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, 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
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 through the curated BS to talk timing, authenticity, and bouncing back after setbacks. From CRM failures to career detours, Ben brings the real talk with a dose of humor. Hit play and sub...
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 home from the airport to share some bidding tips. Flight Advice closes with a skydiver pilot wondering if it’s time to trade jumpers for smokejumpers with the USFS—and what that caree...
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’...
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 a wild tale of aviation adventure, mechanical mayhem, and resourceful fixes. No mailbag or flight advice this time—just pure story time from the stick...
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 ...
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...
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-to-air formation over SoCal and the Grand Canyon (yep, with a Bonanza), CRM, and why Armando turned down the “double-or-...
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, and swap credit-card hacks for pilots living on per-diem. Flight-Advice gets heavyweight help from James Onieal of Raven Careers, who steers a listener through the mine-field of a United Flight-O...
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...
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 ...
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 mailbag, they respond to listeners with questions about juggling a corporate flying gig while working for a major airline, updates from a newly minted high school grad CFI, and a debate on whethe...
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
Show...
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 sha...
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. Pilots, take notes… and maybe double-check your insurance policy.
Forrest Owens | Aviatio...
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.
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 gig flying in Dubai is a golden ticket or a trap. The guys break it down with laughs...
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 advice.
Visit Tim's website for more information or to schedule a consult.
Show Notes
...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 corporate aviation, revealing how timing, networking, and persistence are the real flight...
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. Broyhill drops some spicy takes on military-to-civilian leadership advice.
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