
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
| Publishes | Weekly | Episodes | 196 | Founded | 7 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | LeisureAviation | |||

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 impacts for airl... more
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 the Mailbag, ... more
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 dropping soon... more
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 CFI logjams t... more
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Interesting guests, but I could do without all the musings.
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
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
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!!!
Used to be a great podcast but now they have turned into some MAGA brainwashed cult. Subtle comments about it but you can tell. Also calling GROK a good AI model when Musk has publicly said he is changing it to agree with his agenda and the MAGA agenda is crazy.
Key themes from listener reviews, highlighting what works and what could be improved about the show.
How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.
Apple Podcasts | #14 | |
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Apple Podcasts | #29 | |
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Apple Podcasts | #64 |
Recent interactions between the hosts and their guests.
Listeners, social reach, demographics and more for this podcast.
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Content primarily focuses on discussions relevant to professional pilots, including career development, aircraft operation, and industry trends. The hosts, experienced pilots themselves, frequently engage with guests from various aviation sectors, sharing insights on pilot compensation, financial planning, and the challenges of navigating a career in aviation. Throughout the episodes, there is often humor interspersed with practical advice, making the discussions relatable for pilots at different stages of their careers. The podcast uniquely combines light-hearted storytelling with genuine industry insight, catering to corporate, airline, and charter pilots alike. Listeners can expect to hear a mix of personal anecdotes, expert advice, and ... more
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1. Pilot to Pilot
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3. Aviation News Talk – Pilot Stories, Safety Tips & General Aviation News
4. Ready 4 Pushback
5. I Learned About Flying From That
21.FIVE launched 7 years ago and published 196 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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Recent guests on 21.FIVE include:
1. Brian Small
2. Tim Schoenauer
3. Dr. Chris Broyhill
4. Timothy P. Pope
5. Tim Pope
6. Captain Benny
7. Colonel Bushong
8. Seth Lake
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