21.FIVE - Professional Pilots Podcast

21.FIVE - Professional Pilots Podcast

21Five Podcast

Episodes 212
Avg. Duration 1h 13m
Activity Highly Active
Apple Rating 4.9 (372)
Since Apr 2019
Latest Episode Jun 2026

Outreach Signals

Open to Sponsors Features Guests

Publishing Details

Schedule
Weekly
Format
Episodic
Consistency
70%
Hosting
rss.libsyn.com

Contact & Outreach

About This 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

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Recent Episodes

212. Would You Trade Seniority for Better Stories?

Jun 09, 2026 55m

Summer scheduling chaos is in full swing as Dylan and Max talk vacation bidding wizardry, Teterboro's RNAV to Runway 1, NDB war stories, New York hotel-room misery, and a suspiciously affectionate…

211. When Does Paying for Training Actually Make Sense?

Jun 02, 2026 1h 20m

Dylan and Max talk Alaska dreams, Southwest's new nonstop to Anchorage, lake lodge podcast fantasies, and Max's brave decision to bypass the discounted Marriott burger for Yemeni cuisine. In the…

210. What Should Pilots Do When the Paycheck Stops?

May 19, 2026 37m

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…

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

May 13, 2026 1h 2m

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…

208. How Should Pilots Compete After Spirit's Shutdown?

May 05, 2026 59m

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…

207. Would You Sign a Five-Year Non-Prorated Training Contract?

Apr 28, 2026 58m

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…

206. Is your leadership style actually just manipulation?

Apr 21, 2026 1h 8m

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…

205. Is Airport Parking the Worst Part of Being an Airline Pilot?

Apr 14, 2026 56m

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…

204. What Can We Learn Before the Final Report Arrives?

Apr 07, 2026 42m

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…

203. Is Commuting Worth Three Years of Seniority?

Mar 24, 2026 1h 1m

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…

202. Would You Start Over at a Fractional in Your 40s?

Mar 17, 2026 1h 23m

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…

201. Why Are Wrong-Airport Landings Still Happening?

Mar 10, 2026 41m

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.…

200. Live show: James Onieal answers listener questions

Mar 04, 2026 1h 38m

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…

199.5 How Do You Build Fortune 100-Level Flight Ops at your Small Flight Department?

Feb 24, 2026 55m

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),…

199. At What Point Should You Just Eat the Hotel Food?

Feb 10, 2026 1h 15m

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…

S1E198 198. What Does "Stay Flexible" Actually Mean for Pilot Spouses?

Feb 04, 2026 56m

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…

197. What's Changing with Airline Pilot Retirement in 2026?

Jan 27, 2026 54m

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…

196. How Much Chaos Can You Fit Into One Runway?

Jan 13, 2026 1h 49m

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…

195. Would You Let the King Air Land Itself?

Jan 06, 2026 1h 45m

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…

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

Dec 23, 2025 1h 26m

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…

Frequently Asked Questions

How many episodes does 21.FIVE - Professional Pilots Podcast have?

21.FIVE - Professional Pilots Podcast has published 212 episodes since April 2019, covering topics in Aviation, Leisure.

Is 21.FIVE - Professional Pilots Podcast still active?

21.FIVE - Professional Pilots Podcast is currently highly active with new episodes weekly. Average episode length is 1h 13m.

How do I contact 21.FIVE - Professional Pilots Podcast for sponsorship or guest appearances?

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