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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189. Can You Survive 900 Hours a Year on a One-Hour Callout?
Episode 189
Tuesday, November 4, 2025 • Duration 01:51:18
Max kicks off his annual training rant—breaking down the highs, lows, and downright absurd moments of recurrent at "the training center." Dylan adds perspective on flight training efficiency and why a great instructor makes all the difference. The mailbag delivers everything from a new layover guide in Portsmouth to a 14-year-old aircraft dealer to a Marine pilot navigating a tricky transition to the airlines, plus a Learjet Pilot with a 1 hour call-out seeks guidance. In Flight Advice, a hard-working pilot is stalled out waiting for the industry to start moving again. Show Notes
0:00 Intro
5:42 Annual Training Rant
28:00 Watches & Shoes
34:13 The Cub & Random Thoughts
54:12 Reviews & Comments
55:13 AI Music & Mailbag
1:38:57 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.
188. How Can Pilots Build Wealth Beyond the Flight Deck?
Episode 188
Tuesday, October 28, 2025 • Duration 56:48
Tim Pope, CFP® and founder of 360 Aviation Advisors, joins Dylan and Max to talk about how pilots can make smarter financial moves—on and off the line. From variable pay to early retirement and crashpad cash flow, Tim breaks down what makes pilot finances uniquely tricky and how to stay ahead of turbulence. The crew also dives into taxes, scheduling volatility, and the "golden handcuff" problem in today's airline contracts. Tune in for real-world money talk that every professional pilot should hear before their next recurrent.
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
3:45 360 Aviation Advisors
6:04 End-Of-Year To-Do
14:46 Income, 529s, Roth IRAs
21:48 Super Saver vs Super Spender
49:18 Pilot's Portfolio
Our Sponsors
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 to learn more.
Feedback & Contact
179. What Happened to Those "Hard Days Off" You Promised Me?
Episode 179
Tuesday, August 19, 2025 • Duration 59:29
Dylan and Max connect from hotel rooms across the West, with Max prepping for his Cub camping trip to Idaho and Dylan testing out foam ear tips for his ProFlight headset (link in the show notes). In the Mailbag, listeners weigh in on commuting trade-offs, a gear-down hydraulic improvisation involving bottled water, and flying under Bravo airspace with "raw dog radios." Flight Advice tackles a business aviation bait-and-switch: hard days off evaporating into 24/7 on-call duty. The hosts dig into leverage, contracts, and how to sniff out a toxic flight department.
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.
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 to learn more.
Feedback & Contact
88. Flying for the Fractionals: 125,000 reasons to stop commuting
Episode 88
Tuesday, November 15, 2022 • Duration 01:13:20
Mailbag: Comments on our BizAv retention episode, Ted calls in to discuss some photos, Review of @FlyFLevelPilot Document Holder [6:00] // Flexjet's Director of Training, Jim Dunn, updates us on increased pay, benefits, and upgrade times at Flexjet. Training discussion: Using Flight data for training, handling takeoff performance, training circle to land, and RNP-AR approaches [20:20] // Story Time with Jim: Handling an uncontained engine failure [53:17] // Flight Advice: Navigating open enrollment with Tim Pope [59:00]
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. Visit harveywatt.com to learn more!
87. BizAv Pilot Retention: Creative ideas to keep talent
Episode 87
Tuesday, November 1, 2022 • Duration 01:29:31
Dylan and Max share some stories from night flying // Mailbag: USAF Study on pilot healthcare avoidance, Stories from offline airline diverts [10:55] // NBAA DOC members Eric Canup, David Keys, and Brian Koester join us to recap NBAA BACE and discuss one of the hottest topics at the show: Pilot retention and compensation [19:20] // Story Time with Dave: Brake failure in an A300 going into LGA [1:17:30] // Flight Advice: I failed airline training, now what? [1:23:00]
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. Visit harveywatt.com to learn more!
Advanced Aircrew Academy enables flight operations to fulfill their training needs in the most efficient and affordable way—in any location at any time. We do this by providing high-quality professional pilot, flight attendant, flight coordinator, maintenance, and line service training modules delivered via the web using a world-class online aviation training system. Visit to learn more!
