21.FIVE - Professional Pilots Podcast
Education & Explainer
About
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, or anywhere in between, you'll love our fresh and often funny take on all things aviation.Come find us online at 21fivepodcast.com and connect with us via Insta/Facebook/Twitter: @21fivepodcast
Episodes
- 209. Should You Trade Quality of Life for Airline Seniority?
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,…
- 208. How Should Pilots Compete After Spirit's Shutdown?
James Onieal from Raven Career Development joins Dylan and Max to unpack Spirit Airlines' wind down and what it means for Spirit pilots, regional pilots, CFIs, and anyone trying to move up the aviation ladder. The conversation gets into wh…
- 207. Would You Sign a Five-Year Non-Prorated Training Contract?
Max recaps a wild GA camping trip involving gale-force winds and a midnight arboreal emergency, while Dylan discusses the "superpower" of vibe-coding your own aviation tools with AI . The Mailbag tackles the dilemma of choosing between a q…
- 206. Is your leadership style actually just manipulation?
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 th…
- 205. Is Airport Parking the Worst Part of Being an Airline Pilot?
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,…
- 204. What Can We Learn Before the Final Report Arrives?
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, find…
- 203. Is Commuting Worth Three Years of Seniority?
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 int…
- 202. Would You Start Over at a Fractional in Your 40s?
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 actuall…
- 201. Why Are Wrong-Airport Landings Still Happening?
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,…
- 200. Live show: James Onieal answers listener questions
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 a…
- 199.5 How Do You Build Fortune 100-Level Flight Ops at your Small Flight Department?
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 w…
- 199. At What Point Should You Just Eat the Hotel Food?
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, airl…
- 198. What Does "Stay Flexible" Actually Mean for Pilot Spouses?
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 Sco…
- 197. What's Changing with Airline Pilot Retirement in 2026?
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 impac…
- 196. How Much Chaos Can You Fit Into One Runway?
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 th…
- 195. Would You Let the King Air Land Itself?
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 dr…
- 194. What Will Pilot Hiring Really Look Like in 2026?
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 CF…
- 193. Can One Industry-Wide SOP Manual Raise the Bar for Business Aviation?
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 t…
- 192. Is $9,000 Worth Missing Christmas Morning With the Kids?
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 h…
- 191. Should You Sign a $75K Contract Just to Chase PIC Time?
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…
- 190. What's Next for BizAv Pilot Compensation?
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…
- 189. Can You Survive 900 Hours a Year on a One-Hour Callout?
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 differe…
- 188. How Can Pilots Build Wealth Beyond the Flight Deck?
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 make…
- 187. Is turbine PIC in 91/135 the fastest lane to legacy?
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, cock…
- 186. First Officers: How Do You Speak Up Without Getting Shut Down?
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 traini…
- 185. Late-Bloomer Pilot: Fractional, Regional, or Wait It Out?
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 carou…
- 184. How Do You Stay Resilient After Career Setbacks? w/ Capt Benny
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 throu…
- 183. Can a Skydiver Pilot Make the Jump to the Big Leagues?
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 h…
- 182. When the Flight Department's Broken, Do You Stay or Go?
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-wor…
- 181. How Many Things Can Go Wrong on in the Idaho Backcountry?
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…
- 180. Is Pilot Hiring Heating Up Again?
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 ha…
- 179. What Happened to Those "Hard Days Off" You Promised Me?
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 commu…
- 178. What did the Mr Beast Challenge Pilot Do for 100 Days in a Jet?
Corporate pilot (and MrBeast 100-day jet winner ) Armando Carrion jumps in to unpack the ops behind living on a Hawker 800 for 100 straight days—no devices, no Netflix, just Part 91 brainpower and a lot of extension cords. We get into air-…
- 177. Should You Spend $8K on a Seaplane Rating or a CFI?
This week, Dylan and Max talk Oshkosh FOMO, a rogue taxiway takeoff, and some serious Midwestern rental car struggles. Mailbag highlights a listener mapping out his aviation career path and asking if it's possible to fly both corporate and…
- 176. Will a United Internship Trump Turbine Time?
Max sweats through fence repairs in 110 °F while plotting an Idaho back-country Super Cub adventure, and Dylan tries (unsuccessfully) to review a "dad-grade" sun-hoodie. In the Mailbag we read spicy reviews, debate the sanity of commuting,…
- 175. Should You Drop $5 K on an ATP-CTP Now?
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 real…
- 174. B-17 to F-4: A 102-Year-Old WWII Aviator's Incredible Journey
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 Tu…
- 173. Descend Via Phraseology, Aviation YouTube Deep Dive, and CFI Survival Tips
Dylan and Max are recording from hotel rooms across the country and catching up after some time off. They kick things off with a deep dive into aviation YouTube, comparing backcountry flying with ferrying retired Airbuses from Asia. In the…
- 172. What does it take to reinstate your lapsed CFI?
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 FOI…
- 171. What's the Right Way to Be a Low-Time SIC in BizAv?
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 d…
- 170. What Should You Do When the FAA Calls?
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…
- 169. Should You Bet Your Career on an Aviation Degree?
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 featur…
- 168. Should You Chase Turbine Time in Dubai?
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…
- 167. What Happens When the Market and Your Airline Career Both Stall?
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.…
- 166. Why Aren't More Pilots Talking About Healthspan?
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 s…
- 165. Should You Really Jump Ship for 15 Grand More?
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 wi…
- 164. How Do You Network in Aviation If You're an Introvert?
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…
- 163. Should You Panic or Prep? James Onieal Breaks It Down
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 coc…
- 162. Can You Really Plan for an Unplannable Career?
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 mailb…
- 161. Is This the Craziest Warbird Recovery Attempt Ever?
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 riggin…