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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

57:44

182. When the Flight Department’s Broken, Do You Stay...

21.FIVE - Professional Pilots Podcast ·

2025/09/16

A listener asks the question every pro pilot eventually faces: should you stay put and try to fix what’s broken in your flight department, or cut bait and move on? Dylan and Max bring in Jenny Showalter and Jim Lara to explore the real-world tradeoffs. From career coaching to leadership insights, they share what to weigh before pulling the ripcord—or digging in to make change happen. It’s candid talk about loyalty, burnout, and how to navigate tough calls in business aviation. To contact Jenny

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01:33:28

180. Is Pilot Hiring Heating Up Again?

21.FIVE - Professional Pilots Podcast ·

2025/08/26

Dylan and Max sit down with James Onieal of Raven Careers for a wide-ranging industry update. James breaks down the latest pilot hiring trends across legacies, regionals, and corporate operators—and why networking still beats any resume hack. From CFIs grinding to 1,500 hours to regionals debating upgrade timing, to cadet program uncertainties and the “pilot leverage index,” this episode maps out what the next 12 months could look like. Tune in for sharp insights and some laughs along the way—your

en

59:29

179. What Happened to Those “Hard Days Off” You...

21.FIVE - Professional Pilots Podcast ·

2025/08/19

Dylan and Max connect from hotel rooms across the West, with Max prepping for his Cub camping trip to Idaho and Dylan testing out foam ear tips for his ProFlight headset (link in the show notes). In the Mailbag, listeners weigh in on commuting trade-offs, a gear-down hydraulic improvisation involving bottled water, and flying under Bravo airspace with “raw dog radios.” Flight Advice tackles a business aviation bait-and-switch: hard days off evaporating into 24/7 on-call duty. The hosts dig into

en

55:13

175. Should You Drop $5 K on an ATP-CTP Now?

21.FIVE - Professional Pilots Podcast ·

2025/07/08

Max walks into a 737 cockpit guarded by a five-inch hula girl and promptly invents the “Shakira Scale” for bumps in flight . Listener mailbag hits everything from the best starter credit card for flight instructors to whether a degree really matters and if paying $5 K for ATP-CTP is smart when you’re 49 and eyeing the next hiring wave . In Flight Advice, a military helo pilot with only ten working years left asks whether to chase a major or ride the fractional lifestyle . Plus: back-country flower

en

52:56

174. B-17 to F-4: A 102-Year-Old WWII Aviator’s...

21.FIVE - Professional Pilots Podcast ·

2025/07/01

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

en

01:17:07

172. What does it take to reinstate your lapsed CFI?

21.FIVE - Professional Pilots Podcast ·

2025/06/10

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

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47:43

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

21.FIVE - Professional Pilots Podcast ·

2025/06/03

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

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47:38

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

21.FIVE - Professional Pilots Podcast ·

2025/05/20

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

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01:03:12

164. How Do You Network in Aviation If You're an...

21.FIVE - Professional Pilots Podcast ·

2025/04/08

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

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01:26:35

163. Should You Panic or Prep? James Onieal Breaks It...

21.FIVE - Professional Pilots Podcast ·

2025/04/01

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

en

01:03:24

159. Is Aviation Insurance Finally Getting Cheaper?...

21.FIVE - Professional Pilots Podcast ·

2025/03/04

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

en

01:09:04

157. What’s It Really Like Flying the 787...

21.FIVE - Professional Pilots Podcast ·

2025/02/12

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

en

01:22:36

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

21.FIVE - Professional Pilots Podcast ·

2025/02/04

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

en

01:14:00

154. Could You Survive 100 Days in a Falcon 2000?

21.FIVE - Professional Pilots Podcast ·

2025/01/21

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

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01:16:50

150. Flight Advice Fiesta!

21.FIVE - Professional Pilots Podcast ·

2024/12/10

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

en

57:38

147. Can Strong Leadership Save Your Flight Department?

21.FIVE - Professional Pilots Podcast ·

2024/11/19

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

en

54:16

146. Flying for the Regional vs. Flying for the...

21.FIVE - Professional Pilots Podcast ·

2024/11/13

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

en

49:25

145. How Much Should You Really Be Earning? Salary...

21.FIVE - Professional Pilots Podcast ·

2024/11/05

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?"

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37:27

137. What Should Pilots Do with Election-Year Market...

21.FIVE - Professional Pilots Podcast ·

2024/09/03

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

en

01:08:50

133. Should You Sign an Airline Training Contract?

21.FIVE - Professional Pilots Podcast ·

2024/07/09

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

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148 results

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