Best 21Five Podcast Podcasts (2025)

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171. What's the Right Way to Be a Low-Time SIC in BizAv? 47:43

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1d ago47:43

47:43

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:…

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170. What Should You Do When the FAA Calls? 1:05:59

8d ago1:05:59

1:05:59

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. Pilo…

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169. Should You Bet Your Career on an Aviation Degree? 47:38

15d ago47:38

47:38

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…

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168. Should You Chase Turbine Time in Dubai? 1:04:42

22d ago1:04:42

1:04:42

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…

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167. What Happens When the Market and Your Airline Career Both Stall? 55:42

29d ago55:42

55:42

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 …

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166. Why Aren’t More Pilots Talking About Healthspan? 1:02:42

1M ago1:02:42

1:02:42

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 corp…

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165. Should You Really Jump Ship for 15 Grand More? 57:33

1M ago57:33

57:33

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. Broyh…

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164. How Do You Network in Aviation If You're an Introvert? 1:03:12

2M ago1:03:12

1:03:12

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 t…

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163. Should You Panic or Prep? James Onieal Breaks It Down 1:26:35

2M ago1:26:35

1:26:35

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 c…

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162. Can You Really Plan for an Unplannable Career? 1:08:50

2M ago1:08:50

1:08:50

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 Ad…

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161. Is This the Craziest Warbird Recovery Attempt Ever? 1:46:43

3M ago1:46:43

1:46:43

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—en…

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160. Want to Fly Biz Jets After Airline Retirement? Here’s the Reality 1:03:29

3M ago1:03:29

1:03:29

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 Fligh…

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159. Is Aviation Insurance Finally Getting Cheaper? w/ Tom Hauge 1:03:24

3M ago1:03:24

1:03:24

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 …

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158. What’s Going on with All These Aviation Accidents? 1:10:28

3M ago1:10:28

1:10:28

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 a…

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157. What’s It Really Like Flying the 787 Internationally? w/ Ted 1:09:04

4M ago1:09:04

1:09:04

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 P…

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156. Does an A&P Give You a Leg Up in Business Aviation? 1:22:36

4M ago1:22:36

1:22:36

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 …

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155. The Air National Guard: Is This the ultimate career hack for pilots? 58:44

4M ago58:44

58:44

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…

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154. Could You Survive 100 Days in a Falcon 2000? 1:14:00

4M ago1:14:00

1:14:00

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 indu…

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153. From Garage Invention to Aviation Must-Have: The AeroTow Story 32:24

5M ago32:24

32:24

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, a…

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152. 2025 Pilot Hiring: What's Happening And What Should I be Doing About It? 1:32:44

5M ago1:32:44

1:32:44

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…

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151. From Cargo to Carry-Ons: Flying ACMI in a 747 and Building Better Bags 1:03:53

6M ago1:03:53

1:03:53

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 p…

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150. Flight Advice Fiesta! 1:16:50

6M ago1:16:50

1:16:50

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 …

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149. What’s the Buzz in BizAv? Market Update with Brooks 1:13:39

6M ago1:13:39

1:13:39

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 tr…

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148. Fuel Leaks, Flight Sims, and Airline Internships—Oh My! 56:50

6M ago56:50

56:50

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 aspirin…

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147. Can Strong Leadership Save Your Flight Department? 57:38

7M ago57:38

57:38

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 e…