86. Winter is coming - Are you ready?
Episode 86
Tuesday, October 18, 2022 • Duration 01:02:34
The latest from Donavan Batiste, Dylan gets stuck in an F-18 Simulator with his 6-year-old at the controls, and Max reviews our listener's new coffee company, FBO Coffee // Mailbag: Feedback on the Coast Guard Interview, A sobering message from a pilot with ALS, More on Formula 1 logistics, and a young airman wonders how to find what segment of aviation to settle in to [11:40] // Ryan, Winter Ops subject matter expert for Advanced Aircrew Academy, joins us to run through a quick refresher on winter ops, de-icing, and runway contamination [21:15] // Story Time with Ryan: Skywriting fail [51:00] // Flight Advice: Mother of 2 looking for a family-friendly flying job [55:45]
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. Visit harveywatt.com to learn more!
85. What does an airline dispatcher do? What every 121 pilot needs to know
Episode 85
Tuesday, October 4, 2022 • Duration 01:27:40
Max educates Dylan on the changes in LOA requirements for RNP/AR approaches. Mailbag: Skywest pay correction, Regional vs Fractional/LCC/ACMI thoughts, EASA Conversion info [9:50] // Matt Duxbury, Major Airline Dispatcher, joins us to pull back the curtain on what it is dispatchers do for a 121 operation. [25:30] // How do you calculate hold fuel, monitor weather, and ATC delays, and find the best rides for passengers? Matt explains it all // Story Time with Matt: Wife calls dispatch to locate pilot husband on a trip... [1:14:30] // Flight Advice: Airline dispatcher wants to transition to the cockpit [1:19:15]
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. Visit to learn more!
84. Investigating Aeromedical Reform
Episode 84
Tuesday, September 20, 2022 • Duration 01:09:29
Mailbag: Fired from corporate job after giving notice, Which regional should a CFI go to, and Max reveals his Coffee Routine [8:40] // Flight Advice: Leave a regional for FlexJet to stop commuting? [22:50] // The Pilots Pandemic Podcast hosts Maddie and Emma join us to talk about what's being done to address pilot mental health [27:20] // Emma shares her family story and promotes their petition for change // Story time: Max and Dylan buy a wake foil board [1:05:30]
83. What's it like to be a fixed wing pilot in the US Coast Guard?
Episode 83
Wednesday, September 7, 2022 • Duration 01:29:42
SWA Photo Airdrop, Max pitches a new segment, and we're hiring for a producer! // Mailbag: Playing over/under with Mesa Airlines' new pay rates [19:00] // Flight Advice: Leaving for a new job: Dealing with guilt and leaving behind a weak pilot [26:00] // Ron Bledsoe, Chief Pilot @ US Coast Guard, joins us to share his experience as a fixed-wing pilot for the USCG [38:00] // We learn about the different types of flying the Coast Guard does as well as the Coast Guard's new reserve program // Story time: We get several great stories from Ron's career [1:15:20]
82. How can BizAv tackle Fitness for Duty and Pilot Mental health with Jenny Showalter
Episode 82
Tuesday, August 23, 2022 • Duration 01:23:15
What do you do when you're paired with a lousy sim partner in training? // Mailbag: Success at OBAP, an Awesome Job Opportunity, and thoughts on dropping out of college to focus on flying // Jenny Showalter joins us to discuss Fitness for Duty, Pilot Mental Health, and how it relates to BizAv // Jenny helps us with some Flight Advice: Should a listener leave his good pt 91 job to commute to an LCC? // Story time with Jenny: Cheap Pilots and Rock Stars, the glamorous life of working at an FBO
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. Visit 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.
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, 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.
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.
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.
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.
ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.
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.
Advanced Aircrew Academy enables flight operations to fulfill their training needs in the most efficient and affordable way—in any location at any time. We do this by providing high-quality professional pilot, flight attendant, flight coordinator, maintenance, and line service training modules delivered via the web using a world-class online aviation training system. Visit aircrewacademy.com to learn more!
Tim Pope is a CERTIFIED FINANCIAL PLANNER™ and a pilot. His financial planning practice provides services to aviation professionals and aviation 401k plans. Tim helps clients pursue their financial goals by defining them, organizing & optimizing resources, planning, implementing, and monitoring their financial plan. Visit www.tpope.ceterainvestors.com to learn more. Click Here to Schedule a Meeting
Do you have feedback, suggestions, or a great aviation story to share? Email us info@21fivepodcast.com Check out our Instagram feed @21FivePodcast for more great content and to see 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 is a CERTIFIED FINANCIAL PLANNER™ and a pilot. His financial planning practice provides services to aviation professionals and aviation 401k plans. Tim helps clients pursue their financial goals by defining them, organizing & optimizing resources, planning, implementing, and monitoring their financial plan. Visit www.tpope.ceterainvestors.com to learn more. Click Here to Schedule a Meeting
Do you have feedback, suggestions, or a great aviation story to share? Email us info@21fivepodcast.com Check out our Instagram feed @21FivePodcast for more great content and to see 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.
