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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

45:12

221. Are You Leaving Money on the Table Before Year-End?

21.FIVE - Professional Pilots Podcast ·

2026/09/29

Tim Pope of 360 Aviation Advisors joins Dylan and Max to talk open enrollment, year-end financial planning, and one of the biggest career decisions pilots eventually face: when to upgrade. For professional pilots, the numbers matter—but so do schedule, seniority, reserve, weekends off, and the quality-of-life calculus that never fits neatly into a spreadsheet. They dig into disability coverage, estate planning, 401(k) and Roth strategies, AI-generated financial questions, and whether captain pay is

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01:01:42

219. Why Is the Business Jet Market So Tight Right Now?

21.FIVE - Professional Pilots Podcast ·

2026/09/08

Brooks Pettit of Vaerus Jet Sales joins Dylan and Max to break down what is really happening in the business aircraft market. For professional pilots and flight departments, he covers tight inventory, strong demand, financing, tax-driven transactions, and why planning ahead matters. They also get into Challenger 3500 delivery positions, bonus depreciation, tariffs, AI-driven market research, and the realities of buying and selling aircraft in a fast-moving market. Listen in for a practical look at

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01:15:16

218. Can You Trust a Pilot on the Road?

21.FIVE - Professional Pilots Podcast ·

2026/09/01

Max checks in from a musty Missouri hotel while earning his Light Sport Repairman certificate, and the guys detour through GA maintenance, Starbase, RTA wizardry, and the ongoing decline of 123.45 as a social network. Mailbag covers Sugar Alpha, Qantas' ultra-long-haul A350 plans, where Spirit's pilots and traffic may have landed, and whether 21.Five needs a Discord server. In Flight Advice, Dylan and Max tackle the stereotype that pilots are destined to cheat—and how couples can build trust,

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37:23

210. What Should Pilots Do When the Paycheck Stops?

21.FIVE - Professional Pilots Podcast ·

2026/05/19

Timothy P. Pope joins Dylan and Max to talk through the financial side of Spirit's shutdown and what professional pilots can learn from it. For airline and bizav pilots, the big takeaway is simple but not always fun: stabilize first, optimize later. The crew digs into emergency funds, burn rate, 401(k) rollovers, IRA traps, benefits, life insurance, and why raiding retirement money is usually the nuclear option you try very hard to avoid. Listen, subscribe, and maybe give your emergency fund a

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01:02:34

209. Should You Trade Quality of Life for Airline...

21.FIVE - Professional Pilots Podcast ·

2026/05/13

Dylan and Max kick things off with DoubleTree cookie restraint, San Diego seafood, 40-plus Vegas strategy, DJ juice, and the emerging menace of the commuter life vest. In the Mailbag, listeners bring dumpster-diving charter pilot stories, bankruptcy bassoon suggestions, skydiving-adjacent book recommendations, and a heavy airline-industry "what if" about another major demand shock. Dylan also recaps his first Atlantic crossing in years, complete with CPDLC confusion, Gander relief, and some unpaid

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55:06

199.5 How Do You Build Fortune 100-Level Flight Ops...

21.FIVE - Professional Pilots Podcast ·

2026/02/24

Dylan and Max sit down with Aaron, Software Architect at Airplane Manager, to talk business aviation ops tech and where AI is headed. If you're running lean (two pilots, one tail, no dispatcher), this is the roadmap for reducing busywork without losing operational control. They dig into integrations, offline trip tools, and why "apps" might just become background APIs. Listen in and subscribe for more pilot-to-pilot ops talk. Check out the software Dylan and Max both use to run their departments:

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01:26:41

194. What Will Pilot Hiring Really Look Like in 2026?

21.FIVE - Professional Pilots Podcast ·

2025/12/23

James Onieal from Raven Career Development returns to break down what pilot hiring is shaping up to look like in 2026. We dig into majors, regionals, corporate paths, and why movement can feel slow right up until it suddenly isn't. From CFI logjams to corporate and furlough realities, this episode is all about timing, strategy, and expectations. Subscribe and listen to stay ahead of the hiring curve. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term

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59:59

193. Can One Industry-Wide SOP Manual Raise the Bar...

21.FIVE - Professional Pilots Podcast ·

2025/12/16

This episode introduces the new NBAA Standard Operating Procedures (SOP) Manual and why it's a big deal for business aviation. Dylan and Max are joined by Brian Small of FlightSafety International and Tim Schoenauer of CAE to explain how the manual was developed, who it's for, and how operators can actually use it—not just shelf it. They break down the regulatory intent, training implications, and where this fits into real-world Part 91 and 135 operations. If you've ever wondered what "good SOPs"

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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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