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21.FIVE - Professional Pilots Podcast

21Five Podcast
Aviation
Business Aviation
Southwest Airlines
Financial Planning
Aviation Safety
Flight Training
Pilot Training
Aviation Industry
Aviation Training
Airlines
Professional Pilots
Aircomp Calculator
Air Traffic Control
Pilot Compensation
Airline Industry
Pilot Hiring Trends
ACMI
Roth IRA
Flight Operations
Artificial Intelligence

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 hilar... more

PublishesWeeklyEpisodes217Founded7 years ago
Number of ListenersCategories
AviationLeisure

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Artwork for 21.FIVE

Latest Episodes

Rob Zettel joins Dylan and Max to tell the story of flying MiG-21s and MiG-23s with the USAF's secretive Red Eagles under the Constant Peg program. For professional pilots, it's a fascinating look at training, aircraft handling, risk management, and ... more

Max gets wrecked by a closed mariscos truck, discovers there are still 727 flight engineers in the wild, and goes full test-pilot mode in his Cub after finding Bush Air's backcountry training content. In the Mailbag, we hear about expat pilot furloug... more

James Onieal of Raven Careers returns to break down the current pilot hiring market across the majors, regionals, cargo operators, fractionals, and cadet programs. He explains why hiring remains competitive, why ATP-CTP is becoming a practical minimu... more

Dylan and Max return from aggressively vacationing with biplane rides, glacier dog sledding, Telluride approaches, and a real single-engine checkride landing at Prescott. They break down United's unusual diversion into Luke Air Force Base, swap diver... more

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Recent Guests

Dan Smith
Assistant Professor of Practice Aviation and the Director of Aviation at University of Nebraska at Kearney
University of Nebraska at Kearney
Episode: 211. When Does Paying for Training Actually Make Sense?
Timothy Pope
Financial advisor to Professional Pilots, hosts Pilots Portfolio
Pilots Portfolio / Professional Pilots
Episode: 210. What Should Pilots Do When the Paycheck Stops?
Kyle Freiberger
President of First Class Leaders
First Class Leaders
Episode: 206. Is your leadership style actually just manipulation?
Mike Sferrazza
Director of Training and Strategy, First Class Leaders
First Class Leaders
Episode: 206. Is your leadership style actually just manipulation?
Juan Browne
Creator of Blancolirio YouTube channel, aviation commentator
Blancolirio
Episode: 204. What Can We Learn Before the Final Report Arrives?
Dan Boedigheimer
Subject matter expert on aviation safety topics
Advanced Aircrew Academy
Episode: 201. Why Are Wrong-Airport Landings Still Happening?
Brian Small
Director of Regulatory Affairs for Flight Safety
Flight Safety
Episode: 193. Can One Industry-Wide SOP Manual Raise the Bar for Business Aviation?
Tim Schoenauer
Senior Director of Global Training Solutions at CAE
CAE
Episode: 193. Can One Industry-Wide SOP Manual Raise the Bar for Business Aviation?
Tim Pope
Financial advisor with a focus on aviation professionals
360 Aviation Advisors
Episode: 188. How Can Pilots Build Wealth Beyond the Flight Deck?

Hosts

Dylan
Host of professional pilots show with a background in flight instruction, airlines, and business aviation
Max
Co-host with Dylan; focuses on aviation topics with a mix of stories and practical career advice

Reviews

4.9 out of 5 stars from 596 ratings
  • Great podcast

    Love the podcast!! As a student pilot with aspirations to fly for the majors I love hearing from people in the industry and what their life is like.

    Apple Podcasts
    5
    Drew.aviator514
    United Statesa month ago
  • I saw Max in the wild!

    I am an avid listener of the 21.Five show and I always enjoy the salty humor, occasional political innuendo and general good aviation vibes. During a recent trip to one of SWA’s hot spots, my FO was showing me the secret routes from the terminal to the hotel. During our discussions of various hazards the we would endure during our 12-15 minute walk through the underground hallway including possible flooding, closed subway stations, falling ceiling tiles and various molds and mildew, we spotted a... more

    Apple Podcasts
    5
    A flier
    United States2 months ago
  • Line up for kisses

    Great show gentlemen! In comment to ep 212, I too have witnessed the lineup of flight attendants meeting the Captain and receiving kisses on the cheek while on layover in NYC. More commonly in SEA and SFO are the Japanese and Korean crews lined up and bowing to each other before they enter the crew vans. I imagine it is part of an inspection before they report for work with the high visibility and emphasis on saving face in Asian cultures. Unfortunately, no video evidence.

