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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

01:08:52

206. Is your leadership style actually just...

21.FIVE - Professional Pilots Podcast ·

2026/04/21

Dylan and Max sit down with Kyle Freiberger and Mike Sferrazza from First Class Leaders to bridge the gap between technical proficiency and effective aviation leadership . This episode explores why traditional CRM often fails to address the human element and how pilots at any rank can cultivate influence through self-awareness and emotional intelligence . The guys dive into the "Take the Lead" framework, the DISC behavioral tool, and the critical shift from defending your intentions to owning your

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56:13

205. Is Airport Parking the Worst Part of Being an...

21.FIVE - Professional Pilots Podcast ·

2026/04/14

This week Dylan and Max kick things off with Atlantic Bucks, the new IRS reporting threshold, and a spirited rant about airport parking, employee lots, and the endless misery of hotel vans. In the mailbag, they dig into helicopter careers, the real risk-versus-reward tradeoffs, and what that path looks like compared with airplanes. Flight Advice gets into career strategy for a maintenance pro trying to break into flying and a young regional FO deciding between staying put, jumping to 135, or chasing

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42:29

204. What Can We Learn Before the Final Report Arrives?

21.FIVE - Professional Pilots Podcast ·

2026/04/07

Juan Browne of the blancolirio YouTube channel joins Dylan and Max to talk about how he breaks down aviation accidents and incidents in near real time. For professional pilots, it’s a sharp discussion on separating facts from opinion, finding teachable moments, and managing the gap before the NTSB final report arrives. They get into ADS-B, ATC audio, comment-section corrections, GA repeat offenders like VFR into IMC and loss of control, plus a few backcountry Husky war stories. Check out the Juan

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01:01:22

203. Is Commuting Worth Three Years of Seniority?

21.FIVE - Professional Pilots Podcast ·

2026/03/24

Why is Max recording at night, and why does every aviation headline lately feel like another runway-incursion autopsy? This episode covers TSA chaos at Sky Harbor, a rough New York accident discussion, eVTOL optimism, and Max’s descent into experimental-airplane condition inspection misery. In the Mailbag, the guys debate NBAA landing-distance math, hear a loud call to bring back listener stories, and defend Max’s musings like true professionals. In Flight Advice, they tackle a brutal career

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01:23:32

202. Would You Start Over at a Fractional in Your 40s?

21.FIVE - Professional Pilots Podcast ·

2026/03/17

This week Dylan and Max dig into the recent Challenger 650 accident in Bangor and the very real pressure corporate crews can feel when winter ops get sporty. In the Mailbag, they hit union negotiations, whether helicopter flying is actually a smart career pivot, a truly elite ripped-pants-in-cruise story, and a listener correction on landing the Osprey. For Flight Advice, they tackle a big mid-career question: if you had to start over in your late 40s, is a fractional the better move than going back

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41:04

201. Why Are Wrong-Airport Landings Still Happening?

21.FIVE - Professional Pilots Podcast ·

2026/03/10

Dan Boedigheimer from Advanced Aircrew Academy joins Dylan and Max to break down why wrong-airport and wrong-surface landings still happen, and what professional pilots can do to stay ahead of them. For Part 91 and bizav crews especially, it’s a practical discussion on building better habits when nobody is spoon-feeding you the safety data. They get into visual approach traps, pilot monitoring duties, stabilized approach discipline, workload, fatigue, and what actually makes recurrent safety

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01:38:32

200. Live show: James Onieal answers listener questions

21.FIVE - Professional Pilots Podcast ·

2026/03/04

Dylan and Max are joined by James Onieal (Raven Careers) for Episode 200, covering everything from conferences and networking to cadet programs, cargo hiring, and fractional life. They also dig into the latest conflict in the Middle East and what rising oil prices could mean for airline pilots—from hiring pressure and route economics to the broader ripple effects across the industry. The conversation gets into why pathway programs can be helpful, but also how debt-heavy options can limit your

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01:15:21

199. At What Point Should You Just Eat the Hotel Food?

21.FIVE - Professional Pilots Podcast ·

2026/02/10

Dylan and Max recap a jet-lagged Japan ski mission, widebody travel wins and fails, and the realities of surviving brutal time zone changes. In the Mailbag, they dig into Saab war stories, Autoland edge cases, NBAA training standards, airline-branded watches, and career wins from listeners making the jump into jets. The Flight Advice segment centers on a sobering accident discussion and the risks of slipping from airline discipline into lightly regulated operations. As always, it’s equal parts

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56:24

198. What Does “Stay Flexible” Actually Mean for...

21.FIVE - Professional Pilots Podcast ·

2026/02/04

Late-night musings from Dylan and Max: corrections on “newest airports,” a touchdown-point math fix, and Max’s Cub antics after an oil change—including a surprise landing on BLM dirt near Lake Pleasant. Then: the inaugural JSX ATR into Scottsdale, a Japan trip preview, a wild “Gleaming the Cube” airport intro, Jepp AMM taxi chart nerd-out, ForeFlight layoff chatter, and Airplane Manager’s new AI. The mailbag brings career moves, SOP love, a real-world bird strike at rotation, and finally: Flight

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54:08

197. What’s Changing with Airline Pilot Retirement in...

21.FIVE - Professional Pilots Podcast ·

2026/01/27

Financial planner Timothy P. Pope of 360 Aviation Advisors returns to break down 2026 retirement updates that matter to pro pilots. From new Roth catch-up rules to Southwest's bold move on NEC contributions, he digs into the real tax impacts for airline crews. Bonus: comparisons across the majors, advice for CFI's just starting out, and a hangar office update. Listen in and get smarter about your money. Show Notes 0:00 Intro 3:23 What’s New: Retirement Considerations 13:26 Southwest Airlines &

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01:49:16

196. How Much Chaos Can You Fit Into One Runway?

21.FIVE - Professional Pilots Podcast ·

2026/01/13

San Diego continues its reign as the busiest single-runway “how is this legal?” airport, plus we nerd out on new terminals, recurrent training wins, and a Challenger sim surprise when Dylan’s seat decided to yeet itself at ~90 knots. In the Mailbag, we hit ferry flying as a niche career path, a home-buying reality check from Diamond Dog Tim Pope (mortgage recasts, baby), and a training-center SOP rant that’s painfully relatable. We also kick off the 2026 ops-manual push with the “latest touchdown

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01:45:17

195. Would You Let the King Air Land Itself?

21.FIVE - Professional Pilots Podcast ·

2026/01/06

First show of 2026: we talk Garmin Autoland in a King Air and why internet speculation is the fastest way to sound like a jabroni. We also hit the chaos of international ops (Mexico permits/APIS pain) and tease the Chicago Layover Guide dropping soon. In the Mailbag: Coeur d’Alene layover intel, a legendary lav story, Pilot Pete confusion gets cleaned up, airline-switching “sunk cost” drama, and surviving an unhinged sim instructor. Flight Advice is a big one: a 2,000-hr pilot with a baby inbound

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58:28

192. Is $9,000 Worth Missing Christmas Morning With...

21.FIVE - Professional Pilots Podcast ·

2025/12/09

Dylan and Max kick off this PM edition with holiday-on-the-road war stories: Cowboys Thanksgiving trips, O’Hare blizzards, Vegas taxi laps, and that deranged border tether balloon that literally broke loose over Sierra Vista. The mailbag hits everything from FlightSafety’s Master Aviator modules and Shorts 360 island hopping, to 50-something career-changers, disc golf and pickleball layover hacks, and using tools like Notebook LM without getting your manuals on the evening news. In Flight Advice, a

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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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