21.FIVE - Professional Pilots Podcast

Max goes back to basics in recurrent training, Ted checks in from his increasingly fortified garage, and the guys dig into the FAA's move away from single-pilot exemptions on legacy Citations. The Mailbag keeps the pilot-marriage conversation going with listener strategies for trust, communication, and life on the road. For Flight Advice, Ben asks how to consolidate paper, Garmin Pilot, and MyFlightbook records before starting his first Part 135/fractional flying job, leading to a discussion about owning your data, backups, and keeping a clean interview-ready logbook. 
Show Notes
0:00 Intro
3:34 Captain Stabbing
5:36 Special Phone Call
22:01 FAA News
31:26 SR-71 Rumor
36:20 Reviews & Comments
38:17 Mailbag
52:06 Flight Advice
Our Sponsors
Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.
Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.
Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.
The AirComp Calculator™ is business aviation's only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more.
Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.
Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline's plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more.
VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.
ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.
 
Feedback & Contact
Have feedback, suggestions, or a great aviation story to share? Email us at info@21fivepodcast.com. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates).
The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.

Tim Pope of 360 Aviation Advisors joins Dylan and Max to talk open enrollment, year-end financial planning, and one of the biggest career decisions pilots eventually face: when to upgrade. For professional pilots, the numbers matter—but so do schedule, seniority, reserve, weekends off, and the quality-of-life calculus that never fits neatly into a spreadsheet. They dig into disability coverage, estate planning, 401(k) and Roth strategies, AI-generated financial questions, and whether captain pay is worth trading away a senior FO schedule. Listen in and subscribe for more conversations built around the decisions professional pilots actually have to make.
Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.
Show Notes
0:00 Intro
3:48 Benefit Season & Estate Plans
7:37 Health & Year-End Targets
16:57 AI in Financial Planning & Tax Check In
24:13 Quality of Life vs Money
35:47 Airplane Purchase Spreadsheet
39:19 When to Work With Tim
 
Our Sponsors
Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.
Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.
Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.
The AirComp Calculator™ is business aviation's only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more.
Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.
Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline's plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more.
VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.
ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.
 
Feedback & Contact
Have feedback, suggestions, or a great aviation story to share? Email us at info@21fivepodcast.com. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates).
The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.

This week we ditch the usual format and go full storytime, starting with Max's annual Idaho backcountry mission involving Cub flying, pack rafts, mechanical drama, questionable fuel logistics, hungry foxes, and one extremely unwelcome skunk. Dylan counters with a 24-hour Anchorage layover full of 747s, floatplanes, bush planes, F Street Station, and some proper Alaska aviation sightseeing. Then he brings Gavin along in the right seat of the CJ2 for a father-son run to Roswell, complete with copilot duties and UFO tourism. Mailbag and Flight Advice will be back next episode.
Show Notes
0:00 Intro
5:37 Max's Trip To Idaho
31:39 45 Ranch & Night Visitor
43:43 Plans to Return?
52:12 Dylan's Alaskan Adventure
58:00 New Favorite Copilot
 
Our Sponsors
Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.
Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.
Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.
The AirComp Calculator™ is business aviation's only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more.
Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.
Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline's plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more.
VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.
ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.
 
Feedback & Contact
Have feedback, suggestions, or a great aviation story to share? Email us at info@21fivepodcast.com. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates).
The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.

Brooks Pettit of Vaerus Jet Sales joins Dylan and Max to break down what is really happening in the business aircraft market. For professional pilots and flight departments, he covers tight inventory, strong demand, financing, tax-driven transactions, and why planning ahead matters. They also get into Challenger 3500 delivery positions, bonus depreciation, tariffs, AI-driven market research, and the realities of buying and selling aircraft in a fast-moving market. Listen in for a practical look at the transaction side of business aviation, then subscribe for more conversations from the cockpit and the flight department.
Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.
Show Notes
0:00 Intro
3:15 August Market Update & Inventory
14:53 New vs Used
20:53 New Airplane Deliveries
24:34 Interest Rates & Tariffs
28:06 Coaching: Airplane Transaction Scenario
35:51 Using AI in Sales
44:19 Brooks' Musings
Our Sponsors
Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.
Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.
Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.
The AirComp Calculator™ is business aviation's only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more.
Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.
Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline's plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more.
VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.
ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.
 
Feedback & Contact
Have feedback, suggestions, or a great aviation story to share? Email us at info@21fivepodcast.com. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates).
The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.

Max checks in from a musty Missouri hotel while earning his Light Sport Repairman certificate, and the guys detour through GA maintenance, Starbase, RTA wizardry, and the ongoing decline of 123.45 as a social network. Mailbag covers Sugar Alpha, Qantas' ultra-long-haul A350 plans, where Spirit's pilots and traffic may have landed, and whether 21.Five needs a Discord server. In Flight Advice, Dylan and Max tackle the stereotype that pilots are destined to cheat—and how couples can build trust, recognize real red flags, and keep the hotel-bar lifestyle from becoming a relationship MEL.
Mentioned in this episode:
Land or Go Around: https://www.instagram.com/land_or_go_around/
Temu-style quadcopter video: https://www.youtube.com/watch?v=bUkvDe0x47A&t=15s
Husk.irl AI troll account: https://www.facebook.com/profile.php?id=61577492686970
Show Notes
0:00 Intro & AMP Training
12:16 Networking In The Sky
17:22 Max's Musings: Overnights in Harlingen
21:53 News: Allegiant Contracts & Ebola
24:11 Listener Reviews & Comments
28:29 Mailbag
43:03 Flight Advice: Cheating Stigma
57:36 Temu Quadcopter?!?
Our Sponsors
Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.
Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.
Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.
The AirComp Calculator™ is business aviation's only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more.
Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.
Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline's plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more.
VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.
ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.
 
Feedback & Contact
Have feedback, suggestions, or a great aviation story to share? Email us at info@21fivepodcast.com. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates).
The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.