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21.FIVE - Professional Pilots Podcast

21Five Podcast
Aviation Safety
Business Aviation
Pilot Hiring Trends
PJP Facebook Group
Pilot Mental Health
EVTOL
Flight Training
Southwest Airlines
Aviation
FAA Regulations
Flight Operations Quality Assurance
Designated Pilot Examiner (DPE)
Electric Air Taxis
Non-Rev Flying
Airline Industry
Cargo Pilots
Airline Hiring
Airlines
Professional Pilots
Gulfstream Aerospace

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

PublishesWeeklyEpisodes202Founded7 years ago
Number of ListenersCategories
AviationLeisure

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Artwork for 21.FIVE

Latest Episodes

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 actually a smart c... more

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, it's a prac... more

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 and what ris... more

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 losi... more

Key Facts

Accepts Guests
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Contact Information
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Number of Listeners
Find out how many people listen to this podcast per episode and each month.

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Recent Guests

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?
Captain Benny
Pilot influencer known for his humorous takes on aviation culture
Fly, Benny Fly
Episode: 184. How Do You Stay Resilient After Career Setbacks? w/ Capt Benny
James Onieal
Career coach and industry expert from Raven Careers
Raven Careers
Episode: 180. Is Pilot Hiring Heating Up Again?
Colonel Bushong
102-year-old WWII aviator and aircraft commander on a B-17
390th Memorial Museum
Episode: 174. B-17 to F-4: A 102-Year-Old WWII Aviator's Incredible Journey
Seth Lake
Airline Pilot and Designated Pilot Examiner
Episode: 172. What does it take to reinstate your lapsed CFI?
Forrest Owens
Aviation legal counsel and attorney specializing in aviation law
Law office of Forrest Owens
Episode: 170. What Should You Do When the FAA Calls?
Tim Pope
Financial advisor specializing in investment management for professional pilots
360 Aviation Advisors
Episode: 167. What Happens When the Market and Your Airline Career Both Stall?
Vernon Rich
Runs a fabrication shop, specializes in metal work and airplane recovery projects.
Episode: 161. Is This the Craziest Warbird Recovery Attempt Ever?

Hosts

Dylan
Host of the podcast, a professional pilot with a background in flight instructing and business aviation. Engages listeners with humorous anecdotes and valuable insights from the aviation industry.
Max
Co-host of the show, a professional pilot with experience in various aviation sectors. Known for his engaging humor and insightful contributions to discussions on aviation topics.

Reviews

4.9 out of 5 stars from 558 ratings
  • It’s A Whole Thing 😆

    I can’t recommend this podcast highly enough to anyone who is or aspires to be a professional pilot. I’ve been listening for over 3 years.

    From industry updates to career advice to gear reviews and layover guides, it’s a great way to get plugged into the industry.

    Apple Podcasts
    5
    StevoG85
    United Statesa month ago
  • Long winded

    Interesting guests, but I could do without all the musings.

    Apple Podcasts
    4
    Anon@mouse99
    United States2 months ago
  • A Must Listen for anyone thinking about professional aviation

    This one is now at the top of my weekly podcast (and I’m a cohost of a different Aviation podcast). I’m currently in the search for a flying job as a career 2.0er.

    Great discussions every week about a wide variety of topics and great guests. Ep 193 with James O’Nieal cinched up the deal for me to sign up for their concierge program.

    Thanks for the great pod!

    Ben S

    Apple Podcasts
    5
    Bsinger339
    United States2 months ago
  • Keep the good vibes going!

    Dylan, Max, Khaleesi and Reggie!

    I guess after listening for your podcast for several years now and after you recently supported me and my team’s around the world flight virtual adventure I suppose it’s time I finally write a review of your amazing podcast. First off seeing the show morph over the years really shows the “flexibility” you guys have to stay ahead of typical aviation podcasts out there. Always love whenever James O’Niell or Timothy Pope comes on because the amount of knowledge ... more

    Apple Podcasts
    5
    Shanetk
    United States3 months ago
  • OG listener

    So, I’ve been listening since day 1. You two have a fantastic product that covers every facet of professional aviation. And, it keeps getting better. Both in production and content.

    Keep up the awesome content!

    ps. Max’s musing is F’n gold!!!

    Apple Podcasts
    5
    C5_Pete
    United States3 months ago

Listeners Say

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

Many have highlighted the mix of industry insights and personal anecdotes that create an enjoyable listening experience.
However, a few critiques mention a preference for less personal commentary during episodes, suggesting a desire for a more focused approach.
Reviews indicate that the podcast is considered one of the best in the aviation niche, often recommended for those in the field or aspiring to enter it.
Listeners appreciate the engaging discussions and humor shared by the hosts, finding it a valuable resource for professional development in aviation.

Chart Rankings

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

Apple Podcasts
#21
United States/Leisure/Aviation
Apple Podcasts
#243
United States/Leisure
Apple Podcasts
#36
Canada/Leisure/Aviation
Apple Podcasts
#79
United Kingdom/Leisure/Aviation
Apple Podcasts
#11
Australia/Leisure/Aviation
Apple Podcasts
#54
Italy/Leisure/Aviation

Talking Points

Recent interactions between the hosts and their guests.

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.
194. What Will Pilot Hiring Really Look Like in 2026?
Q: What factors should pilots consider when evaluating job offers?
Pilots need to assess not just the job offers but also the cultural fit and instability that could lead to higher rejection rates in interviews.
194. What Will Pilot Hiring Really Look Like in 2026?
Q: What is the current state of regional pilot hiring?
The discussion reveals that regional hiring is expected to surge, especially as major airlines ramp up hiring, benefiting those in the pipeline.

Audience Metrics

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

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About 21.FIVE

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

The content caters specifically to professional pilots, presenting a diverse range of discussions that blend humor, personal anecdotes, and expert opinions. Common themes include the challenges and experiences faced by pilots in various sectors such as business aviation, airlines, and flight instruction. Episodes cover pivotal industry developments, financial planning for pilots, and personal stories that highlight the realities of an aviation career. Notably, the hosts frequently engage with industry experts, providing valuable insights on topics such as pilot hiring trends, compensation, and operational efficiencies. The podcast creatively balances entertainment with informational depth, making it appealing not just for current pilots, bu... more

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Which podcasts are similar to 21.FIVE?

These podcasts share a similar audience with 21.FIVE:

1. Ready 4 Pushback
2. Pilot’s Portfolio
3. Pilot to Pilot
4. Aviation Careers Podcast
5. Opposing Bases: Air Traffic Talk

How many episodes of 21.FIVE are there?

21.FIVE launched 7 years ago and published 202 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact 21.FIVE?

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What guests have appeared on 21.FIVE?

Recent guests on 21.FIVE include:

1. Brian Small
2. Tim Schoenauer
3. Captain Benny
4. James Onieal
5. Colonel Bushong
6. Seth Lake
7. Forrest Owens
8. Tim Pope

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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