Advanced Aircrew Academy enables flight operations to fulfill their training needs in the most efficient and affordable way—in any location at any time. We do this by providing high-quality professional pilot, flight attendant, flight coordinator, maintenance, and line service training modules delivered via the web using a world-class online aviation training system. Visit aircrewacademy.com to learn more!
Tim Pope is a CERTIFIED FINANCIAL PLANNER™ and a pilot. His financial planning practice provides services to aviation professionals and aviation 401k plans. Tim helps clients pursue their financial goals by defining them, organizing & optimizing resources, planning, implementing, and monitoring their financial plan. Visit www.tpope.ceterainvestors.com to learn more. Click Here to Schedule a Meeting
Do you have feedback, suggestions, or a great aviation story to share? Email us info@21fivepodcast.com Check out our Instagram feed @21FivePodcast for more great content and to see 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.
Advanced Aircrew Academy enables flight operations to fulfill their training needs in the most efficient and affordable way—in any location at any time. We do this by providing high-quality professional pilot, flight attendant, flight coordinator, maintenance, and line service training modules delivered via the web using a world-class online aviation training system. Visit aircrewacademy.com to learn more!
Tim Pope is a CERTIFIED FINANCIAL PLANNER™ and a pilot. His financial planning practice provides services to aviation professionals and aviation 401k plans. Tim helps clients pursue their financial goals by defining them, organizing & optimizing resources, planning, implementing, and monitoring their financial plan. Visit www.tpope.ceterainvestors.com to learn more. Click Here to Schedule a Meeting
Do you have feedback, suggestions, or a great aviation story to share? Email us info@21fivepodcast.com Check out our Instagram feed @21FivePodcast for more great content and to see 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.
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. Visit harveywatt.com to learn more!
Advanced Aircrew Academy enables flight operations to fulfill their training needs in the most efficient and affordable way—in any location at any time. We do this by providing high-quality professional pilot, flight attendant, flight coordinator, maintenance, and line service training modules delivered via the web using a world-class online aviation training system. Visit aircrewacademy.com to learn more!
Tim Pope is a CERTIFIED FINANCIAL PLANNER™ and a pilot. His financial planning practice provides services to aviation professionals and aviation 401k plans. Tim helps clients pursue their financial goals by defining them, organizing & optimizing resources, planning, implementing, and monitoring their financial plan. Visit www.tpope.ceterainvestors.com to learn more. Click Here to Schedule a Meeting
Do you have feedback, suggestions, or a great aviation story to share? Email us info@21fivepodcast.com Check out our Instagram feed @21FivePodcast for more great content and to see 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.
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. Visit harveywatt.com to learn more!
Advanced Aircrew Academy enables flight operations to fulfill their training needs in the most efficient and affordable way—in any location at any time. We do this by providing high-quality professional pilot, flight attendant, flight coordinator, maintenance, and line service training modules delivered via the web using a world-class online aviation training system. Visit aircrewacademy.com to learn more!
Tim Pope is a CERTIFIED FINANCIAL PLANNER™ and a pilot. His financial planning practice provides services to aviation professionals and aviation 401k plans. Tim helps clients pursue their financial goals by defining them, organizing & optimizing resources, planning, implementing, and monitoring their financial plan. Visit www.tpope.ceterainvestors.com to learn more. Click Here to Schedule a Meeting
Do you have feedback, suggestions, or a great aviation story to share? Email us info@21fivepodcast.com Check out our Instagram feed @21FivePodcast for more great content and to see 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.
Advanced Aircrew Academy enables flight operations to fulfill their training needs in the most efficient and affordable way—in any location at any time. We do this by providing high-quality professional pilot, flight attendant, flight coordinator, maintenance, and line service training modules delivered via the web using a world-class online aviation training system. Visit aircrewacademy.com to learn more!
Tim Pope is a CERTIFIED FINANCIAL PLANNER™ and a pilot. His financial planning practice provides services to aviation professionals and aviation 401k plans. Tim helps clients pursue their financial goals by defining them, organizing & optimizing resources, planning, implementing, and monitoring their financial plan. Visit www.tpope.ceterainvestors.com to learn more. Click Here to Schedule a Meeting
Do you have feedback, suggestions, or a great aviation story to share? Email us info@21fivepodcast.com Check out our Instagram feed @21FivePodcast for more great content and to see 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.
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