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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

56:48

188. How Can Pilots Build Wealth Beyond the Flight Deck?

21.FIVE - Professional Pilots Podcast ·

2025/10/28

Tim Pope, CFP® and founder of 360 Aviation Advisors, joins Dylan and Max to talk about how pilots can make smarter financial moves—on and off the line. From variable pay to early retirement and crashpad cash flow, Tim breaks down what makes pilot finances uniquely tricky and how to stay ahead of turbulence. The crew also dives into taxes, scheduling volatility, and the "golden handcuff" problem in today's airline contracts. Tune in for real-world money talk that every professional pilot should hear

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01:15:42

187. Is turbine PIC in 91/135 the fastest lane to...

21.FIVE - Professional Pilots Podcast ·

2025/10/21

We kick off with Southwest red-eye shenanigans, hot/high GA drama departing PRC in a 150, and Max’s backcountry “mesa strip” adventure (with hard data from the STOL-mate). The Mailbag is full: 2,500-hour 135 pilots debating regionals, cockpit sun-shade gear, commuting to MEM in your own A36, first flights post-PPL, time-building without a CFI, and making that first 91/135 SIC→PIC jump. Flight Advice tackles the big one: take a regional CJO now or accept a 135 upgrade for immediate PIC while a baby’s

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57:35

185. Late-Bloomer Pilot: Fractional, Regional, or...

21.FIVE - Professional Pilots Podcast ·

2025/10/07

Dylan opens from an echo chamber (literally) and the guys kick around first impressions of Gulfstream’s newly announced G300 versus the G280—windows, avionics, “longest cabin,” and whether depreciation and warranty keep the new-metal carousel spinning. Mailbag hits everything from those mysterious skid marks on SNA 20R and whether an RJ type helps more than becoming a check instructor, to Phoenix haboobs, GA commuting from the islands, and a listener swag request. Flight Advice: a 40-year-old “late

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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151 results

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