navigating a tricky transition to the airlines, plus a Learjet Pilot with a 1 hour call-out seeks guidance. In Flight Advice, a

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01:11:04

186. First Officers: How Do You Speak Up Without...

21.FIVE - Professional Pilots Podcast ·

2025/10/15

Colin and Mara'D—both airline FOs and cast members from The Rehearsal—join Max and Dylan to dissect the tricky dynamics of speaking up in the right seat. Why is it so hard, and what makes it easier? The crew digs into SOP gaps, CRM training, real-world examples like Asiana 214, and the subtle art of being a chameleon in the cockpit. Plus: bizav vs. 121 culture, and how personality plays a bigger role than you think. Connect with Colin on Instagram Connect with Mara'D on Instagram Check out Season 2

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01:05:50

184. How Do You Stay Resilient After Career Setbacks?...

21.FIVE - Professional Pilots Podcast ·

2025/09/30

Benjamin Bailey (@flybenfly) joins Max and Dylan for an honest, hilarious deep dive into aviation’s influencer world, airline interview faceplants, and the realism gap on pilot social media. For professional pilots, this episode cuts through the curated BS to talk timing, authenticity, and bouncing back after setbacks. From CRM failures to career detours, Ben brings the real talk with a dose of humor. Hit play and subscribe for the stories you're not getting on your For You page. Follow Ben on

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01:01:18

183. Can a Skydiver Pilot Make the Jump to the Big...

21.FIVE - Professional Pilots Podcast ·

2025/09/23

Max rants about St. Louis still acting like it’s O’Hare, but enjoys the accomodations. The mailbag covers creative GA commuting strategies and whether backcountry camping flights belong on a professional resume. Ted calls in on his drive home from the airport to share some bidding tips. Flight Advice closes with a skydiver pilot wondering if it’s time to trade jumpers for smokejumpers with the USFS—and what that career path really looks like. Show Notes 0:00 Intro 5:19 Max’s Musings 13:24 Reviews &

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54:53

181. How Many Things Can Go Wrong on in the Idaho...

21.FIVE - Professional Pilots Podcast ·

2025/09/02

Max returns from the Idaho backcountry with a Cub full of stories—starter failures, in-flight repairs, surprise rafting, wildlife rescues, and nearly becoming the emergency contact for a hiker with a head injury. This standalone episode is a wild tale of aviation adventure, mechanical mayhem, and resourceful fixes. No mailbag or flight advice this time—just pure story time from the sticks. Strap in and enjoy the highs (and literal downdrafts) of off-the-grid bush flying. Show Notes 0:00 Intro 3:35

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01:23:13

178. What did the Mr Beast Challenge Pilot Do for 100...

21.FIVE - Professional Pilots Podcast ·

2025/08/12

Corporate pilot (and MrBeast 100-day jet winner) Armando Carrion jumps in to unpack the ops behind living on a Hawker 800 for 100 straight days—no devices, no Netflix, just Part 91 brainpower and a lot of extension cords. We get into air-to-air formation over SoCal and the Grand Canyon (yep, with a Bonanza), CRM, and why Armando turned down the “double-or-nothing” 100-day extension. We also talk post-win realities: maintenance bills, management, and why the airplane is probably headed to a new

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55:02

177. Should You Spend $8K on a Seaplane Rating or a CFI?

21.FIVE - Professional Pilots Podcast ·

2025/07/29

This week, Dylan and Max talk Oshkosh FOMO, a rogue taxiway takeoff, and some serious Midwestern rental car struggles. Mailbag highlights a listener mapping out his aviation career path and asking if it’s possible to fly both corporate and airline gigs at once (spoiler: not easy). Flight Advice tackles how to best spend $8K of National Guard tuition money—seaplane rating, CFI, backcountry flying, or something else entirely? Plus, Starlink outages and the return of our favorite sunshade gear review

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56:47

176. Will a United Internship Trump Turbine Time?

21.FIVE - Professional Pilots Podcast ·

2025/07/22

Max sweats through fence repairs in 110 °F while plotting an Idaho back-country Super Cub adventure, and Dylan tries (unsuccessfully) to review a “dad-grade” sun-hoodie. In the Mailbag we read spicy reviews, debate the sanity of commuting, and swap credit-card hacks for pilots living on per-diem. Flight-Advice gets heavyweight help from James Onieal of Raven Careers, who steers a listener through the mine-field of a United Flight-Ops internship vs. PC-12 135 gig vs. aerial-survey multi-time. Plus:

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59:42

173. Descend Via Phraseology, Aviation YouTube Deep...

21.FIVE - Professional Pilots Podcast ·

2025/06/24

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"

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01:05:59

170. What Should You Do When the FAA Calls?

21.FIVE - Professional Pilots Podcast ·

2025/05/27

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

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01:04:42

168. Should You Chase Turbine Time in Dubai?

21.FIVE - Professional Pilots Podcast ·

2025/05/13

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

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55:42

167. What Happens When the Market and Your Airline...

21.FIVE - Professional Pilots Podcast ·

2025/05/06

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

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01:02:42

166. Why Aren’t More Pilots Talking About Healthspan?

21.FIVE - Professional Pilots Podcast ·

2025/04/29

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

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57:33

165. Should You Really Jump Ship for 15 Grand More?

21.FIVE - Professional Pilots Podcast ·

2025/04/22

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

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01:08:50

162. Can You Really Plan for an Unplannable Career?

21.FIVE - Professional Pilots Podcast ·

2025/03/25

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

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01:46:43

161. Is This the Craziest Warbird Recovery Attempt Ever?

21.FIVE - Professional Pilots Podcast ·

2025/03/18

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

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01:03:29

160. Want to Fly Biz Jets After Airline Retirement?...

21.FIVE - Professional Pilots Podcast ·

2025/03/11

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

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01:10:28

158. What’s Going on with All These Aviation Accidents?

21.FIVE - Professional Pilots Podcast ·

2025/02/25

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

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