    Cheers! Jesse

    Apple Podcasts
    5
    Gutie04
    United States3 months ago
  • New Sticker Idea

    I think you’ve found your next sticker idea: „Wake up wrecked in the Hilton somewhere!“ - The 21.5 Show.

    Love the show, been listening for a long time now. I recommend it to all the aspiring pilots I work with or speak with. From student pilots to guys like me trying go from Marine Corps V22s (Shout out to Dan mentioned in a previous episode) to the Majors. Keep up the great work guys! Always informative and entertaining. „Fake it ‚til you make it!“ Semper Fidelis. Mark.

    Apple Podcasts
    5
    Noswet261
    United States4 months ago
  • Top of the heap

    Best aviation podcast out there at the moment. Nice work guys. Us pro pilots enjoy your perspective and relevant humor. James “right” O’Neal tho. Maybe jettison him. Dude is impossible to listen to. Otherwise, Great job fellas. Love the show.

    Apple Podcasts
    5
    Crazy192837
    United States4 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Fans appreciate practical advice on training, compensation, and navigating disruptions.
Guests and hosts balance humor with serious industry insights, keeping topics approachable.
Listeners repeatedly cite the show as engaging and informative for career planning in aviation.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#7
United States/Leisure/Aviation
Apple Podcasts
#177
United States/Leisure
Apple Podcasts
#24
Canada/Leisure/Aviation
Apple Podcasts
#56
United Kingdom/Leisure/Aviation
Apple Podcasts
#18
Italy/Leisure/Aviation
Apple Podcasts
#50
Germany/Leisure/Aviation

Talking Points

Recent interactions between the hosts and their guests.

210. What Should Pilots Do When the Paycheck Stops?
Q: Can you talk a little bit about...the emergency fund and how pilots should approach stability during disruption?
Tim outlines that knowing exact monthly burn rate and trimming non-essentials creates a safety buffer, reduces anxiety, and buys time to land a new job or pivot, while keeping the family's needs met.
208. How Should Pilots Compete After Spirit's Shutdown?
Q: James, welcome to the program. Maybe just give us your initial observations about what happened this weekend.
Spirit ceased operations; the layoff and closure have broad implications for pilot employment paths, with many pilots facing uncertainty about bailouts, absorption by legacy carriers, and the need to reorient their resumes and interview approach.
198. What Does "Stay Flexible" Actually Mean for Pilot Spouses?
Q: What should a pilot spouse consider if their partner is starting a new job?
The spouse should evaluate whether to keep their job or leave it for the pilot's career, considering the potential for commuting and how that impacts their quality of life and family dynamics.
198. What Does "Stay Flexible" Actually Mean for Pilot Spouses?
Q: What does it mean to stay flexible as a pilot spouse?
Staying flexible means adapting to the unpredictable schedule of the pilot, especially when it can vary significantly based on seniority and operational demands.
197. What's Changing with Airline Pilot Retirement in 2026?
Q: When should one engage a financial advisor during their pilot career?
When they find themselves earning a solid income, realize the stakes of financial decisions are higher, or their finances are unorganized, they should consider reaching out to a professional.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About 21.FIVE

What is 21.FIVE about and what kind of topics does it cover?

Two professional pilots host a candid, informal show focused on real-world aviation careers, training, compensation, and industry dynamics. Episodes pair practical career advice with lighthearted banter, deep dives into pay, contracts, leadership, safety, and disruption (e.g., carrier shutdowns, layoffs, or training bottlenecks), and plenty of listener questions and guest perspectives. Notable threads include seniority versus quality of life, data-driven salary discussions, and leadership development for pilots, all delivered with humor and approachable storytelling that appeals to current and aspiring aviation professionals. The format often blends actionable guidance with entertaining anecdotes, making it a useful resource for career plan... more

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How many episodes of 21.FIVE are there?

21.FIVE launched 7 years ago and published 217 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on 21.FIVE?

Recent guests on 21.FIVE include:

1. Dan Smith
2. Timothy Pope
3. Kyle Freiberger
4. Mike Sferrazza
5. Juan Browne
6. Dan Boedigheimer
7. Brian Small
8. Tim Schoenauer

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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